636-72-6

Basic information

• Product Name: 2-Thiophenemethanol
• Synonyms: 2-(2-HYDROXYETHYL)THIOPHENE;2-(HYDROXYMETHYL)THIOPHENE;2-THENYL ALCOHOL;2-THIENYL CARBINOL;2-THIENYLETHANOL;2-THIENYLMETHANOL;2-THIOPHENEMETHANOL;2-THIOPHENETHANOL
• CAS NO: 636-72-6
• Molecular Formula: C₅H₆OS
• Molecular Weight: 114.17
• EINECS: 226-452-0
• Product Categories: Sulphur Derivatives;Thiophene&Benzothiophene;Alkohols;Heterocyclic Compounds;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes
• Mol File: 636-72-6.mol
• Article Data: 65

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 207 °C(lit.)
• Flash Point: 214 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.205 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.139mmHg at 25°C
• Refractive Index: n20/D 1.564(lit.)
• Storage Temp.: Store at 0°C
• PKA: 13.89±0.10(Predicted)
• Water Solubility: 40 g/L (20 ºC)
• Sensitive: Air Sensitive
• BRN: 383595
• CAS DataBase Reference: 2-Thiophenemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiophenemethanol(636-72-6)
• EPA Substance Registry System: 2-Thiophenemethanol(636-72-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26
• WGK Germany: 3
• F: 13
• Hazardous Substances Data: 636-72-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to light yellow liquid

Uses

Different sources of media describe the Uses of 636-72-6 differently. You can refer to the following data:
1. No commercially developed applications.
2. 2-?Thiophenemethanol is a heterocyclic building block used in pharmaceutical and organic synthesis. It is a component of the synthesis of styrylheterocycle analogs of reservatrol which act as apoptosis-inducing agents. Also used in the preparation of diverse 2-aminothiophenes displaying biologically active antiproliferative activity.

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

Synthetic route

thiophene-2-carbaldehyde (98-03-3) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With hydrogen; phosphotungstic acid 44-hydrate; [Fe(C5H4P(i-Pr)2)2Rh(C8H12)]BF4 In water; isopropyl alcohol at 20℃; under 5171.62 Torr; for 16h;	100%
With isopropyl alcohol; hydrotalcite at 81.84℃; for 3h; Kinetics; Further Variations:; Temperatures; Reagents; ratio educt:reagent;	100%
With trichlorosilane; N,N-dimethyl-formamide In dichloromethane at 0℃; for 6h;	99%

C20H20BO4S4(1-)*Na(1+) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With water	100%

thiophene-2-carbaldehyde (98-03-3) → 2-thiophenylcarboxylic acid (527-72-0) + 2-thiophenemethanol (636-72-6)

Conditions	Yield
Stage #1: thiophene-2-carbaldehyde With potassium hydroxide for 0.0833333h; Cannizzaro Reaction; Milling; Inert atmosphere; Sealed tube; Green chemistry; Stage #2: With hydrogenchloride In water for 0.0833333h; Green chemistry;	A 98% B 98%
With aluminum oxide; water; sodium hydroxide at 100℃; for 0.0333333h; Cannizzaro Reaction; Microwave irradiation;	A 47% B 47%
With aluminum oxide; sodium hydroxide; water for 0.00416667h; Irradiation; Yield given; Yields of byproduct given;

(thiophen-2-yl)methyl acetate (13679-77-1) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With zirconocene dichloride; diisobutylaluminium hydride In tetrahydrofuran at -20℃; Inert atmosphere; regioselective reaction;	97%
With lipase B from Candida antarctica immobilized on Immobead 150 In aq. phosphate buffer at 40℃; for 0.333333h; pH=7.4;	87%

4,4,5,5-tetramethyl-2-(thiophen-2-ylmethoxy)-1,3,2-dioxaborolane → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With silica gel In hexane; ethyl acetate	96%
With silica gel at 25℃; Inert atmosphere; Glovebox;	94%
With water; silica gel In methanol at 60℃; Inert atmosphere;	88%

trimethyl-(thiophen-2-ylmethoxy)-silane → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With Nafion-H(R); silica gel In hexane at 20℃; for 0.666667h;	95%
With silica chromate; silica gel In dichloromethane at 20℃; for 0.75h;	70%

(CH3CNO)2(CH3CNOH)2Co(C5H5N)(OOCH2C4H3S) → thiophene-2-carbaldehyde (98-03-3) + 2-thiophenemethanol (636-72-6)

