25705-52-6

Basic information

• Product Name: (R)-phenylglycine hydrochloride
• Synonyms: (R)-phenylglycine hydrochloride;(R)-2-AMino-2-phenylacetic acid hydrochloride;(R)-Phenylglycine HCl
• CAS NO: 25705-52-6
• Molecular Formula: C₈H₉NO₂*ClH
• Molecular Weight: 187.6235
• EINECS: 247-195-0
• Mol File: 25705-52-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 288.7°Cat760mmHg
• Flash Point: 128.4°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 8.86E-06mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (R)-phenylglycine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-phenylglycine hydrochloride(25705-52-6)
• EPA Substance Registry System: (R)-phenylglycine hydrochloride(25705-52-6)

Safety Data

• Hazardous Substances Data: 25705-52-6(Hazardous Substances Data)

Usage

General Description

(R)-phenylglycine hydrochloride is a chemical compound that is the hydrochloride salt form of (R)-phenylglycine, an organic compound with a phenyl group attached to a glycine molecule. It is commonly used as a chiral auxiliary in the asymmetric synthesis of various pharmaceuticals and agrochemicals. As a chiral compound, (R)-phenylglycine hydrochloride is important in the preparation of enantiomerically pure compounds, which are essential for the development of many modern drugs. This chemical is also used in the production of chiral drugs, as well as in research and development in the pharmaceutical and agrochemical industries.

InChI:InChI=1/C8H9NO2.ClH/c10-8(11)6-9-7-4-2-1-3-5-7;/h1-5,9H,6H2,(H,10,11);1H

Upstream product

• 29129-67-7 (S)-2-azido-2-phenylacetic acid 
• 144744-23-0 (3R,5S,6R)-2,3,5,6-Tetrahydro-3,5,6-triphenyl-1,4-oxazin-2-one 
• 219924-26-2 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-({(R)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylcarbamoyl]-phenyl-methyl}-formyl-amino)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 226388-27-8 (R)-α-(N,N-dibenzylamino)-α-phenylacetic acid 
• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 393588-13-1 (2R,αR)-2-phenyl-2-(N-benzyl-N-α-methylbenzylamino)ethanoic acid 
• 393588-04-0 (2R,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)-3-phenylpropanol 
• 33125-05-2 Boc-D-Phg-OH 
• 14371-10-9 (E)-3-phenylpropenal 
• 137284-11-8 (2R)-2-N-(tert-butoxycarbonyl)amino-2-phenylethanal 
• 65253-04-5 (-)-8-phenylmenthol 
• 172925-28-9 trans-(S)-1-phenyl-1,5-hexadien-3-ol 
• 127358-17-2 (3R,5R,6S)-2,3,5,6-Tetrahydro-3,5,6-triphenyl-1,4-oxazin-2-one 
• 116911-14-9 (2S,3S)-3-azido-3-phenyl-propane-1,2-diol 

Downstream Products

• 79795-33-8 C₁₅H₁₅N₂O₃P 
• 79795-33-8 C₁₅H₁₅N₂O₃P 
• 6489-76-5 D-(-)-N-carbamoyl phenyl glycine 
• 33125-05-2 Boc-D-Phg-OH 
• 15686-71-2 cefalexin 
• 1007880-00-3 (R)-2-(3-cyclopentylureido)-2-phenylacetic acid 
• 54193-09-8 HPGly 
• 1007879-96-0 (R)-tert-butyl 2-(3-cyclopentylureido)-2-phenylacetate 
• 26553-34-4 N-trichloroethoxycarbonyl-D-phenylglycine 

Relevant articles and documents

Axially chiral dicarboxylic acid-catalyzed asymmetric imino aza-enamine reaction/oxidation as a Strecker reaction surrogate

Axially chiral dicarboxylic acid-catalyzed highly enantioselective imino aza-enamine reaction was elaborated into a surrogate of the asymmetric Strecker reaction building on the fact that the N,N-dialkylhydrazone moiety can be easily converted to the cyanide moiety by treatment with peracid.

Asymmetric allylboration of α,β-enals as a surrogate for the enantioselective synthesis of allylic amines and α-amino acids

(Chemical Equation Presented) Optically pure allylic amines have been synthesized from α,β-unsaturated aldehydes via allylboration with (-)-B-allyldiisopinocampheylborane, followed by Overman rearrangement. By incorporating crotyl and alkoxyallylboration, functionalization at δ-position was readily accomplished. By applying this methodology, the synthesis of several chiral α-amino acids has been achieved.

Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

An efficient protocol for the transformation of homochiral α-hydroxy-β-amino esters to their α-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino 1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-α-methylbenzyl protected α-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the α-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides α-amino acids in 94-98% e.e.