1-Phenylethylamine

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1-Phenylethylamine[1]
Chemical structure of 1-Phenylethylamine
Names
IUPAC name
1-phenylethan-1-amine
Other names
(±)-1-Phenylethylamine; (±)-α-Methylbenzylamine
Identifiers
618-36-0 YesY
ChEBI CHEBI:670 YesY
ChEMBL ChEMBL278059 YesY
ChemSpider 7130 YesY
Jmol-3D images Image
Image
KEGG C02455 YesY
Properties
C8H11N
Molar mass 121.18 g·mol−1
Density 0.94 g/mL
Melting point -10
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

1-Phenylethylamine is a monoamine compound. Individual enantiomers of this basic compound are useful for performing chiral resolution of acidic compounds by forming diastereomeric salts and for performing chiral hydrogenations of ketones resulting in enantiopure amines.

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]

Reductive amination acetophenone ammonia

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

See also[edit]

References[edit]

  1. ^ 1-Phenylethylamine - PubChem Public Chemical Database
  2. ^ John C. Robinson, Jr. and H. R. Snyder (1955). "α-Phenylethylamine". Org. Synth. ; Coll. Vol. 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". Org. Synth. ; Coll. Vol. 17, p. 76