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

Description

(R)-1-(4-Chlorophenyl)ethylamine, also known as (R)-(+)-1-(4-Chlorophenyl)ethylamine, is a chiral compound that exists as a clear colorless to yellowish liquid. It is characterized by its distinct (R)-configuration, which is crucial for its applications in various industries due to the importance of stereochemistry in chemical reactions and biological activities.

Uses

Used in Organic Synthesis:
(R)-1-(4-Chlorophenyl)ethylamine is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of reactions, making it a valuable building block for creating complex molecules.
Used in Pharmaceutical Industry:
(R)-1-(4-Chlorophenyl)ethylamine is utilized as an important raw material in the development of pharmaceuticals. Its chiral nature is particularly relevant in the synthesis of drugs that require specific stereochemistry for their intended biological activity, ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Agrochemicals:
In the agrochemical industry, (R)-1-(4-Chlorophenyl)ethylamine serves as a crucial intermediate for the production of various agrochemicals, such as pesticides and herbicides. Its incorporation into these products can enhance their effectiveness and selectivity, leading to improved crop protection and reduced environmental impact.
Used in Dyestuff:
(R)-1-(4-Chlorophenyl)ethylamine is also employed in the dyestuff industry, where it contributes to the synthesis of dyes with specific color properties and stability. Its chiral nature can influence the color and performance of the resulting dyes, making it an essential component in the development of high-quality colorants.
Used as a Chiral Reagent:
(R)-1-(4-Chlorophenyl)ethylamine is used as a chiral reagent in various chemical processes. Its (R)-configuration can be exploited to induce asymmetry in other molecules, leading to the formation of enantiomerically pure products. This is particularly important in the synthesis of enantiomerically pure compounds for pharmaceutical, agrochemical, and other applications where the stereochemistry of the molecule is critical for its function.

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

Upstream product

• 99-91-2 para-chloroacetophenone 
• 1956-39-4 (E)-1-(4-chlorophenyl)ethanone oxime 
• 35588-60-4 p-chloro-(R,S)-1-phenylethylamine 
• 948018-43-7 (R)-N-(3,5-dimethyl-4-methoxyphenyl)-(1-(4-chlorophenyl)ethyl)amine 
• 948018-29-9 N-(3,5-dimethyl-4-methoxyphenyl)-1-(4-chlorophenyl)ethylideneamine 
• 937371-83-0 (E)-1-(4-chlorophenyl)ethanone O-benzyl oxime 
• 4187-56-8 (S)-1-(p-chlorophenyl)ethylamine 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 71426-50-1 Syn-α-Brom-p-chlor-acetophenon oxim 
• 1434603-01-6 (Z)-1-(4-chlorophenyl)ethanone O-benzyloxime 
• 105879-62-7 2(R)-(-)-4-chlorophenylpropanoic acid 
• 1529-41-5 3-chloro-benzeneacetonitrile 
• 622-98-0 4-chloro(ethylbenzene) 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 

Downstream Products

• 787633-99-2 (R,S)-α-(4-chlorophenyl)-α-[(R)-N-[1-(4-chlorophenyl)ethyl]amino]acetic acid methyl ester 
• 787633-96-9 (3S)-3-(4-Chlorophenyl)-4-[(R)-1-(4-chlorophenyl)ethyl]-7-iodo-1,3-dihydro-1,4-benzodiazepine-2,5-dione 
• 851664-11-4 (4-Chloro-phenyl)-{[(R)-1-(4-chloro-phenyl)-ethyl]-[(E)-(3-phenyl-acryloyl)]-amino}-acetic acid methyl ester 
• 851664-13-6 (4-Chloro-phenyl)-{[(R)-1-(4-chloro-phenyl)-ethyl]-[(E)-(3-phenyl-acryloyl)]-amino}-acetic acid 
• 787633-77-6 (3S)-1,3-dihydro-3-(4-chlorophenyl)-4-[(R)-1-(4-chlorophenyl)ethyl]-7-phenyl-1,4-diazepine-2,5-dione 
• 851664-12-5 {[(E)-3-(2-Bromo-phenyl)-acryloyl]-[(R)-1-(4-chloro-phenyl)-ethyl]-amino}-(4-chloro-phenyl)-acetic acid methyl ester 
• 851664-14-7 {[(E)-3-(2-Bromo-phenyl)-acryloyl]-[(R)-1-(4-chloro-phenyl)-ethyl]-amino}-(4-chloro-phenyl)-acetic acid 
• 851664-18-1 (S)-7-(2-Bromo-phenyl)-3-(4-chloro-phenyl)-4-[(R)-1-(4-chloro-phenyl)-ethyl]-3,4-dihydro-1H-[1,4]diazepine-2,5-dione 

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.