88347-90-4

Basic information

• Product Name: Cysteine, S-phenyl-, hydrochloride
• CAS NO: 88347-90-4
• Molecular Formula: C9H11NO2S.ClH
• Molecular Weight: 233.719
• Mol File: 88347-90-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Cysteine, S-phenyl-, hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Cysteine, S-phenyl-, hydrochloride(88347-90-4)
• EPA Substance Registry System: Cysteine, S-phenyl-, hydrochloride(88347-90-4)

Safety Data

• Hazardous Substances Data: 88347-90-4(Hazardous Substances Data)

Upstream product

• 20640-68-0 2-acetylamino-3(phenylthio)propionic acid 
• 931-59-9 benzenesulfenyl chloride 
• 108-98-5 thiophenol 
• 42801-75-2 α-Chlor-β-(phenylthio)propansaeure-methylester 
• 88347-74-4 α-Azido-β-(phenylthio)propansaeure-methylester 
• 1352924-03-8 (R)-3-(phenylthio)-2-((4'S,5'R)-4'-hydroxy-5'-methoxy-4',5'-dimethyl-2'-oxooxazolidin-3'-yl)propanoic acid methyl ester 

Downstream Products

• 34317-61-8 S-phenyl-L-cysteine 

Relevant articles and documents

A biomimetic approach to lanthionines

The asymmetric sulfa-Michael additions of appropriately protected l- and d-cysteine derivatives to new chiral dehydroamino acid derivatives have been developed as key steps in the synthesis of biologically important cysteine derivatives, such as lanthionine (Lan) and β-methyllanthionine (MeLan), which are unusual bis-α-amino acids found in the emerging lantibiotics such as nisin.

Amino Acids, 12. - Syntheses of DL-Cysteines from Acrylic Acid Derivatives

The addition of sulfenyl chlorides 1 to 2-alkenoic acid esters 2 gives mixtures of 2(3)-chloro-3(2)-thioalkenoic acid esters 3/4, whereas the addition of thiols 7 to methyl 2-chloro-2-propenoate (6) results in the formation of methyl 2-chloro-3-thiopropanoates 3 only.The dependence of the isomerization of 3 to 4 on the reaction conditions was investigated; at higher temperatures the formation of 4 is especially favored.At temperatures below 55 deg C the 2-azido compounds 8 are obtained without isomerization from 3 by reaction with sodium azide in the presence of a PT catalyst.Cysteine derivatives 9 or 10, resp., are obtained by hydrogenation of 8 with H2S/pyridine/H2O or with H2/Re2S; the overall yields of 9 or 10, resp., starting from 6 are as high as 70percent.DL-Cysteine is obtained in good overall yields as hydrochloride hydrate 16 by HCl-catalyzed hydrolysis of the 2-thiazolines 15a*HCl and 15e, which are prepared by HCl-catalyzed addition of thioacetamide (11a) to α-chloroacrylic acid (12) or the amide 13 and consecutive ring closure.