43189-37-3

Basic information

• Product Name: (R)-4-CHLORO PHENYLGLYCINE
• Synonyms: (R)-Amino-(4-chlorophenyl)acetic acid;D(-)-4-Chlorophenylglycine;(R)-2-amino-2-(4-chlorophenyl)acetic acid;(R)-4-chlorophenylgycine;100g of D-4-Chlorophenylglycine (CAS# 43189-37-3);(R)-2-(4-Chlorophenyl)glycine;Benzeneacetic acid, .alpha.-amino-4-chloro-, (.alpha.R)-;H-D-Phg(4-Cl)-OH
• CAS NO: 43189-37-3
• Molecular Formula: C₈H₈ClNO₂
• Molecular Weight: 185.61
• Mol File: 43189-37-3.mol

Chemical Properties

• Boiling Point: 328.8 °C at 760 mmHg
• Flash Point: 152.7 °C
• Appearance: /
• Density: 1.393 g/cm³
• Vapor Pressure: 7.45E-05mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.81±0.10(Predicted)
• CAS DataBase Reference: (R)-4-CHLORO PHENYLGLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-CHLORO PHENYLGLYCINE(43189-37-3)
• EPA Substance Registry System: (R)-4-CHLORO PHENYLGLYCINE(43189-37-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Hazardous Substances Data: 43189-37-3(Hazardous Substances Data)

Usage

Uses

(R)-4-Chlorophenylglycine

InChI:InChI=1/C8H8ClNO2/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7H,10H2,(H,11,12)/t7-/m1/s1

Upstream product

• 43189-43-1 (R)-Amino-(4-chloro-phenyl)-acetic acid methylester 
• 67-66-3 chloroform 
• 104-88-1 4-chlorobenzaldehyde 
• 119825-44-4 (R)-2-Amino-N-tert-butyl-2-(4-chloro-phenyl)-acetamide; hydrochloride 
• 144744-27-4 (3R,5S,6R)-2,3,5,6-Tetrahydro-3-(p-chlorophenyl)-5,6-diphenyl-1,4-oxazin-2-one 
• 112022-98-7 N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(R)-p-chloro-phenylglycine-N'-tert-butyl-amide 
• 6212-33-5 2-(4-Chlorophenyl)glycine 
• 102333-75-5 2-amino-2-(4-chlorophenyl)acetamide 
• 92303-74-7 4-chloro-(RS)-phenylglycinamide hydrochloride 
• 56464-72-3 2-amino-2-(p-chlorophenyl)acetonitrile 
• 1073-67-2 4-vinylbenzyl chloride 
• 7138-34-3 p-chloromandelic acid 
• 856214-68-1 4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)benzylideneamine 
• 112022-98-7 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-{[(R)-tert-butylcarbamoyl-(4-chloro-phenyl)-methyl]-formyl-amino}-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 

Downstream Products

• 6212-33-5 2-(4-Chlorophenyl)glycine 
• 53994-85-7 (R)-2-((tert-butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid 
• 1147391-02-3 (R)-4-(4-chlorophenyl)oxazolidin-2-one 
• 1067658-27-8 (R)-2-amino-2-(4-chlorophenyl)ethanol 
• 1395847-72-9 (R)-N-(1-(4-chlorophenyl)-2-hydroxyethyl)pent-4-enamide 
• 1395847-77-4 (S)-4-tert-butyl 1-((R)-2-(4-chlorophenyl)-2-(pent-4-enamido)ethyl) 2-allylsuccinate 
• 1395847-80-9 tert-butyl 2-((3R,11S,E)-3-(4-chlorophenyl)-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetate 
• 1396152-06-9 N-(4-chlorobenzyl)-2-((3R,11S,E)-3-(4-chlorophenyl)-5,12-dioxo-1-oxa-4-azacyclododec-8-en-11-yl)acetamide 
• 1429382-71-7 (R)-tert-butyl (1-(4-chlorophenyl)-2-hydroxyethyl)carbamate 
• 1429382-72-8 (R)-tert-butyl 1-(4-chlorophenyl)-2-oxoethylcarbamate 
• 1429382-73-9 tert-butyl (1R,2R)-2-(3-chloro-5-fluorophenyl)-1-(4-chlorophenyl)-2-hydroxyethylcarbamate 
• 1429382-74-0 tert-butyl (1R,2S)-2-(3-chloro-5-fluorophenyl)-1-(4-chlorophenyl)-2-hydroxyethylcarbamate 
• 1429387-27-8 tert-butyl (1R,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-2-hydroxyethylcarbamate 
• 1429397-50-1 (1R,2R)-2-amino-1-(3-chlorophenyl)-2-(4-chlorophenyl)ethanol hydrochloride 

Relevant articles and documents

One-Pot Enantioselective Synthesis of d-Phenylglycines from Racemic Mandelic Acids, Styrenes, or Biobased l-Phenylalanine via Cascade Biocatalysis

