2,5-DIMETHYL-THIOPHENE-3-CARBALDEHYDE Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C7H8OS/c1-5-3-7(4-8)6(2)9-5/h3-4H,1-2H3

InChIKey

WVIQPBIZBQRJAD-UHFFFAOYSA-N

SMILES

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

LogP

1.874 (est)

CAS DataBase Reference

26421-44-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2934999090

2,5-DIMETHYL-THIOPHENE-3-CARBALDEHYDE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2,5-dimethyl-3-thiophenecarboxaldehyde from 2,5-dimethylthiophene and 1,1-dichlorodimethyl ether: a solution of 2,5-dimethylthiophene (7.80 g, 69.5 mmol) in dichloromethane (DCM, 15 mL) was added simultaneously and slowly to a solution of titanium tetrachloride (TiCl4, 19.1 mL) in dichloromethane (DCM, 20 mL). mL) solution were added simultaneously and slowly dropwise to a dichloromethane (DCM, 20 mL) solution of titanium tetrachloride (TiCl4, 19.1 mL), keeping the reaction temperature below 5 °C. The reaction mixture was stirred at 0 °C for 2 h, followed by slow warming to room temperature for 30 min. The reaction mixture was poured into ice water acidified with hydrochloric acid (HCl, 20 mL). The mixture was partitioned with dichloromethane and water, the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by Kugelrohr distillation (membrane pump, set temperature ca. 175 °C) gave 2,5-dimethyl-3-thiophenecarboxaldehyde as a colorless liquid (5.81 g, 60% yield).1H NMR (CDCl3) δ 9.93 (s, 1H), 7.00 (d, J = 1.1 Hz, 1H), 2.70 (s, 3H), 2.40 (d, J = 0.4 Hz, 3H). Mass spectrum measured value: [M + H]+ = 141.1.

References

[1] Russian Chemical Bulletin, 2005, vol. 54, # 5, p. 1208 - 1213
[2] Patent: WO2017/155909, 2017, A1. Location in patent: Paragraph 0067

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