27298-99-3

Basic information

• Product Name: (R)-1-(4-CHLOROPHENYL)ETHYLAMINE
• Synonyms: (R)-4-CHLORO-ALPHA-METHYLBENZYLAMINE;(R)-(+)-4-CHLORO A-METHYLBENZYLAMINE;(R)-1-(4-CHLOROPHENYL)ETHANAMINE;(R)-(+)-1-(4-CHLOROPHENYL)ETHYLAMINE;(R)-1-(4-CHLOROPHENYL)ETHYLAMINE;(R)-4-Chloro-alpha-methylbenzylamine~ClophaR(tm;ClophaR\(tm;(r)-4-chloro-à-methylbenzylamine
• CAS NO: 27298-99-3
• Molecular Formula: C₈H₁₀ClN
• Molecular Weight: 155.62
• EINECS: -0
• Mol File: 27298-99-3.mol
• Article Data: 40

Chemical Properties

• Melting Point: 222-224 °C
• Boiling Point: 232 °C
• Flash Point: 115°C
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.110 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0842mmHg at 25°C
• Refractive Index: n20/D 1.543(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.82±0.10(Predicted)
• Water Solubility: VERY LOW SOLUBILITY
• Sensitive: Air Sensitive
• BRN: 2412317
• CAS DataBase Reference: (R)-1-(4-CHLOROPHENYL)ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(4-CHLOROPHENYL)ETHYLAMINE(27298-99-3)
• EPA Substance Registry System: (R)-1-(4-CHLOROPHENYL)ETHYLAMINE(27298-99-3)

Safety Data

• Hazard Codes: C,N,T
• Statements: 34-51/53-22-43-41-38-23
• Safety Statements: 26-36/37/39-45-61
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 27298-99-3(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to yellowish liquid

Uses

(R)-(+)-1-(4-Chlorophenyl)ethylamine, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is used as a chiral reagent.

InChI:InChI=1/C8H10ClN/c1-6(10)7-2-4-8(9)5-3-7/h2-6H,10H2,1H3/t6-/m1/s1

Upstream product

• 35588-60-4 p-chloro-(R,S)-1-phenylethylamine 
• 948018-43-7 (R)-N-(3,5-dimethyl-4-methoxyphenyl)-(1-(4-chlorophenyl)ethyl)amine 
• 1956-39-4 (E)-1-(4-chlorophenyl)ethanone oxime 
• 108-24-7 acetic anhydride 
• 622-98-0 4-chloro(ethylbenzene) 
• 108-05-4 vinyl acetate 
• 5405-41-4 ethyl 3-hydroxybutyrate 
• 141-78-6 ethyl acetate 
• 3938-96-3 ethyl 2-methoxyacetate 
• 108-22-5 Isopropenyl acetate 
• 123-25-1 succinic acid diethyl ester 
• 106-65-0 Dimethyl succinate 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 1529-41-5 3-chloro-benzeneacetonitrile 

Downstream Products

• 787633-99-2 (R,S)-α-(4-chlorophenyl)-α-[(R)-N-[1-(4-chlorophenyl)ethyl]amino]acetic acid methyl ester 
• 787633-72-1 α-(4-chlorophenyl)-α-[(R)-N-[1-(4-chlorophenyl)ethyl]amino]acetic acid methyl ester hydrochloride 
• 1187776-93-7 C₃₃H₄₄ClN₃O₂ 
• 1198107-11-7 (R)-N-(1-(4-chlorophenyl)ethyl)benzamide 
• 92520-15-5 (R)-N-[1-(4-chlorophenyl)ethyl]acetamide 
• 1143532-53-9 (R)-4-amino-N-(1-(4-chlorophenyl)ethyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide 
• 1394070-79-1 4-(5-bromo-2-chloropyrimidin-4-yl)-N-((R)-1-(4-chlorophenyl)ethyl)morpholine-3-carboxamide 
• 787633-96-9 (3S)-3-(4-Chlorophenyl)-4-[(R)-1-(4-chlorophenyl)ethyl]-7-iodo-1,3-dihydro-1,4-benzodiazepine-2,5-dione 
• 737000-80-5 C₉H₈ClNS 
• 1143536-01-9 (R)-tert-butyl 4-(1-(4-chlorophenyl)ethylcarbamoyl)-4-cyanopiperidine-1-carboxylate 
• 1012057-76-9 (R)-4-((1-(4-chlorophenyl)ethyl)amino)-7-methoxyquinazolin-6-ol 
• 1093101-68-8 (R)-N-(1-(4-chlorophenyl)ethyl)-6-methyl-5-nitroisoquinolin-1-amine 
• 1031721-42-2 (R)-1-(4-trifluoromethylphenyl)-3-[(1R)-1-(4-chlorophenyl)-ethylamino]-5-(3-trifluoromethoxyphenyl)-1,5-dihydropyrrol-2-one 

