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ChemicalBook--->CAS DataBase List--->154566-69-5

154566-69-5

154566-69-5 Structure

154566-69-5 Structure
IdentificationBack Directory
[Name]

5-METHYL-4-BROMOTHIOPHEN-2-YLBORONIC ACID
[CAS]

154566-69-5
[Synonyms]

(4-Bromo-5-methylthiophen-2-yl)
3-Bromo-2-methyl-5-thienylboronic acid
4-Bromo-5-methylthiophene-2-boronic acid
5-METHYL-4-BROMOTHIOPHEN-2-YLBORONIC ACID
4-Bromo-5-methyl-2-thiopheneboronic acid
(4-BroMo-5-Methylthiophen-2-yl)boronic acid
(4-bromo-5-methyl-2-thiophenyl)boronic acid
Boronic acid, B-(4-bromo-5-methyl-2-thienyl)-
[Molecular Formula]

C5H6BBrO2S
[MDL Number]

MFCD09952079
[MOL File]

154566-69-5.mol
[Molecular Weight]

220.88
Chemical PropertiesBack Directory
[storage temp. ]

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
[HS Code ]

2934999090
Spectrum DetailBack Directory
[Spectrum Detail]

5-METHYL-4-BROMOTHIOPHEN-2-YLBORONIC ACID(154566-69-5)1HNMR
Hazard InformationBack Directory
[Synthesis]

3,5-DIBROMO-2-METHYLTHIOPHENE

29421-73-6

5-METHYL-4-BROMOTHIOPHEN-2-YLBORONIC ACID

154566-69-5

The general procedure for the synthesis of 4-bromo-5-methylthiophene-2-boronic acid from 3,5-dibromo-2-methylthiophene was as follows: 3,5-dibromo-2-methylthiophene (12.8 g, 50 mmol) was dissolved in anhydrous ether (240 mL) under argon protection and degassed. The solution was cooled to -78 °C and n-butyllithium (n-BuLi, 20.4 mL, 50 mmol, 2.5 M hexane solution) was added slowly and dropwise. The reaction mixture was stirred continuously at -78 °C for 30 min. Subsequently, tributyl borate (12.68 g, 50 mmol) was added and the reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, 1 M HCl aqueous solution (200 mL) was added for acidification, and the ether phase was separated and extracted. The ether phase was washed three times with 1 M NaOH aqueous solution (3 x 70 mL). The NaOH phases were combined, concentrated and the pH was adjusted with HCl to 1. Under this acidic condition, the target product 4-bromo-5-methylthiophene-2-boronic acid precipitated as a beige solid in 76% yield.

[References]

[1] European Journal of Organic Chemistry, 2011, # 18, p. 3301 - 3312
[2] Acta Crystallographica Section C: Crystal Structure Communications, 2005, vol. 61, # 10, p. o599-o601
[3] Canadian Journal of Chemistry, 2007, vol. 85, # 1, p. 12 - 20
[4] Journal of Molecular Structure, 2007, vol. 833, # 1-3, p. 23 - 29
[5] Dyes and Pigments, 2010, vol. 84, # 1, p. 25 - 35
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