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4-Aminodiphenylamine

CAS：101-54-2
MW:184.23708
MF：C12H12N2

p-Aminodiphenylamine hydrochloride was formerlyused as a hair dye. Sensitization, when deteeted bypatch testing, is relatively low in hairdressers. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 4-Aminodiphenylamine

1.2 Synonyms: 1,2-Benzenediamine, N-phenyl-; 1,4-Benzenediamine, N-phenyl-; 4-(Phenylamino)aniline; 4-amino-diphenylamin; 4-N-phenylbenzene-1,4-diamine; Azoic Diazo Component 22; azoic diazo no. 22; EINECS 202-951-9; Fast Blue R Salt; fastbluersalt; FastblueRTbase; Luxan Black R; MFCD00007850; N1-Phenylbenzene-1,4-diamine; N-Phenyl-1,2-benzenediamine; N-phenyl-1,2-phenylenediamine; N-Phenyl-1,4-benzenediamine; N-Phenyl-1,4-phenylenediamine; N-PHENYLBENZENE-1,2-DIAMINE; n-phenyl-o-phenylenediamine; N-Phenyl-p-Phenylenediamine; o-semidine; p-Aminodiphenylamine; VARIAMINE BLUE RT; Variamine Blue RT Base; Variamine Blue RT Salt; ZR DMR;

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1.3 CAS No.: 101-54-2

1.4 CID: 7564

1.5 EINECS: 202-951-9

1.6 Molecular Formula: C12H12N2

1.7 Inchi: InChI=1S/C12H12N2/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9,14H,13H2

1.8 InChkey: ATGUVEKSASEFFO-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)NC2=CC=C(C=C2)N

1.10 Isomers Smiles: C1=CC=C(C=C1)NC2=CC=C(C=C2)N

2. Properties

2.1 Solubility: ethanol: soluble10mg/mL, clear, very dark red (Violet to brown to black solution)

2.2 Viscosity: 1.76X10-2 Pa.s at 25 °C

2.3 Appearance: Odorless purple-black solid or flake or dark purple chips

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: Dark grey flake

2.6 Color/Form: Needles (alcohol)
Purple powder
Purple needles

2.7 Contact Allergens: This substance was formerly used as a hair dye.Sensitization, when detected by patch testing, is relativelylow in hairdressers.

2.8 Decomposition: When heated to decompostion it emits toxic fumes of NOx.

2.9 Heat of Combustion: -6.29X10+9 J/kmol

2.10 Heat of Vaporization: 9.26X10+7 J/kmol at 25 °C

2.11 PH: 8.9 (0.5g/l, H2O, 20℃)

2.12 pKa: 5.20±0.10(Predicted)

2.13 Water Solubility: Slightly soluble

2.14 Spectral Properties: MAX ABSORPTION (95% ALCOHOL): 281 NM (LOG E= 4.18)
IR: 10875 (Sadtler Research Laboratories IR Grating Collection)
UV: 4561 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 3267 (Sadtler Research Laboratories Spectral Collection)
MASS: 72879 (NIST/EPA/MSDC Mass Spectral Database 1990 version)

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2.15 Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, plastics.

2.16 StorageTemp: Store below +30°C.

2.17 Surface Tension: 3.08X10-2 N/m at 25 °C

3. Use and Manufacturing

3.1 Definition: ChEBI: An aromatic amine that is the 4-amino derivative of diphenylamine.

3.2 Description: 4-Aminodiphenylamine (CAS 101-54-2) is a chemical compound that appears as a white to light brown crystalline powder. It has a basic structure consisting of an amino group (-NH2) attached to two phenyl groups. This compound is sparingly soluble in water, but it can dissolve in organic solvents such as ethanol and acetone. 4-Aminodiphenylamine has a melting point of approximately 102-105°C and a boiling point of around 360-365°C.

Applicable Fields
4-Aminodiphenylamine is primarily used in the production of dyes and pigments. It serves as a precursor in the synthesis of various azo dyes, which are widely employed in the textile, printing, and coloring industries. The mechanism of action involves the reaction of 4-aminodiphenylamine with diazonium salts to form azo compounds, which exhibit vibrant colors.

Storage Conditions
Store in a cool, dry place.

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3.3 General Description: Odorless purple-black solid or flake or dark purple chips.

3.4 Purification Methods: It crystallises from EtOH with m 66o, and from ligroin with m 75o. It can be distilled at high vacuum. [Beilstein 13 IV 113.] 4-Aminodiphenylamine Preparation Products And Raw materials Raw materials

3.5 Usage: Dye intermediate, pharmaceuticals, photographic chemicals.

4. Safety and Handling

4.1 Octanol/Water Partition Coefficient: log Kow = 1.82 (est)

4.2 Fire Hazard: 4-Aminodiphenylamine is combustible.

4.3 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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4.4 Formulations/Preparations: HAIR DYES ARE PREPARED BY COMBINING 2,6-DIAMINOPYRIDINE OR ITS SALT, P-AMINODIPHENYLAMINE OR ITS SALT, AND 2,5-DIAMINOPYRIDINE OR ITS SALT AT THE MOLE RATIO OF 1:2:3.

