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2-Aminobiphenyl

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2-Aminobiphenyl Basic information

Product Name:
2-Aminobiphenyl
Synonyms:
  • 2-amino-1,1’-biphenyl
  • 2-Aminobifenyl
  • 2-aminobiphenyl(forsugardetermination)
  • 2-Phenylbenzenamine
  • 2-Aminobiphenyl,97%
  • 2-aminophenylbenzen
  • 2-AMINOBIPHENYL, FOR FLUORESCENCE
  • biphenyl,2-amino-
CAS:
90-41-5
MF:
C12H11N
MW:
169.22
EINECS:
201-990-9
Product Categories:
  • Biphenyl & Diphenyl ether
  • Amines
  • Amines and Anilines
  • Aromatics
  • Mutagenesis Research Chemicals
Mol File:
90-41-5.mol
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2-Aminobiphenyl Chemical Properties

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)
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Safety Information

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

MSDS

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2-Aminobiphenyl Usage And Synthesis

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.]

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