ethyl thiophen-2-ylacetate
2-thiophenethanol
Conditions | Yield |
---|---|
With phenylsilane; cobalt(II) diacetate tetrahydrate; sodium triethylborohydride In 1,2-dimethoxyethane; toluene at 25℃; for 15h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; | 100% |
Stage #1: ethyl thiophen-2-ylacetate With sodium tetrahydroborate In tetrahydrofuran at 70℃; for 0.25h; Stage #2: In tetrahydrofuran; methanol at 70℃; for 0.15h; | 94% |
With ethylmagnesium bromide; poly(methylhydrosiloxane); bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran; diethyl ether for 17.5h; Ambient temperature; | 89% |
methyl 2-thiopheneacetate
2-thiophenethanol
Conditions | Yield |
---|---|
Stage #1: methyl 2-thiopheneacetate With diethylzinc; lithium chloride In tetrahydrofuran; hexane at 20℃; for 6h; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; hexane; water at 20℃; for 8h; Inert atmosphere; chemoselective reaction; | 98% |
Stage #1: methyl 2-thiopheneacetate With sodium tetrahydroborate In tetrahydrofuran at 70℃; for 0.25h; Stage #2: In tetrahydrofuran; methanol at 70℃; for 0.15h; | 97% |
With strain of the zygomycete fungus S. racemosum MUT 770 In dimethyl sulfoxide for 72h; Enzymatic reaction; | 96% |
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 6h; | 97% |
With tricarbonyl(η(4)-cycloocta-1,5-diene)iron; phenylsilane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; UV-irradiation; chemoselective reaction; | 95% |
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In chloroform at 60℃; for 2h; Inert atmosphere; | 73% |
oxirane
2,5-dilithiothiophene
A
2-thiophenethanol
B
2,2′-(thiophene-2,5-diyl)diethanol
Conditions | Yield |
---|---|
In hexane 1) -10 deg C, 2 h, 2) r.t., 24 h; | A 95% B 5% |
2-[2-(tert-butyldimethylsilyloxy)ethyl]thiophene
2-thiophenethanol
Conditions | Yield |
---|---|
With Povidone-Iodine In methanol at 30℃; for 1h; Solvent; Temperature; | 91% |
2,2,2-trichloro-1-(thien-2-yl)-ethanol
2-thiophenethanol
Conditions | Yield |
---|---|
With lithium borohydride; sodium hydroxide In isopropyl alcohol Temperature; Jocic Reaction; Heating; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
Stage #1: thiophene With sodium; polyethylene; isoprene In tetrahydrofuran; toluene at -1 - 1℃; for 3.5h; Stage #2: oxirane In tetrahydrofuran; toluene at 19 - 21℃; for 2h; Stage #3: With water; ammonium chloride In tetrahydrofuran; toluene at 0 - 22℃; for 0.25h; Product distribution / selectivity; Cooling with ice-methanol bath; | 83% |
Stage #1: thiophene With cis-Octadecenoic acid; sodium; isopropenylbenzene In tetrahydrofuran; toluene at -1 - 1℃; for 3.5h; Stage #2: oxirane In tetrahydrofuran; toluene at 19 - 21℃; for 2h; Stage #3: With water In tetrahydrofuran; toluene at 0 - 20℃; for 0.166667 - 0.25h; Product distribution / selectivity; Cooling with ice-methanol bath; | 83% |
Stage #1: thiophene With cis-Octadecenoic acid; sodium; 2,3-dimethyl-buta-1,3-diene In tetrahydrofuran; toluene at -1 - 1℃; for 2h; Stage #2: oxirane In tetrahydrofuran; toluene at 20℃; for 0.333333h; Stage #3: With water In tetrahydrofuran; toluene at 0 - 13℃; for 0.5h; Product distribution / selectivity; | 83% |
With n-butyllithium In tetrahydrofuran; hexane at 0℃; | 68% |
With n-butyllithium; diethyl ether |
Conditions | Yield |
---|---|
Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: ethyleneglycol sulfate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With sulfuric acid In tetrahydrofuran; hexane for 3h; Heating; Further stages.; | 79% |
