PRODUCTS

NITROBENZOIC ACID

2-Nitrobenzoic acid is used NH2-protecting reagent.
2-Nitrobenzoic Acid is used as a reagent in the synthesis of several organic compounds including that of novel triazoles and a tetrazole of escitalopram which act as cholinesterase inhibitors.
2-Nitrobenzoic acid is also used in the one pot synthesis of 1,4-disubstituted 1,2,3-triazoles.

Molecular formula: C₇H₅NO₄
Molecular weight ~167.12 g/mol

Isomer               CAS       EC Number   Melting Point (°C)   Solubility (H₂O)   pKa (in water)   Density (g/cm³)
2-Nitrobenzoic acid (o-)   552-16-9   209-004-9   146–148           ~6.8–7.8 g/L       ~2.16       ~1.58
3-Nitrobenzoic acid (m-)   121-92-6   204-508-5   139–141           ~0.24 g/100 mL (15 °C)   ~3.47       ~1.49
4-Nitrobenzoic acid (p-)   62-23-7       200-526-2   ~237–242       <0.1 g/100 mL (26 °C)   ~3.41       ~1.58

SYNONYMS:
2-NITROBENZOIC ACID SYNONYMS:
O-NITROBENZOIC ACID, 2-nitrobenzoic, 2-NITRODRACYLIC ACID, 2-Nitrobenzoicacid,95%, Nitrobenzoic aci, 2-nitro-benzoicaci, o-Nitrobenaoicacid, o-nitro-benzoicaci, RARECHEM AL BO 0202, ORTHO-NITROBENZOATE, O-nitrobenzoic acid, 2-nitrobenzoic acid, 2-nitrodracylic acid, 2-Nitrobenzoicacid, Nitrobenzoic aci, 2-nitro-benzoicaci, o-Nitrobenaoicacid, o-nitro-benzoicaci, ORTHO-NITROBENZOATE, 2-NITROBENZOIC ACID, 552-16-9, o-Nitrobenzoic acid, Benzoic acid, 2-nitro-, ortho-nitrobenzoic acid, CCRIS 2334, NSC 9576, EINECS 209-004-9, DTXSID5025738, CHEBI:25620, AI3-08821, S6S4653K7Z, NSC-9576, UNII-S6S4653K7Z, NITROBENZOIC ACID, 2-, CCRIS-2334, DTXCID005738, oNitrobenzoic acid, oCarboxynitrobenzene, Nitrobenzoicacid, o, orthonitrobenzoic acid, Benzoic acid, onitro, Benzoic acid, 2nitro, BENZOIC ACID,2-NITRO MFC7 H5 N1 O4, 209-004-9, InChI=1/C7H5NO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10, SLAMLWHELXOEJZ-UHFFFAOYSA-N, 2-nitrobenzoicacid, o-Carboxynitrobenzene, Benzoic acid, o-nitro-, 2-nitro-benzoic acid, MFCD00007137, 2-nitro benzoic acid, -nitrobenzoic acid, nitro benzoic acid, 6-nitro-benzoic acid, 2-Nitrobenzoic acid, 95%, Oprea1_474365, SCHEMBL78205, SCHEMBL220779, SCHEMBL246196, SCHEMBL436389, CHEMBL114719, orb1685669, SCHEMBL2722499, SCHEMBL7560618, SCHEMBL17461588, SCHEMBL29696138, 2-Nitrobenzoic acid - Technical, NSC9576, 2-Nitrobenzoic acid-ring-ul-14c, HY-Y0891, Tox21_201020, AC-652, SBB058380, STL168882, AKOS000119255, CS-W020072, FN38281, NCGC00091364-01, NCGC00091364-02, NCGC00258573-01, AS-11055, CAS-552-16-9, FN172456, SY005662, DB-024127, N0155, NS00022362, ST50186531, EN300-18349, BENZOIC ACID,2-NITRO MFC7 H5 N1 O4, D71183, 2-Nitrobenzoic acid, purum, >=97.0% (HPLC), 2-Nitrobenzoic acid, technical, >=85% (HPLC), AB-131/40245354, 2-Nitrobenzoic acid, Vetec(TM) reagent grade, 94%, Q19810380, Z57160141, 2-Nitrobenzoic acid, 95%, Contains 3- and 4-isomers, F3096-1719, 104810-18-6, O-nitrobenzoic acid, 2-nitrobenzoic acid, 2-nitrodracylic acid, 2-Nitrobenzoicacid, Nitrobenzoic aci, 2-nitro-benzoicaci, o-Nitrobenaoicacid, o-nitro-benzoicaci, ORTHO-NITROBENZOATE

