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3,4-Dichloroaniline is used as an intermediate for pesticides and dyes.
3,4-Dichloroaniline is primarily used as an intermediate in the manufacture of herbicides, pesticides, pharmaceuticals, dyes, pigments, and specialty chemicals.
3,4-Dichloroaniline is one of the most important precursors for the synthesis of several chloroacetanilide herbicides and other crop protection products, where the dichlorinated aromatic ring contributes to biological activity and chemical stability.
CAS Number: 95-76-1
EC Number: 202-448-4
Molecular Formula: C₆H₅Cl₂N
Molecular Weight: 162.02 g/mol
SYNONYMS:
3,4-Dichloroaniline, 3,4-DCA, 3,4-Dichlorobenzenamine, 1-Amino-3,4-dichlorobenzene, 4,5-Dichloroaniline, Benzenamine, 3,4-dichloro-, 3,4-dca, 3，4-Dichloroanihne, 4,5-Dichloroaniline, Gefitinib-1, 3.4-Dichloroan, 3,4-Dichloroanil, 3,4-Dichloranilin, AKOS BBS-00003672, 3,4-Dichloraniline, 3,4-DICHLOROANILINE, 3,4-DICHLOROANILINE, 95-76-1, 3,4-Dichlorobenzenamine, 3,4-Dichloraniline, 3,4-Dichloranilin, Benzenamine, 3,4-dichloro-, 4,5-Dichloroaniline, 1-Amino-3,4-dichlorobenzene, 3,4-DCA, Aniline, 3,4-dichloro-, 4-Amino-1,2-dichlorobenzene, DTXSID7021815, m,p-dichloroaniline, LY 004892, 20KR9WJ4NS, CHEBI:16767, NSC-247, DTXCID001815, RefChem:485966, 202-448-4, 3,4-Dichlorophenylamine, MFCD00007768, NSC 247, 3,4-Dichloro-phenylamine, EN300-17401, m.p-Dichloroaniline, CAS-95-76-1, 3,4 dichloroaniline, CCRIS 2395, HSDB 1319, 3,4-dichlorobenzeneamine, EINECS 202-448-4, UNII-20KR9WJ4NS, BRN 0636837, diuron TP3, 3,4dichloroaniline, 3.4-Dichloroaniline, 3,4 -dichloroaniline, 3,4-di-chloroaniline, 3,4-dichloro-aniline, WLN: ZR CG DG, Epitope ID:131788, EC 202-448-4, 3,4-Dichloroaniline, 98%, MLS002152880, 1,2-Dichloro-4-aminobenzene, ANILINE,3,4-DICHLORO, SCHEMBL203854, NSC247, SCHEMBL1196211, SCHEMBL1807689, SCHEMBL6492679, DICHLOROANILINE, 3,4-, CHEMBL1319813, SCHEMBL29417504, BDBM626052, 3,4-DICHLOROANILINE [MI], STR00826, 3,4-DICHLOROANILINE [HSDB], Tox21_202115, Tox21_302839, MSK001330, SBB040495, STK387110, AKOS000119137, CS-W020574, EBC-153117, MSK001330-100A, PS-5109, MSK001330-1000A, NCGC00091758-01, NCGC00091758-02, NCGC00256341-01, NCGC00259664-01, SMR000155324, DB-030884, D0324, NS00000077, ST45255275, C02791, F022132, 3,4-Dichloroaniline 100 microg/mL in Acetonitrile, Q13427547, Z56926514, 3,4-Dichloroaniline Solution in Acetonitrile, 100ug/mL, 3,4-Dichloroaniline, PESTANAL(R), analytical standard, F2190-0456, 3,4-Dichloroaniline Solution in Acetonitrile, 1000ug/mL, 1-Amino-3,4-Dichlorobenzene, 3,4-Dichlorobenzenamine, 3,4-DCA, InChI=1/C6H5Cl2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H, LV5, 3,4-Dichlorobenzenamine, 3,4-Dichlorophenylamine, 4,5-Dichloroaniline, 4-Amino-1,2-dichlorobenzene, m,p-Dichloroaniline, 3,4-Dichloroaniline, 1-amino-3,4-dichlorobenzene, 3,4-Dichloroaniline, Benzenamine, 3,4-dichloro-, 95-76-1, 3,4-DCA, Benzenamine, 3,4-dichloro-, 1-Amino-3,4-dichlorobenzene, 3,4-Dichloranilin, 3,4-Dichloraniline, 3,4-Dichlorobenzenamine, 3,4-Dichlorobenzeneamine, 3,4-Dichlorophenylamine, 3,4-dicloroanilina, 4,5-Dichloroaniline, 4-Amino-1,2-dichlorobenzene, ANILINE, 3,4-DICHLORO-, m,p-Dichloroaniline, NSC 247, BRN 0636837, EINECS 202-448-4, m.p-Dichloroaniline, UNII-20KR9WJ4NS, 3,4-Dichlorobenzenamine, 3,4-Dichloro-4-benzenamine, 3,4-DCA, 3,4-DiHalide, 3,4-Dichloraniline, DCA, alpha,3,4-Trichlorotoluene
