1-Phenylethylamine - Misplaced Pages

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1-Phenylethylamine
Names
Chemical structure of 1-Phenylethylamine
Preferred IUPAC name 1-Phenylethan-1-amine
Other names (±)-1-Phenylethylamine (±)-α-Methylbenzylamine
Identifiers
CAS Number	618-36-0 (R/S) 3886-69-9 (R)-(+) 2627-86-3 (S)-(−)
3D model (JSmol)	(R/S): Interactive image (R)-(+): Interactive image (S)-(−): Interactive image
ChEBI	CHEBI:670
ChEMBL	ChEMBL278059
ChemSpider	7130
ECHA InfoCard	100.009.588
KEGG	C02455
PubChem CID	7408 (R/S) 643189 (R)-(+) 75818 (S)-(−)
UNII	HZ9DM6B2MT (R/S) V022ZK8GZ5 (R)-(+) 05780F90V3 (S)-(−)
CompTox Dashboard (EPA)	DTXSID40862301
InChI InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N (R/S): InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3Key: RQEUFEKYXDPUSK-UHFFFAOYSA-N (R)-(+): InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m1/s1Key: RQEUFEKYXDPUSK-SSDOTTSWSA-N (S)-(−): InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m0/s1Key: RQEUFEKYXDPUSK-ZETCQYMHSA-N
SMILES (R/S): CC(C1=CC=CC=C1)N (R)-(+): C(C1=CC=CC=C1)N (S)-(−): C(C1=CC=CC=C1)N
Properties
Chemical formula	C₈H₁₁N
Molar mass	121.183 g·mol
Density	0.94 g/mL
Melting point	-65 C
Boiling point	187 °C (369 °F; 460 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Corrosive
Related compounds
Related stereoisomers	(R)-(+)- (CAS ) (S)-(−)- (CAS )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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.

Preparation and optical resolution

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

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

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

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.

References

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

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Category:

Phenethylamines

Preparation and optical resolution

See also

References