3-NITROBENZOIC ACID SYNONYMS:
m-Nitrobenzoic acid, 3-NITROBENZOIC ACID, 121-92-6, m-Nitrobenzoic acid, Benzoic acid, 3-nitro-, Benzoic acid, m-nitro-, m-Nitrobenzenecarboxylic acid, Metanitrobenzoic acid, meta-Nitrobenzoic acid, M-CARBOXYNITROBENZENE, DTXSID0025737, NSC-9801, H318ZW7612, DTXCID605737, 204-508-5, 3-Nitro-benzoic acid, MFCD00007251, CAS-121-92-6, CCRIS 2335, HSDB 6028, NSC 9801, EINECS 204-508-5, BRN 0908644, AI3-09015, UNII-H318ZW7612, 3-nitro benzoic acid, WLN: WNR CVQ, 3-NITROBENZOICACID, SCHEMBL132618, CHEMBL274839, SCHEMBL2170995, SCHEMBL2204741, SCHEMBL3049742, SCHEMBL4827704, SCHEMBL7406647, SCHEMBL17347335, SCHEMBL29490968, NSC9801, CHEBI:231494, 3-NITROBENZOIC ACID [HSDB], BCP08709, HY-Y1313, STR01384, Tox21_201238, Tox21_303250, SBB058220, STK301724, 3-Nitrobenzoic acid, puriss., 99%, AKOS000119012, AC-2834, CS-W020596, FN70301, PS-5143, NCGC00091521-01, NCGC00091521-02, NCGC00091521-03, NCGC00257168-01, NCGC00258790-01, 3-Nitrobenzoic acid, ReagentPlus(R), 99%, N0154, NS00019769, ST45061531, EN300-18006, BENZOIC ACID,3-NITRO MFC7 H5 N1 O4, 3-Nitrobenzoic acid, purum, >=98.0% (HPLC), 3-Nitrobenzoic acid, Vetec(TM) reagent grade, 98%, Q4634183, Z57127479, F2191-0133, InChI=1/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10, 27178-83-2

4-NITROBENZOIC ACID SYNONYMS:
4-Nitrobenzoic acid, p-Nitrobenzoic acid, benzoic acid, 4-nitro, nitrodracylic acid, 4-nitrodracylic acid, 1-carboxy-4-nitrobenzene, p-nitro, p-nitrobenzoicacid, p-nitrobenzenecarboxylic acid, kyselina p-nitrobenzoova, 4-NITROBENZOIC ACID, Benzoic acid, p-nitro-, p-Nitrobenzoic acid, Nitrodracylic acid, 4-Nitrobenzoic acid, Kyselina p-nitrobenzoova, 1-Carboxy-4-nitrobenzene, 4-Nitrodracylic acid, p-Nitrobenzenecarboxylic acid, p-Nitrodracylic acid, NSC 7707, 4-NITROBENZOIC ACID, PNBA, 4-Nitrobenzoic, p-nitrobenzoic, PARA-NITROBENZOATE, -Nitrobenzoic Acid, 19/KG, nitrodracylicacid, 4-Nitrobenzoesure, Nitrodracylic acid, p-Nitrobenzoic acid, 62-23-7, Benzoic acid, 4-nitro-, Nitrodracylic acid, 4-Nitrodracylic acid, 1-Carboxy-4-nitrobenzene, p-Nitrobenzenecarboxylic acid, Benzoic acid, p-nitro-, p-Nitrodracylic acid, para-nitrobenzoic acid, G83NWR61OW, DTXSID3020966, CHEBI:262350, NSC-7707, DTXCID90966, 200-526-2, Kyselina p-nitrobenzoova, MFCD00007352, 4-Nitro-benzoic acid, NSC 7707, CHEMBL101263, CAS-62-23-7, 4-Nitrobenzoicacid, p-nitro benzoic acid, CCRIS 1185, HSDB 2140, Kyselina p-nitrobenzoova [Czech], EINECS 200-526-2, UNII-G83NWR61OW, AI3-00149, p-nitro-benzoicacid, 4NB, p-Carboxynitrobenzene, p-nitro-benzoic acid, 4-Nitro benzoic acid, WLN: WNR DVQ, EC 200-526-2, 4-Nitrobenzoic acid, 98%, SCHEMBL43476, 4-Nitrobenzenecarboxylic acid, PARA NITROBENZOIC ACID, MLS002454442, SCHEMBL180511, orb1745271, SCHEMBL3282224, SCHEMBL10590027, SCHEMBL15630318, NSC7707, HMS3041D05, HY-Y0607, STR01385, Tox21_201258, Tox21_300131, BDBM50405310, SBB058196, STL168880, 4-Nitrobenzoic acid, puriss., 99%, 4-NITROBENZOIC ACID [USP-RS], AKOS000118872, AKOS015831344, AKOS024268501, CS-W020075, FN30591, PB43175, NCGC00091607-01, NCGC00091607-02, NCGC00091607-03, NCGC00091607-04, NCGC00253917-01, NCGC00258810-01, AC-10993, BP-30196, PD033171, SMR001252222, SY002161, N0156, NS00015670, ST50406177, EN300-18011, C18625, D70606, 4-Nitrobenzoic acid, purum, >=98.0% (HPLC), AE-562/40227261, 4-Nitrobenzoic Acid(Discontinued,See C4X-25793), 4-Nitrobenzoic acid, Vetec(TM) reagent grade, 98%, Q2823227, 4-AMINOBENZOIC ACID IMPURITY A [EP IMPURITY], Z57127484, F2191-0089, 4-Nitrobenzoic acid, United States Pharmacopeia (USP) Reference Standard, InChI=1/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10)

