4-Bromo-2-thiophenemethanol
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4-Bromo-2-thiophenemethanol
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CAS No:
79757-77-0
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Formula:
C5H5BrOS
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Chemical Name:
4-Bromo-2-thiophenemethanol
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Synonyms:
2-Thiophenemethanol,4-bromo-;4-Bromo-2-thiophenemethanol;4-Bromo-2-(hydroxymethyl)thiophene;4-Bromothenyl alcohol;(4-Bromothiophen-2-yl)methanol;(4-Bromothien-2-yl)methanol
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CAS No:
Safety Information
20/21/22-36/37/38-41-22
26-36/37/39-39
Xn
|Warning|H302+H312+H332 (50%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-Bromo-2-thiophenemethanol Use and Manufacturing
Step l:(4-Bromothiophen-2-yl)methanol (3_26_2): [00212] Sodium borohydride (5.20 g, 0.137 mol) was added to a solution of 4-bromo-thiophene-2-carbaldehyde 3_26_1 (25.0 g, 0.131 mol) in anhydrous tetra- hydrofuran (400 mL) at room temperature and the resulting mixture was stirred at room temperature for 1.5 hours. The reaction was quenched by carefully adding a saturated ammonium chloride solution (100 mL) at room temperature. The mixture was extracted into ethyl acetate and the extract was washed with brine, dried over sodium sulfate, and concentrated to give the product (25.02 g, 99percent yield) which was used in the next step without further purification. [00213] NMR (400 MHz, CDC1Step 1: 4-Bromothiophen-2-yl)methanolSodium borohydride (594 mg, 15.7 mmol) was added to a solution of 2- bromothiophene carboxaldehyde (2.5 g, 13 mmol) in a mixture toluene/ethanol (16 mL, 1 : 1) at 0°C. The reaction mixture was stirred for 2 hours at room temperature then partitioned between water (20 mL) and ethyl acetate (20 mL). The aqueous phase was separated and extracted with ethyl acetate (2 x 30 mL). The combined organic phases were washed with a saturated solution of sodium chloride (2 x 20 mL), dried over sodium sulphate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using petroleum ether/ethyl acetate (7 : 3) as eluent. The title product was obtained as a white solid (2.47 g, 98percent). *H NMR (CDCIA 4-Bromothiophene-2-carboxaldehyde (4 g, 18.8 mmol) was dissolved in dichloromethane/methanol (9/1, v/v, 100 mL) and the solution was cooled to 0C. To this was added sodium borohydride (0.35 g 9.4 mmol) and the mixture stirred for 3 h at rt. The reaction mixture was neutralized by addition of 1N HCl, extracted with dichloromethane, and the extracts dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (EtOAc: n-hexane, 1:4) to give the title compound (3.5 g, 97percent).1H NMR (CDCl3) ' 4.52 (s, 2H), 7.19 (m, 1H), 7.42 (m, 1H).???FAB MS: 194 [M+1]+Referential Example 5
Computed Properties
Molecular Weight:193.06
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:191.92445
Monoisotopic Mass:191.92445
Topological Polar Surface Area:48.5
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