Conditions	Yield
In methanol decomposition of the complex by refluxing in methanol under N2 for 6-8 h; evapn. of the solvent, extn. of the organic compounds with ether, gas chromatography;	A 5% B 95%

(4-bromothiophen-2-yl)methanol (79757-77-0) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 2h; Inert atmosphere;	95%

tetrahydropyranyl ether of 2-thiophenemethanol (121851-24-9) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
ammonium cerium(IV) nitrate In alkaline aq. solution; acetonitrile at 70℃; for 2h; pH=8; Decomposition;	91%

tert-butyl dimethyl(thiophen-2-ylmethoxy)silane → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With tetrabutyl ammonium fluoride In methanol at 30℃; for 1h;	90%

2-thiophenecarboxaldehyde diacetate (63011-97-2) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 20℃; for 4h; chemoselective reaction;	88%

(5-bromothien-2-yl)methanol (79387-71-6) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 10h; Inert atmosphere;	85%

thiophene-2-carboxylic acid methyl ester (5380-42-7) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
Stage #1: thiophene-2-carboxylic acid methyl ester With sodium triethylborohydride In diethyl ether; toluene at 20℃; for 8h; Inert atmosphere; Stage #2: With sodium hydroxide In methanol; diethyl ether; toluene at 20℃; for 2h; Reagent/catalyst; Solvent; Time;	78%
With lithium aluminium tetrahydride In diethyl ether at -10℃; for 1h;	1.07 g

thiophene-2-carbaldehyde (98-03-3) + propargyl bromide (106-96-7) → (+/-)-1-(2-thienyl)-3-butyn-1-ol (38597-97-6) + 2-thiophenemethanol (636-72-6)

Conditions	Yield
With ammonium chloride; calcium chloride; zinc In tetrahydrofuran; water for 1h;	A 74% B 15 % Spectr.
With ammonium chloride; calcium chloride; zinc In tetrahydrofuran; water for 1h;	A 74 % Spectr. B 15 % Spectr.

2-thiophenylcarboxylic acid (527-72-0) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;	64%
Stage #1: 2-thiophenylcarboxylic acid With trimethylphenylsilane; C69H55ClP3Ru In tetrahydrofuran at 60℃; for 16h; Glovebox; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 1h; Glovebox; chemoselective reaction;	60%
Multi-step reaction with 2 steps 2: 1.07 g / LiAlH4 / diethyl ether / 1 h / -10 °C View Scheme

2-thenyl bromide (45438-73-1) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With oxygen; eosin y In dimethyl sulfoxide at 25℃; for 12h; Irradiation;	61%

thiophene-2-carbaldehyde (98-03-3) → 2-thiophenemethanol (636-72-6) + (1S,2S)-1-(2-thienyl)-1,2-propanediol (189032-31-3) + (1S,2R)-1-(thiophen-2-yl)propane-1,2-diol

Conditions	Yield
brewers' yeast; Yields of byproduct given;	A 52% B n/a C n/a
brewers' yeast; Yield given;	A 52% B n/a C n/a

Ethyl thiophene-2-carboxylate (2810-04-0) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium tert-butylate; hydrogen In tetrahydrofuran; 2-methyltetrahydrofuran at 45℃; under 3750.38 Torr; for 2.5h; Autoclave;	52%
Multi-step reaction with 2 steps 1: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C24H23ClCrIrNO3 / dichloromethane / 15 h / 25 °C / Schlenk technique; Glovebox; Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / Inert atmosphere View Scheme

5-methyl-2-thienyl-2,3-dihydro-1,3-benzazaphosphole + 5-methyl-2-thienyl-2,3-dihydro-1,3-benzazaphosphole → 5-methyl-2-(thien-2-yl)-1H-1,3-benzazaphosphole (1443767-97-2) + 2-thiophenemethanol (636-72-6)

Conditions	Yield
With toluene-4-sulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Inert atmosphere; Reflux;	A 50% B n/a

thiophene-2-carbaldehyde (98-03-3) + 3,4,5-triamino-1,2,6-thiadiazine 1,1-dioxide (61403-61-0) → 2-thiophenemethanol (636-72-6) + 4-amino-6-(2-thienyl)-1H,5H-imidazo<4,5-c>1,2,6-thiadiazine 2,2-dioxide (116256-01-0) + 4-amino-6,7-di(2'-thienyl)-8H-pyrazino<2,3-c>-1,2,6-thiadiazine 2,2-dioxide (116544-19-5)

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Product distribution; Heating; other solvent;	A n/a B 36% C 32%
In N,N-dimethyl-formamide for 8h; Heating;	A n/a B 36% C 32%
In acetic acid for 8h; Heating;	A n/a B 33% C 32%