Nitrobenzoic Acid is a derivative of benzoic acid.
Nitrobenzoic Acid is commercially important.

Nitrobenzoic Acid is about ten times more acidic than the parent benzoic acid.
Nitrobenzoic Acid can be prepared through the oxidation of styrene in boiling nitric acid.
The salts and esters of nitrobenzoic acids are known as nitrobenzoates.

Nitrobenzoic acid is an organic compound that consists of a benzoic acid molecule with a nitro group (-NO2) attached to the benzene ring.
Nitrobenzoic Acid is an important intermediate in the synthesis of various pharmaceutical and industrial compounds.

2-NITROBENZOIC ACID (o-NITROBENZOIC ACID)
2-Nitrobenzoic acid or o-nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H.
2-Nitrobenzoic acid is prepared by oxidation of 2-nitrotoluene with nitric acid.

2-Nitrobenzoic acid consists of a carboxylic acid group and a nitro group in the ortho configuration.
Reduction of the nitro group into an amine produces anthranilic acid.

2-Nitrobenzoic acid is a yellowish white crystals with an intensely sweet taste.
2-Nitrobenzoic acid is a nitrobenzoic acid carrying the nitro substituent at position 2.

2-Nitrobenzoic acid is functionally related to a benzoic acid.
2-Nitrobenzoic acid is a conjugate acid of a 2-nitrobenzoate.

2-Nitrobenzoic acid is a off-white powder.
2-Nitrobenzoic acid is a nitrobenzoic acid carrying the nitro substituent at position 2.

2-Nitrobenzoic acid is yellowish white crystals with an intensely sweet taste.
2-Nitrobenzoic acid is a insoluble in water.

3-NITROBENZOIC ACID (m-NITROBENZOIC ACID)
3-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H.
3-Nitrobenzoic acid is an aromatic compound and under standard conditions, it is an off-white solid.

The two substituents are in a meta position with respect to each other, giving the alternative name of m-nitrobenzoic acid.
3-Nitrobenzoic acid can be useful as it is a precursor to 3-aminobenzoic acid, which is used to prepare some dyes.

3-nitrobenzoic acid is a nitrobenzoic acid having the nitro group at the 3-position.
3-Nitrobenzoic acid is a conjugate acid of a 3-nitrobenzoate.

3-Nitrobenzoic acid is soluble in water.
3-Nitrobenzoic acid is insoluble in acetic acid.

4-NITROBENZOIC ACID (p-NITROBENZOIC ACID)
4-Nitrobenzoic acid appears as odorless pale yellow crystals.
4-Nitrobenzoic acid is a nitrobenzoic acid having the nitro group at the 4-position.

4-Nitrobenzoic acid is functionally related to a benzoic acid.
4-Nitrobenzoic acid is a conjugate acid of a 4-nitrobenzoate.

4-Nitrobenzoic acid (p-nitrobenzoic acid) is a carboxylic acid derivative.
4-Nitrobenzoic acid participates in the biosynthesis of the antibiotic aureothin.

Infrared Fourier transform spectroscopic studies suggest that the molecules of 4-nitrobenzoic acid gets adsorbed on the surfaces of fine silver powder as carboxylate.
4-Nitrobenzoic acid is a light yellow crystalline powder.

4-Nitrobenzoic acid is a nitrobenzoic acid having the nitro group at the 4-position.
4-Nitrobenzoic acid is a versatile aromatic compound known for its distinctive nitro group, which enhances its reactivity and utility in various chemical applications.

4-Nitrobenzoic acid (C7H5NO4) is a carboxylic acid derivative and an aromatic organic compound.
At room temperature, 4-Nitrobenzoic acid appears as a white crystalline solid with no significant odor.

