69308-37-8

Basic information

• Product Name: (R)-4-AMINO-3-(4-CHLOROPHENYL)BUTANOIC ACID
• Synonyms: Benzenepropanoic acid, β-(aminomethyl)-4-chloro-, (βR)-;D-Baclofen;l-Baclofen;(R)-4-Amino-3-(4-chlorophenyl)butyric acid;4-azanyl-3-(4-chlorophenyl)butanoic acid;(βR)-β-(AMinoMethyl)-4-chlorobenzenepropanoic Acid;STX 209;Benzenepropanoic acid, b-(aMinoMethyl)-4-chloro-, (bR)-
• CAS NO: 69308-37-8
• Molecular Formula: C₁₀H₁₂ClNO₂
• Molecular Weight: 213.66
• Product Categories: GABA/Glycine receptor;Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 69308-37-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 171-174°C
• Boiling Point: 364.3 °C at 760 mmHg
• Flash Point: 174.1 °C
• Appearance: /
• Density: 1.285g/cm³
• Vapor Pressure: 6.01E-06mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Store at RT
• PKA: 4.04±0.10(Predicted)
• Water Solubility: Practically insoluble in water
• CAS DataBase Reference: (R)-4-AMINO-3-(4-CHLOROPHENYL)BUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-AMINO-3-(4-CHLOROPHENYL)BUTANOIC ACID(69308-37-8)
• EPA Substance Registry System: (R)-4-AMINO-3-(4-CHLOROPHENYL)BUTANOIC ACID(69308-37-8)

Safety Data

• RIDADR: 2811
• RTECS: DA8339450
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 69308-37-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 69308-37-8 differently. You can refer to the following data:
1. (R)-baclofen is a derivative of gamma-aminobutyric acid primarily used to treat spasticity.
2. R-Enantiomer of Baclofen. Specific GABA-B receptor agonist. Muscle relaxant (skeletal).

Biological Activity

More active enantiomer of ( RS )-Baclofen ((RS)-4-Amino-3-(4-chlorophenyl)butanoic acid) , a selective GABA B agonist.

InChI:InChI=1/C10H12ClNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14)/t8-/m0/s1

Upstream product

• 200720-85-0 (E)-(S)-3-(4-Chloro-phenyl)-hex-4-enoic acid ethyl ester 
• 1141-23-7 3-(p-chlorophenyl)glutaramic acid 
• 1134-47-0 4-amino-3-(4-chlorophenyl)butanoic acid 
• 123632-35-9 (R)-(-)-4-(4-chlorophenyl)pyrrolidin-2-one 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 71639-13-9 diethyl 2-(3-nitrophenylethyl)malonate 
• 101671-01-6 1-nitro-2-(4-chlorophenyl)ethylene 
• 104-88-1 4-chlorobenzaldehyde 
• 63701-55-3 (R)-(-)-baclofen hydrochloride 
• 159156-87-3 4-hydroxy-3-(p-chlorophenyl)butyronitrile 
• 159156-85-1 1-acetoxy-2-(p-chlorophenyl)-3-mesyloxypropane 
• 159156-88-4 4-mesyloxy-3-(p-chlorophenyl)butyronitrile 
• 159156-86-2 4-acetoxy-3-(p-chlorophenyl)butyronitrile 

Downstream Products

• 847353-27-9 (3R)-4-{[(1R)-2-methyl-1-(2-methylpropanoyloxy)propoxy]carbonylamino}-3-(4-chlorophenyl)butanoic acid 
• 847353-30-4 [3H]-Arbaclofen placarbil 
• 123632-35-9 (R)-(-)-4-(4-chlorophenyl)pyrrolidin-2-one 
• 1252761-95-7 (R)-4-(4-chloro-3-iodophenyl)pyrrolidin-2-one 
• 1252761-94-6 tert-butyl (R)-4-(4-chloro-3-iodophenyl)-2-oxopyrrolidine-1-carboxylate 
• 1252761-96-8 tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate 
• 1252762-31-4 tert-butyl (R)-4-(4-chloro-3-hydroxyphenyl)-2-oxopyrrolidine-1-carboxylate 
• 1252763-01-1 (R)-4-amino-3-(4-chloro-3-(pyridin-4-ylmethoxy)phenyl)butanoic acid 
• 1252761-51-5 (R)-4-(4-chloro-3-nitrophenyl)pyrrolidin-2-one 
• 1252761-21-9 (R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-one 

Relevant articles and documents

Chiral separation and modeling of baclofen, bupropion, and etodolac profens on amylose reversed phase chiral column

Chiral resolution of baclofen, bupropion, and etodolac profens was obtained with amylose derivatized chiral reversed stationary phase (carbamate groups). The eluent used for bupropion and etodolac was MeOH–water (20:80, v/v) and for baclofen was water–methanol (95:5, v/v). The eluent run rates, finding wavelength and temperature, were 1.0?mL/min, 220?nm and 27?±?1?°C for all the eluents. The magnitude of the retardation factors for S- and R-enantiomers of baclofen, bupropion, and etodolac were 1.37, 2.62, 2.25, 3.25, 1.8, and 3.0. The magnitudes of separation and resolution factors were 1.90, 1.44, and 1.67 and 2.77, 2.35, and 2.04. Limits of detection and quantitation were 1.0–2.0 and 5.1–10.0?μg/mL. Chiral recognition mechanisms were recognized by simulation and high-performance liquid chromatography (HPLC) experiments. It was seen that hydrogen interactions, hydrophobic interactions, and π–π exchanges were the chief interactions for chiral recognition mechanisms. The described methods may be exploited for the chiral separation of baclofen, bupropion, and etodolac profens in any unknown sample.

COCRYSTALS OF (R)-BACLOFEN

The invention relates to novel cocrystals of (R)-Baclofen and processes for preparation thereof, and in particular to cocrystals of (R)-Baclofen with cinnamic acid, benzoic acid, salicylic acid and ferulic acid. It also refers to pharmaceutical compositions containing said cocrystals and to a use of said cocrystals or pharmaceutical compositions for the treatment of a disease or disorder selected from spasticity due to multiple sclerosis, spinal cord injury or cerebral palsy, and alcoholism.

Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position

With the assistance of hydrogen bonds, the first asymmetric hydrogenation of β-cyanocinnamic esters is developed, affording chiral β-cyano esters with excellent enantioselectivities (up to 99% ee). This novel methodology provides an efficient and concise synthetic route to chiral GABA-derivatives such as (S)-Pregabalin, (R)-Phenibut, (R)-Baclofen. Interestingly, in this system, the catalyst with a single H-bond donor performs better than that with double H-bond donors, which is a novel discovery in the metalorganocatalysis area.