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422460

Sigma-Aldrich

2-Thiazolecarboxaldehyde

97%

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About This Item

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

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Quality Level

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.)

functional group

aldehyde

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

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This Item
163821365270259659
assay

97%

assay

≥97%

assay

97%

assay

99%

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

form

liquid

form

solid

form

liquid

form

liquid

refractive index

n20/D 1.574 (lit.)

refractive index

-

refractive index

n20/D 1.553 (lit.)

refractive index

n20/D 1.534 (lit.)

bp

61-63 °C/15 mmHg (lit.)

bp

-

bp

113 °C/3 mmHg (lit.)

bp

248 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

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).[1][2]

Application

2-Thiazolecarboxaldehyde may be used as a reactant in the following syntheses:
  • Benzothiazine N-acylhydrazones, having potential antinociceptive and anti-inflammatory activity.[3]
  • Thiazole-2-yl-(amino)methylphosphonate diethyl esters.[4]
  • Imino ester by reacting with L-leucine t-butyl ester hydrochloride.[5]
Useful building block for taxane analogs.[6]

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

154.4 °F - closed cup

flash_point_c

68 °C - closed cup


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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)
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
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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