4-Methyl-5-thiazolecarboxaldehyde
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4-Methyl-5-thiazolecarboxaldehyde
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CAS No:
82294-70-0
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Formula:
C5H5NOS
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Chemical Name:
4-Methyl-5-thiazolecarboxaldehyde
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Synonyms:
5-Thiazolecarboxaldehyde,4-methyl-;4-Methyl-5-thiazolecarboxaldehyde;4-Methyl-5-formyl-1,3-thiazole;4-Methyl-5-formylthiazole;4-Methylthiazole-5-carbaldehyde
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CAS No:
Characteristics
58.2
1.1
light yellow crystal
1.3±0.1 g/cm3
75 °C
228.1ºC at 760 mmHg
91.8±21.8 °C
1.601
Slightly soluble in water.
Safety Information
NONH for all modes of transport
3
R41;R43
S26-S39
Xi:Irritant
P280-P305 + P351 + P338
H318
|Danger|H318 (95%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|P280, P305+P351+P338, and P310|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory.
4-Methyl-5-thiazolecarboxaldehyde Use and Manufacturing
General procedure: A solution of amine 2 (5 mmol) in THF (3 mL) was added dropwise over 20 min to a solution of t-BuONO (7.5 mmol) and DMSO (0.5 mmol) in THF (7 mL) at 30 °C. The mixture was stirred at 30 °C until the starting materials 2 were consumed (monitored by TLC). The solvent was evaporated, and the yields of the low boiling point products were determined by GC; the high boiling point products were isolated by column chromatography on silica gel (hexane/ethyl acetate).General procedure: Under N2 atmosphere, to the solution of FTSM (1) (57 mg, 0.2 mmol) in CH2Cl2 (1.2 mL) at 78 C was slowly added KHMDS (0.24 mL, 1.0 M in THF, 0.24 mmol). After stirring at 78 C for20 min, a solution of aldehyde 3 (0.24 mmol) in CH2Cl2 (0.4 mL)was added. The reaction mixture was stirred at 78 C for 6 h, quenched with CF3CO2H (0.5 mL) at 94 C, diluted with H2O (5 mL), and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated under vacuum. The residue was purified by flash column chromatography on silica gel with petroleum ether/EtOAc (form 10:1 to 3:1, v/v) as eluent to afford the major isomer syn-4
Computed Properties
Molecular Weight:127.17
XLogP3:1.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:127.00918496
Monoisotopic Mass:127.00918496
Topological Polar Surface Area:58.2
Heavy Atom Count:8
Complexity:96.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-Methyl-5-thiazolecarboxaldehyde
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