1-Phenylethylamine

1-Phenylethylamine is the organic compound with the formula C6H5CH(NH2)CH3. Classified as a monoamine, this colorless liquid is often used in chiral resolutions. Like benzylamine, it is highly basic and forms stable ammonium salts and imines.

1-Phenylethylamine[1]
Names
Preferred IUPAC name
1-Phenylethan-1-amine
Other names
  • (±)-1-Phenylethylamine
  • (±)-α-Methylbenzylamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.588
KEGG
UNII
Properties
C8H11N
Molar mass 121.183 g·mol−1
Density 0.94 g/mL
Melting point -65 C 
Boiling point 187 °C (369 °F; 460 K)
Hazards
Main hazards Corrosive
Related compounds
Related stereoisomers
(R)-(+)- (CAS [3886-69-9])
(S)-(–)- (CAS [2627-86-3])
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

This compound may be prepared by the reductive amination of acetophenone under various standard conditions for this type of reaction. One major route for this chemical uses the Mignonac reaction, a one-pot protocol using hydrogen gas as the reducing agent:[2]

The Leuckart reaction, using ammonium formate, is another method for this transformation.[3][4]

See also

  • 2-Phenylethylamine

References

  1. 1-Phenylethylamine - PubChem Public Chemical Database
  2. John C. Robinson, Jr. and H. R. Snyder (1955). "α-Phenylethylamine". Organic Syntheses.; Collective Volume, 3, p. 717
  3. Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. pp. 223–224. ISBN 9780582444072.
  4. A. W. Ingersoll (1937). "α-Phenylethylamine". Organic Syntheses.; Collective Volume, 17, p. 76
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