4052-59-9

Basic information

• Product Name: (-)-2-thienylglycine
• Synonyms: (-)-2-thienylglycine;(-)-α-Amino-2-thiopheneacetic acid;(-)-alpha-Amino-2-thiopheneacetic acid;2-Thiopheneacetic acid, alpha-amino-, (-)-;Einecs 223-758-6
• CAS NO: 4052-59-9
• Molecular Formula: C₆H₇NO₂S
• Molecular Weight: 157.19028
• EINECS: 223-758-6
• Mol File: 4052-59-9.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 311.8 °C at 760 mmHg
• Flash Point: 185.94 °C
• Appearance: /
• Density: 1.418 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: (-)-2-thienylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2-thienylglycine(4052-59-9)
• EPA Substance Registry System: (-)-2-thienylglycine(4052-59-9)

Safety Data

• Hazardous Substances Data: 4052-59-9(Hazardous Substances Data)

Usage

Purification Methods

Recrystallise 2-(2-thienyl)glycine by dissolving it in H2O (1g in 3 mL), adjusting the pH to 5.5 with aqueous NH3, diluting with MeOH (20 mL), stirring, adjusting the pH to 5.5 and cooling to 0o. Also recrystallise it from small volumes of H2O. [R-isomer: Nishimura et al. Nippon Kagaku Zasshi 82 1688 1961, S-isomer: Johnson & Panetta Chem Abstr 63 14869 1965, Johnson & Hardcastle Chem Abstr 66 10930 1967, RS-isomer: LiBassi et al. Gazz Chim Ital 107 253 1977.] The (±) N-acetyl derivative has m 191o (from H2O) [Schouteenten et al. Bull Soc Chim Fr II 248, II 252 1978].

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

Upstream product

• 4075-59-6 2-thiopheneglyoxylic acid 
• 126402-94-6 2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-[((R)-tert-butylcarbamoyl-thiophen-2-yl-methyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester 
• 1355742-75-4 (S)-2-benzyloxycarbonylamino-2-(thiophen-2-yl)-acetonitrile 
• 65700-48-3 N-carbamyl-D-(-)2-thienylglycine 
• 110728-00-2 C₁₄H₁₃NO₃S 
• 26878-13-7 methyl 2-thienylglyoxylate 
• 1027925-78-5 2-tert-butoxycarbonylamino-2-thiophen-2-yl-malonic acid diethyl ester 
• 408346-66-7 diethyl 2-amino-2-(2-thienyl)-malonate 
• 101004-88-0 (Benzhydrylidene-amino)-thiophen-2-yl-acetic acid ethyl ester 
• 98-03-3 thiophene-2-carbaldehyde 
• 97036-25-4 (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(2-thienyl)acetonitril 
• 97036-29-8 (2S)-(-)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(2-thienyl)essigsaeure 
• 97036-27-6 (2R)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(2-thienyl)acetonitril 
• 97036-23-2 (4S,5S)-(+)-2,2-Dimethyl-4-phenyl-5-<(2-thienylmethylen)amino>-1,3-dioxan 

Downstream Products

• 112395-52-5 N-<(o-nitrophenyl)sulfenyl>-D,L-2-thienylglycine 
• 171661-56-6 2-amino-2-(thiophen-2-yl)ethan-1-ol 
• 891789-96-1 C₂₀H₁₅ClN₄O₂S 
• 1035868-78-0 C₁₅H₁₁NO₂S₂ 
• 416879-89-5 (Ph3P)PdCl(η(2)-N,O-NH2CH(2-thienyl)COO) 
• 4052-59-9 (R)-amino(thiophen-2-yl)acetic acid 
• 4052-59-9 (2S)-amino(2-thienyl)acetic acid 
• 1469538-27-9 2-phenyl-5-(thiophen-2-yl)pyrazolo[1,5-c]quinazoline 
• 102241-69-0 3,3'-(thiophen-2-ylmethylene)bis(indole) 
• 13533-27-2 4-methoxy-N-(thiophen-2-ylmethylene)aniline 
• 1391629-03-0 (3S,6R)-4-(5-(4-fluorophenyl)isoxazole-3-carbonyl)-3-isobutyl-6-(thiophen-2-yl)piperazin-2-one 
• 59966-06-2 L-α-[[[(4-methoxyphenyl)-methoxy]carbonyl]amino]-2-thiopheneacetic acid 
• 14675-98-0 N-Boc-amino(2-thienyl)acetic acid 
• 162927-66-4 4-(2-thienyl)-2-(trifluoromethyl)-3-oxazolin-5-one 

Relevant articles and documents

Reductive amination of ketonic compounds catalyzed by Cp*Ir(III) complexes bearing a picolinamidato ligand

Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.

Primary amines by transfer hydrogenative reductive amination of ketones by using cyclometalated IrIII catalysts

Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer-hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer-hydrogenative DRA has been realised for β-keto ethers, leading to the corresponding β-amino ethers. In addition, non-natural α-amino acids could also be obtained in excellent yields with this method. Reduce the work! A broad range of ketones have been successfully aminated to afford primary amines under transfer-hydrogenation conditions by using ammonium formate as the amine source and 0.1 mol % of a cyclometalated IrIII catalyst (see scheme). Copyright

Enantioselective hydrocyanation of N-protected aldimines

Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly]2[(S)-binap]/C6H5OLi system or a bimetallic complex [Li{Ru[(S)-phgly]2[(S)-binap]}]Cl affords the amino nitriles in 92 - 99% ee. The reaction is carried out in tert-C 4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500 - 5000 at -20 to 0°C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.