87636-30-4

Basic information

• Product Name: 2-Thiazolemethanol, -alpha--(1-methylethyl)-
• Synonyms: 2-Thiazolemethanol, -alpha--(1-methylethyl)-
• CAS NO: 87636-30-4
• Molecular Formula: C₇H₁₁NOS
• Molecular Weight: 0
• Mol File: 87636-30-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Thiazolemethanol, -alpha--(1-methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiazolemethanol, -alpha--(1-methylethyl)-(87636-30-4)
• EPA Substance Registry System: 2-Thiazolemethanol, -alpha--(1-methylethyl)-(87636-30-4)

Safety Data

• Hazardous Substances Data: 87636-30-4(Hazardous Substances Data)

Upstream product

• 3034-53-5 2-bromo-1,3-thiazole 
• 78-84-2 isobutyraldehyde 
• 288-47-1 1,3-thiazole 
• 87636-28-0 2-(2-Methyl-1-trimethylsilanyloxy-propyl)-thiazole 

Relevant articles and documents

Highly diastereoselective synthesis of 2-(1-N-Boc-aminoalkyl)thiazole-5-carboxylates by reduction of tert-butylsulfinyl ketimines

Positional isomers of naturally occurring peptide subunits were synthesized via highly diastereoselective reduction of tert-butylsulfinyl ketimines as a key reaction. While NaBH4 reduction of ketimines derived from 2-thiazolyl ketones afforded the (RS,R)-isomer with moderate diastereoselectivity, L-Selectride reduction afforded the (RS,S)-isomer as the sole product. In contrast, ketimines derived from tert-butyl 2-thiazolyl ketone afforded the (RS,R)-isomer with low diastereoselectivity by both NaBH4 and L-Selectride reduction. Stereochemistry of the reaction was discussed based on calculation of the conformational energies for ketimines.

NEW PERSPECTIVES IN THIAZOLE CHEMISTRY

Carbon-carbon bond forming reactions at C-2 of the thiazole ring have been carried using two strategies, one involving the addition of organometallic reagents (lithium carbanions of esters, Grignard salts, silyl enol ethers, silyl ketene acetals, silylazoles) to N-acylthiazolium salts; the other involving the addition of carbon electrophiles (ketenes, acyl chlorides, anhydrides, aldehydes) to N-acylthiazolium ylides generated in situ.The reactions have been applied to 1,3-thiazole and 2-trimethylsilyl-1,3-thiazole, the latter being more reactive than the former toward electrophiles.This methodology constitutes a new entry to a variety of functionalized thiazoles and thiazolines which are potential building blocks for the synthesis of natural compounds and analogues of biologically active molecules (penems, arylpropionic acids).Some ring transformations of thiazoles induced by carbon-sulfur bond cleavage are also described.The fundamental role played by the sulfur atom of the thiazole ring in the observed reactions is pointed out and briefly discussed.