A
2-thiophenethanol
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 12h; Heating; | A 74% B 13% C 9% |
2-thiophenethanol
Conditions | Yield |
---|---|
Stage #1: thiophen-2-yl-acetic acid propyl ester With sodium tetrahydroborate In tetrahydrofuran at 70℃; for 0.25h; Stage #2: In tetrahydrofuran; methanol at 70℃; for 0.15h; | 68% |
Thiophene-2-acetic acid
1,1,3,3-Tetramethyldisiloxane
2-thiophenethanol
Conditions | Yield |
---|---|
Stage #1: Thiophene-2-acetic acid; 1,1,3,3-Tetramethyldisiloxane With C24H23ClCrIrNO3; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 40℃; for 15h; Schlenk technique; Glovebox; Inert atmosphere; Stage #2: With water In dichloromethane at 25℃; for 1h; | 68% |
Conditions | Yield |
---|---|
Stage #1: 2-Chloromethylthiophene With chloro-trimethyl-silane; ethylene dibromide; zinc In tetrahydrofuran at 70℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran at 70℃; for 6h; Schlenk technique; Inert atmosphere; | 45% |
oxirane
thiophene
A
2-thiophenethanol
B
2,2′-(thiophene-2,5-diyl)diethanol
Conditions | Yield |
---|---|
With n-butyllithium; diethyl ether |
Conditions | Yield |
---|---|
With sodium amalgam; benzene unter Stickstoff; |
Conditions | Yield |
---|---|
With diethyl ether |
Conditions | Yield |
---|---|
With diethyl ether |
methyl 2-thiopheneacetate
A
2-thiophenethanol
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; sodium hydroxide; polymethylhydrosiloxane 1.) 65 deg C, 23 h, 2.) THF, 12 h; Yield given. Multistep reaction. Yields of byproduct given; |
D-Fructose
GLUTATHIONE
A
Thiophene-2-thiol
B
Tetrahydrothiophen-3-one
C
2-ethylthiophene
D
2-Methylpyrazine
E
5-Methylfurfural
F
2-thiophenethanol
G
1-(2-furyl)-1-ethanone
H
2-methylthiophene-3-thiol
I
2-Acetylpyrrole
J
2-methylfuran-3-thiol
Conditions | Yield |
---|---|
In water at 160℃; for 2h; pH=7.5; Maillard reaction; |
Conditions | Yield |
---|---|
With (2-methyl-4-phenyl-1-oxabuta-1,3-diene)tricarbonyliron(0); 1,1,3,3-tetramethyldisilazane In toluene at 50℃; for 24h; Inert atmosphere; chemoselective reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: Dess-Martin periodane / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: sodium hydroxide; lithium borohydride / isopropyl alcohol / Heating; Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium hydroxide; lithium borohydride / isopropyl alcohol / Heating; Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With 2-methyltetrahydrofuran; iodine; zinc for 1h; | 112 g |
2-thiophenethanol
methanesulfonyl chloride
2-(thiophen-2-yl)ethyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 10℃; for 1h; | 100% |
With triethylamine In dichloromethane at 0℃; for 0.5h; | 100% |
With triethylamine In dichloromethane at 25℃; for 2.25h; Cooling with ice; | 99% |
2-thiophenethanol
tert-butyldimethylsilyl chloride
2-[2-(tert-butyldimethylsilyloxy)ethyl]thiophene
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 100% |
With dmap; triethylamine In dichloromethane 1.) 0 deg C, 30 min, 2.) RT, 18 h; | 99% |
With dmap; triethylamine In dichloromethane | 98% |
2-thiophenethanol
acetic anhydride
acetic acid-(2-[2]thienyl-ethyl ester)
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; dmap In dichloromethane at 0 - 20℃; for 3h; | 100% |
With sulfuric acid | |
With dmap; triethylamine In dichloromethane at 20℃; for 0.5h; |
