127733-42-0

Basic information

• Product Name: Benzenemethanamine, 2-chloro-α-methyl-, (αR)-
• Synonyms: Benzenemethanamine, 2-chloro-α-methyl-, (αR)-;(R)-1-(2-Chlorophenyl)ethylamine;(R)-1-(2-Chlorophenyl)ethanaMine hydrochloride;(R)-1-(2-CHLOROPHENYL)ETHANAMINE-HCl;(R)-2-Chloro-alpha-methylbenzenemethanamine;BenzeneMethanaMine,2-chloro-a-Methyl-, (aR)-;(1R)-1-(2-CHLOROPHENYL)ETHAN-1-AMINE-HCL;(1R)-1-(2-CHLOROPHENYL)ETHAN-1-AMINE
• CAS NO: 127733-42-0
• Molecular Formula: C₈H₁₀ClN
• Molecular Weight: 155.627
• Mol File: 127733-42-0.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 217℃
• Flash Point: 93℃
• Appearance: /
• Density: 1.122
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.50±0.10(Predicted)
• CAS DataBase Reference: Benzenemethanamine, 2-chloro-α-methyl-, (αR)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, 2-chloro-α-methyl-, (αR)-(127733-42-0)
• EPA Substance Registry System: Benzenemethanamine, 2-chloro-α-methyl-, (αR)-(127733-42-0)

Safety Data

• Hazardous Substances Data: 127733-42-0(Hazardous Substances Data)

Usage

General Description

Benzenemethanamine, 2-chloro-α-methyl-, (αR)- is a specific enantiomer of a compound known as 2-chloroamphetamine, which is a psychoactive drug with stimulant and entactogenic effects. This particular enantiomer is the (αR)- form, which means it has a specific orientation of atoms around the chiral center. It is commonly used in scientific research to study its effects on neurotransmitters and brain function, particularly its interactions with serotonin receptors and its potential as a treatment for certain mental health disorders. The compound is also classified as a controlled substance due to its potential for abuse and dependence.

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

Upstream product

• 13524-04-4 2'-chloro-sec-phenethyl alcohol 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 1149756-73-9 2-methylpropane-2-sulfinic acid [1-(2-chlorophenyl)ethylidene]amide 
• 39959-67-6 1-(2-Chloro-phenyl)-ethylamine 
• 83834-86-0 N-[1-(2-chloro-phenyl)-ethyl]-formamide 
• 87227-77-8 bishydrochloride salt of cis-1,4-diamino-but-2-ene 
• 2856-63-5 2-Chlorophenylacetonitrile 
• 1239016-36-4 (R)-2-(2-chlorophenyl)propanoic acid 

Downstream Products

• 68285-26-7 (S)-α-(o-chlorophenyl)ethylamine 
• 39959-67-6 (R)-α-(o-chlorophenyl)ethylamine 
• 1131737-05-7 1-(2,6-dichlorophenyl)ethan-1-amine 
• 1637437-40-1 C₂₁H₁₉ClN₄O 

Relevant articles and documents

Resolution of 1-arylalkylamines with 3-O-hydrogen phthalate glucofuranose derivatives: Role of steric bulk in a family of resolving agents

The development of three new acidic resolving agents which are hydrogen phthalates of 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose 1, 1,2:5,6-di-O-cyclohexylidene-α-d-glucofuranose 2 and 1,2-O- cyclohexylidene-5,6-O-diphenylmethylidene-α-d-glucofuranose 3 is shown for the resolution of 1-arylalkylamines 7a-k. The salts between 1, 2 and (RS)-1-arylalkylamines 7a-k selectively crystallize 1?(S) 7a-j and 2?(S) 7a-h salts, allowing us to recover the corresponding bases (S) 7a-j and (S) 7a-h, respectively, in good yield and enantiomeric excess (73-95% ee). Whereas, the salts between 3 and (RS)-1-arylalkylamines 7a-c,g-i,k selectively crystallize 3?(S)-7a-c,g-i salts to recover the corresponding bases (S)-7a-c,g-i in poor enantiomeric excess (4-35% ee). The difference between the resolving ability of 1 and 2 for 1-arylalkylamines 7a-h is very slight, but there is considerable difference compared to ortho-substituted 1-arylalkylamines 7i and 7j. The role of substituents on a family of resolving agents 1, 2 and 3 is also discussed to interpret their resolving ability.

One-Pot C-H Arylation/Lactamization Cascade Reaction of Free Benzylamines

An efficient method has been developed for the synthesis of seven-membered biaryl lactams involving Pd-catalyzed, native amine-directed, ortho-arylation of benzylamines followed by in situ lactamization. This cascade sequence is enabled by the use of 2-iodobenzoates, which facilitates C-H arylation from the free amine under conditions that typically require an improved directing group approach. This reaction is characterized by a broad substrate scope with good functional group tolerance. The need for an ester versus carboxylic acid-functionalized coupling partner is also explored, as is the potential for synthesizing eight-membered biaryl lactams. Various applications are also investigated, including access to the aza-brassinolide core.

Carbon Dioxide-Mediated C(sp2)-H Arylation of Primary and Secondary Benzylamines

C-C bond formation by transition metal-catalyzed C-H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C-C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to allowing this transformation to proceed under relatively mild conditions, and mechanistic studies indicate that it (CO2) is directly involved in the rate-determining step. Furthermore, the milder temperatures furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, an interesting chelate effect is shown to facilitate selective monoarylation.