422460
2-Thiazolecarboxaldehyde
97%
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About This Item
Formule empirique (notation de Hill) :
C4H3NOS
Numéro CAS:
Poids moléculaire :
113.14
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22
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Essai
97%
Forme
liquid
Indice de réfraction
n20/D 1.574 (lit.)
pb
61-63 °C/15 mmHg (lit.)
Densité
1.288 g/mL at 25 °C (lit.)
Groupe fonctionnel
aldehyde
Température de stockage
2-8°C
Chaîne SMILES
O=Cc1nccs1
InChI
1S/C4H3NOS/c6-3-4-5-1-2-7-4/h1-3H
Clé InChI
ZGTFNNUASMWGTM-UHFFFAOYSA-N
Description générale
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.
Code de la classe de stockage
10 - Combustible liquids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
154.4 °F - closed cup
Point d'éclair (°C)
68 °C - closed cup
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Les clients ont également consulté
The Morita-Baylis-Hillman Reaction: Advances and Contributions from Brazilian Chemistry.
Santos MS, et al.
Current Organic Synthesis, 12(6), 830-852 (2015)
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
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
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