2-Aminobiphenyl Property

Melting point:

47-50 °C(lit.)

Boiling point:

299 °C(lit.)

Density 

1.44

vapor density 

5.9 (vs air)

vapor pressure 

2 mm Hg ( 140 °C)

refractive index 

1.613-1.615

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Crystals or Crystalline Powder

pka

3.82(at 22℃)

color 

Purple to brown

Water Solubility 

<0.01 g/100 mL at 21 ºC

BRN 

471874

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

TWBPWBPGNQWFSJ-UHFFFAOYSA-N

LogP

2.84

CAS DataBase Reference

90-41-5(CAS DataBase Reference)

NIST Chemistry Reference

[1,1'-Biphenyl]-2-amine(90-41-5)

EPA Substance Registry System

2-Biphenylamine (90-41-5)

Safety

Hazard Codes 

Xn

Risk Statements 

22-40-52/53-21/22/36/37/38/40-20

Safety Statements 

36/37-61

WGK Germany 

3

RTECS 

DV5530000

Autoignition Temperature

842 °F

TSCA 

Yes

HS Code 

29214980

Hazardous Substances Data

90-41-5(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2340 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H351Suspected of causing cancer

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

2-Aminobiphenyl Chemical Properties,Usage,Production

Description

2-Aminobiphenyl (2-APB) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored even black. Palladacycles obtained from 2-aminobiphenyl are popular catalysts for cross-coupling.

Chemical Properties

colourless to purple crystalline solid. Soluble in alcohol, ether and benzene, insoluble in water. Can be volatilized with water vapor. Flash point >110℃.

Uses

2-Aminobiphenyl has a mutagenic potency. It is a substrate for UGTs (UDP-glucuronosyltransferases), including UGT1A4, UGT2B13 and UGT2B16.

Preparation

2-Aminodiphenyl is prepared by hydrogenation of 2-nitrobiphenyl.
NEW SYNTHESIS OF 2-AMINOBIPHENYLS
Reflux 2-nitrobiphenyl, ethanol and stannous chloride in a water bath for 3h, recover the ethanol, cool the residue, add 40% liquid alkali to make it strongly alkaline, separate the oil layer, extract the aqueous layer with ether, dry the extract with anhydrous calcium chloride, filter and recover the ether, wash with ethanol to obtain the crude product, then distill the crude product under reduced pressure to obtain 2-aminobiphenyl.

Application

2-Aminobiphenyl is used as raw materials for organic synthesis. manufacture of carbazole resin, synthetic rubber.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 5, p. 829, 1973
Tetrahedron Letters, 36, p. 125, 1995 DOI: 10.1016/0040-4039(94)02191-D

General Description

2-aminobiphenyl appears as colorless or purplish crystals. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Aminodiphenyl neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Hazard

Toxic by ingestion, inhalation, and skin absorption. A carcinogen.

Fire Hazard

2-Aminodiphenyl is probably combustible.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by ingestion.Mutation data reported. When heated to decomposition, itemits toxic fumes of NOx.

Purification Methods

Crystallise it from aqueous EtOH (charcoal). [Beilstein 12 IV 3223.]