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422460

Sigma-Aldrich

2-Thiazolecarboxaldehyde

97%

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About This Item

Formula empirica (notazione di Hill):
C4H3NOS
Numero CAS:
10200-59-6
Peso molecolare:
113.14
Numero MDL:
MFCD00142924
Codice UNSPSC:
12352100
ID PubChem:
24866433
NACRES:
NA.22

Livello qualitativo

100

Saggio

97%

Stato

liquid

Indice di rifrazione

n20/D 1.574 (lit.)

P. ebollizione

61-63 °C/15 mmHg (lit.)

Densità

1.288 g/mL at 25 °C (lit.)

Gruppo funzionale

aldehyde

Temperatura di conservazione

2-8°C

Stringa SMILE

O=Cc1nccs1

InChI

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

Categorie correlate

Descrizione generale

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).

Applicazioni

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.

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

154.4 °F - closed cup

Punto d’infiammabilità (°C)

68 °C - closed cup

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Certificati d'analisi (COA)

Lot/Batch Number
MKCF7118
MKBT3230V
MKBH5972
MKBG6814
MKBF0973

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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)
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)
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
The Morita-Baylis-Hillman Reaction: Advances and Contributions from Brazilian Chemistry.
Santos MS, et al.
Current Organic Synthesis, 12(6), 830-852 (2015)
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
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