1-Phenylethylamine
Names | |
---|---|
Preferred IUPAC name 1-Phenylethan-1-amine | |
Other names
| |
Identifiers | |
CAS Number |
|
3D model (JSmol) |
|
ChEBI |
|
ChEMBL |
|
ChemSpider |
|
ECHA InfoCard | 100.009.588 |
KEGG |
|
PubChem CID |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
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 their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) 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:[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
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
- 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
- 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)
- Stimulants: Chlorphentermine
- Cloforex
- Clortermine
- Etolorex
- Mephentermine
- Pentorex
- Phentermine
Entactogens: MDPH - MDMPH
Others: Cericlamine
- 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
(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
- 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