2-(diazomethyl)thiophene (5919-31-3) → 2-thiophenemethanol (636-72-6) + (Z)-1-Isopropenyl-1-methyl-2-(2-thienyl)cyclopropan (76836-84-5, 76836-85-6) + (E)-1-Isopropenyl-1-methyl-2-(2-thienyl)cyclopropan (76836-84-5, 76836-85-6) + thiophene-2-carboxaldehyde azine (24523-46-4)

Conditions	Yield
With 2,3-dimethyl-buta-1,3-diene In diethyl ether for 10h; Irradiation; Yields of byproduct given;	A 4% B n/a C n/a D 27%
In diethyl ether for 10h; Irradiation; Yields of byproduct given;	A 4% B n/a C n/a D 27%

2-(diazomethyl)thiophene (5919-31-3) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → 2-thiophenemethanol (636-72-6) + (Z)-1-Isopropenyl-1-methyl-2-(2-thienyl)cyclopropan (76836-84-5, 76836-85-6) + (E)-1-Isopropenyl-1-methyl-2-(2-thienyl)cyclopropan (76836-84-5, 76836-85-6) + thiophene-2-carboxaldehyde azine (24523-46-4)

Conditions	Yield
In diethyl ether for 10h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;	A 4% B n/a C n/a D 27%

thiophene-2-carbaldehyde (98-03-3) + ethanol (64-17-5) → Ethyl thiophene-2-carboxylate (2810-04-0) + 2-thiophenemethanol (636-72-6)

Conditions	Yield
carbonylhydridetris(triphenylphosphine)rhodium(I) for 504h; Heating;	A 25% B 7%

thiophene-2-carbaldehyde (98-03-3) + formaldehyd (50-00-0) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With methanol; sodium hydroxide

2-Chloromethylthiophene (765-50-4) → bis(thienylmethyl) ether (35250-78-3) + 2-thiophenemethanol (636-72-6)

Conditions	Yield
With sodium hydroxide; sodium acetate

2-Chloromethylthiophene (765-50-4) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With sodium hydroxide; sodium acetate

formaldehyd (50-00-0) + 2-thienylmagnesium iodide (89180-57-4) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With diethyl ether

thiophen-2-ylmethanamine monohydrochloride (7404-63-9) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With water; silver nitrate

formaldehyd (50-00-0) + thiophen-2-yl magnesium bromide (5713-61-1) → 2-thiophenemethanol (636-72-6)

Conditions	Yield
With diethyl ether

2-thiophenemethanol (636-72-6) → 2-thenyl bromide (45438-73-1)

Conditions	Yield
With boron tribromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	100%
With phosphorus tribromide In diethyl ether at 0 - 20℃; for 1h;	89%
With hydrogen bromide; acetic acid In diethyl ether at 0 - 20℃; for 16h; Inert atmosphere;	85%

triphenylphosphine hydrobromide (6399-81-1) + 2-thiophenemethanol (636-72-6) → 2-thienylmethyltriphenylphosphonium bromide (23259-98-5)

Conditions	Yield
In chloroform for 1h; Heating;	100%
In chloroform Reflux;	95%
In chloroform for 6h; Heating;

titanium(IV) isopropylate (546-68-9) + 2-thiophenemethanol (636-72-6) → C16H24O4S2Ti (1346523-10-1)

Conditions	Yield
In cyclohexane Inert atmosphere; Reflux;	100%
In cyclohexane for 0.5h; Schlenk technique; Inert atmosphere; Reflux;	100%

2-thiophenemethanol (636-72-6) → thiophene-2-carbaldehyde (98-03-3)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 80℃; for 8h;	99%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-methyl-N-[3-(4'-diacetoxyiodo)phenoxy-1-propyl]pyrrolidinium 4-methylbenzenesulfonate In dichloromethane at 20℃; for 3h;	99%
With Pd(0) nanoparticle supported on aminopropyl grafted silica-based mesocellular foam; air In para-xylene at 110℃; under 760.051 Torr; for 10h;	99%

2-thiophenemethanol (636-72-6) + 1,1'-carbonyldiimidazole (530-62-1) → imidazole-1-carboxylic acid thiophen-2-ylmethyl ester

Conditions	Yield
In ethyl acetate at 20℃; for 7h;	99%

2-thiophenemethanol (636-72-6) → thiophene-2-carbonitrile (1003-31-2)

