288-47-1 Usage
Description
Thiazole is a heterocyclic compound containing a five-membered ring with sulfur and nitrogen heteroatoms, C3SNH3. It is a colorless volatile liquid with a foul odor and has a green, sweet, nutty, tomato note. Thiazole resembles pyridine in its reactions and is found in various natural sources such as roasted chicken, chicken fat, boiled and cooked beef, grilled and roasted beef, pork liver, beer, cognac, grape brandy, rum, coffee, roasted barley, roasted filbert, roasted peanut, soybean, popcorn, oat products, rice bran, buckwheat, malt, wort, dried bonito, crab, crayfish, and Chinese quince.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 288-47-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,8 and 8 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 288-47:
(5*2)+(4*8)+(3*8)+(2*4)+(1*7)=81
81 % 10 = 1
So 288-47-1 is a valid CAS Registry Number.
InChI:InChI=1/C3H3NS/c1-2-5-3-4-1/h1-3H
288-47-1Relevant articles and documents
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Iversen
, p. 484 (1972)
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PYRAZINE DERIVATIVE AND APPLICATION THEREOF IN INHIBITING SHP2
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, (2022/01/23)
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Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis
Hayes, Hannah L. D.,Wei, Ran,Assante, Michele,Geogheghan, Katherine J.,Jin, Na,Tomasi, Simone,Noonan, Gary,Leach, Andrew G.,Lloyd-Jones, Guy C.
supporting information, p. 14814 - 14826 (2021/09/13)
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.
Reduction of Aryl Halides into Arenes with 2-Propanol Promoted by a Substoichiometric Amount of a tert-Butoxy Radical Source
Ueno, Ryota,Shimizu, Takashi,Shirakawa, Eiji
supporting information, p. 741 - 744 (2016/03/12)
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.
