(S)-1-(4-Chlorophenyl)ethylamine

Base Information

• Chemical Name: (S)-1-(4-Chlorophenyl)ethylamine
• CAS No.: 4187-56-8
• Molecular Formula: C8H10ClN
• Molecular Weight: 155.627
• Hs Code.: 29211990
• European Community (EC) Number: 609-965-8
• UNII: 5Y5RW6RLW9
• DSSTox Substance ID: DTXSID50962028
• Nikkaji Number: J57.024I
• Wikidata: Q72456860
• Mol file: 4187-56-8.mol

Synonyms:(S)-1-(4-Chlorophenyl)ethylamine;4187-56-8;(S)-1-(4-chlorophenyl)ethanamine;(1S)-1-(4-chlorophenyl)ethanamine;(S)-1-(4-chlorophenyl)ethan-1-amine;(s)-(-)-1-(4-chlorophenyl)ethylamine;(S)-4-Chloro-alpha-methylbenzylamine;5Y5RW6RLW9;(S)-4-Chlorophenylethylamine;(1S)-1-(4-chlorophenyl)ethan-1-amine;Benzenemethanamine,4-chloro-a-methyl-,(aS)-;UNII-5Y5RW6RLW9;Benzenemethanamine, 4-chloro-.alpha.-methyl-, (.alpha.S)-;SCHEMBL140922;C8 H10 Cl N;DTXSID50962028;CHEBI:194663;AMY37527;(1S)-1-(4-chlorophenyl)ethylamine;(S)-1-(4-chloro-phenyl)ethylamine;(S)-1-(4-chlorophenyl)-ethylamine;(S)-4-Chloro-alpha-methybenzylamine;MFCD00671640;(-)-alpha-(p-Chlorophenyl)ethylamine;(S)-1-(4-chloro-phenyl)-ethylamine;AKOS015840114;AC-9530;(S)-1-(4-chloro-phenyl)-ethyl amine;[(1S)-1-(4-chlorophenyl)ethyl]amine;(S)-4-Chloro- alpha -methylbenzylamine;AC-26776;AS-11102;A6877;CS-0000297;Bencenmetanamina, 4-cloro-?-metil-, (?s)-;EN300-112621;F14931;(-)-.ALPHA.-(P-CHLOROPHENYL)ETHYLAMINE;(S)-4-Chloro-alpha-methylbenzylamine, >=95.0%;Benzenemethanamine, 4-chloro-alpha-methyl-, (alphaS)-;(S)-4-Chloro-alpha-methylbenzylamine, ChiPros(R), produced by BASF, >=95%

Chemical Property of (S)-1-(4-Chlorophenyl)ethylamine

Chemical Property:

• Appearance/Colour: Clear colorless to yellowish liquid
• Vapor Pressure: 0.0842mmHg at 25°C
• Melting Point: 136-137 °C
• Refractive Index: n20/D 1.543(lit.)
• Boiling Point: 225.9 °C at 760 mmHg
• PKA: 8.82±0.10(Predicted)
• Flash Point: 100.9 °C
• PSA: 26.02000
• Density: 1.122 g/cm³
• LogP: 3.06000
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: VERY LOW SOLUBILITY
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 155.0501770
• Heavy Atom Count: 10
• Complexity: 97.4

Purity/Quality:

99% ^*data from raw suppliers

(S)-1-(4-Chlorophenyl)ethylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N, C
• Hazard Codes: T,N,C
• Statements: 25-37/38-41-51/53-34-22-43-38-37-23
• Safety Statements: 26-39-45-61-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=C(C=C1)Cl)N
• Isomeric SMILES: C[C@@H](C1=CC=C(C=C1)Cl)N
• Uses: It is used as a substrate in palladium catalysts on alkaline-earth supports for racemization and dynamic kinetic resolution of benzylic amines.

Technology Process of (S)-1-(4-Chlorophenyl)ethylamine

There total 29 articles about (S)-1-(4-Chlorophenyl)ethylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.1%

p-chloro-(R,S)-1-phenylethylamine (35588-60-4) → (S)-1-(p-chlorophenyl)ethylamine (4187-56-8) + (R)-1-(4-chlorophenyl)ethylamine (27298-99-3)

Guidance literature:

With 6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl) hydrogen phthalate; In isopropyl alcohol; Heating;

DOI:10.1016/j.tetasy.2003.12.038

Reference yield: 46.0%

isopropyl 2-propoxyacetate (1121583-62-7) + p-chloro-(R,S)-1-phenylethylamine (35588-60-4) → (S)-1-(p-chlorophenyl)ethylamine (4187-56-8) + (R)-2-propoxy-N-(1-(4-chlorophenyl)ethyl)acetamide

Guidance literature:

With lipase B from Candida antarctica immobilized on acrylic beads; In toluene; at 30 ℃; for 8h; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tet.2018.05.032

Reference yield: 46.0%

isopropyl methoxyacetate (17640-21-0) + p-chloro-(R,S)-1-phenylethylamine (35588-60-4) → N-[1-(4-chlorophenyl)ethyl]methoxyacetamide (192210-96-1) + (S)-1-(p-chlorophenyl)ethylamine (4187-56-8)

Guidance literature:

With Novozym 435; at 23 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Molecular sieve; Enzymatic reaction;

DOI:10.1016/j.tetasy.2012.02.008

upstream raw materials:

p-chloro-(R,S)-1-phenylethylamine

para-chloroacetophenone

(E)-1-(4-chlorophenyl)ethanone oxime

isopropyl methoxyacetate

Downstream raw materials:

(R)-N-[1-(4-chlorophenyl)-ethyl]-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid amide

(1S,3R)-2,2-dichloro-N-[(S)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide

(R)-tert-butyl 2-(((S)-1-(4-chlorophenyl)ethyl)carbamoyl)pyrrolidine-1-carboxylate

3-[(S)-1-(4-chloro-phenyl)-ethylamino]-1-phenyl-propan-1-one

Refernces

• 1、 Oláh, Márk,Kovács, Dániel,Katona, Gabriel,Hornyánszky, Gábor,Poppe, László. "Optimization of 2-alkoxyacetates as acylating agent for enzymatic kinetic resolution of chiral amines". . p. 3663 - 3670. Retrieved 2018/06/04.
• 2、 Jin, Ying-Ji,Choi, Yunseo,Chen, Qian,Shirbhate, Mukesh Eknath,Huang, Haofei,Kim, Youngmee,Kim, Sung-Jin,Jun, Moo-Jin,Koo, Eon Cheol,Kim, Kwan Mook. "Chirality switching in the crystallization of 1-(4-chlorophenyl) ethylamine with binaphthoic acid by ketimine formation". . p. 1690 - 1695. Retrieved 2016/10/13.