PRODUCTS

DIPHENYLAMINE

Diphenylamine is an important aromatic compound used in both industrial formulations and fine chemical synthesis.
Diphenylamine's ability to slow oxidative deterioration makes it especially valuable in elastomers, oils, polymers, and related performance materials.
Diphenylamine also serves as a useful precursor for producing substituted amines, colorants, additives, and specialty organic derivatives.

CAS Number: 122-39-4
EC Number: 204-539-4
Molecular Formula: C12H11N
Molecular Weight: 169.23

Synonyms: Diphenylamine, N-Phenylaniline, 122-39-4, N,N-DIPHENYLAMINE, N-Phenylbenzenamine, Anilinobenzene, Phenylaniline, Scaldip, Big Dipper, N-Phenylbenzeneamine, Benzenamine, N-phenyl-, Aniline, N-phenyl-, No-Scald, Benzene, anilino-, Difenylamin, Deccoscald 282, Naugalube 428L, N-Fenylanilin, Shield DPA, No-Scald DPA 283, Benzene, (phenylamino)-, No scald, N-Phenylbenzenamine, styrenated, DTXSID4021975, (phenylamino)benzene, C.I. 10355, 9N3CBB0BIQ, C6H5-NH-C6H5, CHEBI:4640, CI 10355, NSC-215210, DTXCID001975, RefChem:5769, 204-539-4, Pyridyl-biphenylyl-acetamide, Styrenated diphenylamine, DIPHENYL-AMINE, MFCD00003014, NSC 215210, Diphenylamine solution, Difenylamin [Czech], DIPHENYL AMINE, Caswell No. 398, N-Fenylanilin [Czech], 25656-57-9, CAS-122-39-4, CCRIS 4699, Diphenylamine indicator, HSDB 1108, DIPHENYLAMINE, ACS, EINECS 204-539-4, UNII-9N3CBB0BIQ, EPA Pesticide Chemical Code 038501, phenyl aniline, Anilino-Benzene, AI3-00781, (Diphenyl)amine, n-phenyl-aniline, N-(phenyl)aniline, n,n-diphenyl amine, N,N-di-phenylamine, n-phenyl-benzenamine, Diphenylamine, p.a., (phenylamino)-Benzene, No scald dpa 283, Ph2NH, Naugard(R) 635, Cetirizine Impurity 57, Diphenylamine, >=98%, WLN: RMR, Diphenylamine, ACS grade, Diphenylamine solution R1, N-Phenylbenzenamine, 9CI, SCHEMBL229, DIPHENYLAMINE [MI], Epitope ID:115002, EC 204-539-4, Oprea1_815288, SCHEMBL49629, SCHEMBL69437, SCHEMBL72023, MLS002152913, BIDD:ER0338, CHEMBL38688, SCHEMBL226139, orb3029566, QSPL 033, SCHEMBL3003404, SCHEMBL7090460, SCHEMBL11470761, SCHEMBL12467721, 2-Biphenylyl-N-pyridyl-Acetamide, N,N-DIPHENYLAMINE [HSDB], PDK0048, HMS1788N11, HMS3034E05, MSK21093, Tox21_201611, Tox21_301026, EBC-44028, NSC215210, SBB058673, STK301666, Diphenylamine, ACS reagent, >=99%, Diphenylamine, ReagentPlus(R), 99%, AKOS000119099, NC-0220, NCGC00090889-01, NCGC00090889-02, NCGC00090889-03, NCGC00090889-04, NCGC00090889-05, NCGC00254928-01, NCGC00259160-01, AC-16417, SMR000777939, Diphenylamine 10 microg/mL in Cyclohexane, D0872, D1229, Diphenylamine 100 microg/mL in Acetonitrile, NS00010366, ST45053747, Diphenylamine, Vetec(TM) reagent grade, 98%, EN300-18732, H57845, Diphenylamine 1000 microg/mL in Dichloromethane, Diphenylamine, PESTANAL(R), analytical standard, AE-641/01947044, Q412265, Z90121252, F2190-0411, Diphenylamine, puriss. p.a., redox indicator, ACS reagent, reag. Ph. Eur., >=98% (GC), InChI=1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13, 122-39-4, 204-539-4, 508755, Aniline, N-phenyl-, Benzenamine, N-phenyl-, Difenylamin, DIPHENYL AMINE, Diphenyl-amine, Diphenylamine, DPA, N-Fenylanilin, N-Phenyl-Aniline, N-Phenyl-Benzenamine, N-Phenylanilin, N-Phenylaniline, N-Phénylaniline, N-Phenylbenzenamine, (phenylamino)-Benzene, (phenylamino)benzene, 100 mg, 107-05-1, 25656-57-9, 270-485-3, 37055-51-9, 537-67-7, 548756-68-9, 579-92-0, 68442-68-2, 7293-45-0, 86352-05-8, 98%, 99234-91-0, ACS, and garden onion., Anilinobenzene, Benzene, (phenylamino)-, Big Dipper, Cayman, DFA, di(phenyl)amine, Difenylamin, Diphenpyramide, DIPHENYAMINE, Diphenylamine indicator, diphenylamine-d10, Diphenylaminemissing, EINECS 204-539-4, EINECS 270-485-3, N,N-diphenylamine, N-phenyl-ben<wbr/>zenamine, N-Phenylaniline, Anilinobenzene, N-Phenylbenzeneamine, N-Phenylbenzenamine, 9CI, N-Phenylbenzeneamine, Naugalube 428L, No scald, No-Scald, Oprea1_815288, phenylaminobenzene, Phenylaniline, pWLN: RMR, RMR, Scaldi, Scaldip, Shield DPA, 二苯胺

