10200-59-6

Basic information

• Product Name: 1,3-Thiazole-2-carbaldehyde
• Synonyms: 2-THIAZOLECARBOXALDEHYDE;2-THIAZOLECARBOXYALDEHYDE;2-FORMYLTHIAZOLE;1,3-THIAZOLE-2-CARBALDEHYDE;THIAZOLE-2-CARBALDEHYDE;THIAZOLE-2-CARBOXALDEHYDE;1,3-Thiazole-2-carboxaldehyde;2-ThiazoleCarboxaldehyde(=2-FormylThiazole)
• CAS NO: 10200-59-6
• Molecular Formula: C₄H₃NOS
• Molecular Weight: 113.14
• EINECS: 1592732-453-0
• Product Categories: Aldehydes;Thiazoles, Isothiazoles &Benzothiazoles;API;Thiazoles;Thiazole;Thiazoles, Isothiazoles & Benzothiazoles;Boronic Acid;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Building Blocks
• Mol File: 10200-59-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 61-63 °C15 mm Hg(lit.)
• Flash Point: 154 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.288 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.187mmHg at 25°C
• Refractive Index: n20/D 1.574(lit.)
• Storage Temp.: Refrigerator (+4°C)
• PKA: 0.44±0.10(Predicted)
• Water Solubility: soluble
• CAS DataBase Reference: 1,3-Thiazole-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Thiazole-2-carbaldehyde(10200-59-6)
• EPA Substance Registry System: 1,3-Thiazole-2-carbaldehyde(10200-59-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26-23-36
• WGK Germany: 3
• Hazardous Substances Data: 10200-59-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

2-Thiazolecarboxaldehyde is a useful building block for taxane analogs.

Synthesis Reference(s)

Synthesis, p. 998, 1987 DOI: 10.1055/s-1987-28146

General Description

2-Thiazolecarboxaldehyde is a thiazole aldehyde derivative. It undergoes Baylis–Hillman reaction with methyl acrylate catalyzed by DABCO (1,4-diazabicyclo[2.2.2]octane). The reaction mechanism has been studied by electrospray ionization mass spectrometry (ESI-MS).

InChI:InChI=1/C4H3NOS/c6-3-4-5-1-2-7-4/h1-3H

Upstream product

• 3034-53-5 2-bromo-1,3-thiazole 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 134271-22-0 2-Dibromomethylthiazole 
• 288-47-1 1,3-thiazole 
• 2591-86-8 N-Formylpiperidine 
• 68-12-2 N,N-dimethyl-formamide 
• 54101-88-1 thiazolo<3,2-c><1,2,3>triazole 
• 40610-14-8 2-lithiothiazole 
• 16733-85-0 thiazole-2-carboxamide 
• 14542-12-2 (1,3-thiazol-2-yl)methanol 
• 96-50-4 2-thiazolylamine 
• 75-17-2 formaldoxime 

Downstream Products

• 13838-75-0 N-thiazol-2-ylmethylene-aniline 
• 188806-18-0 N-(4-methoxybenzyl)-C-(2-thiazolyl)nitrone 
• 917-23-7 5,15,10,20-tetraphenylporphyrin 
• 637041-83-9 ethyl 1-cyclohexyl-1H-benzimidazole-5-carboxylate 
• 879-52-7 phenyl-thiazol-2-yl-methanol 
• 294872-67-6 (4-Methoxy-phenyl)-[1-thiazol-2-yl-meth-(E)-ylidene]-amine 
• 719297-14-0 methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-1-[(thiazol-2-yl)methyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 298182-17-9 C₃₂H₃₇N₅O₂S 
• 915923-11-4 2-((1,3-thiazole-2-ylmethyl)amino)ethanol 
• 728917-28-0 N,N-diethyl-4-{(3-nitrophenyl)[1-(1,3-thiazol-2-ylmethyl)piperidin-4-ylidene]methyl}benzamide 
• 915920-14-8 N-(1,3-thiazol-2-ylmethyl)cyclopropanamine 
• 280768-77-6 N-(5-Chloropyridin-2-yl)-2-[[1-(2-thiazolylmethyl)piperidin-4-ylcarbonyl]amino]benzamide 
• 866640-87-1 (5-methyl-2-phenyloxazol-4-ylmethyl)thiazol-2-ylmethylamine 

Relevant articles and documents

Facile preparation and reactivity of polymer-supported N-(2-lodyl-phenyl)- acylamide, an Efficient Oxidizing System

(Chemical Equation Presented) A simple three-step preparation of polymer-supported N-(2-iodyl-phenyl)-acylamide (NIPA resin) starting from 2-iodoaniline is described. The resin was obtained with good loading levels (0.7-0.8 mmol g-1) and has been successfully used for efficient oxidation of a diverse collection of alcohols. Thus, treating alcohols with 1.0 equiv of the resin in 1,2-dichloroethane under reflux for 30-60 min allowed rapid and in most cases complete conversion to the corresponding carbonyl compound.

Selective metallation of thiophene and thiazole rings with magnesium amide base

The chemoselective magnesiation of thiophene and thiazole derivatives were reported using magnesium chloride. Organomagnesium compounds were used at relatively higher temperatures. The results showed that hydrogen-magnesium exchange reaction of thiophene derivatives with iPr2NMgCl proceeded selectively.

Synthesis of nonlinear optical chromophores containing electron-excessive and -deficient heterocyclic bridges. The auxiliary donor-acceptor effects

Push-pull substituted nonlinear optical chromophores with thiazole and thiophene rings and interposed ethylene units as π-conjugated bridges were synthesized. The effects of the nature and location of the heterocycles on the energy of the charge transfer transition for the chromophores are discussed.

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