1-Phenylethylamine

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1-Phenylethylamine
1-phenethylamine.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3 Yes check.svgY
    Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N Yes check.svgY
  • (R/S):InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3
    Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N
  • (R)-(+):InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m1/s1
    Key: RQEUFEKYXDPUSK-SSDOTTSWSA-N
  • (S)-(−):InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m0/s1
    Key: RQEUFEKYXDPUSK-ZETCQYMHSA-N
  • (R/S):CC(C1=CC=CC=C1)N
  • (R)-(+):C[C@H](C1=CC=CC=C1)N
  • (S)-(−):C[C@@H](C1=CC=CC=C1)N
Properties
C8H11N
Molar mass 121.183 g·mol−1
Density 0.94 g/mL
Melting point -65 C[ citation needed ]
Boiling point 187 °C (369 °F; 460 K)
Hazards
Occupational safety and health (OHS/OSH):
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

1-Phenylethylamine is the organic compound with the formula C6H5CH(NH2)CH3. This primary amine is a colorless liquid is often used in chiral resolutions. Like benzylamine, it is relatively basic and forms stable ammonium salts and imines.

Contents

Preparation and optical resolution

1-Phenylethylamine may be prepared by the reductive amination of acetophenone: [1]

C6H5C(O)CH3 + NH3 + H2 → C6H5CH(NH2)CH3 + H2O

The Leuckart reaction, using ammonium formate, is another method for this transformation. [2]

L-malic acid is used to resolve 1-Phenylethylamine, a versatile resolving agent in its own right. The dextrorotatory enantiomer crystallizes with the malate, leaving the levorotatory form in solution. [3]

See also

Related Research Articles

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References

  1. ↑ John C. Robinson, Jr. and H. R. Snyder (1943). "α-Phenylethylamine". Organic Syntheses . 23: 68. doi:10.15227/orgsyn.023.0068 .
  2. ↑ Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. pp. 223–224. ISBN   9780582444072.
  3. ↑ A. W. Ingersoll (1937). "d- and l-α-Phenylethylamine". Organic Syntheses. 17: 80. doi:10.15227/orgsyn.017.0080.
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