Diphenylamine is an aromatic amine composed of two phenyl groups attached to a single nitrogen atom.
Diphenylamine is typically a colorless to pale crystalline solid that may darken on exposure to air and light.

Diphenylamine is widely used as an antioxidant, stabilizer, chemical intermediate, and starting material in the production of dyes, rubber chemicals, lubricants, and specialty organic compounds.:
Diphenylamine is a light tan to brown solid with a pleasant odor.

Diphenylamine, as an important intermediate in organic chemistry, is commonly used in pharmaceutical, agricultural, and pigment production.
Diphenylamine plays an effective role in the synthesis of redox derivatives in various reactions.

Diphenylamines formed as a result of the reaction of diphenylamine with nitrogen-containing compounds are critical for various industrial applications.
Safety in laboratory settings requires caution when working with this substance; direct contact with eyes, skin, and respiratory tract should be avoided.
Diphenylamine is a chemical compound with a light yellow-brown color pigment, temporary printing properties, and low viscosity.

Diphenylamine is an aromatic amine containing two phenyl substituents.
Diphenylamine has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.

Diphenylamine has a role as a ferroptosis inhibitor, an antioxidant, a radical scavenger, a carotogenesis inhibitor, an EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor and an antifungal agrochemical.
Diphenylamine is an aromatic amine, a secondary amino compound and a bridged diphenyl fungicide.

Diphenylamine is found in coriander.
Diphenylamine is used for control of superficial scald in stored apples Diphenylamine is the organic compound with the formula (C6H5)2NH.

Diphenylamine is a colourless solid, but samples are often yellow due to oxidized impurities.
Diphenylamine is a weak base, with a KB of 10 14.

With strong acids, Diphenylamine forms the water soluble salt.
Diphenylamine belongs to the family of Aromatic Homomonocyclic Compounds.
These are aromatic compounds containig only one ring, which is homocyclic.

Diphenylamine is an organic compound with the formula (C6H5)2NH.
Diphenylamine is a derivative of aniline, consisting of an amine bound to two phenyl groups.

Diphenylamine is a colorless solid, but commercial samples are often yellow due to oxidized impurities.
Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water.

Diphenylamine is used mainly for its antioxidant properties.
Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.

Diphenylamine is defined as the genetic material that mediates transformation, serving as a "pure gene" that can transfer information between organisms, significantly contributing to the field of molecular biology.

Diphenylamine is an organic compound with the formula (C6H5)2NH.
Diphenylamine is a derivative of aniline, consisting of an amine bound to two phenyl groups.

Uses of Diphenylamine:
Diphenylamine is used as an antioxidant, stabilizer of explosives, fungicide, and analytical chemical reagent.
Diphenylamine is also used in the manufacture of dyes and pesticides.
Diphenylamine is used to make dyes, to stabilize nitrocellulose explosives and celluloid, to treat screwworm topically (veterinary), and to test for nitrate or nitrite poisoning.

