13781-67-4

Basic information

• Product Name: Thiophene-3-ethanol
• Synonyms: 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;2-(3-Thienyl)ethanol, 99% 25GR;2-(3-Thienyl)ethanol, 99% 5GR
• CAS NO: 13781-67-4
• Molecular Formula: C₆H₈OS
• Molecular Weight: 128.19
• EINECS: 237-434-7
• Product Categories: Thiophen;Heterocycles;Thiophens;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research)
• Mol File: 13781-67-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 110-111 °C14 mm Hg(lit.)
• Flash Point: 199 °F
• Appearance: Clear colorless to yellow-brown/Liquid
• Density: 1.144 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.177mmHg at 25°C
• Refractive Index: n20/D 1.552(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.92±0.10(Predicted)
• Water Solubility: Sparingly soluble in water(0.059 g/L at 25°C).
• BRN: 107080
• CAS DataBase Reference: Thiophene-3-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene-3-ethanol(13781-67-4)
• EPA Substance Registry System: Thiophene-3-ethanol(13781-67-4)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 13781-67-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to yellowish-brown liquid

Uses

Different sources of media describe the Uses of 13781-67-4 differently. You can refer to the following data:
1. 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.
2. 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.

InChI:InChI=1/C5H6OS/c6-3-5-1-2-7-4-5/h1-2,4,6H,3H2

Synthetic route

thiophen-3-yl-acetic acid (6964-21-2) → 3-(2-hydroxyethyl)thiophene (13781-67-4)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Stage #2: With water In tetrahydrofuran; ethyl acetate	99%
With lithium aluminium tetrahydride	98%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Schlenk technique; Inert atmosphere;	98%

thiophen-3-yl-acetic acid methyl ester (58414-52-1) → 3-(2-hydroxyethyl)thiophene (13781-67-4)

Conditions	Yield
Stage #1: thiophen-3-yl-acetic acid methyl ester With 1,1,3,3-Tetramethyldisiloxane; vanadium(V) oxytriisopropoxide In toluene at 100℃; for 26h; Inert atmosphere; Sealed tube; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene for 2h; Inert atmosphere;	74%
In tetrahydrofuran; water; ethyl acetate

3-Bromothiophene (872-31-1) + ethyleneglycol sulfate (1072-53-3) → 3-(2-hydroxyethyl)thiophene (13781-67-4)

Conditions	Yield
Stage #1: 3-Bromothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: ethyleneglycol sulfate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With sulfuric acid In tetrahydrofuran; hexane for 4h; Heating; Further stages.;	53%

oxirane (75-21-8) + 3-thienyl lithium (1192-06-9) → 3-(2-hydroxyethyl)thiophene (13781-67-4)

Conditions	Yield
With diethyl ether at -70℃;
In tetrahydrofuran; diethyl ether at -70 - 20℃; for 1h;

oxirane (75-21-8) + 3-Bromothiophene (872-31-1) → 3-(2-hydroxyethyl)thiophene (13781-67-4)

3-(2-hydroxyethyl)thiophene (13781-67-4) + methanesulfonyl chloride (124-63-0) → 3-thiopheneethanol methanesulfonate (ester) (114896-64-9)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h;	100%
With triethylamine In dichloromethane at 0℃; for 0.25h;	99%
With triethylamine In dichloromethane at 0℃; for 0.25h;	99%

3-(2-hydroxyethyl)thiophene (13781-67-4) + p-toluenesulfonyl chloride (98-59-9) → 2-(thiophen-3-yl)ethyl 4-methylbenzenesulfonate (40412-09-7)

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In toluene at 0 - 35℃; for 12h;	93%
With triethylamine In dichloromethane at 0 - 20℃; for 5h;	90%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 1-Iodonaphthalene (90-14-2) → 3-(2-(naphthalen-1-yloxy)ethyl)thiophene (960395-49-7)

Conditions	Yield
With copper(l) iodide; 3,4,7,8-Tetramethyl-o-phenanthrolin; caesium carbonate In toluene at 110℃; for 24h;	99%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 4-nitrobenzaldehdye (555-16-8) → 5,7-dihydro-7-(4-nitrophenyl)-4H-thieno[2,3-c]pyran (1220970-39-7)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction;	99%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 4-cyanobenzaldehyde (105-07-7) → 4-(5,7-dihydro-4H-thieno[2,3-c]pyran-7-yl)benzonitrile (1220970-41-1)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction;	99%

3-(2-hydroxyethyl)thiophene (13781-67-4) + diethylphosphonoacetic acid (3095-95-2) → 2-(thiophen-3-yl)ethyl 2-(diethoxyphosphoryl)acetate

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere;	99%

3-(2-hydroxyethyl)thiophene (13781-67-4) → 3-(2'-iodoethyl) thiophene (114896-65-0)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane for 3h; Ambient temperature;	98%
With 1H-imidazole; triphenylphosphine diiodide In dichloromethane Ambient temperature;
Multi-step reaction with 2 steps 1: 53 percent / PBr3 / benzene / 5 h / Ambient temperature 2: 92 percent / NaI / acetone / 96 h / 50 °C View Scheme

