2-Aminobiphenyl

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.[1] Palladacycles obtained from 2-aminobiphenyl are popular catalysts for cross-coupling.[2]

2-Aminobiphenyl

Names
Preferred IUPAC name [1,1'-Biphenyl]-2-amine
Identifiers
CAS Number	90-41-5
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL296021
ChemSpider	6748
ECHA InfoCard	100.001.810
EC Number	201-990-9
PubChem CID	7015
UNII	8LQM58EBRY
CompTox Dashboard (EPA)	DTXSID3030189
InChI InChI=1S/C12H11N/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H,13H2 Key: TWBPWBPGNQWFSJ-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C2=CC=CC=C2N
Properties
Chemical formula	C12H11N
Molar mass	169.227 g·mol^−1
Appearance	white solid
Density	1.077 g/cm^3
Melting point	51 °C (124 °F; 324 K)
Boiling point	299 °C (570 °F; 572 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H351, H412
GHS precautionary statements	P201, P202, P264, P270, P273, P281, P301+312, P308+313, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is prepared by hydrogenation of 2-nitrobiphenyl.[3]

See also

• 4-Aminobiphenyl
• Herrmann's catalyst

References

1. M. J. S. Dewar; R. B. K. Dewar; Z. L. F. Gaibel (1966). "10-Methyl-10,9-borazarophenanthrene". Org. Synth. 46: 65. doi:10.15227/orgsyn.046.0065.
2. Bruneau, A.; Roche, M.; Alami, M.; Messaoudi, S. (2015). "2-Aminobiphenyl Palladacycles: The "Most Powerful" Precatalysts in C–C and C–Heteroatom Cross-Couplings". ACS Catalysis. 5: 1386-1396. doi:10.1021/cs502011x.
3. G. David Mendenhall; Peter A. S. Smith (1966). "2-Nitrocarbazole". Org. Synth. 46: 85. doi:10.15227/orgsyn.046.0085.