2-Hexylthiophene Chemical Properties

Melting point:

-39.15°C (estimate)

Boiling point:

228-230°C

Density 

0.932 g/mL at 25 °C

refractive index 

1.4960

FEMA 

4137 | 2-HEXYLTHIOPHENE

Flash point:

107°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

color 

Colorless to light yellow

Odor

at 0.10 % in dipropylene glycol. floral fruity gassy green meaty

Odor Type

sulfurous

Water Solubility 

Soluble in most organic solvents and ethanol Soluble . Insoluble in water.

λmax

234nm(EtOH)(lit.)

JECFA Number

1764

BRN 

110220

InChIKey

QZVHYFUVMQIGGM-UHFFFAOYSA-N

LogP

5.01

CAS DataBase Reference

18794-77-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26-37/39

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HS Code 

38220090

MSDS

• Language:English Provider:ALFA

2-Hexylthiophene Usage And Synthesis

Chemical Properties

Light yellow liquid

Chemical Properties

Colorless to pale yellow liquid; meat-like aroma

Occurrence

Reported found in beef, cranberry, mushroom and turkey.

Uses

2-n-Hexylthiophene is used as a important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals.

Definition

ChEBI: 2-Hexylthiophene is a heteroarene.

Aroma threshold values

High strength odor, sulfurous type; recommend smelling in a 0.10% solution or less

Synthesis

To a solution of thiophene (5.0 g, 60 mmol) in tetrahydrofuran (THF, 50 mL) was added slowly and dropwise n-butyllithium (n-BuLi, 40.6 mL, 65 mmol, 1.6 M hexane solution) at -78 °C and under nitrogen protection. The reaction mixture was stirred at -78 °C for 1 hour. Subsequently, 1-bromohexane (10.7 g, 65 mmol) was slowly added to the reaction system and the reaction mixture was gradually warmed to room temperature and stirring was continued for 12 hours. After completion of the reaction, the reaction was quenched with water and the product was extracted with ether. The organic phase was washed sequentially with water and saturated saline, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The crude product was purified by rapid column chromatography on silica gel, using hexane as eluent, to give 2-hexylthiophene (2a) as a colorless liquid. Yield: 8.3 g (82% yield). The product was characterized as follows: IR (KBr, cm-1): 3071 (sp2 C-H stretching vibration), 2921-2854 (sp3 C-H stretching vibration), 1470 (C=C stretching vibration); 1H NMR (300 MHz, CDCl3, δ/ppm): 7.08 (d, 1H, J=4.8Hz), 6.88 (dd, 1H J=4.8Hz), 6.69 (d, 1H, J=3.3Hz), 2.81 (t, 2H, J=7.7Hz), 1.68-1.61 (m, 2H), 1.34-1.26 (m, 6H), 1.02-0.98 (t, 3H, J=1.8Hz); EIMS m/z (relative abundance): 168 (100, M+).

References

[1] Organic Letters, 2002, vol. 4, # 12, p. 2067 - 2070
[2] Journal of Organic Chemistry, 2009, vol. 74, # 7, p. 2718 - 2725
[3] Inorganic Chemistry, 2018, vol. 57, # 3, p. 1527 - 1534
[4] Chinese Chemical Letters, 2011, vol. 22, # 7, p. 819 - 822
[5] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 11, p. 3810 - 3816

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