| Identification | More | [Name]
2-N-HEXYLTHIOPHENE | [CAS]
18794-77-9 | [Synonyms]
2-HEXYLTHIOPHENE
2-N-HEXYLTHIOPHENE
ALPHA-HEXYLTHIOPHENE
FEMA 4137
2-hexyl-thiophen
Thiophene, 2-hexyl- | [EINECS(EC#)]
242-579-4 | [Molecular Formula]
C10H16S | [MDL Number]
MFCD00022535 | [Molecular Weight]
168.3 | [MOL File]
18794-77-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
-39.15°C (estimate) | [Boiling point ]
228-230°C | [density ]
0,935 g/cm3 | [FEMA ]
4137 | [refractive index ]
1.4960 | [Fp ]
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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
NA 1993 / PGIII | [WGK Germany ]
3 | [HS Code ]
38220090 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to pale yellow liquid; meat-like aroma
| [Chemical Properties]
Light yellow liquid | [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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