3,4-Dichloroaniline (3,4-DCA) is a chlorinated aromatic amine consisting of an aniline ring substituted with chlorine atoms at the 3- and 4-positions.
3,4-Dichloroaniline is an important industrial intermediate used primarily in the synthesis of herbicides, pharmaceuticals, dyes, pigments, and specialty organic chemicals.
Due to the presence of both an amino group and two chlorine substituents, 3,4-Dichloroaniline exhibits versatile chemical reactivity, making it valuable for electrophilic and nucleophilic substitution reactions, diazotization, and condensation processes.
3,4-Dichloroaniline, 1-amino- 3,4- dichlorobenzene, is a gray to dark-brown crystalline solid at room temperature.
3,4-dichloroaniline appears as light tan to dark gray crystals or brown solid.
The melting point of 3,4-Dichloroaniline is 71-72 °C.
3,4-dichloroaniline is a dichloroaniline having the two chloro-substituents at the 3- and 4-positions.
3,4-Dichloroaniline has a role as a xenobiotic and an epitope.
3,4-Dichloroaniline is functionally related to a 1,2-dichlorobenzene.
3,4-Dichloroaniline is an organic compound with the formula C6H3Cl2(NH2).
3,4-Dichloroaniline is one of several isomers of dichloroaniline.
3,4-Dichloroaniline is a white solid although commercial samples often appear gray.
3,4-Dichloroaniline is a precursor to dyes, agricultural chemicals, and drugs including the antimalarial chlorproguanil and the herbicides propanil, linuron, DCMU, and diuron.
3,4-Dichloroaniline is a light tan to dark gray crystals or brown solid.
3,4-Dichloroaniline darkens in storage.
3,4-Dichloroaniline is insoluble in water.
3,4-Dichloroaniline occurs as a pesticide metabolite.
3,4-Dichloroaniline is not listed in the EU pesticide database.
The certified reference material (CRM) is intended to be used as a calibrant for chromatography and other analytical techniques.
3,4-Dichloroaniline is a gray to brown crystalline solid, which is a critical intermediate for manufacturing several important herbicides, including diuron and propanil, as well as dyes.
3,4-Dichloroaniline is a chlorinated derivative of aniline used as an intermediate in pharmaceutical and agrochemical synthesis.
3,4-Dichloroaniline occurs as an off-white crystal or powder.
USES and APPLICATIONS of 3,4-DICHLOROANILINE:
3,4-Dichloroaniline is used in the preparation of the herbicide propanil (P760840).
3,4-Dichloroaniline may be employed as derivatization reagent for the HPLC analysis of perfluorooctanoic acid (PFOA).
3,4-Dichloroaniline is used as an intermediate for pesticides and dyes.
