2-Aminobiphenyl

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
2-Aminobiphenyl Structure
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
Fp >230 °F
storage temp. Store below +30°C.
solubility Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
pka3.82(at 22℃)
form Crystals or Crystalline Powder
color Purple to brown
Water Solubility <0.01 g/100 mL at 21 ºC
BRN 471874
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyTWBPWBPGNQWFSJ-UHFFFAOYSA-N
LogP2.84
CAS DataBase Reference90-41-5(CAS DataBase Reference)
NIST Chemistry Reference[1,1'-Biphenyl]-2-amine(90-41-5)
EPA Substance Registry System2-Biphenylamine (90-41-5)
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 Temperature842 °F
TSCA Yes
HS Code 29214980
Hazardous Substances Data90-41-5(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 2340 mg/kg
MSDS Information
ProviderLanguage
o-phenylaniline English
ACROS English
SigmaAldrich English
ALFA English
2-Aminobiphenyl Usage And Synthesis
Description2-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 Propertiescolourless to purple crystalline solid. Soluble in alcohol, ether and benzene, insoluble in water. Can be volatilized with water vapor. Flash point >110℃.
Uses2-Aminobiphenyl has a mutagenic potency. It is a substrate for UGTs (UDP-glucuronosyltransferases), including UGT1A4, UGT2B13 and UGT2B16.
Preparation2-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.
Application2-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 Description2-aminobiphenyl appears as colorless or purplish crystals. (NTP, 1992)
Air & Water ReactionsInsoluble in water.
Reactivity Profile2-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.
HazardToxic by ingestion, inhalation, and skin absorption. A carcinogen.
Fire Hazard2-Aminodiphenyl is probably combustible.
Flammability and ExplosibilityNonflammable
Safety ProfileModerately toxic by ingestion.Mutation data reported. When heated to decomposition, itemits toxic fumes of NOx.
Purification MethodsCrystallise it from aqueous EtOH (charcoal). [Beilstein 12 IV 3223.]
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