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1-Phenylethylamine

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1-Phenylethylamine
Names
Chemical structure of 1-Phenylethylamine
Preferred IUPAC name 1-Phenylethan-1-amine
Other names 1-Phenylethylamine α-Phenylethylamine α-Methylbenzylamine 1-PEA α-PEA
Identifiers
CAS Number	618-36-0 (R/S)^Y 3886-69-9 (R)-(+)^Y 2627-86-3 (S)-(−)^Y
3D model (JSmol)	(R/S): Interactive image (R)-(+): Interactive image (S)-(−): Interactive image
ChEBI	CHEBI:670^Y
ChEMBL	ChEMBL278059^Y
ChemSpider	7130^Y
ECHA InfoCard	100.009.588
KEGG	C02455^Y
PubChem CID	7408 (R/S) 643189 (R)-(+) 75818 (S)-(−)
UNII	HZ9DM6B2MT (R/S)^Y V022ZK8GZ5 (R)-(+)^Y 05780F90V3 (S)-(−)^Y
CompTox Dashboard(EPA)	DTXSID40862301
InChI InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3^Y Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N^Y (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
SMILES (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
Chemical formula	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 theirstandard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

1-Phenylethylamine (1-PEA orα-PEA), also known asα-methylbenzylamine, is the organic compound with the formula C₆H₅CH(NH₂)CH₃. Thisprimary amine is a colorless liquid is often used inchiral resolutions. Likebenzylamine, it is relatively basic and forms stable ammonium salts andimines.

Preparation and optical resolution

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1-Phenylethylamine may be prepared by thereductive amination ofacetophenone:^[1]

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

TheLeuckart reaction, usingammonium formate, is another method for this transformation.^[2]

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