Thiophene-3-ethanol Chemical Properties

Boiling point:

110-111 °C14 mm Hg(lit.)

Density 

1.144 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.552(lit.)

Flash point:

199 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

14.92±0.10(Predicted)

form 

Liquid

color 

Clear colorless to yellow-brown

Specific Gravity

1.144

Water Solubility 

Sparingly soluble in water(0.059 g/L at 25°C).

BRN 

107080

InChIKey

YYPNNBPPDFTQFX-UHFFFAOYSA-N

LogP

1.07

CAS DataBase Reference

13781-67-4(CAS DataBase Reference)

NIST Chemistry Reference

3-Thiopheneethanol(13781-67-4)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

F 

10

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Thiophene-3-ethanol Usage And Synthesis

Chemical Properties

Clear colorless to yellowish-brown liquid

Uses

3-Thiopheneethanol is used as a reagent in the synthesis of pH-responsive near-IR emitting conjugated polymer nanoparticles for cellular imaging and controlled-drug delivery. 3-Thiopheneethanol is also used as a reagent in the preparation of potent respiratory syncytial virus RNA polymerase inhibitors.

Uses

3-Thiopheneethanol [3-(2-hydroxyethyl)thiophene] was used in the synthesis of various ether and ester derivatives such as 3-(2-(benzyloxy)ethyl)thiophene, 3-[2-((triphenylmethyl)oxy)ethyl]thiophene, 3-[2-((trimethylsilyl)oxy)ethyl]thiophene, 3-[2-((dimethyl-tert-butylsilyl)oxy)ethyl]thiophene, 3-(2-acetoxyethyl)thiophene and 3-(2-(benzoyloxy)ethyl)thiophene.

Synthesis

Step 2: Synthesis of 2-(thiophen-3-yl)ethanol 1. to LiAlH4 (4.56 g, 0.12 mol) was added tetrahydrofuran (200 mL) at 0 °C and the mixture was stirred. 2. Slowly add THF solution of 2-(thiophen-3-yl)acetic acid (14.2 g, 0.1 mol dissolved in 100 mL of THF) dropwise to the above mixture, keeping the temperature at 0 °C. 3. after the dropwise addition was completed, the reaction mixture was continued to be stirred at 0 °C for 2 hours. 4. EtOAc (200 mL) was slowly added to the reaction mixture followed by water (5 mL) to quench the reaction. 5. The resulting suspension was filtered through diatomaceous earth and the filtrate was dried with anhydrous sodium sulfate. 6. The dried filtrate was concentrated to dryness to give 2-(thiophen-3-yl)ethanol (12.44 g, yield: 99%). 7. The product was characterized by 1H NMR (MeOD, 400 MHz): δ 5.92-5.87 (m, 1H), 5.69-5.66 (m, 1H), 5.57 (s, 1H), 2.90 (d, J=14.0 Hz, 1H), 2.38 (d, J=14 Hz, 1H), 1.55-1.42 (m, 2H).

References

[1] Patent: US2011/76291, 2011, A1. Location in patent: Page/Page column 148
[2] Synthesis, 2005, # 2, p. 267 - 271
[3] Synthesis (Germany), 2015, vol. 47, # 24, p. 3972 - 3982
[4] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 256, p. 439 - 448
[5] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1568 - 1575

Thiophene-3-ethanol(13781-67-4)Related Product Information

• Thiophene
• Ethyl acetate
• Thianaphthene
• 2-(METHYLSULFONYL)ETHANOL
• Ethanol
• Cephalothin sodium
• Thifensulfuron methyl
• 2-Thiophenecarboxaldehyde
• Tetrahydrothiophene
• 2-Thiazolecarboximidamide
• 2-Thiophenecarboxylic acid
• 2,5-Thiophenedicarboxylic acid
• Tioxolone
• 2,3-THIOPHENEDICARBOXALDEHYDE
• THIOPHENE-2-CARBOXALDOXIME
• 4-(2-THIAZOLYLAZO)RESORCINOL
• THIOPHENE-2-THIOCARBOXAMIDE
• N'-HYDROXY-2-THIOPHENECARBOXIMIDAMIDE