Home Cart Sign in  
Chemical Structure| 930-96-1 Chemical Structure| 930-96-1
Chemical Structure| 930-96-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

Synonyms: 3-Bromothiophene-2-carbaldehyde

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of 3-Bromothiophene-2-carboxaldehyde

CAS No. :930-96-1
Formula : C5H3BrOS
M.W : 191.05
SMILES Code : O=CC1=C(Br)C=CS1
Synonyms :
3-Bromothiophene-2-carbaldehyde
MDL No. :MFCD00126680
InChI Key :BCZHCWCOQDRYGS-UHFFFAOYSA-N
Pubchem ID :2797079

Safety of 3-Bromothiophene-2-carboxaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-Bromothiophene-2-carboxaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 930-96-1 ]
  • Downstream synthetic route of [ 930-96-1 ]

[ 930-96-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 24287-92-1 ]
  • [ 68-12-2 ]
  • [ 1860-99-7 ]
  • [ 930-96-1 ]
  • [ 930-97-2 ]
References: [1] Synthetic Communications, 2009, vol. 39, # 18, p. 3315 - 3323.
  • 2
  • [ 930-96-1 ]
  • [ 40985-58-8 ]
References: [1] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255.
  • 3
  • [ 930-96-1 ]
  • [ 70260-17-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium tetrahydroborate In methanol at 0℃; for 2 h;
Stage #2: With ammonium chloride In ethyl acetate
To a solution of 3- bromothiophene-2-carbaldehyde (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 firs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.
100% With sodium tetrahydroborate In methanol at 0℃; for 2 h; [00473] To a solution of 3-bromothiophene-2-carbaldehyde (6) (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 hrs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.
92% With sodium tetrahydroborate In ethanol at 0 - 20℃; for 24 h; Inert atmosphere Stirring of 3-bromothiophene-2-carboxaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) at 0 ° C under argon, and adding sodium borohydride (NaBH 4 , 3.4 g, 90.1 mmol) and stirred at room temperature for 24 hours. An aqueous solution of ammonium chloride was added to the oily solid obtained by concentration of the reaction mixture under reduced pressure, and the organic layer was extracted with ethyl acetate. After the extract was dried over magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure to give a crude material. The crude product was purified by a silica gel column chromatography (ethyl acetate / hexane (volume ratio) = 2 / 8) to thereby obtain 3-bromothiophene-2-methanol (the compound (3-1), The yield was 9.3 g, and the yield was 92percent)
92% at 0 - 20℃; for 24 h; Inert atmosphere A solution of 3-bromothiophene-2-carboxaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) was stirred at 0 ° C under an argon atmosphere, and sodium borohydride (NaBH 4 , 3.4 g, 90.1 mmol) and stirred at room temperature for 24 hours. An aqueous solution of ammonium chloride was added to the obtained oily solid, and the organic layer was extracted with ethyl acetate. After the extract was dried over magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure to give a crude material. The crude product was purified by silica gel column chromatography (ethyl acetate / hexane (volume ratio) = 2/8), whereby 3-bromothiophene-2-methanol (the compound (3) -1), yield 9.3 g, yield 92percent).
92% With sodium tetrahydroborate In ethanol at 0 - 20℃; for 24 h; Inert atmosphere In an argon environment,A solution of 3-bromothiophene-2-carbaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) was stirred at 0 ° C.Sodium borohydride (NaBH4, 3.4 g, 90.1 mmol) was added on one side.Stir at room temperature for 24 hours.The oily solid obtained by concentrating the reaction liquid under reduced pressure is added to an aqueous solution of ammonium chloride.The organic layer was extracted with ethyl acetate.Drying the extract with magnesium sulfate,After filtering,The filtrate was concentrated under reduced pressure to give a crude product.The crude product was purified by column chromatography (ethyl acetate/hexane (volume ratio) = 2/8).And the target compound 3-bromothiophene-2-methanol was obtained.(Compound (3-1), yield 9.3 g, yield 92percent).

References: [1] Patent: WO2011/156640, 2011, A2, . Location in patent: Page/Page column 134.
[2] Patent: WO2013/86451, 2013, A2, . Location in patent: Paragraph 00473.
[3] Patent: TW2018/43157, 2018, A, . Location in patent: Paragraph 0229-0232.
[4] Patent: TW2018/41922, 2018, A, . Location in patent: Paragraph 0239; 0240; 0241; 0242.
[5] Patent: TW2018/41923, 2018, A, . Location in patent: Paragraph 0213; 0214; 0215; 0216.
[6] Journal of the American Chemical Society, 2014, vol. 136, # 19, p. 7132 - 7139.
[7] Chemical Communications, 2015, vol. 51, # 18, p. 3842 - 3845.
 

Historical Records

Technical Information

Categories