3,4-Dichloroaniline is primarily used as an intermediate in the manufacture of herbicides, pesticides, pharmaceuticals, dyes, pigments, and specialty chemicals.
3,4-Dichloroaniline is one of the most important precursors for the synthesis of several chloroacetanilide herbicides and other crop protection products, where the dichlorinated aromatic ring contributes to biological activity and chemical stability.
3,4-Dichloroaniline is widely utilized in fine chemical manufacturing as a precursor for high-value chemical products.
In pharmaceutical manufacturing, 3,4-Dichloroaniline serves as a valuable building block for the preparation of active pharmaceutical ingredients and heterocyclic compounds through diazotization, reduction, condensation, and substitution reactions.
The amino functionality provides excellent versatility for constructing more complex molecular structures used in medicinal chemistry.
The dye and pigment industry utilizes 3,4-dichloroaniline as a precursor for azo dyes and colorants, where diazonium chemistry enables the production of brightly colored and chemically resistant pigments.
3,4-Dichloroaniline is also employed in specialty organic synthesis for producing antioxidants, polymer additives, advanced intermediates, laboratory reagents, and custom fine chemicals.
3,4-Dichloroaniline is used as an intermediate for pesticides and dyes and is produced by catalytic hydrogenation of 3,4-dichloronitrobenzene with noble metal catalysts under pressure.
Various types of additives prevent dehalogenation during production and reactors must be fabricated with special steel alloys to inhibit corrosion.
In research laboratories, 3,4-dichloroaniline is widely used as a reference material for studying aromatic amine chemistry, environmental degradation pathways, analytical methods, and toxicological assessments.
PROPERTIES of 3,4-DICHLOROANILINE:
3,4-Dichloroaniline is an aromatic amine that combines the nucleophilic character of the amino group with the electron-withdrawing effects of two chlorine substituents.
This molecular arrangement provides a useful balance between chemical stability and synthetic reactivity, making 3,4-Dichloroaniline an important intermediate in numerous industrial processes.
The amino group readily participates in diazotization, acylation, alkylation, condensation, and substitution reactions, while the chlorine atoms influence regioselectivity and improve the stability of reaction intermediates.
Compared with unsubstituted aniline, 3,4-dichloroaniline exhibits lower basicity, greater hydrophobicity, and enhanced thermal stability.
3,4-Dichloroaniline demonstrates good compatibility with a wide range of organic solvents and maintains stability under recommended storage conditions.
3,4-Dichloroaniline's aromatic framework allows selective functionalization for the production of complex specialty chemicals, while its relatively low volatility facilitates safer handling in industrial environments.
BENEFITS of 3,4-DICHLOROANILINE:
3,4-Dichloroaniline offers several technical advantages in industrial chemistry:
Valuable intermediate for herbicide production
Important precursor for pharmaceutical synthesis
Excellent building block for azo dye manufacture
Reactive amino functional group
Good thermal and chemical stability
Suitable for diazotization and coupling reactions
Compatible with numerous organic solvents
Useful precursor for specialty aromatic compounds
High-purity commercial grades available
Versatile intermediate for fine chemical manufacturing
Good process stability during industrial synthesis
3,4-Dichloroaniline supports production of high-value specialty chemicals
CHARACTERISTICS of 3,4-DICHLOROANILINE:
Chlorinated aromatic amine
Crystalline organic solid
White to light beige appearance
Slight aromatic amine odor
Weak aromatic base
Moderately lipophilic
Slightly soluble in water
Soluble in many organic solvents
Reactive amino functional group
Chemically stable under normal conditions
Combustible organic solid
Industrial chemical intermediate
Widely used in agrochemical and pharmaceutical synthesis
Suitable for diazotization and electrophilic substitution chemistry
PREPARATION of 3,4-DICHLOROANILINE:
3,4-Dichloroaniline is produced by catalytic hydrogenation of 3,4-dichloronitrobenzene with noble metal catalysts under pressure.
