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422460

Sigma-Aldrich

2-Thiazolecarboxaldehyde

97%

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About This Item

Fórmula empírica (Notação de Hill):
C4H3NOS
Número CAS:
10200-59-6
Peso molecular:
113.14
Número MDL:
MFCD00142924
Código UNSPSC:
12352100
ID de substância PubChem:
24866433
NACRES:
NA.22

Ensaio

97%

Formulário

liquid

índice de refração

n20/D 1.574 (lit.)

p.e.

61-63 °C/15 mmHg (lit.)

densidade

1.288 g/mL at 25 °C (lit.)

grupo funcional

aldehyde

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

O=Cc1nccs1

InChI

1S/C4H3NOS/c6-3-4-5-1-2-7-4/h1-3H

chave InChI

ZGTFNNUASMWGTM-UHFFFAOYSA-N

Categorias relacionadas

Descrição geral

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).

Aplicação

2-Thiazolecarboxaldehyde may be used as a reactant in the following syntheses:
  • Benzothiazine N-acylhydrazones, having potential antinociceptive and anti-inflammatory activity.
  • Thiazole-2-yl-(amino)methylphosphonate diethyl esters.
  • Imino ester by reacting with L-leucine t-butyl ester hydrochloride.
Useful building block for taxane analogs.

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

154.4 °F - closed cup

Ponto de fulgor (°C)

68 °C - closed cup

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Certificados de análise (COA)

Lot/Batch Number
MKCF7118
MKBT3230V
MKBH5972
MKBG6814
MKBF0973

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Synthesis of new thiazole-2,-4, and-5-yl-(amino) methylphosphonates and phosphinates: unprecedented cleavage of thiazole-2 derivatives under acidic conditions.
Olszewski TK and Boduszek B.
Tetrahedron, 66(45), 8661-8866 (2010)
Yasuyuki Takeda et al.
Bioorganic & medicinal chemistry letters, 14(12), 3209-3215 (2004-05-20)
To improve the metabolic stability of 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both iv and po administration, we designed and synthesized new taxane analogues. Most of the synthetic compounds maintained excellent antitumor activity
Online mechanistic investigations of catalyzed reactions by electrospray ionization mass spectrometry: a tool to intercept transient species in solution.
Santos LS.
European Journal of Organic Chemistry, 2008(2), 235-253 (2008)
The Morita-Baylis-Hillman Reaction: Advances and Contributions from Brazilian Chemistry.
Santos MS, et al.
Current Organic Synthesis, 12(6), 830-852 (2015)
Armel A Agbodjan et al.
The Journal of organic chemistry, 73(8), 3094-3102 (2008-03-25)
A practical asymmetric synthesis of a highly substituted N-acylpyrrolidine on multi-kilogram scale is described. The key step in the construction of the three stereocenters is a [3+2] cycloaddition of methyl acrylate and an imino ester prepared from l-leucine t-butyl ester
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