4-Nitrobenzoic acid's molecular structure features a benzene ring substituted with a nitro group (-NO2) at the para position and a carboxylic acid group (-COOH), which imparts both aromaticity and acidic properties to the compound.

As such, 4-Nitrobenzoic acid belongs to the broader chemical classes of aromatic hydrocarbons and carboxylic acid derivatives.
4-Nitrobenzoic acid was first synthesized in the 19th century through the nitration of benzoic acid using a mixture of concentrated nitric acid and sulfuric acid under controlled conditions.

This process introduces a nitro group onto the benzene ring of benzoic acid, specifically at the para position due to the electron-withdrawing effect of the carboxylic acid group.

Although not commonly derived from natural sources, certain plants containing nitroaromatic compounds may theoretically produce similar structures under specific metabolic pathways.

Industrial preparation typically involves the aforementioned nitration method, utilizing benzoic acid as the starting material and conducting the reaction under carefully monitored temperatures to ensure selectivity and yield.
In summary, 4-Nitrobenzoic acid represents a versatile aromatic carboxylic acid derivative with applications spanning multiple industries.

USES and APPLICATIONS of NITROBENZOIC ACID:
USES and APPLICATIONS of 2-NITROBENZOIC ACID (p-NITROBENZOIC ACID)
Reagent in organic synthesis (e.g., protecting groups, and for synthesizing triazole/tetrazole derivatives)
Also produced via oxidation of 2-nitrotoluene

2-Nitrobenzoic acid is also used in the one pot synthesis of 1,4-disubstituted 1,2,3-triazoles.
2-Nitrobenzoic acid is employed as a synthetic reagent and can function as a growth supplement for Pseudomonas fluorescens strain KU-7.
2-Nitrobenzoic acid also finds its use as a reagent for protection of amine groups and in organic synthesis.

USES and APPLICATIONS of 3-NITROBENZOIC ACID (p-NITROBENZOIC ACID)
3-Nitrobenzoic acid was used to investigate the role of ozone as additional decomposition or finishing reagent in the degradation of o-, m- and p-nitrobenzoic acids.

USES and APPLICATIONS of 4-NITROBENZOIC ACID (p-NITROBENZOIC ACID)
4-Nitrobenzoic Acid is used in the synthesis of anti-Trypanosoma cruzi agents in the treatment of chagas disease.
4-Nitrobenzoic acid is widely utilized in the synthesis of dyes, pharmaceuticals, and agrochemicals, making it an essential building block in organic chemistry.

4-Nitrobenzoic acid's ability to undergo electrophilic substitution reactions allows for the introduction of various functional groups, facilitating the development of more complex molecules.
Researchers often leverage 4-nitrobenzoic acid in the preparation of nitro-substituted derivatives, which are valuable in the production of advanced materials and specialty chemicals.

In addition to its synthetic applications, 4-nitrobenzoic acid serves as a reagent in analytical chemistry, particularly in the determination of amines and alcohols.
4-Nitrobenzoic acid's unique properties, such as solubility in organic solvents and stability under various conditions, make it an ideal choice for laboratory use.

With its broad range of applications, 4-nitrobenzoic acid stands out as a crucial compound for professionals seeking reliable and effective solutions in their research and industrial processes.
4-Nitrobenzoic acid's synthesis history dates back to classical organic chemistry techniques, while its utility continues to grow in modern contexts.

Industrially, 4-Nitrobenzoic acid finds extensive application across various sectors.
In the pharmaceutical industry, 4-Nitrobenzoic acid serves as an intermediate for synthesizing drugs and antibiotics.
Within the chemical sector, 4-Nitrobenzoic acid acts as a precursor for dyes, pigments, and other fine chemicals.

Additionally, 4-Nitrobenzoic acid plays a role in the production of agrochemicals, such as herbicides and pesticides.
4-Nitrobenzoic acid is a precursor to 4-nitrobenzoyl chloride; used in manufacturing of anesthetic procaine, folic acid, and para-aminobenzoic acid (PABA)
4-Nitrobenzoic acid is used in dye intermediates.

NITROBENZOIC ACIDS AND DERIVATIVES:
Organic compounds that consist of benzoic acid with a nitro group substitution; a nitro group has a nitrogen atom bonded to two oxygen groups in a single and a double bond.
Includes compounds that are directly derived from nitrobenzoic acid.

ISOMERS OF NITROBENZOIC ACID:
The three isomers of nitrobenzoic acid are:
2-Nitrobenzoic acid is prepared by oxidation of 2-nitrotoluene.
3-Nitrobenzoic acid is a precursor to 3-aminobenzoic acid, which in turn is used to prepare some dyes.

