4-METHYLTHIOPHENE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

136-138 ºC

Boiling point:

274 ºC

Density 

1.319

Flash point:

119 ºC

storage temp. 

2-8°C(protect from light)

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.18±0.20(Predicted)

color 

White to Off-White

Safety Information

HS Code 

2934999090

4-METHYLTHIOPHENE-3-CARBOXYLIC ACID Usage And Synthesis

Synthesis

At -78 °C, n-butyllithium (n-BuLi, 1.6 M hexane solution, 14.6 mL, 23.3 mmol) was slowly added dropwise to a stirred solution of 3-bromo-4-methylthiophene (2.7 g, 15.6 mmol) in tetrahydrofuran (THF, 35 mL). After the dropwise addition was completed, the reaction mixture was kept stirred at -78 °C for 15 minutes, followed by continued stirring for 30 minutes. Next, carbon dioxide gas (CO2) was passed into the reaction mixture for 10 minutes and stirring was continued at the same temperature for 20 minutes. Upon completion of the reaction, the mixture was slowly warmed to 0 °C and the reaction was quenched with 1 M aqueous sodium hydroxide (NaOH) solution (60 mL), followed by washing with ethyl acetate (EtOAc, 2 x 50 mL). The aqueous phase was acidified to pH about 5 and extracted with dichloromethane (DCM, 2 × 50 mL). The organic layers were combined, washed sequentially with water (100 mL) and saturated saline (100 mL), dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure. Finally, the residue was purified by column chromatography (silica gel as stationary phase, 8% methanol/dichloromethane as eluent) to afford the target product 4-methylthiophene-3-carboxylic acid (1.5 g, 70% yield) as a white solid.

References

[1] Patent: WO2015/129926, 2015, A1. Location in patent: Page/Page column 78

4-METHYLTHIOPHENE-3-CARBOXYLIC ACID(78071-30-4)Related Product Information

• ETHYL 2-AMINO-4-METHYLTHIOPHENE-3-CARBOXYLATE
• 2-AMINO-4-PHENYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER
• 2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER
• ETHYL 2-AMINO-4,5-DIMETHYLTHIOPHENE-3-CARBOXYLATE
• 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER
• THIOPHENE-3,4-DICARBOXYLIC ACID
• DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE
• ETHYL 2-[(2-CHLOROACETYL)AMINO]-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE
• ETHYL 2-AMINO-4-(2-FURYL)THIOPHENE-3-CARBOXYLATE
• ETHYL 2-AMINO-4-(2-THIENYL)THIOPHENE-3-CARBOXYLATE
• ETHYL 2-ACETAMIDO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE
• 3-AMINO-4H-THIENO[3,4-C]CHROMEN-4-ONE
• ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate
• AKOS 89941
• BUTTPARK 91\08-100
• ETHYL 2-[(2-CHLOROACETYL)AMINO]-4-METHYLTHIOPHENE-3-CARBOXYLATE
• ETHYL 2-[2-(2,4-DICHLOROPHENOXY)ACETAMIDO]-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE
• AURORA 3766