Diphenylamine is widely used as an antioxidant and stabilizer in a variety of industrial materials, particularly in lubricants, rubber products, polymers, and petroleum-based formulations where it helps reduce oxidative degradation.
Diphenylamine is also used as a chemical intermediate in the manufacture of dyes, pigments, pharmaceuticals, agrochemical intermediates, and other nitrogen-containing aromatic compounds.

In the rubber industry, diphenylamine derivatives are employed as antidegradants to improve resistance to heat, oxygen, and aging.
Diphenylamine is used in lubricant and fuel additive formulations to enhance oxidative stability and extend service life.

Diphenylamine also serves as a starting material for the production of specialty antioxidants used in plastics, elastomers, and synthetic oils.
In analytical chemistry, Diphenylamine has been used as a reagent in certain colorimetric and redox-based tests.
Diphenylamine is additionally employed in research and fine chemical synthesis for preparing substituted aromatic amines and other functional organic molecules.

Industry Uses:
Stabilizing agent
Dye
Intermediate
Other
Chemical reaction regulator
Antioxidant
Processing aids not otherwise specified

Consumer Uses:
Lubricating agent
Other
Energy Releasers (explosives, motive propellant)
Antioxidant
Dye

Applications of Diphenylamine:
Diphenylamine may be used in the preparation of diphenylamine reagent, which is employed for the quantitative estimation of nucleic acid (DNA) from various biological sources by colorimetric method.
Diphenylamine can undergo palladium-catalyzed intramolecular cyclization to form carbazole.
Diphenylamine may also be used as a starting material in the synthesis of triphenylamine.

Testing for DNA:
The Dische test uses diphenylamine to test for DNA, and can be used to distinguish DNA from RNA.

Apple scald inhibitor:
Diphenylamine is used as a pre- or postharvest scald inhibitor for apples applied as an indoor drench treatment.
Apple scald is physical injury that manifests in brown spots after fruit is removed from cold storage.
Diphenylamine's anti-scald activity is the result of its antioxidant properties, which protect the apple skin from the oxidation products of α-farnesene during storage.

Stabilizer for smokeless powder:
In the manufacture of smokeless powder, diphenylamine is commonly used as a stabilizer such that the gunshot residue analysis seeks to quantify traces of diphenylamine.
Diphenylamine functions by binding nitrogen oxide degradation products, forming compounds like nitrodiphenylamine.
In this way, DPA prevents these degradation products from accelerating further degradation.

Antioxidant:
Alkylated diphenylamines function as antioxidants in lubricants approved for use in machines, in which contact with food is not ruled out.
Alkylated diphenylamines and other derivatives are used as antiozonants in the manufacture of rubber products, reflecting the antioxidant nature of aniline derivatives.

Redox indicator:
Many diphenylamine derivatives are used as redox indicators that are particularly useful in alkaline redox titrations.
The diphenylaminesulfonic acid is a simple prototype redox indicator, owing to its improved aqueous solubility compared with diphenylamine.
Attempts have been made to explain the color changes associated with the oxidation of diphenylamine.

In a related application, diphenylamine is oxidized by nitrate to give a similar blue coloration in the diphenylamine test for nitrates.

Dyes:
Several azo dyes like Metanil Yellow, Disperse Orange 1, and Acid orange 5 are derivatives of diphenylamine.
Diphenylamine is also used as a dye mordant.
A dye mordant is any substance that helps dyes to adhere to fabrics.

Preparation and Reactivity of Diphenylamine:

Diphenylamine is produced by heating a mixture of aniline and anilinium chloride:
C6H5NH2 + C6H5NH3Cl → (C6H5)2NH + NH4Cl

Diphenylamine is a weak base, with a Kb of 10−14.
With strong acids, it forms salts.
For example, treatment with sulfuric acid gives the bisulfate [(C6H5)2NH2]+[HSO4]− as a white or yellowish powder with m.p. 123–125 °C (253–257 °F).

Diphenylamine undergoes various cyclisation reactions.
With sulfur, Diphenylamine gives phenothiazine, a precursor to pharmaceuticals.

(C6H5)2NH + 2 S → S(C6H4)2NH + H2S

Oxidative dehydrogenation give carbazole:
(C6H5)2NH + 0.5 O2 → (C6H4)2NH + H2O

Arylation with iodobenzene gives triphenylamine.

