tert-butyl 4,5-dibromothiophen-2-ylcarbamate

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tert-butyl 4,5-dibromothiophen-2-ylcarbamate Basic information
Product Name:tert-butyl 4,5-dibromothiophen-2-ylcarbamate
Synonyms:tert-butyl 4,5-dibromothiophen-2-ylcarbamate;1,1-dimethylethyl (4,5-dibromo-2-thienyl)carbamate;Carbamic acid, N-(4,5-dibromo-2-thienyl)-, 1,1-dimethylethyl ester
CAS:943321-93-5
MF:C9H11Br2NO2S
MW:357.06
EINECS:
Product Categories:
Mol File:943321-93-5.mol
tert-butyl 4,5-dibromothiophen-2-ylcarbamate Structure
tert-butyl 4,5-dibromothiophen-2-ylcarbamate Chemical Properties
Boiling point 317.4±42.0 °C(Predicted)
density 1.782±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka12.09±0.70(Predicted)
Safety Information
MSDS Information
tert-butyl 4,5-dibromothiophen-2-ylcarbamate Usage And Synthesis
Synthesis
4,5-DIBROMOTHIOPHENE-2-CARBOXYLIC ACID

6324-10-3

tert-Butanol

75-65-0

tert-butyl 4,5-dibromothiophen-2-ylcarbamate

943321-93-5

GENERAL STEPS: To a solution of 4,5-dibromothiophene-2-carboxylic acid (9.8 mmol, 2.8 g) in tert-butanol (20 mL) were sequentially added diphenylphosphoryl azide (DPPA, 12.5 mmol, 2.7 mL) and triethylamine (29 mmol, 4.2 mL). The reaction mixture was heated to 85 °C and stirred for 12 h under nitrogen protection. Upon completion of the reaction, it was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. Purification of the crude product by fast column chromatography (silica gel as stationary phase, hexane/ethyl acetate=10:1 as eluent) afforded tert-butyl (4,5-dibromothiophen-2-yl)carbamate (2.6 g, 74% yield) as a white solid. m/z LC-MS (electrospray ionization): 357 [M+H]+.

References[1] Patent: WO2007/76423, 2007, A2. Location in patent: Page/Page column 92
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 8, p. 2244 - 2248
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5567 - 5571
tert-butyl 4,5-dibromothiophen-2-ylcarbamate Preparation Products And Raw materials
Raw materialstert-Butanol-->4,5-Dibromothiophene-2-carboxylic acid
Tag:tert-butyl 4,5-dibromothiophen-2-ylcarbamate(943321-93-5) Related Product Information
(5-Bromo-thiophen-2-yl)-carbamic acid tert-butyl ester tert-Butyl (4-bromothiophen-2-yl)carbamate N-Boc-2-amino-3-bromothiophene tert-Butyl thiophen-2-ylcarbamate (5-Chloro-thiophen-2-yl)-carbamic acid tert-butyl ester tert-Butyl (5-bromo-3-methylthiophen-2-yl)carbamate