2-Aminobiphenyl

Synonym(s):2-Aminodiphenyl, 2-Phenylaniline;2-Biphenylylamine;2-Phenylaniline

CAS NO.：90-41-5
Empirical Formula: C12H11N
Molecular Weight: 169.22
MDL number: MFCD00007701
EINECS: 201-990-9
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-12 17:17:06

What is 2-Aminobiphenyl?

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℃.

The Uses of 2-Aminobiphenyl

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

What are the applications of Application

2-Aminobiphenyl is an amine that has mutagenic potency

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.

What are the applications of 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.]

Properties of 2-Aminobiphenyl

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.
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 information for 2-Aminobiphenyl

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07 Health Hazard GHS08
GHS Hazard Statements	H302:Acute toxicity,oral H351:Carcinogenicity H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P201:Obtain special instructions before use. P202:Do not handle until all safety precautions have been read and understood. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P273:Avoid release to the environment. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P308+P313:IF exposed or concerned: Get medical advice/attention.