Conditions	Yield
Stage #1: 2-thiophenemethanol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 3h; Inert atmosphere;	99%
With copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium hydroxide at 100℃; for 24h;	96%
With ammonia; oxygen In ethanol; water for 3h; Reflux;	91%

2-thiophenemethanol (636-72-6) + prenyl halide → prenyl 2-thiophenemethyl ether

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;	99%

2-thiophenemethanol (636-72-6) + ethylenediamine (107-15-3) → 2-(thiophen-2-yl)-4,5-dihydro-1H-imidazole (45753-18-2)

Conditions	Yield
Stage #1: 2-thiophenemethanol With iodine; potassium carbonate In tert-butyl alcohol at 70℃; for 8h; Stage #2: ethylenediamine In tert-butyl alcohol at 70℃; for 2h;	99%

2-thiophenemethanol (636-72-6) + benzyl bromide (100-39-0) → 2-((benzyloxy)methyl)thiophene (184040-47-9)

Conditions	Yield
Stage #1: 2-thiophenemethanol With sodium hydride In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; for 3h; Schlenk technique; Inert atmosphere;	99%
With tetra-(n-butyl)ammonium iodide; sodium hydroxide at 40 - 50℃; for 7h;	83%
In tetrahydrofuran	78%

2-thiophenemethanol (636-72-6) + aniline (62-53-3) → N-(thiophen-2-ylmethyl)aniline (40625-28-3)

Conditions	Yield
With copper; potassium hydroxide In toluene at 180℃; for 48h; Inert atmosphere;	99%
With potassium hydroxide In neat (no solvent) at 80℃; for 12h; Green chemistry;	91%
With zinc(II) nitrate hexahydrate; potassium tert-butylate In toluene at 140℃; for 36h; Sealed tube; Inert atmosphere; Schlenk technique;	91%

carbon disulfide (75-15-0) + 2-thiophenemethanol (636-72-6) → C6H5OS3(1-)*K(1+)

Conditions	Yield
With potassium hydroxide In diethyl ether at 20℃; for 12h;	99%

2-thiophenemethanol (636-72-6) → 2-Hydroxymethyl-5-iodothiophene (13781-27-6)

Conditions	Yield
With N-iodo-succinimide; toluene-4-sulfonic acid In ethanol at 25℃; for 0.166667h; Green chemistry; regioselective reaction;	98%
With iodine; mercury(II) oxide In toluene for 3h;	95%
With iodine; mercury(II) oxide In benzene for 1h;
With iodine; mercury(II) oxide In toluene Inert atmosphere; Schlenk technique;

2-thiophenemethanol (636-72-6) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 1-(thiophen-2-ylmethylene)-2-(2,4-dinitrophenyl)hydrazine

Conditions	Yield
Stage #1: 2-thiophenemethanol With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen In acetonitrile at 20℃; for 1h; Stage #2: (2,4-dinitro-phenyl)-hydrazine With hydrogenchloride In water; acetonitrile for 1h;	98%
Stage #1: 2-thiophenemethanol With peracetic acid; C9H17NO5S(1-)*C11H12IN2(1+); acetic acid In 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 8h; Stage #2: (2,4-dinitro-phenyl)-hydrazine With sulfuric acid In diethyl ether; ethanol; water	86%

2-thiophenemethanol (636-72-6) + benzamide (55-21-0) → N-(thiophen-2-yl-methyl)benzamide (4595-96-4)

Conditions	Yield
With C44H39IrN2P(1+)*C32H12BF24(1-); caesium carbonate In toluene at 120℃; for 12h; Inert atmosphere;	98%
With C23H24ClIrN3OS(1+)*F6P(1-); caesium carbonate In toluene at 120℃;	96%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In toluene at 130℃; for 12h;	86%
With caesium carbonate In toluene at 130℃; for 12h; Inert atmosphere; Schlenk technique;	185 mg
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In toluene at 130℃; for 12h;

4-methylbenzensulphonamide potassium salt (29281-83-2) + 2-thiophenemethanol (636-72-6) → 4-methyl-N-(thiophen-2-ylmethyl)benzenesulfonamide (545358-50-7)

Conditions	Yield
With potassium hydroxide at 130℃; for 25h; Schlenk technique; Inert atmosphere;	98%

2-thiophenemethanol (636-72-6) + pivaloyl chloride (3282-30-2) → thiophen-2-ylmethyl pivalate

Conditions	Yield
With dmap In dichloromethane at 24℃; Inert atmosphere;	98%
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere;	0.85 g

diphenylphosphinamide (5994-87-6) + 2-thiophenemethanol (636-72-6) → P,P-diphenyl-N-(thiophen-2-ylmethyl)phosphinic amide (1283087-86-4)

