68-39-3

Basic information

• Product Name: DL-CYCLOSERINE
• Synonyms: (+-)-4-amino-3-isossazolidone;DL-4-AMINO-3-ISOXAZOLIDINONE;DL-CYCLO-SER;DL-CYCLOSERINE;DL-4-aminoisoxazolidin-3-one;3-Oxoisooxazolidin-4-amine;3-Isoxazolidinone,4-amino-(9CI);4-Amino-3-isoxazolidinone, 4-Amino-3-isoxazolidone
• CAS NO: 68-39-3
• Molecular Formula: C₃H₆N₂O₂
• Molecular Weight: 102.09
• EINECS: 200-687-9
• Product Categories: VARIOUSAMINE;Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 68-39-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 147°C
• Appearance: /crystalline
• Density: 1.278 g/cm³
• Refractive Index: 1.474
• Storage Temp.: −20°C
• Solubility: Water (Sparingly)
• PKA: 14.36±0.40(Predicted)
• Stability: Unstable in DMSO solution
• CAS DataBase Reference: DL-CYCLOSERINE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-CYCLOSERINE(68-39-3)
• EPA Substance Registry System: DL-CYCLOSERINE(68-39-3)

Safety Data

• WGK Germany: 3
• RTECS: NY2974900
• Hazardous Substances Data: 68-39-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

rac Cycloserine is a antibacterial (tuberculostatic).

Definition

ChEBI: A member of the class of oxazolidines that is isoxazoldin-3-one which is substituted at position 4 by an amino group.

InChI:InChI=1/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)

Upstream product

• 27010-92-0 DL-β-aminoxyalanine methyl ester dihydrochloride 
• 6344-12-3 4-(5-chloro-2-hydroxy-benzylideneamino)-isoxazolidin-3-one 
• 103758-42-5 N-benzyloxycarbonyl-O-(toluene-4-sulfonyl)-DL-serine benzyloxyamide 
• 120854-55-9 3-chloro-DL-alanine hydroxyamide 

Downstream Products

• 1448530-39-9 3-(3-oxoisoxazolidin-4-yl)-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 
• 1448530-52-6 (E)-3-(3-oxoisoxazolidin-4-yl)-2-styryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 
• 359004-20-9 tert-butyl N-(3-oxoisoxazolidin-4-yl)carbamate 
• 1187-83-3 3-Aminooxy-alanin 
• 129661-56-9 methyl-1 (isoxazolidinone-3 imino-4 methyl)-2 nitro-5 imidazole 
• 578-95-0 10H-acridin-9-one 
• 35558-81-7 4-(4-bromo-benzylideneamino)-isoxazolidin-3-one 
• 14996-34-0 α-N-acetyl-D-cycloserine 

Relevant articles and documents

Preparation of D-cycloserine and 13C-labeled D-cycloserine

D-Cycloserine (DCS), a second stage drug for the treatment of tuberculosis, is synthesized in 19.8% overall yield from DL-serine methyl ester. This synthetic route gives both enantiomers of cycloserine via a corrected and improved one pot resolution procedure using D- and L-tartaric acids. The route is used to synthesize a 13C-labeled derivative for use in biological studies.