Relevant articles and documents

Chirality switching in the crystallization of 1-(4-chlorophenyl) ethylamine with binaphthoic acid by ketimine formation

Axially chiral binaphthoic acid (BNA) was studied as a resolving agent for a stereoselective crystallization of 1-(4-chlorophenyl)ethylamine (CPEA). The diastereomeric pair of (R)-BNA/(S)-CPEA crystallizes in methylene chloride, on the other hand, the pair of (S)-BNA/(S)-CPEA crystallizes in acetone. The switch of the solubility of the diastereomeric pair is due to the imine formation with acetone. The very low solubility of the BNA/imine pair appears to be responsible for the fast and complete imine formation. The crystal structure of the BNA part in both crystals of the diastereomers maintains a same feature. Asymmetric chiral channels and pockets composed by intermolecular packing of BNA molecules appear in the crystal structures, and the robustness of them seem to contribute to the recognition of the chirality of CPEA with high selectivity.

Enzymatic Primary Amination of Benzylic and Allylic C(sp3)-H Bonds

Aliphatic primary amines are prevalent in natural products, pharmaceuticals, and functional materials. While a plethora of processes are reported for their synthesis, methods that directly install a free amine group into C(sp3)-H bonds remain unprecedented. Here, we report a set of new-to-nature enzymes that catalyze the direct primary amination of C(sp3)-H bonds with excellent chemo-, regio-, and enantioselectivity, using a readily available hydroxylamine derivative as the nitrogen source. Directed evolution of genetically encoded cytochrome P411 enzymes (P450s whose Cys axial ligand to the heme iron has been replaced with Ser) generated variants that selectively functionalize benzylic and allylic C-H bonds, affording a broad scope of enantioenriched primary amines. This biocatalytic process is efficient and selective (up to 3930 TTN and 96percent ee), and can be performed on preparative scale.

The enzymatic resolution of 1-(4-chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide

The kinetic resolution of (R,S)-1-(4-chlorophenyl)ethylamine was accomplished using a commercial lipase from Candida antarctica (Novozym 435). The performance of this lipase was investigated for the enantioselective amidation of (R,S)-1-(4-chlorophenyl)ethylamine, leaving the target product (S)-1-(4-chlorophenyl)ethylamine in its unreacted form. The effects of various types of solvents and an acyl donor, the molar ratio of the substrate to the acyl donor, and the reaction temperature were studied. The optimum reaction conditions were found to result in amidation with methyl 2-tetrahydrofuroate at 40°C in methyl tert-butyl ether, with a substrate/acyl donor molar ratio of 1:2.4. The conversion rate of (R,S)-1-(4-chlorophenyl)ethylamine was 52%, with an enantiomeric excess of 99% towards the unreacted substrate in a reaction time of 22?hours. Finally, using optically pure (S)-1-(4-chlorophenyl)ethylamine as the raw material, the chemical synthesis of (S)-N-(1-(4-chlorphenyl)ethyl)-2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)acetamide, a novel triazolopyrimidine herbicide, was achieved, and the total yield and purity were 83.5% and 95.3%, respectively.