History of Diphenylamine:
Diphenylamine was discovered by A. W. Hofmann in 1864 amongst the products of dry distillation of aniline dyes; it was first purposefully synthesized through deamination of a mix of aniline and its salts by a group of French chemists two years later.[24]

In 1872, diphenylamine was suggested as a means to detect nitrous acid in sulfuric acid due to its blue coloration in the presence of oxidizing agents.
By 1875, Diphenylamine was also being used to detect nitrites and nitrates in drinking water.

In 1924, diphenylamine is discovered to be useful in detecting DNA via the Dische test by Zacharias Dische.
In 1947, diphenylamine was registered in the US as a pesticide.

Stability and Reactivity of Diphenylamine:

Chemical Stability:
Stable under normal recommended storage and handling conditions.

Reactivity:
No dangerous reactions are expected when handled and stored appropriately.

Conditions to Avoid:
Excessive heat, ignition sources, and prolonged exposure to incompatible substances.

Incompatible Materials:
Strong oxidizing agents.

Hazardous Decomposition Products:
Thermal decomposition or combustion may generate carbon monoxide, carbon dioxide, nitrogen oxides, and irritating fumes.

Handling and Storage of Diphenylamine:

Safe Handling:
Avoid breathing dust or vapors and prevent contact with skin and eyes.
Handle with adequate ventilation and use suitable personal protective equipment.

Storage Conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated location away from incompatible materials.

First Aid Measures of Diphenylamine:

Inhalation:
Move the affected person to fresh air and seek immediate medical attention.

Skin Contact:
Remove contaminated clothing and wash the affected area thoroughly with plenty of water.

Eye Contact:
Rinse cautiously with water for several minutes and obtain medical attention.

Ingestion:
Rinse the mouth and seek immediate medical assistance.
Do not induce vomiting unless directed by medical personnel.

Firefighting Measures of Diphenylamine:

Suitable Extinguishing Media:
Use water spray, carbon dioxide, dry chemical powder, or suitable foam.

Specific Hazards:
Combustion may produce carbon oxides, nitrogen-containing fumes, and other irritating decomposition products.

Protective Equipment:
Firefighters should wear full protective clothing and self-contained breathing apparatus.

Accidental Release Measures of Diphenylamine:

Personal Precautions:
Ensure adequate ventilation, avoid dust formation, and wear appropriate protective equipment.

Environmental Precautions:
Prevent release into drains, surface water, soil, or sewer systems.

Cleanup Methods:
Carefully sweep or collect the spilled material without generating dust and place it in a suitable closed container for disposal.
Diphenylamine should not be released into the environment.

Exposure Controls/Personal Protection of Diphenylamine:

Engineering Controls:
Use adequate general ventilation or local exhaust ventilation.

Eye Protection:
Wear safety glasses or chemical goggles.

Hand Protection:
Wear suitable chemical-resistant gloves.

Skin Protection:
Wear appropriate protective clothing.

Respiratory Protection:
Use suitable particulate respiratory protection, such as a P2-type filter, when dust exposure cannot be adequately controlled.

Identifiers of Diphenylamine:
Article No.: 03501
Grade: AR/ACS
Purity: 99%
CAS No.: 122-39-4
Molecular Formula: C12H11N
Molecular Weight: 169.23
H.S. Code: 2921.4410

CAS Number: 122-39-4
Abbreviations: DPA
Beilstein Reference: 508755
ChEBI: CHEBI:4640
ChEMBL: ChEMBL38688
ChemSpider: 11003
ECHA InfoCard: 100.004.128
EC Number: 204-539-4
Gmelin Reference: 67833
KEGG: C11016
PubChem CID: 11487
RTECS number: JJ7800000
UNII: 9N3CBB0BIQ
UN number: 2811 3077
CompTox Dashboard (EPA):
DTXSID4021975 Edit this at Wikidata
InChI
InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
Key: DMBHHRLKUKUOEG-UHFFFAOYSA-N
InChI=1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
Key: DMBHHRLKUKUOEG-UHFFFAOYAJ
SMILES: c1ccc(cc1)Nc2ccccc2

CAS: 122-39-4
IUPAC Name: N-phenylaniline
Molecular Formula: C12H11N
InChI Key: DMBHHRLKUKUOEG-UHFFFAOYSA-N
SMILES: N(C1=CC=CC=C1)C1=CC=CC=C1
Molecular Weight (g/mol): 169.23

