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Thiophene-3-ethanol

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CAS:13781-67-4
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Products Intro: Product Name:2-(3-Thienyl)ethanol
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Thiophene-3-ethanol Basic information
Product Name:Thiophene-3-ethanol
Synonyms:2-(3-Thienyl)ethanol, 3-(2-Hydroxyethy;3-(2-Hydroxyethyl)thiophene 98%;2-(thiophen-3-yl)ethanol;2-(3-Thienyl)ethanol, 3-(2-Hydroxyethyl)thiophene;2-(Thiophene-3-yl)ethanol;2-(3-Thienyl)ethanol,99%;2-(3-Thienyl)ethanol ,98%;2-(Thien-3-yl)ethan-1-ol
CAS:13781-67-4
MF:C6H8OS
MW:128.19
EINECS:237-434-7
Product Categories:Thiophen;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Heterocycles;Thiophens;1
Mol File:13781-67-4.mol
Thiophene-3-ethanol Structure
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.)
Fp 199 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
pka14.92±0.10(Predicted)
form Liquid
color Clear colorless to yellow-brown
Specific Gravity1.144
Water Solubility Sparingly soluble in water(0.059 g/L at 25°C).
BRN 107080
InChIKeyYYPNNBPPDFTQFX-UHFFFAOYSA-N
LogP1.07
CAS DataBase Reference13781-67-4(CAS DataBase Reference)
NIST Chemistry Reference3-Thiopheneethanol(13781-67-4)
Safety Information
Safety Statements 23-24/25
WGK Germany 3
10
HS Code 29349990
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Thiophene-3-ethanol Usage And Synthesis
Chemical PropertiesClear colorless to yellowish-brown liquid
Uses3-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.
Uses3-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
3-Thiopheneacetic acid

6964-21-2

Thiophene-3-ethanol

13781-67-4

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
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