METHYL 5-BROMO-1,3-THIAZOLE-4-CARBOXYLATE 97 Chemical Properties

Melting point:

98-101

Boiling point:

276℃

Density 

1.759

Flash point:

121℃

storage temp. 

Inert atmosphere,2-8°C

pka

-1.48±0.10(Predicted)

form 

solid

color 

Light yellow to orange

InChI

InChI=1S/C5H4BrNO2S/c1-9-5(8)3-4(6)10-2-7-3/h2H,1H3

InChIKey

AUJMFWXVFMHABB-UHFFFAOYSA-N

SMILES

S1C(Br)=C(C(OC)=O)N=C1

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HS Code 

2934100090

METHYL 5-BROMO-1,3-THIAZOLE-4-CARBOXYLATE 97 Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 5-bromo-4-thiazolecarboxylate from methyl 2-amino-5-bromothiazole-4-carboxylate: Methyl 2-amino-5-bromothiazole-4-carboxylate (1.0 equiv, 100 mg, 0.42 mmol) was dissolved in anhydrous DMF (0.8 mL). The reaction mixture was heated to 80 °C under nitrogen protection. A solution of tert-butyl nitrite (1.2 eq, 60 μL, 0.50 mmol) in DMF (0.8 mL) was slowly added dropwise to the hot solution. After several minutes of reaction, no gas escaped indicating completion of the reaction. The reaction mixture was cooled to room temperature and then sampled directly onto a preloaded silica gel column. Rapid column chromatographic separation was carried out sequentially using hexane and ethyl acetate/hexane (2:8, v/v) as eluents to afford methyl 5-bromothiazole-4-carboxylate as a yellow solid (49 mg, 53% yield). The product was analyzed by LCMS (ES) showing a purity of 95%, m/z 222 [M]+, 224 [M+2]+.

References

[1] Patent: WO2008/28168, 2008, A2. Location in patent: Page/Page column 157
[2] Patent: US2009/93465, 2009, A1. Location in patent: Page/Page column 49
[3] Patent: US2009/239859, 2009, A1. Location in patent: Page/Page column 138

METHYL 5-BROMO-1,3-THIAZOLE-4-CARBOXYLATE 97(913836-22-3)Related Product Information

• Methyl 5-broMothiophene-3-carboxylate
• Ethyl 5-bromothiazole-4-carboxylate
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• METHYL 2-BROMOTHIAZOLE-4-CARBOXYLATE
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• Methyl 2-amino-5-bromothiazole-4-carboxylate
• METHYL 5-BROMO-1,3-THIAZOLE-4-CARBOXYLATE 97
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