Formal Name: N-phenyl-benzenamine
CAS Number: 122-39-4
Synonyms: NSC 215210
Molecular Formula: C12H11N
Formula Weight: 169.2
Purity: ≥98%
Formulation: A solid
Chloroform: Slightly Soluble
Methanol: Slightly Soluble
λmax: 284 nm
SMILES: C1(NC2=CC=CC=C2)=CC=CC=C1
InChi Code: InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
InChi Key: DMBHHRLKUKUOEG-UHFFFAOYSA-N

Linear Formula: (C6H5)2NH
CAS Number: 122-39-4
Molecular Weight: 169.22
NACRES: NA.21
PubChem Substance ID: 24854569
UNSPSC Code: 12352100
EC Number: 204-539-4
MDL number: MFCD00003014
Beilstein/REAXYS Number: 508755
Assay: ≥99%

Properties of Diphenylamine:
Chemical formula: C12H11N
Molar mass: 169.227 g·mol−1
Appearance: White, off-white
Odor: Floral
Density: 1.2 g/cm3
Melting point: 53 °C (127 °F; 326 K)
Boiling point: 302 °C (576 °F; 575 K)
Solubility in water: 0.03%
Vapor pressure: 1 mmHg (108 °C)
Acidity (pKa): 0.79 of conjugate acid (Ph2NH2+)[4]
Magnetic susceptibility (χ): −109.7·10−6 cm3/mol

Product Name: Diphenylamine, ACS reagent, ≥99%
grade: ACS reagent
Quality Segment: 200
vapor density: 5.82 (vs air)
vapor pressure: 1 mmHg ( 108 °C)
assay: ≥99%
autoignition temp.: 1175 °F
ign. residue: ≤0.03%
bp: 302 °C (lit.)
mp: 50-53 °C (lit.)
solubility: alcohol: passes test
anion traces: nitrate (NO3-): passes test
suitability: passes test for sensitivity to nitrate
SMILES string: N(c1ccccc1)c2ccccc2
InChI: 1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
InChI key: DMBHHRLKUKUOEG-UHFFFAOYSA-N
Gene Information: human ... UGT1A4(54657)

Physical state at 20 °C: Solid
Colour: Cream coloured powder
Odour: Floral odor
Melting point/ Freezing point [°C]: 50 - 53 °C
Flash point [°C]: 153 °C
Boiling point [°C]: 302 °C
Vapour pressure mm/Hg: 1 mm Hg @ 1080C
Vapour density: 5.82
Density [g/cm3]: 1.16
Solubility in water [% weight]: Insoluble in water
Partition coefficient Log Pow octanol / water at 20°C: 3.5

Molecular Weight: 169.22 g/mol
XLogP3: 3.5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 2
Exact Mass: 169.089149355 Da
Monoisotopic Mass: 169.089149355 Da
Topological Polar Surface Area: 12 Å²
Heavy Atom Count: 13
Complexity: 116
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Computed by PubChem
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Diphenylamine:
Appearance: White to off white flakes/powder, darkening on exposure to light
Purity (by GC): Min 99%
Melting range: 52.5 - 54 °C
Solubility in ethanol: Passes test
Sulphated ash: Max 0.03%
Nitrate (NO3): Passes test
Aniline (C6H5.NH2): Max 0.01%
Sensitivity for nitrate (NO3): Min 1:1600000 (Passes ACS test)
Copper (Cu): Max 0.001%
Iron (Fe): Max 0.001%
Nickel (Ni): Max 0.001%
Lead (Pb): Max 0.001%

GC: >=98.5 %
Appearance (Color): White to yellow to beige
Appearance (Form): Crystalline powder or crystals or flakes
Infrared spectrum: Conforms
Melting point: 52°C to 55°C

Related compounds of Diphenylamine:

Related Amine:
Aniline

Names of Diphenylamine:

Preferred IUPAC name:
N-Phenylaniline

Other names:
(Diphenyl)amine
Diphenylamine (deprecated)
Diphenylazane
N-Phenylbenzenamine
Anilinobenzene
(Phenylamino)benzene
N,N-Diphenylamine
C.I. 10355
Phenylbenzenamine