ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Thiophene compounds 3-Thienylmethanol

3-Thienylmethanol

Product Name3-Thienylmethanol
CAS71637-34-8
MFC5H6OS
MW114.17
EINECS275-741-8
MOL File71637-34-8.mol

Chemical Properties

Boiling point	86-88 °C/10 mmHg (lit.)
Density	1.211 g/mL at 25 °C (lit.)
refractive index	n20/D 1.564(lit.)
Flash point	213 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
pka	14.49±0.10(Predicted)
form	clear liquid
color	Colorless to Almost colorless
Water Solubility	Slightly soluble in water.
BRN	106460
InChI	InChI=1S/C5H6OS/c6-3-5-1-2-7-4-5/h1-2,4,6H,3H2
InChIKey	BOWIFWCBNWWZOG-UHFFFAOYSA-N
SMILES	C1SC=CC=1CO
CAS DataBase Reference	71637-34-8(CAS DataBase Reference)
NIST Chemistry Reference	3-Thiophenemethanol(71637-34-8)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	3
HS Code	29349990
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

3-Thiophenemethanol was used in the preparation of 3-substituted thiophene conducting copolymers which has potential applications in electrochromic displays. It was also used in the synthesis of 4-(thiophene-3-ylmethoxy)phthalonitrile.

Definition

ChEBI: 3-Thiophenemethanol is a heteroarene.

General Description

Comparision of electrochemical polymerization properties of 3-thiophenemethanol and 3-methylthiophene has been reported.

Synthesis

18791-78-1

71637-34-8

The general procedure for the synthesis of 3-thiophene methanol from 3-bromothiophene-4-carboxaldehyde was as follows: 3-bromothiophene-4-carboxaldehyde (930 mg, 5.0 mmol), sodium acetate (820 mg, 10.0 mmol), methanol (30 mL), and palladium chloride (45 mg) were mixed in a balloon-covered glass vial filled with hydrogen. The reaction mixture was stirred at 35 °C for 4 h before being filtered and washed with methanol. Subsequently, the solvent was removed by reduced pressure distillation and the residue was dissolved in water, neutralized with solid sodium bicarbonate and extracted with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate and filtered. Finally, the solvent was removed by reduced pressure distillation and the residue was purified by column chromatography to give 3-thiophene methanol (428 mg, 78% yield).

References

[1] Tetrahedron Letters, 2012, vol. 53, # 29, p. 3798 - 3801

Preparation Products And Raw materials

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