It can be prepared by nitration of benzoic acid.
It also can be prepared by treating benzaldehyde under nitration conditions, a process that initially converts the aldehyde to the acid.
4-Nitrobenzoic acid is a precursor to 4-aminobenzoic acid, which is in turn used to prepare the anesthetic procaine.

4-Nitrobenzoic acid is prepared by oxidation of 4-nitrotoluene.
Nitrobenzoic acids are derivatives of benzoic acid.
Two are commercially important.

They are about ten times more acidic than the parent benzoic acid.
Nitrobenzoic acid can be prepared through the oxidation of styrene in boiling nitric acid.
The salts and esters of nitrobenzoic acids are known as nitrobenzoates.

Nitrobenzoic acids are benzoic acid derivatives where one hydrogen is replaced by a nitro group (–NO₂) at different positions:
2-Nitrobenzoic acid (ortho-nitrobenzoic acid, o-nitrobenzoic acid).
3-Nitrobenzoic acid (meta-nitrobenzoic acid, m-nitrobenzoic acid).
4-Nitrobenzoic acid (para-nitrobenzoic acid, p-nitrobenzoic acid).

Each variant shares the formula C₇H₅NO₄ and molar mass ~167.12 g/mol.

5 MUST KNOW FACTS FOR NITROBENZOIC ACID:
The nitro group on nitrobenzoic acid is an electron-withdrawing substituent, which increases the acidity of the carboxylic acid group.

Nitrobenzoic acid can exist in three isomeric forms: ortho-, meta-, and para-nitrobenzoic acid, each with slightly different physical and chemical properties.

Nitrobenzoic acid is commonly used as a precursor in the synthesis of various pharmaceutical intermediates, such as analgesics and antidepressants.

The presence of the nitro group on the benzene ring makes nitrobenzoic acid more susceptible to nucleophilic aromatic substitution reactions compared to benzoic acid.

Nitrobenzoic acid can undergo reduction reactions to form amino-substituted benzoic acid derivatives, which are important building blocks in organic synthesis.

EXPLAIN HOW THE NITRO GROUP ON NITROBENZOIC ACID AFFECTS THE ACIDITY OF THE CARBOXYLIC ACID GROUP:
The nitro group on nitrobenzoic acid is an electron-withdrawing substituent, which means it pulls electron density away from the benzene ring.
This increased electron-withdrawing effect stabilizes the conjugate base of the carboxylic acid group, making the proton more easily released and the overall compound more acidic compared to benzoic acid.
The electron-withdrawing nature of the nitro group decreases the electron density around the carboxylic acid group, making the hydrogen more labile and the compound more acidic.

DESCRIBE THE POTENTIAL REACTIVITY OF NITROBENZOIC ACID IN NUCLEOPHILIC AROMATIC SUBSTITUTION REACTIONS:
The presence of the nitro group on the benzene ring of nitrobenzoic acid makes the ring more susceptible to nucleophilic aromatic substitution reactions.
The nitro group is an activating, ortho/para-directing substituent, which means it increases the reactivity of the ring towards nucleophilic attack, particularly at the ortho and para positions relative to the nitro group.
This enhanced reactivity is due to the electron-withdrawing nature of the nitro group, which makes the benzene ring more electrophilic and, therefore, more prone to nucleophilic addition-elimination reactions.

DISCUSS THE POTENTIAL USE OF NITROBENZOIC ACID AS A PRECURSOR IN THE SYNTHESIS OF PHARMACEUTICAL INTERMEDIATES:
Nitrobenzoic acid is a valuable intermediate in the synthesis of various pharmaceutical compounds, such as analgesics and antidepressants.
The nitro group can be selectively reduced to an amino group, creating amino-substituted benzoic acid derivatives that serve as important building blocks in organic synthesis.

These amino-substituted benzoic acids can then be further functionalized and incorporated into the structures of various pharmaceutical agents.
The versatility of nitrobenzoic acid as a precursor, combined with the reactivity of the nitro group, makes it a valuable compound in the development of new pharmaceutical drugs and intermediates.

