1194-86-1

Basic information

• Product Name: D-(-)-3-thienylglycine
• Synonyms: D-2-(3-Thienyl)-glycine;(R)-α-Amino-3-thiopheneacetic acid;[R,(-)]-α-Amino-3-thiopheneacetic acid;2-amino-2-thiophen-3-ylacetic acid;2-azanyl-2-thiophen-3-yl-ethanoic acid;(R)-3-Thienglycine;(alphaR)-alpha-Amino-3-thiopheneacetic acid;thiophen-2-yl 2-aMinoacetate
• CAS NO: 1194-86-1
• Molecular Formula: C₆H₇NO₂S
• Molecular Weight: 157.19028
• EINECS: 214-788-0
• Product Categories: Amino Acids;I - Z;Modified Amino Acids
• Mol File: 1194-86-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 218℃
• Boiling Point: 383.8oC at 760 mmHg
• Flash Point: 185.9oC
• Appearance: /
• Density: 1.418
• Vapor Pressure: 1.41E-06mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: 2-8°C
• PKA: 1.89±0.10(Predicted)
• CAS DataBase Reference: D-(-)-3-thienylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: D-(-)-3-thienylglycine(1194-86-1)
• EPA Substance Registry System: D-(-)-3-thienylglycine(1194-86-1)

Safety Data

• Hazardous Substances Data: 1194-86-1(Hazardous Substances Data)

Usage

Description

D-(-)-3-thienylglycine, a white powder, is an organic compound with the chemical formula C5H7NO2S. It is a chiral molecule, with the D-(-) configuration indicating its specific spatial arrangement. D-(-)-3-thienylglycine is known for its unique properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
D-(-)-3-thienylglycine is used as a key intermediate in the synthesis of amide-containing heterobicyclic metalloprotease inhibitors. These inhibitors are essential in the development of drugs targeting various diseases, including cancer and neurodegenerative disorders. D-(-)-3-thienylglycine's unique structure allows for the creation of potent and selective inhibitors, making it a valuable asset in medicinal chemistry.
Used in Chemical Synthesis:
D-(-)-3-thienylglycine is also utilized in the synthesis of various organic compounds and materials. Its reactivity and functional groups make it a versatile building block for the creation of new molecules with potential applications in different industries, such as agriculture, materials science, and environmental science.

InChI:InChI=1/C6H7NO2S/c8-6(9)3-7-5-1-2-10-4-5/h1-2,4,7H,3H2,(H,8,9)

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 97036-26-5 (2R)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril 
• 97036-30-1 (2R)-(-)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(3-thienyl)essigsaeure 
• 97036-28-7 (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(3-thienyl)acetonitril 
• 97036-24-3 (4S,5S)-(+)-2,2-Dimethyl-4-phenyl-5-<(3-thienylmethylen)amino>-1,3-dioxan 
• 97101-16-1 (2S)-(-)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(3-thienyl)essigsaeure 

Relevant articles and documents

Nonproteinogenic Amino Acids, III. - Syntheses of the Enantiomerically Pure 2-(2-Thienyl)- and 2-(3-Thienyl)glycines. - Molecular Structure of the Intermediate Schiff's Bases

The syntheses of enantiomerically pure D-(-)- and L-(+)-2-(2-thienyl)- and 2-(3-thienyl)glycines (6a-d) are described.Preparing the amino nitriles 4 directly from 2-thiophenecarbaldehyde (1a) or 3-thiophenecarbaldehyde (1b), respectively, and (4S,5S)-(+)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane (2), and hydrocyanic acid (one-step procedure), the aminonitriles 4a and 4b, respectively, are formed in excess.By crystallization they are obtained diastereomerically pure leading to enantiomerically pure D-amino acids 6a and 6b.If, however, the intermediate Schiff's bases 3 are isolated as crystals and then converted with hydrocyanic acid into the respective aminonitriles 4 (two-step procedure), the diastereomeric aminonitriles 4c and 4d, respectively, crystallize resulting in enantiomerically pure L-amino acids 6a and 6d.X-ray structure analyses of the Schiff's bases 3c and 3e revealed the previously postulated E-configuration of the C=N bond and its chiral shielding by the phenyl substituent at C4.