288-47-1

Basic information

• Product Name: Thiazole
• Synonyms: 1,3-THIAZOLE;FEMA 3615;FEMA NUMBER 3615;THIAZOLE;Thiazole,98%;THIAZOLE 99+%;THIAN-4-ONEOXIME
• CAS NO: 288-47-1
• Molecular Formula: C₃H₃NS
• Molecular Weight: 85.12762
• EINECS: 206-021-3
• Product Categories: C3 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Thiazoles, Isothiazoles &Benzothiazoles;Thiazole;Building Blocks;Halogenated;Organohalides;Thiazoles, Isothiazoles & Benzothiazoles;Alphabetical Listings;Flavors and Fragrances;Q-Z;Building Blocks;Heterocyclic Building Blocks;Thiazoles
• Mol File: 288-47-1.mol

Chemical Properties

• Melting Point: -33°C
• Boiling Point: 117-118 °C(lit.)
• Flash Point: 72 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.2 g/mL at 25 °C(lit.)
• Vapor Pressure: 21.6mmHg at 25°C
• Refractive Index: n20/D 1.538(lit.)
• Storage Temp.: Flammables area
• PKA: 2.44(at 20℃)
• Water Solubility: slightly soluble
• Sensitive: Air & Light Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,9307
• BRN: 103852
• CAS DataBase Reference: Thiazole(CAS DataBase Reference)
• NIST Chemistry Reference: Thiazole(288-47-1)
• EPA Substance Registry System: Thiazole(288-47-1)

Safety Data

• Hazard Codes: Xn,F
• Statements: 10-22-37/38-41
• Safety Statements: 16-26-39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: XJ1290000
• F: 8-10-23
• TSCA: T
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 288-47-1(Hazardous Substances Data)

Usage

Uses

1. Flavoring Agent and Dye Preparation:
Thiazole is used as a flavoring agent and in the preparation of dyes and rubber accelerators. It provides a unique flavor and aroma to various products, enhancing their sensory qualities.
2. Vitamin Thiamine (B1) Component:
Thiazole serves as a component of the vitamin thiamine (B1), which is essential for various metabolic processes in the human body.
3. Protected Formyl Group in Natural Product Synthesis:
Thiazole acts as a protected formyl group used in natural product synthesis, allowing for the development of complex organic compounds with specific functional groups.
4. Organometallic Complex Preparation:
Thiazole reacts with alkyl lithium and Grignard's reagent to prepare organometallic complexes, which are important intermediates in organic synthesis.
5. Electrophilic and Nucleophilic Aromatic Substitution:
Thiazole is involved in electrophilic aromatic substitution and nucleophilic aromatic substitution at C-5 and C-2 positions, respectively, allowing for the functionalization of the thiazole ring in various chemical reactions.
6. Alkylation and Catalyst in Organic Reactions:
Thiazole undergoes alkylation to form thiazolium cation, which is used as a catalyst in the Stetter reaction and the Benzoin condensation, important organic reactions for the synthesis of complex molecules.
7. Preparation of Alagebrium:
Thiazole is also involved in the preparation of alagebrium, a compound with potential therapeutic applications.
8. Recognition Motifs for Metal Ions:
Thiazoles are used to create novel recognition motifs for interaction with divalent and trivalent metal ions in siderophores or antibiotics, which can have applications in the development of new drugs and therapies.
9. Organic Synthesis of Fungicides, Dyes, and Rubber Accelerators:
Thiazole is used in the organic synthesis of fungicides, dyes, and rubber accelerators, contributing to the development of various industrial products.

Air & Water Reactions

Slightly water soluble.

Reactivity Profile

Thioisocyanates, such as Thiazole, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat.

InChI:InChI=1/C3H3NS/c1-2-5-3-4-1/h1-3H

Upstream product

• 40018-26-6 1,4-dithiane-2,5-diol 
• 50-00-0 formaldehyd 
• 3034-52-4 2-chlorothiazole 
• 53089-10-4 2,2-diethoxy-1-formylaminoethane 
• 107-20-0 2-chloroethanal 
• 77287-34-4 formamide 
• 3034-53-5 2-bromo-1,3-thiazole 
• 64-17-5 ethanol 
• 603-35-0 triphenylphosphine 
• 5053-24-7 2-methylthio-1,3-thiazole 
• 105-53-3 diethyl malonate 
• 4175-78-4 2,5-dibromo-1,3-thiazole 
• 34259-99-9 4-bromo-1,3-thiazole 
• 96-50-4 2-thiazolylamine 

Downstream Products

• 24295-03-2 2-Acetylthiazole 
• 5304-34-7 2-(3-thiazolium)-1-phenylethanone bromide 
• 3034-53-5 2-bromo-1,3-thiazole 
• 14190-59-1 1,3-thiazole-2-carboxylic acid 
• 89323-88-6 2-(2-Hydroxyethyl)thiazole 
• 14542-12-2 (1,3-thiazol-2-yl)methanol 
• 5304-35-8 3-[2-(4-nitro-phenyl)-2-oxo-ethyl]-thiazolium; bromide 
• 89464-29-9 2-(1-hydroxypropyl)thiazole 
• 87636-30-4 2-methyl-1-(thiazol-2-yl)propan-1-ol 
• 68913-64-4 2-phenyl-5-trityl-thiazole 
• 1826-13-7 5-phenylthiazole 
• 1826-11-5 2-phenylthiazole 
• 1826-12-6 4-phenyl-thiazole 
• 79265-30-8 2-(trimethylsilyl)thiazole 

