2-Aminobiphenyl

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/cm3
Melting point	51 °C (124 °F; 324 K)
Boiling point	299 °C (570 °F; 572 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H351, H412
Precautionary statements	P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, 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

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]

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

References

^ 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.
^ 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.
^ G. David Mendenhall; Peter A. S. Smith (1966). "2-Nitrocarbazole". Org. Synth. 46: 85. doi:10.15227/orgsyn.046.0085.

[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.

[1]

[2]

[3]

See also

References