2-Thiopheneethanol Chemical Properties

Boiling point:

108-109 °C/13 mmHg (lit.)

Density 

1.153 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.551(lit.)

Flash point:

214 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Liquid

pka

14.77±0.10(Predicted)

color 

Clear light yellow to gray-green or brownish

Water Solubility 

slightly soluble

BRN 

106985

LogP

1.040 (est)

CAS DataBase Reference

5402-55-1(CAS DataBase Reference)

NIST Chemistry Reference

2-Thiopheneethanol(5402-55-1)

EPA Substance Registry System

2-Thiopheneethanol (5402-55-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-36-26

RIDADR 

UN 3334

WGK Germany 

3

F 

13

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29349990

MSDS

• Language:English Provider:2-(2-Thienyl)ethanol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Thiopheneethanol Usage And Synthesis

Chemical Properties

clear colorless to slightly brown liquid

Uses

2-Thiopheneethanol is a thiophene derivative used in the preparation of oligothiophene isothiocyanates as fluorescent markers for biopolymers. 2-Thiopheneethanol is also used in the preparation of oth er biologically active compounds such as the analgesic Sulfentanyl and the antithrombotic Clopidogrel Hydrogen Sulfate (C587250).

Uses

2-Thiopheneethanol, is used as the antithrombotics thiophene chlorine match piperidine intermediates. It is also used as a ticlopidine Intermediate.

Definition

ChEBI: 2-(2-Thienyl)ethanol is a heteroarene.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 477, 1942 DOI: 10.1021/ja01255a001
The Journal of Organic Chemistry, 59, p. 4323, 1994 DOI: 10.1021/jo00094a056

Synthesis

2.3. Biotransformation experiments: liquid culture inoculum was prepared by pre-culturing the fungal strains in Petri dishes containing malt extract solid medium (MEA: glucose 20 g/L, malt extract 20 g/L, agar 20 g/L, peptone 2 g/L). The fungus was inoculated as a conidial suspension (1 × 10^6 conidia/mL) in a 50 mL conical flask containing 40 mL of malt extract liquid medium. The conical flasks were placed in a constant temperature shaker at 25°C and incubated with oscillation at 110 rpm. After 2 days of preincubation, a DMSO solution with 500 mM substrate was added to give a starting substrate concentration (c0) of 1-5 mM. Three biological replicates were set up for each substrate. After addition of substrate, the experiment continued for 3 days, during which time 1 mL was sampled at predetermined time intervals (typically 24, 48, and 72 h.) After each sampling, the sample was extracted with 500 μL of ethyl acetate (EtOAc), and the organic phase was dried over anhydrous Na2SO4 and analyzed by GC/MS. In some cases (see Section 2.4), the reduction products were separated. Before each set of biotransformation experiments, initial biomass and pH were determined. At the end of the experiment, these parameters were evaluated again. The liquid medium was separated from the biomass by filtration for pH measurements; mycelium was dried at 60°C for 24 h and the dry weight of the biomass was determined. The yield of the product 2-(thiophen-2-yl)ethanol was 72% (3.7 mg) and the yield of the by-product methyl 2-(thiophen-2-yl)acetate was 96% (24.6 mg).1H NMR (400 MHz, CDCl3, TMS): δ = 7.20 (m, 1H, heteroaromatic hydrogens), 6.99 (m, 1H, heteroarylhydrogen), 6.90 (m, 1H, heteroaromatic hydrogen), 3.85 (t, 2H, J=6.2 Hz, CH2OH), 3.02 (t, 2H, J=6.2 Hz, CH2CH2OH). 13C NMR (100 MHz, CDCl3, TMS): δ=140.5, 127.0, 125.8, 124.0, 63.4, 33.3. GC/MS: tR= 9.47 min, m/z 128 (M+, 30%), 110 (5%), 97 (100%).

References

[1] Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 346 - 357
[2] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 85, p. 10514 - 10516,3
[3] European Journal of Organic Chemistry, 2011, # 17, p. 3178 - 3183
[4] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 116, p. 83 - 88
[5] Patent: US2010/16365, 2010, A1. Location in patent: Page/Page column 26

2-Thiopheneethanol(5402-55-1)Related Product Information

• 2-Thiopheneboronic acid
• Ethyl acetate
• 2-Thiophenecarboxylic acid
• Ethanol
• 2-Thiophenecarboxaldehyde
• 2-Thiophenemethylamine
• Thiophenethiol
• 2-Thiopheneacetic acid
• Tetrahydrothiophene
• Cephalothin sodium
• Thifensulfuron
• 2-Thiopheneglyoxylic acid
• Methyl 2-thienylacetate
• 2-(5-CHLORO-3-METHYLBENZO[B]THIOPHEN-2-YL)ACETIC ACID
• 2-Thiophenemethanol
• ETHYL THIOPHENE-2-GLYOXYLATE
• AMINO-THIOPHEN-2-YL-ACETIC ACID
• 2,2'-THENOIN