4.5 Report: NCI Carcinogenesis Bioassay (feed); No Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-82 ,1978. . Reported in EPA TSCA Inventory.

4.6 Safety: Moderately toxic by ingestion. A severe eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x. See also AMINES.
Hazard Codes: Xn,Xi
Risk Statements: 22-36-43-42/43-36/37/38-20/22
R20/22:Harmful by inhalation and if swallowed.
R22:Harmful if swallowed.
R36:Irritating to eyes.
R36/37/38:Irritating to eyes, respiratory system and skin.
R42/43:May cause sensitization by inhalation and skin contact.
R43:May cause sensitization by skin contact.
Safety Statements: 26-36-45-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

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4.7 Specification: N-Phenyl-p-phenylenediamine , its cas register number is 101-54-2. It also can be called Diphenylamine, 4-amino- ; 1,4-Benzenediamine, N-phenyl- ; Variamine Blue RT Base ; and 4-Aminodiphenylamine . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, N-Phenyl-p-phenylenediamine (CAS NO.101-54-2) is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Carbon monoxide, carbon dioxide, nitrogen oxides (NO_x) and ammonia (NH₃).

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4.8 Toxicity

1.	eye-rbt 100 mg/24H SEV	28ZPAK Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,70.
2.	mmo-sat 150 µg/plate	ESKHA5 Eisei Shikenjo Hokoku. Bulletin of the National Hygiene Sciences.(94)(1976),28.
3.	orl-rat LD50:464 mg/kg	NCILB* Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. (Bethesda, MD) NIH-NCI-E-C-72-3252 .
4.	orl-mus LD50:244 mg/kg	TPKVAL Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Sciences. 8 (1966),126.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : CCl4 solution

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

101-54-2Total: 87 Synthesis Route

98-95-3 66 Suppliers

101-54-2 71 Suppliers

71-43-2 202 Suppliers

101-54-2 71 Suppliers

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8. Precursor and Product

precursor:

71-43-2

101-75-7

88-35-7

98-95-3

156-10-5

91-30-5

100-00-5

108-95-2

622-37-7

836-30-6

product:

6201-64-5

793-24-8

101-56-4

156-10-5

1205-71-6

2406-04-4

74-31-7

2367-19-3

88522-60-5

80471-61-0

9. Computed Properties

Molecular Weight：184.23708g/mol
Molecular Formula：C₁₂H₁₂N₂
Compound Is Canonicalized：True
XLogP3-AA：184.100048391
Monoisotopic Mass：184.100048391
Complexity：156
Rotatable Bond Count：2
Hydrogen Bond Donor Count：2
Hydrogen Bond Acceptor Count：2
Topological Polar Surface Area：38
Heavy Atom Count：：14
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBzAAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHAAQAAAACAiBEAAwwILAAACAACRCQACCAAAhAgAIiAAAZIgIIGLAkZGEIAhgkADIyAcQAAAAAACAAAAAAAAAAQAAAAAAAAAAAAAAAA==

10.Other Information

Usage: p-Anilinoaniline is an antioxidant that has shown to cause a reduction of NOx emissions from soybean biodiesel powered DI diesel engines but has increased CO and HC emissions. It is also used to produce dyes, pharmaceuticals, and photographic chemicals and frmerly used as a hair dye.

BRN: 908935

Description: p-Aminodiphenylamine hydrochloride was formerly used as a hair dye. Sensitization, when deteeted by patch testing, is relatively low in hairdressers.

Chemical Properties: Dark grey flake

Uses: Dye intermediate, pharmaceuticals, photographic chemicals.

Uses: 4-Aminodiphenylamine is used as an oxidation dye color in hair dyes. It is also promoted as an efficient reagent for oxidase enzymes, including glucose, lactate, xanthine, and lysine oxidases.

Definition: ChEBI: An aromatic amine that is the 4-amino derivative of diphenylamine.

General Description: Odorless purple-black solid or flake or dark purple chips.

Air & Water Reactions: Insoluble in water.

Reactivity Profile: 4-Aminodiphenylamine is incompatible with strong oxidizers. 4-Aminodiphenylamine is also incompatible with strong acids. 4-Aminodiphenylamine may react with plastics.

Fire Hazard: 4-Aminodiphenylamine is combustible.

Contact allergens: This substance was formerly used as a hair dye. Sensitization, when detected by patch testing, is relatively low in hairdressers.

Purification Methods: It crystallises from EtOH with m 66o, and from ligroin with m 75o. It can be distilled at high vacuum. [Beilstein 13 IV 113.]

11. Toltal 62 Suppliers View more