4-Bromothiophene-2-carboxaldehyde Chemical Properties

Melting point:

44-46 °C (lit.)

Boiling point:

114-115 °C/11 mmHg (lit.)

Density 

1.770 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

Powder or Granules

color 

White to beige

Sensitive 

Air Sensitive

BRN 

108455

InChI

InChI=1S/C5H3BrOS/c6-4-1-5(2-7)8-3-4/h1-3H

InChIKey

PDONIKHDXYHTLS-UHFFFAOYSA-N

SMILES

C1(C=O)SC=C(Br)C=1

CAS DataBase Reference

18791-75-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

22-24/25-36/37/39-26-36

WGK Germany 

3

F 

10-23

TSCA 

N

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:4-Bromo-2-thiophenecarboxaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromothiophene-2-carboxaldehyde Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

4-Bromothiophene-2-carboxaldehyde has been used:

• as building block for the synthesis of tetrahydroisoquinolinones
• in the synthesis of 3-[(4-bromo-2-thienyl)methylenehydrazinocarbonyl]-1H-1,2,4-triazole

Application

4-Bromothiophene-2-carboxaldehyde is an important and commonly used intermediate in medicinal chemistry.

Synthesis

General procedure: a THF solution of 1 M NaHMDS (8.8 mL, 8.8 mmol) was slowly added dropwise to the substrate (6.8 mmol) at 0°C. The reaction mixture was stirred for 30 min at 0 °C, then a solution of anhydrous THF (2 mL) with electrophilic reagent (8.3 mmol) was slowly added and stirring was continued for 3 h at 0 °C. Upon completion of the reaction, the reaction was quenched with saturated NH4Cl solution (5 mL) and diluted with hexane (20 mL). The organic layer was separated and washed with 15 wt% NaCl aqueous solution (10 mL) and subsequently concentrated to give the crude product. The product was purified by fast chromatography using a silica gel column pretreated with Et3N and 0.1% Et3N/4.9% EtOAc/95% hexane as eluent.

Toxicity evaluation

4-Bromothiophene-2-carboxaldehyde has acute oral toxicity and acute dermal toxicity, it causes skin corrosion/irritation and serious eye damage/eye irritation.

References

[1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169
[2] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169

4-Bromothiophene-2-carboxaldehyde(18791-75-8)Related Product Information

• 2-Thiophenecarboxaldehyde
• Tetrahydrothiophene
• Cephalothin sodium
• Thifensulfuron
• 3-Thiophenecarboxaldehyde
• Dibenzothiophene
• Bromine
• 5-BROMOTHIOPHENE-2-CARBOXALDEHYDE,2-BROMOTHIOPHENE-5-CARBOXALDEHYDE
• 5-BROMOTHIOPHENE-2-CARBOXALDEHYDE OXIME
• 3-Bromothiophene-2-carboxaldehyde, GC 97%,3-BROMOTHIOPHENE-2-CARBOXALDEHYDE 98%,3-Bromothiophene-2-carboxaldehyde, 95%+,3-BROMOTHIOPHENE-2-CARBOXALDEHYDE
• 4,5-DIBROMOTHIOPHENE-2-CARBOXALDEHYDE
• 1-(4-BROMO-2-THIENYL)ETHAN-1-ONE
• 3-BROMOTHIOPHENE-2-CARBOXALDEHYDE DIETHYL ACETAL
• METHYL 4-BROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE
• 4,5-DIBROMOTHIOPHENE-2-CARBOXYLIC ACID
• METHYL 4,5-DIBROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE
• METHYL4,5-DIBROMOTHIOPHENE-2-CARBOXYLATE
• METHYL 4-BROMO-3-METHOXYTHIOPHENE-2-CARBOXYLATE