2-thiophenethanol
1-iodo-2-(thien-2-yl)ethane
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane Cooling with ice; | 99% |
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 1.16667h; Inert atmosphere; | 96% |
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 20℃; for 4h; Inert atmosphere; | 88% |
2-thiophenethanol
2-thienylacetaldehyde
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; for 2h; | 99% |
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 2h; | 60% |
With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine In dichloromethane; dimethyl sulfoxide at -15℃; for 0.5h; Parikh-Doering Oxidation; Inert atmosphere; | 11% |
Conditions | Yield |
---|---|
With iron(II) triflate In toluene at 70℃; for 6h; Pictet-Spengler Synthesis; Green chemistry; | 99% |
2-thiophenethanol
2-bromo-5-(2-hydroxyethyl)thiophene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In toluene at -20.16℃; for 2h; Inert atmosphere; Darkness; | 98.5% |
With N-Bromosuccinimide In toluene at -20 - 20℃; | 90% |
With N-Bromosuccinimide In toluene at -20 - 25℃; for 12h; Inert atmosphere; | 90% |
2-thiophenethanol
p-toluenesulfonyl chloride
2-(2-thienyl)ethyl tosylate
Conditions | Yield |
---|---|
With triethylamine at 35℃; Cooling with ice; | 98% |
With triethylamine In toluene at 5 - 30℃; for 20.8333h; Product distribution / selectivity; | 96.37% |
With triethylamine In dichloromethane at -5 - 20℃; for 2h; | 96.5% |
2-thiophenethanol
chlorophosphoric acid diphenyl ester
diphenyl 2-(thiophen-2-yl)ethyl phosphate
Conditions | Yield |
---|---|
With tris(pentafluorophenyl)borate; triethylamine In dichloromethane at 20℃; for 0.5h; | 97% |
Conditions | Yield |
---|---|
With oxygen; triethylamine at 80℃; for 15h; Reagent/catalyst; Temperature; | 96.5% |
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 12h; | 85% |
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; water; acetonitrile at 35℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry; | 85% |
With iridium hexafluoride; sulphate-doped anatase; potassium oxide In dichloromethane at 85℃; Temperature; |
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene at 20℃; for 4h; | 96% |
2-thiophenethanol
Dimethoxymethane
2-(2-methoxymethoxyethyl)thiophene
Conditions | Yield |
---|---|
With lithium chloride; toluene-4-sulfonic acid for 5h; Heating / reflux; | 96% |
2-thiophenethanol
6-chloroquinoline
6-(2-(thiophen-2-yl)ethoxy)quinoline
Conditions | Yield |
---|---|
With CH3O3S(1-)*C31H49OP*C12H9NPd(1+); caesium carbonate In toluene at 90℃; for 16h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; iron(II) acetylacetonate; potassium carbonate In toluene at 130℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; | 96% |
Conditions | Yield |
---|---|
With iron(II) triflate In toluene at 70℃; for 24h; Pictet-Spengler Synthesis; Green chemistry; | 95% |
2-thiophenethanol
2-(2-Bromoethyl)thiophene
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0℃; Schlenk technique; Inert atmosphere; | 94% |
With bromine; triphenylphosphine In dichloromethane at 20℃; | 69% |
64% |
2-thiophenethanol
5-bromosalicylaldehyde dimethyl acetal
2-(2-(4-bromo-2-(dimethoxymethyl)phenoxy)ethyl)thiophene
Conditions | Yield |
---|---|
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In benzene at 0 - 20℃; for 0.5h; | 93.4% |
With di-isopropyl azodicarboxylate; triphenylphosphine In benzene at 0 - 20℃; for 0.5h; | 93.4% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; paraffin for 1h; Ambient temperature; | 93% |
