2-(4-BROMOPHENYL)THIOPHENE Chemical Properties

Melting point:

95-99 °C (lit.)

Boiling point:

307.0±17.0 °C(Predicted)

Density 

1.490±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

powder to crystal

color 

White to Light yellow

Safety Information

RIDADR 

UN 3335

WGK Germany 

3

Hazard Note 

Harmful

HS Code 

2934999090

MSDS

• Language:English Provider:SigmaAldrich

2-(4-BROMOPHENYL)THIOPHENE Usage And Synthesis

Uses

2-(4-Bromophenyl)thiophene is a reagent in the synthesis of 6-O-arylpropargyl diazalides, which has activity against Streptococcus pneumoniae.

Synthesis

General procedure for the synthesis of 2-(4-bromophenyl)thiophene from p-bromoiodobenzene and 2-thiophene boronic acid pinacol ester: 1-bromo-4-iodobenzene (2.0 g, 7.07 mmol), 4,4,5,5-tetramethyl-2-(thiophen-2-yl)-1,3,2-dioxaborolane (2.97 g, 14.1 mmol), Pd(PPh3)4 ( 408 mg, 0.35 mmol) and Na2CO3 (1.49 g, 14.1 mmol) were dissolved in a solvent mixture of toluene (40 mL), THF (15 mL) and H2O (15 mL). The reaction mixture was heated to reflux. Upon completion of the reaction (monitored by TLC), the solvent was removed by distillation under reduced pressure, extracted by addition of H2O (30 mL) and CH2Cl2 (40 mL), the organic layer was separated and dried over anhydrous MgSO4. The crude product was purified by silica gel fast column chromatography to afford 2-(4-bromophenyl)thiophene (1.26 g, 74.6% yield). The spectral data of the obtained product were consistent with the values reported in the literature.1H NMR (400 MHz, CDCl3): δ 7.48 (d, J = 3.6 Hz, 4H), 7.29 (d, J = 4.4 Hz, 2H), 7.07 (dt, J = 1.4, 4.4 Hz, 1H).

References

[1] Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 1, p. 910 - 919
[2] ChemPlusChem, 2017, vol. 82, # 5, p. 742 - 749

2-(4-BROMOPHENYL)THIOPHENE(40133-22-0)Related Product Information

• 2-(4-BROMOPHENYL)THIOPHENE
• ETHYL 2-AMINO-4-(4-BROMOPHENYL)THIOPHENE-3-CARBOXYLATE
• 4-(4-BROMOPHENYL)THIOPHENE-2-CARBOXYLIC&
• 4-(4-BROMOPHENYL)THIOPHENE-2-CARBONYL CHLORIDE
• 6-(4-BROMO-PHENYL)-3H-THIENO[3,2-D]PYRIMIDIN-4-ONE
• 3-AMINO-5-(4-BROMOPHENYL)THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
• 6-(4-BROMOPHENYL)-4-CHLOROTHIENO[3,2-D]PYRIMIDINE
• 5-(4-BROMOPHENYL)THIOPHENE-2-CARBALDEHYDE
• 5-(4-BROMO-PHENYL)-4-METHYL-THIOPHENE-2-CARBOXYLIC ACID
• 3-AMINO-5-(4-BROMO-PHENYL)-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER
• 5-(4-BROMOPHENYL)THIOPHENE-2-CARBOXYLIC ACID
• 5-(4-BROMOPHENYL)THIOPHENE-2-CARBOXYLIC&
• 2-(2-Bromophenyl)thiophene 97%,2-(2-BROMOPHENYL)THIOPHENE
• 5-(4-BROMOPHENYL)THIOPHENE-2-CARBOXYLIC&
• Ethyl 2-amino-4-(3-bromophenyl)thiophene-3-carboxylate
• 4-(4-BROMOPHENYL)THIOPHENE-2-CARBOXYLIC ACID
• 5-(4-BROMOPHENYL)THIOPHENE-2-CARBOHYDRAZIDE,5-(4-BROMOPHENYL)THIOPHENE-2-CARBOXYLIC HYDRAZIDE
• Propyl 2-amino-4-(4-bromophenyl)thiophene-3-carboxylate