3-(2-hydroxyethyl)thiophene (13781-67-4) → methyl 2-(2-bromothiophen-3-yl)ethan-1-ol (111881-86-8)

Conditions	Yield
With N-Bromosuccinimide In fluorobenzene at 20℃; for 24h; Darkness;	98%
With N-Bromosuccinimide In dichloromethane at 20℃; for 0.25h;	95%
With N-Bromosuccinimide; acetic acid In dichloromethane for 0.5h;	91%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 4-methoxy-benzaldehyde (123-11-5) → 5,7-dihydro-7-(4-methoxyphenyl)-4H-thieno[2,3-c]pyran (1220970-40-0)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction;	98%
With bismuth(lll) trifluoromethanesulfonate In toluene at 20 - 80℃; for 1h; oxa-Pictet-Spengler cyclisation;	98%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 4-nitro-benzoic acid (62-23-7) → 2-(thiophene-2-yl) ethyl 4-nitrobenzoate

Conditions	Yield
Stage #1: 3-(2-hydroxyethyl)thiophene; 4-nitro-benzoic acid With ethyl 2-(3,4-dichlorophenyl)azocarboxylate; triphenylphosphine In toluene at 20℃; for 3h; Mitsunobu Displacement; Inert atmosphere; Stage #2: With iron(II) phthalocyanine In toluene at 20℃; for 12h; Inert atmosphere;	98%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 1-methylindole (603-76-9) → 1-(1-methyl-1H-indol-3-yl)-2-(thiophen-3-yl)ethane-1,2-dione

Conditions	Yield
With 1-methyl-piperazine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; zinc trifluoromethanesulfonate In toluene at 110℃; for 6h; Inert atmosphere;	96.2%

3-(2-hydroxyethyl)thiophene (13781-67-4) + carbon monoxide (201230-82-2) + 1,4-diphenyl-1,3-butadiyne (886-66-8) → 2-(thiophen-3-yl)ethyl (E)-2-benzylidene-4-phenylbut-3-ynoate

Conditions	Yield
With (1S)-10-camphorsulfonic acid; palladium diacetate; 2,2'-bis(tert-butyl(pyridin-2-yl)phosphaneyl)-1,1'-binaphthalene In toluene at 40℃; for 20h; Inert atmosphere; Autoclave; High pressure; chemoselective reaction;	96%

3-(2-hydroxyethyl)thiophene (13781-67-4) + phosphonic acid diethyl ester (762-04-9) → diethyl 2-(3-thienyl) ethyl phosphate

Conditions	Yield
With triethylamine In tetrachloromethane for 1.5h; ultrasonic irradiation;	95%

3-(2-hydroxyethyl)thiophene (13781-67-4) → 2-(3'-thiophenyl)-1-bromoethane (57070-76-5)

Conditions	Yield
With triphenylphosphine dibromide 1:1 addition complex In acetonitrile Bromination; Heating;	95%
With 2,6-dimethylpyridine; bromine; triphenylphosphine In dichloromethane at 0℃; for 5h;	95%
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 70℃; for 3h;	86%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-(2-thiophen-3-ylethoxy)benzonitrile (1189815-96-0)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;	95%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;

3-(2-hydroxyethyl)thiophene (13781-67-4) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + trifluoroacetic acid (76-05-1) → 4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran]-1-ium trifluoroacetate (1307248-40-3)

Conditions	Yield
Stage #1: 3-(2-hydroxyethyl)thiophene; N-tert-butyloxycarbonylpiperidin-4-one In dichloromethane at 20℃; Stage #2: trifluoroacetic acid In dichloromethane at 14 - 30℃; for 20.0833h;	95%
In dichloromethane at 14 - 30℃; for 20.0833h;	95%
Stage #1: 3-(2-hydroxyethyl)thiophene; N-tert-butyloxycarbonylpiperidin-4-one In dichloromethane at 20℃; for 0.166667h; Stage #2: trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16.5h;	91%

3-(2-hydroxyethyl)thiophene (13781-67-4) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] (1283095-47-5)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 20.5h;	95%
In tetrahydrofuran; dichloromethane at 25℃;	95%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 1-methyl-1H-indole-2,3-dione (2058-74-4) → 1-methyl-4',5'-dihydrospiro[indoline-3,7'-thieno[2,3-c]pyran]-2-one

Conditions	Yield
With iron perchlorate hexahydrate In tetrahydrofuran at 80℃; for 72h; Friedel-Crafts Alkylation; Inert atmosphere;	95%

3-(2-hydroxyethyl)thiophene (13781-67-4) + ethyl 5-allyloxyindole-2-carboxylate (51086-05-6) → 5-allyloxy-1-[(2-thiophen-3-yl)ethyl]-1H-indole-2-carboxylic acid ethyl ester (385785-67-1)