With sodium hydride In tetrahydrofuran at 50℃; for 1h; | 87% |
With sodium amide In diethyl ether; ammonia at -60 - -50℃; for 0.5h; | 69% |
Stage #1: 2-thiophenethanol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h; |
2-thiophenethanol
2-Methoxyethoxymethyl chloride
2-(2-((2-methoxyethoxy)methoxy)ethyl)thiophene
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; | 93% |
With diisopropylamine In dichloromethane at 0℃; for 4h; Heating / reflux; | 85% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2.5h; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: 2-thiophenethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In tetrahydrofuran; mineral oil at -50 - 20℃; Reagent/catalyst; Temperature; Inert atmosphere; | 93% |
2-thiophenethanol
(E)-2-(3-(thiophen-2-yl)prop-1-enyl)thiophene
Conditions | Yield |
---|---|
With (bis[(2-diisopropylphosphino)ethyl]amine)Mn(CO)2Br; sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 16h; Schlenk technique; Inert atmosphere; | 93% |
With tris(triphenylphosphine)ruthenium(II) chloride; 1,3-bis-(diphenylphosphino)propane; sodium t-butanolate In toluene at 111℃; for 24h; Inert atmosphere; | 56% |
Conditions | Yield |
---|---|
Stage #1: 4-cyanophenylacetic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h; Stage #2: 2-thiophenethanol In dichloromethane at 20℃; | 93% |
Conditions | Yield |
---|---|
With C12H10N(1-)*Pd(2+)*CH3O3S(1-)*C31H49O2P; sodium t-butanolate In 1,4-dioxane at 20℃; for 12h; Sealed tube; Schlenk technique; Inert atmosphere; | 93% |
2-thiophenethanol
carbon monoxide
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; palladium diacetate; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine) In chlorobenzene; acetone at 20 - 80℃; for 30h; Schlenk technique; enantioselective reaction; | 93% |
Conditions | Yield |
---|---|
With C10H10Zr(2+)*2CF3O3S(1-)*C4H8O at 80℃; for 24h; Sealed tube; | 91% |
2-Thiopheneethanol, its cas register number is 5402-55-1. It also can be called 2-(2-Hydroxyethyl)thiophene; 2-(2-Thienyl)ethanol; Ethanol, 2-(2-thienyl)-; Thiophen-2-ethanol. It is a clear colorless to slight colored liquid. It belongs to the Product Categories of Heterocycles; Thiophene&Benzothiophene; Alkohols; Heterocyclic Compounds; Thiophens.
Physical properties about 2-Thiopheneethanol are: (1)ACD/LogP: 1.237; (2)ACD/LogD (pH 5.5): 1.24; (3)ACD/LogD (pH 7.4): 1.24; (4)ACD/BCF (pH 5.5): 5.13; (5)ACD/BCF (pH 7.4): 5.13; (6)ACD/KOC (pH 5.5): 112.23; (7)ACD/KOC (pH 7.4): 112.23; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.568; (12)Molar Refractivity: 35.721 cm3; (13)Molar Volume: 109.236 cm3; (14)Polarizability: 14.161 10-24cm3; (15)Surface Tension: 45.5349998474121 dyne/cm; (16)Density: 1.174 g/cm3; (17)Flash Point: 101.111 °C; (18)Enthalpy of Vaporization: 48.567 kJ/mol; (19)Boiling Point: 223.027 °C at 760 mmHg; (20)Vapour Pressure: 0.0560000017285347 mmHg at 25°C
When you are using 2-Thiopheneethanol, please be cautious about it as the following:
1. Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer);
2. Avoid contact with skin and eyes;
3. Wear suitable protective clothing;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H8OS/c7-4-3-6-2-1-5-8-6/h1-2,5,7H,3-4H2;
(2)InChIKey=VMJOFTHFJMLIKL-UHFFFAOYSA-N;
(3)SmilesOCCc1sccc1;
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