Enantiopure d-phenylglycine and its derivatives are an important group of chiral amino acids with broad applications in thepharmaceutical industry. However, the existing synthetic methods for d-phenylglycine mainly rely on toxic cyanide chemistry and multistep processes. To provide green and safe alternatives, we envisaged cascade biocatalysis for the one-pot synthesis of d-phenylglycine from racemic mandelic acid, styrene, and biobased l-phenylalanine, respectively. Recombinant Escherichia coli (LZ110) was engineered to coexpress four enzymes to catalyze a 3-step reaction in one pot, transforming mandelic acid (210 mM) to give enantiopure d-phenylglycine in 29.5 g L?1 (195 mM) with 93% conversion. Using the same whole-cell catalyst, twelve other d-phenylglycine derivatives were also produced from the corresponding mandelic acid derivatives in high conversion (58–94%) and very high ee (93–99%). E. coli (LZ116) expressing seven enzymes was constructed for the transformation of styrene to enantiopure d-phenylglycine in 80% conversion via a one-pot 6-step cascade biotransformation. Twelve substituted d-phenylglycines were also produced from the corresponding styrene derivatives in high conversion (45–90%) and very high ee (92–99%) via the same cascade reactions. A nine-enzymeexpressing E. coli (LZ143) was engineered to transform biobased l-phenylalanine to enantiopure d-phenylglycine in 83% conversion via a one-pot 8-step transformation. Preparative biotransformations were also demonstrated. The high-yielding synthetic methods use cheap and green reagents (ammonia, glucose, and/or oxygen), and E. coli whole-cell catalysts, thus providing green and useful alternative methods for manufacturing d-phenylglycine. (Figure presented.).

High yield synthesis of d-phenylglycine and its derivatives by nitrilase mediated dynamic kinetic resolution in aqueous-1-octanol biphasic system

A strategy of nitrilase mediated dynamic kinetic resolution toward the synthesis of d-phenylglycine was developed, using aqueous-1-octanol biphasic system. Due to the efficient suppression of the decomposition of phenylglycinonitrile, a maximum yield of 81% is obtained. This result indicates that the nitrilase mediated dynamic kinetic resolution is a promising method toward the synthesis of d-phenylglycine and its derivatives.

Enzymatic synthesis of chiral phenylalanine derivatives by a dynamic kinetic resolution of corresponding amide and nitrile substrates with a multi-enzyme system

Mutant α-amino-ε-caprolactam (ACL) racemase (L19V/L78T) from Achromobacter obae with improved substrate specificity toward phenylalaninamide was obtained by directed evolution. The mutant ACL racemase and thermostable mutant D-amino acid amidase (DaaA) from Ochrobactrum anthropi SV3 co-expressed in Escherichia coli (pACLmut/pDBFB40) were utilized for synthesis of (R)-phenylalanine and non-natural (R)-phenylalanine derivatives (4-OH, 4-F, 3-F, and 2-F-Phe) by dynamic kinetic resolution (DKR). Recombinant E. coli with DaaA and mutant ACL racemase genes catalyzed the synthesis of (R)-phenylalanine with 84% yield and 99% ee from (RS)-phenylalaninamide (400 mM) in 22 h. (R)-Tyrosine and 4-fluoro-(R)-phenylalanine were also efficiently synthesized from the corresponding amide compounds. We also co-expresed two genes encoding mutant ACL racemase and L-amino acid amidase from Brevundimonas diminuta in E. coli and performed the efficient production of various (S)-phenylalanine derivatives. Moreover, 2-aminophenylpropionitrile was converted to (R)-phenylalanine by DKR using a combination of the non-stereoselective nitrile hydratase from recombinamt E. coli and mutant ACL racemase and DaaA from E. coli encoding mutant ACL racemase and DaaA genes. Copyright

Synthesis of Optically Active Arylglycines by Photolysis of Optically Active (β-Hydroxyamino) Carbene-Chromium(0) Complexes

Photolysis of chromium complexes having the optically active amino alcohol (1R,2S)-(-)- or (1S,2R)-(+)-2-amino-1,2-diphenylethanol as the amino group produced aryl-substituted oxazinones in good yield with reasonable diastereoselectivity.Facile separation of diastereoisomers followed by mild reductive cleavage produced several arylglycines, having either electron-donating or withdrawing groups on the aromatic ring, in good overall yield and with excellent enantiomeric excess.

CARBOHYDRATES AS CHIRAL TEMPLATES: ASYMMETRIC UGI-SYNTHESIS OF ALPHA-AMINO ACIDS USING GALACTOSYLAMINES AS THE CHIRAL MATRICES

In the presence of Lewis acid catalysts O-acetyl- (1) and O-pivaloyl- (2) protected β-D-galactopyranosylamines react with aldehydes, isocyanides and carboxylic acids in Ugi-four-component-condensations to give the corresponding N-galactosyl-amino acid amide derivatives 3, 5 in almost quantitative yields.Zinc chloride is the most effective Lewis acid catalyst.At 0 deg C or even at room temperature the (2R,β-D)-diastereomers of the amino acid derivatives 3, 5 are formed with high diastereoselectivity.If the sterically more demanding O-pivaloyl galactosylamine 2 is used at -78 deg C to -25 deg C the stereoselectivity often exeeds 20:1 favouring the (2R,β-D) diastereomers 5.After one recrystallisation pure (R)-amino acid derivatives 5 are obtained in yields of 80-95percent.In addition to the high yields and stereoselectivity the amino acid synthesis described here has the further advantage that it neither requires organometallic reagents and intermediates nor exclusion of oxygen and moisture.Two step acid hydrolysis of the N-galactosylamino acid amide derivatives 5 delivers the enantiomerically pure (R)-amino-acids 8 in high yields.

ASYMMETRIC INDUCTIVE SYNTHESIS OF α-AMINOARYLACETIC ACIDS IN CHIRAL MICELLAR SYSTEM

In the micellar solution of chiral surfactant N-hexadecyl-N-methylephedrine bromide, seven α-aminoarylacetic acids were synthesized from corresponding aldehydes, the e.e.percent being about 28percent.