Identification | Back Directory | [Name]
(2-Bromothien-3-yl)methanol | [CAS]
70260-16-1 | [Synonyms]
(2-Bromo-3-thienyl)methanol 2-Bromothiophene-3-methanol (2-BROMOTHIEN-3-YL)METHANOL 3-Thiophenemethanol, 2-bromo- (2-bromothiophen-3-yl)methanol 2-BROMO-3-HYDROXYMETHYL-THIOPHENE | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C5H5BrOS | [MDL Number]
MFCD09025881 | [MOL File]
70260-16-1.mol | [Molecular Weight]
193.062 |
Chemical Properties | Back Directory | [Boiling point ]
142-145 °C(Press: 18 Torr) | [density ]
1.772±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [pka]
13.77±0.10(Predicted) | [Appearance]
Colorless to light yellow Liquid | [InChI]
InChI=1S/C5H5BrOS/c6-5-4(3-7)1-2-8-5/h1-2,7H,3H2 | [InChIKey]
BOJYRNFSHPAZBL-UHFFFAOYSA-N | [SMILES]
C1(Br)SC=CC=1CO |
Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of (2-bromo-3-thiophene) methanol from 3-thiophene methanol: 3-hydroxymethylthiophene (12, 4.06 g, 35.6 mmol) was dissolved in 18 mL of acetic acid at room temperature, followed by the addition of N-bromosuccinimide (6.34 g, 35.6 mmol), and the reaction was stirred for 45 min. After completion of the reaction, the reaction was quenched with 1 mL of water and the mixture was poured into 250 mL of ether and washed sequentially with 100 mL of water and 100 mL of 10% aqueous NaHCO3. The organic layer was separated, dried with anhydrous Na2SO4 and the solvent was concentrated. Finally, 6.25 g of crude product 13 was obtained in 91% yield, which was directly used in the next reaction without further purification. | [References]
[1] Organic Letters, 2008, vol. 10, # 17, p. 3665 - 3668 [2] Patent: WO2004/65384, 2004, A1. Location in patent: Page 36; 16/19 [3] Chemistry Letters, 2013, vol. 42, # 10, p. 1170 - 1172 [4] Patent: WO2008/17164, 2008, A1. Location in patent: Page/Page column 34 [5] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 2227 - 2238 |
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T&W GROUP
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