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422460

Sigma-Aldrich

2-Thiazolecarboxaldehyde

97%

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About This Item

Empirical Formula (Hill Notation):
C4H3NOS
CAS Number:
10200-59-6
Molecular Weight:
113.14
MDL number:
MFCD00142924
UNSPSC Code:
12352100
PubChem Substance ID:
24866433
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.574 (lit.)

bp

61-63 °C/15 mmHg (lit.)

density

1.288 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

O=Cc1nccs1

InChI

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

InChI key

ZGTFNNUASMWGTM-UHFFFAOYSA-N

Related Categories

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).

Application

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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

154.4 °F - closed cup

Flash Point(C)

68 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

422460-BULK:
422460-VAR:
422460-250MG:
422460-1G:
422460-50G:

Certificates of Analysis (COA)

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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
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)
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)
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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