2-BROMO-5-HYDROXYMETHYLTHIAZOLE Chemical Properties

Melting point:

46-48

Boiling point:

288.3±15.0 °C(Predicted)

Density 

1.899±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder

pka

13.23±0.10(Predicted)

color 

Light yellow

CAS DataBase Reference

687636-93-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Hazard Note 

Irritant

HS Code 

2934100090

2-BROMO-5-HYDROXYMETHYLTHIAZOLE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-bromothiazole-5-methanol from 2-bromo-5-formylthiazole: 2-bromothiazole-5-formaldehyde (3.00 g, 15.62 mmol) was mixed with methanol (50 mL). The mixture was cooled to 0 °C under nitrogen protection and sodium borohydride (0.591 g, 15.62 mmol) was added in batches. The reaction was stirred at this temperature for 2 hours. Subsequently, the reaction system was slowly warmed to room temperature and stirring was continued for 2 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure. To the residue, saturated aqueous ammonium chloride solution was added, and the pH was adjusted to about 6 with 1 M aqueous hydrochloric acid, and then adjusted to about 10 with 1 M aqueous sodium hydroxide. the mixture was extracted with ethyl acetate, and the organic layer was washed sequentially with saturated brine, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with a gradient of ethyl acetate/hexane (10% to 25%) to give 2-bromothiazole-5-methanol as a light yellow oil. Mass spectrum (DCI+) m/z 194,196 (M+H)+.

References

[1] Patent: WO2012/87833, 2012, A1. Location in patent: Page/Page column 125-126
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 25, p. 6303 - 6306
[3] Patent: WO2004/37818, 2004, A1. Location in patent: Page 69 - 70
[4] Patent: WO2007/75749, 2007, A2. Location in patent: Page/Page column 25; 37-39
[5] Patent: WO2009/77990, 2009, A1. Location in patent: Page/Page column 92

2-BROMO-5-HYDROXYMETHYLTHIAZOLE(687636-93-7)Related Product Information

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• Ethyl 2-bromothiazole-5-carboxylate
• 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLIC ACID
• Methyl 2-bromothiazole-5-carboxylate
• 2-Bromothiazole
• 5-Hydroxymethylthiazole
• 2-BROMO-4-HYDROXYMETHYLTHIAZOLE
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• 2-BROMO-4-(TRIFLUOROMETHYL)THIAZOLE-5-CARBOXYLIC ACID ETHYL ESTER
• RARECHEM AL BP 1435