Various types of additives prevent dehalogenation during production and reactors must be fabricated with special steel alloys to inhibit corrosion.
3,4-Dichloroaniline is a dichloroaniline having the two chloro-substituents at the 3- and 4-positions.
REACTIVITY PROFILE of 3,4-DICHLOROANILINE:
3,4-Dichloroaniline is incompatible with oxidizing agetns, acids, acid chlorides and acid anhydrides.
3,4-Dichloroaniline can decompose at low pH.
Hydrochloric acid accelerates decomposition.
3,4-Dichloroaniline reacts at temperatures above 356°F in the presence of ferric chloride.
PREPARATION of 3,4-DICHLOROANILINE:
3,4-Dichloroaniline is produced by hydrogenation of 3,4-dichloronitrobenzene.
3,4-Dichloroaniline is an intermediate in the synthesis of (13C6)N-(3,4-dichlorophenyl)-2,2-dimethylpropanamide.
PHYSICAL and CHEMICAL PROPERTIES of 3,4-DICHLOROANILINE:
Appearance: White to light beige, gray, or pale brown crystalline solid (may darken upon prolonged exposure to air and light)
Odor: Slight aromatic amine odor
Physical State: Crystalline solid at room temperature
Molecular Formula: C₆H₅Cl₂N
Molecular Weight: 162.02 g/mol
Density: Approximately 1.44–1.46 g/cm³ (20°C)
Melting Point: Approximately 43–46°C
Boiling Point: Approximately 272–275°C
Flash Point: Approximately 120–130°C
Autoignition Temperature: Approximately 600°C (estimated)
Vapor Pressure: Very low at room temperature
Vapor Density: Approximately 5.6 (air = 1)
Relative Density: Approximately 1.45
Refractive Index (molten): Approximately 1.61
Water Solubility: Slightly soluble (approximately 500–700 mg/L at 25°C)
Solubility: Soluble in ethanol, methanol, acetone, ether, benzene, toluene, chloroform, and other organic solvents
Log Kow: Approximately 2.8–3.0
Partition Coefficient: Moderately lipophilic
pKa: Approximately 2.8–3.2 (conjugate acid)
Surface Tension: Moderate
Volatility: Low
Chemical Stability: Stable under recommended storage conditions
Reactivity: Reacts with strong oxidizing agents, strong acids, acid chlorides, and diazotizing reagents
Flammability: Combustible solid
Decomposition Products: Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide, and chlorinated aromatic compounds
Oxidation Sensitivity: May slowly discolor upon prolonged exposure to air
Biodegradability: Moderate to slow
Environmental Mobility: Moderate; adsorption to soil increases with organic carbon content
Bioaccumulation Potential: Low to moderate
Chemical Name: 3,4-Dichloroaniline
IUPAC Name: 3,4-Dichlorobenzenamine
Common Name: 3,4-DCA
CAS Number: 95-76-1
EC Number: 202-448-4
Molecular Formula: C₆H₅Cl₂N
Molecular Weight: 162.02 g/mol
CBNumber: CB5696598
Molecular Formula: C6H5Cl2N
Molecular Weight: 162.02
MDL Number: MFCD00007768
MOL File: 95-76-1.mol
Melting point: 69-71 °C(lit.)
Boiling point: 272 °C(lit.)
Density: 1,34 g/cm3
vapor pressure: 97.5Pa at 78℃
refractive index: 1.6140 (estimate)
Flash point: 166 °C
storage temp.: 0-6°C
solubility: 0.73g/l
form: Crystalline Mass and/or Chunks
pka: 2.90±0.10(Predicted)
color: Beige to brown
PH: 7.1 (0.8g/l, H2O)
Water Solubility: 0.06 g/100 mL
Merck: 14,3054
BRN: 636837
Henry's Law Constant: 6.8×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Stability: Stable, but darkens in storage.
Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides.