2-NITROBENZOIC ACID (o-NITROBENZOIC ACID)
CAS Number: 552-16-9
EC/EINECS Number: 209-004-9

Physical & Chemical Properties
Formula: C₇H₅NO₄
Molar Mass: 167.12 g/mol
Appearance: Off-white fine powder; yellowish-white crystals with sweet taste
Melting Point: 146–148 °C
Boiling Point (estimated): 295.7 °C
Density / Specific Gravity: ~1.58 g/cm³
Refractive Index: ~1.6280 (estimate)
Solubility in Water: ~6.8–7.8 g/L (i.e., 0.68–0.78 g/100 mL)
pKa: ~2.16 (at 18 °C)
Stability: Stable; incompatible with strong oxidizing agents, strong bases; may react with cyanides

RELATED COMPOUNDS OF 2-NITROBENZOIC ACID (o-NITROBENZOIC ACID):
*Benzoic acid
*Nitrobenzene
*Anthranilic acid
*3,5-Dinitrobenzoic acid
*3-Nitrobenzoic acid
*4-Nitrobenzoic acid

NOTES OF 2-NITROBENZOIC ACID (o-NITROBENZOIC ACID):
Store 2-Nitrobenzoic acid away from oxidizing agents.
Keep 2-Nitrobenzoic acid the container tightly closed and place it in a cool, dry and well ventilated condition.

REACTIVITY PROFILE OF 2-NITROBENZOIC ACID (o-NITROBENZOIC ACID):
2-Nitrobenzoic acid is incompatible with strong oxidizing agents.
Also incompatible with strong bases.
2-Nitrobenzoic acid may react with cyanides.

PURIFICATION METHODS OF 2-NITROBENZOIC ACID (o-NITROBENZOIC ACID):
Crystallise 2-Nitrobenzoic acid from benzene (twice), n-butyl ether (twice), then water (twice).
Dry and store 2-Nitrobenzoic acid in a vacuum desiccator.
2-Nitrobenzoic acid has also been crystallised from EtOH/H2O.
The amide has m 176.5° (from H2O).
2-Nitrobenzoic acid is employed as a synthetic reagent and can function as a growth supplement for Pseudomonas fluorescens strain KU-7.
2-Nitrobenzoic acid also finds its use as a reagent for protection of amine groups and in organic synthesis.

3-NITROBENZOIC ACID (m-NITROBENZOIC ACID)
CAS Number: 121-92-6
EC/EINECS Number: 204-508-5

Physical & Chemical Properties
Formula: C₇H₅NO₄
Molar Mass: ~167.12 g/mol
Appearance: Cream-colored solid
Melting Point: 139–141 °C
Density: ~1.494 g/cm³
Solubility in Water: ~0.24 g/100 mL at 15 °C
pKa: ~3.47 (in water)
Magnetic Susceptibility: –80.22 ×10⁻⁶ cm³/mol

USES & REACTIVITY OF 3-NITROBENZOIC ACID (m-NITROBENZOIC ACID):
Precursor to 3-aminobenzoic acid (used in dye synthesis)
Hydrogenation yields 3-aminobenzoic acid; nitration of benzoic acid or oxidation routes are used in synthesis
The nitro and carboxyl groups deactivate aromatic ring toward further electrophilic substitution

RELATED COMPOUNDS OF 3-NITROBENZOIC ACID (m-NITROBENZOIC ACID):
*Benzoic acid
*Nitrobenzene
*Anthranilic acid
*3,5-Dinitrobenzoic acid
*2-Nitrobenzoic acid
*4-Nitrobenzoic acid

NOTES OF 3-NITROBENZOIC ACID (m-NITROBENZOIC ACID):
Store 3-Nitrobenzoic acid away from strong oxidizing agents.
Keep 3-Nitrobenzoic acid container tightly closed.
Store 3-Nitrobenzoic acid in cool, dry conditions in well sealed containers.

PROPERTIES OF 3-NITROBENZOIC ACID (m-NITROBENZOIC ACID):
With a pKa of 3.47, 3-nitrobenzoic acid is about ten times more acidic than benzoic acid.
The conjugate base of benzoic acid is stabilised by the presence of the electron withdrawing nitro group which explains its increased acidity in comparison to unsubstituted benzoic acid.
3-Nitrobenzoic acid is typically soluble in oxygenated and chlorinated solvents.

REACTIVITY OF 3-NITROBENZOIC ACID (m-NITROBENZOIC ACID):
The presence of both carboxylic acid and nitro functional groups deactivate the ring with respect to electrophilic aromatic substitution reactions.
Hydrogenation gives 3-aminobenzoic acid.
3-Nitrobenzoic acid appears as off white to yellowish-white crystals.

PREPARATION OF 3-NITROBENZOIC ACID (m-NITROBENZOIC ACID):
3-Nitrobenzoic acid is prepared by nitration of benzoic acid at low temperatures.
Both 2-Nitrobenzoic acid and 4-Nitrobenzoic acid are produced as side products, with yields of approximately 20% and 1.5% respectively.
Since carboxylic acid functional groups are electron withdrawing, during an electrophilic aromatic substitution reaction of nitration, substituents are directed to a meta position which explains this regiochemistry.
A less efficient route involves nitration of methyl benzoate, followed by hydrolysis.
Alternatively, oxidative C-C bond cleavage of 3-nitroacetophenone to the corresponding aryl carboxylic acid, has been demonstrated.
A further synthesis involves the oxidation of 3-nitrobenzaldehyde.

