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2-Thiazolcarboxaldehyd
97%
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About This Item
Empirische Formel (Hill-System):
C4H3NOS
CAS-Nummer:
Molekulargewicht:
113.14
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22
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Qualitätsniveau
Assay
97%
Form
liquid
Brechungsindex
n20/D 1.574 (lit.)
bp
61-63 °C/15 mmHg (lit.)
Dichte
1.288 g/mL at 25 °C (lit.)
Funktionelle Gruppe
aldehyde
Lagertemp.
2-8°C
SMILES String
O=Cc1nccs1
InChI
1S/C4H3NOS/c6-3-4-5-1-2-7-4/h1-3H
InChIKey
ZGTFNNUASMWGTM-UHFFFAOYSA-N
Allgemeine Beschreibung
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).
Anwendung
Useful building block for taxane analogs.
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.
Lagerklassenschlüssel
10 - Combustible liquids
WGK
WGK 3
Flammpunkt (°F)
154.4 °F - closed cup
Flammpunkt (°C)
68 °C - closed cup
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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)
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.
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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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