Relevant articles and documents

An Efficient Synthesis of 1,3-Thiazole

The cyclocondensation of methyl dithiocarbamate with chloroacetaldehyde in aqueous ethanol affords 2-methylthio-1,3-thiazole (82-88percent) which is demethylsulfenylated to 1,3-thiazole (78-81percent) by reaction with lithium in liquid ammonia followed by hydrolysis with aqueous ammonia chloride.

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis

The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2→ ArB(OH)2) and protodeboronation (ArB(OR)2→ ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F,1H, and11B), pH-rate dependence, isotope entrainment,2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous-organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKaof the boronic acid/ester.

Photocatalytic Generation of 2-Azolyl Radicals: Intermediates for the Azolylation of Arenes and Heteroarenes via C-H Functionalization

The 2-azolyl radical, generated from 2-bromoazoles via photocatalysis, is a powerful intermediate for the intermolecular arylation of unmodified (hetero)arenes. The reaction is characterized by mild conditions, operational simplicity, tolerance toward functional and sterically demanding groups, broad scope, and anti-Minisci selectivity. A working mechanism is provided, and a low-solubility amine is essential for successful coupling. The utility of the reaction is demonstrated via late-stage functionalization of methyl estrone and application toward other bromoarenes.

Reduction of Aryl Halides into Arenes with 2-Propanol Promoted by a Substoichiometric Amount of a tert-Butoxy Radical Source

Aryl halides are reduced into the corresponding arenes in high yields, using 2-propanol, cesium carbonate, and di-tert-butyl peroxide (or di-tert-butyl hyponitrite) as a reductant/solvent, a base, and a radical initiator, respectively. This simple system reduces a wide variety of aryl bromides, chlorides, and iodides through single-electron-transfer mechanism with high functional-group tolerance.

Reductive Alkylation of 2-Bromoazoles via Photoinduced Electron Transfer: A Versatile Strategy to Csp2-Csp3 Coupled Products

Access to Csp2-Csp3-coupled products is a challenging goal at the forefront of catalysis. The photocatalytic reductive coupling of aryl bromides with unactivated alkenes is introduced as a convenient method that circumvents any need for synthesis of sp3-hybridized coupling partners. The reaction takes place via photoinduced electron transfer from a tertiary amine to an aryl bromide that fragments to provide an aryl radical and subsequently reacts with an alkene to form a C-C bond. Conveniently, the amine also serves as the final reductant. The method is operationally simple, functional group tolerant, and takes place with selectivities that will allow it to be used in the context of complex molecule synthesis.

Rhodium-catalyzed 2-methylthiolation reaction of thiazoles/oxazoles using 2-(methylthio)thiazole

RhH(PPh3)4 and 1,3-bis(dicyclohexyl)phosphinopropane (dcypp) catalyze the 2-methylthiolation of oxazoles and thiazoles using 2-(methylthio)thiazole as a thiolating reagent. The methylthio transfer reaction is under equilibrium, and various 2-methylthiolated thiazoles and oxazoles were obtained in moderate to good yields by removing thiazole under refluxing o-dichlorobenzene.

Photooxygenation of N-(2-thiazolyl)sulfanilamide, 2-(4-thiazolyl) benzimidazole, and thiacetazone

In the present work, photolysis of N-(2-thiozolyl)sulfanilamide, 2-(4-thiazolyl)benzimidazole and thiacetazone in presence of benzophenone as a sensitizer under 125 W UV Lamp has been reported. Structures of the products have been established by spectral and elemental analysis.

Method for Producing Intermediates for the Production of Novel Macrocycles that are Inhibitors of the Proteasomic Degradation of p27, such as Argyrin and Derivatives Thereof, and Uses of Said Macrocycles

The present invention relates to the use of particular macrocycles that are inhibitors of the proteasomic degradation of p27, in particular argyrin and derivatives thereof, for a treatment in a variety of conditions, such as the induction of immunotolerance, autoimmune diseases, bacterial infections, and proliferative diseases, such as cancers.

Lipopeptide Compounds and Their Use

The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain lipopeptide compounds comprising a cyclic peptide bearing a lipid side chain (for convenience, collectively referred to herein as “LP compounds”), which, inter alia, are antimicrobial, particularly antibacterial. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to provide an antimicrobial function, particularly an antibacterial function, and in the treatment of diseases and conditions that are mediated by microbes, particularly bacteria, that are ameliorated by the antimicrobial function, particularly an antibacterial function, including bacterial diseases, optionally in combination with another agent, for example, another antibacterial agent.