4-NITROBENZOIC ACID (p-NITROBENZOIC ACID)
CAS Number: 62-23-7
EC/EINECS Number: 200-526-2

Physical & Chemical Properties
Formula: C₇H₅NO₄
Molar Mass: 167.1189 g/mol
Appearance: Light yellow crystalline powder
Density: ~1.58 g/cm³
Melting Point: ~237 °C (often quoted 239–242 °C)
Solubility: <0.1 g/100 mL at 26 °C (very poorly soluble in water)
pKa: ~3.41 (in water), ~9.1 (in DMSO)
Magnetic Susceptibility: −78.81 ×10⁻⁶ cm³/mol
Boiling Behavior: Sublimes—does not boil at atmospheric pressure
Additional properties: decomposes at ~350 °C; flash point 201 °C (closed cup); auto-ignition ~300 °C; log P (octanol/water) ~1.89

PRODUCTION METHODS OF 4-NITROBENZOIC ACID (p-NITROBENZOIC ACID)
4-Nitrobenzoic acid is produced commercially by the oxidation of 4-nitrotoluene with molecular oxygen.
Oxidation with 15 % nitric acid at 175 ℃ produces the acid in 88.5 % yield.

An interesting method involves the nitration and subsequent oxidation of polystyrene.
This method uses the steric hindrance of the polymer chain to improve the para to ortho ratio of the product.

USES OF 4-NITROBENZOIC ACID (p-NITROBENZOIC ACID):
*Chemical Synthesis:
4-Nitrobenzoic acid is used as an intermediate in the synthesis of dyes, pigments, and pharmaceuticals.
4-Nitrobenzoic acid is used precursor for the production of 3-aminobenzoic acid and other substituted benzoic acids.

*Pharmaceutical Industry:
4-Nitrobenzoic acid serves as a building block in the synthesis of certain drugs, including anti-inflammatory and antimicrobial compounds.

*Agrochemical Industry:
4-Nitrobenzoic acid is used intermediate for the production of herbicides, pesticides, and other agrochemicals.

*Polymer and Material Science:
4-Nitrobenzoic acid is used in the preparation of functional polymers or polymer additives.

*Laboratory Research:
4-Nitrobenzoic acid is utilized as a standard reagent or intermediate in organic synthesis research.

BENEFITS OF 4-NITROBENZOIC ACID (p-NITROBENZOIC ACID):
*Versatile Intermediate:
Its nitro group allows for further chemical transformations (reduction to amines, substitutions, etc.), making 4-Nitrobenzoic acid highly useful in organic synthesis.

*High Stability:
Relatively stable under normal storage conditions, which makes handling easier for industrial applications.

*Efficiency in Synthesis:
4-Nitrobenzoic acid provides a direct route to a variety of functionalized benzoic acids and aromatic compounds.

*Wide Applicability:
4-Nitrobenzoic acid is useful across multiple industries such as pharmaceuticals, dyes, polymers, and agrochemicals.

PHYSICAL and CHEMICAL PROPERTIES of NITROBENZOIC ACID:
2-NITROBENZOIC ACID (o-NITROBENZOIC ACID)
Physical state: crystalline
Color: yellow
Odor: No data available
Melting point/freezing point: 146-148 °C
Initial boiling point and boiling range: No data available
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: No data available

Flash point: Not applicable
Autoignition temperature: No data available
Decomposition temperature: No data available
pH: No data available
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available

Water solubility: No data available
Partition coefficient: n-octanol/water: No data available
Vapor pressure: No data available
Density: No data available
Relative density: No data available
Relative vapor density: No data available
Particle characteristics: No data available
Explosive properties: No data available

Oxidizing properties: none
Other safety information: No data available
Molecular Weight: 167.12 g/mol
XLogP3: 1.5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 1

Exact Mass: 167.02185764 Da
Monoisotopic Mass: 167.02185764 Da
Topological Polar Surface Area: 83.1 Å²
Heavy Atom Count: 12
Formal Charge: 0
Complexity: 198
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0

Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
CBNumber: CB9853809
Molecular Formula: C7H5NO4
Molecular Weight: 167.12

MDL Number: MFCD00007137
MOL File: 552-16-9.mol
Melting point: 146-148 °C(lit.)
Boiling point: 295.67°C (rough estimate)
Density: 1.58 g/cm3
Refractive index: 1.6280 (estimate)
Storage temp.: Sealed in dry, Room Temperature
Solubility: 7.8 g/l
Form: Fine Powder

pKa: 2.16(at 18℃)
Color: Off-white
Specific Gravity: 1.58
Water Solubility: 6.8 g/L
Merck: 14,6588
BRN: 1910632
Stability: Stable. Incompatible with strong oxidizing agents, strong bases.