InChI: 1S/C6H5Cl2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2
InChIKey: SDYWXFYBZPNOFX-UHFFFAOYSA-N
SMILES: Nc1ccc(Cl)c(Cl)c1
LogP: 2.68 at 20℃
CAS DataBase Reference: 95-76-1(CAS DataBase Reference)
EWG's Food Scores: 3-4
FDA UNII: 20KR9WJ4NS
NIST Chemistry Reference: Benzenamine, 3,4-dichloro-(95-76-1)
EPA Substance Registry System: 3,4-Dichloroaniline (95-76-1)
UNSPSC Code: 41116107
NACRES: NA.24
Molecular Formula / Molecular Weight: C6H5Cl2N = 162.01
Physical State (20 deg.C): Solid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive
CAS RN: 95-76-1
Reaxys Registry Number: 636837
PubChem Substance ID: 87567017
SDBS (AIST Spectral DB): 2093
Merck Index (14): 3054
MDL Number: MFCD00007768
Molecular Weight: 162.01 g/mol
XLogP3: 2.7
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 160.9799046 Da
Monoisotopic Mass: 160.9799046 Da
Topological Polar Surface Area: 26 Ų
Heavy Atom Count: 9
Formal Charge: 0
Complexity: 97.1
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
Linear Formula: Cl2C6H3NH2
CAS Number: 95-76-1
Molecular Weight: 162.02
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24867396
EC Number: 202-448-4
Beilstein/REAXYS Number: 636837
MDL number: MFCD00007768
Assay: 98%
Chemical formula: C6H5Cl2N
Molar mass: 162.01 g·mol−1
Density: 1.57
Melting point: 66–71 °C (151–160 °F; 339–344 K)
Boiling point: 272 °C (522 °F; 545 K)
Solubility in water: 92 mg/l at 20 °C
log P: 2.69
Physical state: solid
Form: crystalline
Color: dark brown
Odor: No data available
Melting point/ range: 69 - 71 °C
Boiling point/boiling range: 272 °C
Flammability: Method: Test N.1: Test method for readily combustible solids
Upper explosion limit / Upper flammability limit: 7,2 %(V) ( 179 °C)
Lower explosion limit / Lower flammability limit: 2,8 %(V) ( 153 °C)
Flash point: 135,00 °C
Method: closed cup
Autoignition temperature: 265 °C
Decomposition temperature: No data available
pH: 7,1
Concentration: 0,8 g/l
Viscosity, dynamic: No data available
Viscosity, kinematic: No data available
Flow time: No data available
Solubility(ies)
Water solubility: 0,58 g/l (20 °C)
GLP: yes
Partition coefficient: noctanol/water: log Pow: 2,7
Method: OECD Test Guideline 107
Bioaccumulation is not expected.
Vapor pressure: < 0,1 hPa (20 °C)
Method: OECD Test Guideline 104
Relative density: No data available
Density: 1,57 g/cm3 (20 °C)
Relative vapour density: 6,49
Explosives: No data available
Oxidizing properties: none
Burning rate: No data available
Self-ignition: > 600 °C
1.013 hPa
does not ignite
Evaporation rate: No data available
Surface tension: 71,78 mN/m, 0,54 g/l, 19,8 °C, Surface tension, GLP: yes
Molecular weight: 162,02 g/mol
Boiling point: 283AdegC
Molecular Formula: C6H5Cl2N
Solubility: Soluble in ethanol, ether, and benzene
Melting Point: 56-58AdegC
Density: 1.49 at 25AdegC Gram per cubic centimeter(g/cm3)
Chemical Name: Other, 3,4 Dichloro Aniline
CAS No: 95-76-1
Appearance: Yellow to brown crystalline powder
FIRST AID MEASURES of 3,4-DICHLOROANILINE:
-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 3,4-DICHLOROANILINE:
-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 3,4-DICHLOROANILINE:
-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 3,4-DICHLOROANILINE:
-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 3,4-DICHLOROANILINE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of 3,4-DICHLOROANILINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