Conditions	Yield
With tributylphosphine; diamide In tetrahydrofuran at 20℃; for 18.3h; Stirring;	94%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 2,2-dimethoxy-propane (77-76-9) → 5,7-dihydro-7,7-dimethyl-4H-thieno[2,3-c]pyran (1220970-47-7)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction;	94%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 1-Bromopentane (110-53-2) → 3-[2-(pentyloxy)ethyl]thiophene

Conditions	Yield
Stage #1: 3-(2-hydroxyethyl)thiophene With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.5h; Stage #2: 1-Bromopentane In dimethyl sulfoxide; mineral oil at 20℃; for 8h;	94%

3-(2-hydroxyethyl)thiophene (13781-67-4) + methyl 5-hydroxy-6-iodopyridine-3-carboxylate (1189816-87-2) → methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinate (1189816-88-3)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃;	93.2%

3-(2-hydroxyethyl)thiophene (13781-67-4) + tert-butylphenylphosphinic acid chloride (4923-85-7) → O-2-(3-thienyl)ethyltert-butylphenylphosphinate

Conditions	Yield
Stage #1: 3-(2-hydroxyethyl)thiophene With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h; Inert atmosphere; Stage #2: tert-butylphenylphosphinic acid chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 6h;	93%

3-(2-hydroxyethyl)thiophene (13781-67-4) + trityl chloride (76-83-5) → 3-(2-trityloxy-ethyl)-thiophene (198278-17-0)

Conditions	Yield
With iron(III) chloride; 1-(n-butyl)-3-methylimidazolium triflate at 20℃; for 3.25h; Ionic liquid;	92%

3-(2-hydroxyethyl)thiophene (13781-67-4) + allyl bromide (106-95-6) → 3-(2-(allyloxy)ethyl)thiophene (136473-37-5)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 50℃; Inert atmosphere;	92%
Stage #1: 3-(2-hydroxyethyl)thiophene With sodium hydride In tetrahydrofuran; mineral oil at 50℃; for 1h; Stage #2: allyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃;	52%

3-(2-hydroxyethyl)thiophene (13781-67-4) → 2,5-dibromo-3-(2-hydroxyethyl)thiophene (207733-28-6)

Conditions	Yield
With tetrabutylammomium bromide; bromine In methanol; dichloromethane at 20℃; for 1h;	91.2%
With N-Bromosuccinimide In toluene at -20 - 20℃;	86%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 40℃; for 3h;	85%

3-(2-hydroxyethyl)thiophene (13781-67-4) + methyl 3-hydroxy-5-isopropoxybenzoate (752242-26-5) → Methyl 3-isopropoxy-5-(2-(3-thienyl)ethoxy)benzoate (852520-41-3)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 3h;	91%
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃;	67%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 20h;	41%

3-(2-hydroxyethyl)thiophene (13781-67-4) → 2-(3'-thienyl)ethyl chloride (7136-58-5)

Conditions	Yield
With pyridine; thionyl chloride In diethyl ether	90%
With tetrachloromethane; tributylphosphine In acetonitrile for 18h; Heating;	84%
With thionyl chloride In chloroform	81.5%
With methanesulfonyl chloride; triethylamine In dichloromethane

3,4-dihydro-2H-pyran (110-87-2) + 3-(2-hydroxyethyl)thiophene (13781-67-4) → 3-<2-(tetrahydropyranyloxy)ethyl>thiophene (160557-19-7)

Conditions	Yield
With toluene-4-sulfonic acid In diethyl ether for 3h; Ambient temperature;	90%
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃;	73%
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃;	73%

Upstream product

• 75-21-8 oxirane 
• 1192-06-9 3-thienyl lithium 
• 872-31-1 3-Bromothiophene 
• 6964-21-2 thiophen-3-yl-acetic acid 
• 1072-53-3 ethyleneglycol sulfate 
• 58414-52-1 thiophen-3-yl-acetic acid methyl ester 

Downstream Products

• 13781-68-5 phenyl-carbamic acid-(2-[3]thienyl-ethyl ester) 
• 212262-18-5 3-[2-(4-bromo-benzyloxy)-ethyl]-thiophene 
• 212262-19-6 N,N-diethyl-4-(2-thiophen-3-yl-ethoxymethyl)-benzenesulfonamide 
• 848360-57-6 2-(2-bromo-3-thienyl)-p-toluenesulfonyl ethanol 
• 212262-24-3 4-(2-thiophen-3-yl-ethoxymethyl)-benzenesulfonyl chloride 
• 1468-84-4 5,6-dihydro-4H-benzothiophen-7-one 
• 1505-47-1 4-(thien-3-yl)butyric acid 
• 198278-17-0 3-(2-trityloxy-ethyl)-thiophene 
• 1206886-69-2 tert-butyldiphenyl(2-(thiophen-3-yl)ethoxy)silane 
• 1221413-86-0 4-(2-(thiophen-3-yl)ethoxy)benzaldehyde 
• 1188309-56-9 2-(thiophen-3-yl)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate 

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