CAS DataBase Reference: 552-16-9(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: S6S4653K7Z
NIST Chemistry Reference: Benzoic acid, 2-nitro-(552-16-9)
EPA Substance Registry System: o-Nitrobenzoic acid (552-16-9)
UNSPSC Code: 12352100
NACRES: NA.22

3-NITROBENZOIC ACID (m-NITROBENZOIC ACID)
Chemical formula C7H5NO4
Molar mass 167.12 g/mol
Appearance cream-colored solid
Density 1.494 g/cm3
Melting point 139 to 141 °C (282 to 286 °F; 412 to 414 K)
Solubility in water 0.24 g/100 mL (15 °C)
Acidity (pKa) 3.47 (in water)
Magnetic susceptibility (χ) −80.22·10−6 cm3/mol

Molecular Weight 167.12 g/mol
XLogP3 1.8
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 1
Exact Mass 167.02185764 Da
Monoisotopic Mass 167.02185764 Da
Topological Polar Surface Area 83.1 Å²
Heavy Atom Count 12

Formal Charge 0
Complexity 198
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1

Compound Is Canonicalized Yes
CAS 121-92-6
IUPAC Name 3-nitrobenzoic acid
Molecular Formula C7H5NO4
InChI Key AFPHTEQTJZKQAQ-UHFFFAOYSA-N
SMILES OC(=O)C1=CC=CC(=C1)N+=O
Molecular Weight (g/mol) 167.12

Synonym 3-nitrobenzoic acid, M-nitrobenzoic acid
Appearance (Color) White to cream or pale yellow
Assay (Aqueous acid-base Titration) ≥98.5 to ≤101.5%
Melting Point 139.5-145.5°C
Form Crystals or powder or crystalline powder
Identification (FTIR) Conforms
Assay (Silylated GC) ≥98.5%

4-NITROBENZOIC ACID (p-NITROBENZOIC ACID)
Linear Formula: O2NC6H4CO2H
CAS Number: 62-23-7
Molecular Weight: 167.12
Beilstein: 973593
EC Number: 200-526-2
MDL number: MFCD00007352
UNSPSC Code: 12352100
PubChem Substance ID: 24869806
NACRES: NA.22

Molecular Weight: 167.12 g/mol
XLogP3: 1.9
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 1
Exact Mass: 167.02185764 Da
Monoisotopic Mass: 167.02185764 Da
Topological Polar Surface Area: 83.1 Å²
Heavy Atom Count: 12

Formal Charge: 0
Complexity: 190
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
CBNumber: CB4252540

Molecular Formula: C7H5NO4
Molecular Weight: 167.12
MDL Number: MFCD00007352
MOL File: 62-23-7.mol
Melting point: 237-240 °C(lit.)
Boiling point: 295.67°C (rough estimate)
Density: 1.61
Bulk density: 700kg/m3

Refractive index: 1.6280 (estimate)
Flash point: 237 °C
Storage temp.: Store below +30°C.
Solubility: 0.42g/l
pKa: 3.41(at 25℃)
Form: Crystalline Powder
Color: Light yellow
pH: 3.1 (0.42g/l, H2O, 20℃)(saturated solution)
Water Solubility: <0.1 g/100 mL at 26 ºC

Merck: 14,6589
BRN: 973593
Specific Activity: 50-60 mCi/mmol
Concentration: 0.1 mCi/ml
Solvent: Ethanol
Stability: Stable.
InChIKey: OTLNPYWUJOZPPA-UHFFFAOYSA-N
LogP: 1.890
CAS DataBase Reference: 62-23-7(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: G83NWR61OW

NIST Chemistry Reference: Benzoic acid, 4-nitro-(62-23-7)
EPA Substance Registry System: p-Nitrobenzoic acid (62-23-7)
UNSPSC Code: 41116107
NACRES: NA.24
Molecular Formula / Molecular Weight: C7H5NO4 = 167.12
Physical State (20 deg.C): Solid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 62-23-7
Reaxys Registry Number: 973593
PubChem Substance ID: 87573539
SDBS (AIST Spectral DB): 1505
MDL Number: MFCD00007352

FIRST AID MEASURES of NITROBENZOIC ACID:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of NITROBENZOIC ACID:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of NITROBENZOIC ACID:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of NITROBENZOIC ACID:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of NITROBENZOIC ACID:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of NITROBENZOIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available