Conditions	Yield
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium hydroxide In toluene at 110℃; for 16h; Inert atmosphere; Sealed tube; Glovebox;	98%
With potassium hydroxide In toluene at 110℃; for 4h;	92%

2-thiophenemethanol (636-72-6) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl dimethyl(thiophen-2-ylmethoxy)silane

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 24h;	97%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	97%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 12h;	95%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 12h;	90%
With 1H-imidazole In N,N-dimethyl-formamide at 23℃; for 2h;	78%

2-thiophenemethanol (636-72-6) + acetic anhydride (108-24-7) → (thiophen-2-yl)methyl acetate (13679-77-1)

Conditions	Yield
With H3[P(Mo3O10)4]*nH2O at 20℃; for 0.166667h;	97%
With pyridine In dichloromethane at 20℃; for 24h; Inert atmosphere;	91%
With thalium(III) chloride tetrahydrate at 20℃; for 0.333333h;	87%
With dmap; triethylamine In dichloromethane at 20℃; for 19h;	86%

2-thiophenemethanol (636-72-6) → thiophene-2-carbaldehyde (98-03-3) + 2-Chloromethylthiophene (765-50-4)

Conditions	Yield
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium nitrite In dichloromethane; water at 20℃; under 760.051 Torr; for 12h; in air;	A 97% B 3%

2-thiophenemethanol (636-72-6) + acetophenone (98-86-2) → 2,6‑diphenyl‑4‑(thiophen‑2‑yl)pyridine (133726-93-9)

Conditions	Yield
Stage #1: 2-thiophenemethanol With 1-methylimidazolium nitrate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 96℃; for 0.0555556h; Ionic liquid; Microwave irradiation; Stage #2: acetophenone With ammonium acetate at 96℃; for 0.133333h; Ionic liquid; Microwave irradiation;	97%

N,N-phenyl-p-toluenesulfonylbenzamide (74542-54-4) + 2-thiophenemethanol (636-72-6) → thiophen-2-yl-methyl benzoate (85455-66-9)

Conditions	Yield
With cesium fluoride In acetonitrile at 100℃; for 15h; Sealed tube;	97%

9H-fluorene (86-73-7) + 2-thiophenemethanol (636-72-6) → 2-((9H-fluoren-9-yl)methyl)thiophene

Conditions	Yield
With potassium tert-butylate In toluene at 120℃; for 24h; Inert atmosphere;	97%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate In toluene at 120℃; for 18h; Inert atmosphere; Sealed tube;	62%

2-thiophenemethanol (636-72-6) → 2-Chloromethylthiophene (765-50-4)

Conditions	Yield
With thionyl chloride In toluene at 20 - 55℃; microwave irradiation;	96%
With thionyl chloride In toluene at 55℃; for 0.333333h; microwave irradiation;	96%
With thionyl chloride at 0 - 75℃; for 4h;	94%

methanol (67-56-1) + 2-thiophenemethanol (636-72-6) → thiophene-2-carboxylic acid methyl ester (5380-42-7)

Conditions	Yield
With dihydrogen peroxide for 3h; Irradiation;	96%
With oxygen at 20℃; for 12h; Irradiation;	93%
With iodine; potassium carbonate for 39h; Heating;	91%

Upstream product

• 765-50-4 2-Chloromethylthiophene 
• 98-03-3 thiophene-2-carbaldehyde 
• 62-53-3 aniline 
• 527-72-0 2-thiophenylcarboxylic acid 
• 32451-19-7 2-thiophen-2-yl-thiazolidine-4-carboxylic acid 
• 554-14-3 2-Methylthiophene 
• 7732-18-5 water 
• 7404-63-9 thiophen-2-ylmethanamine monohydrochloride 
• 121851-24-9 tetrahydropyranyl ether of 2-thiophenemethanol 
• 106-96-7 propargyl bromide 
• 188290-36-0 thiophene 
• 50-00-0 formaldehyd 
• 5919-31-3 2-(diazomethyl)thiophene 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 

Downstream Products

• 874911-05-4 (toluene-4-sulfonyl)-acetic acid thiophen-2-ylmethyl ester 
• 485824-59-7 methyl 2-nitro-5-(thien-2-ylmethoxy)benzoate 
• 386216-83-7 (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-8-(2-thenyloxy)-1H-1,4-benzodiazepine 
• 98-03-3 thiophene-2-carbaldehyde 
• 5918-68-3 (E)-N-phenyl-1-(thiophen-2-yl)methanimine 
• 872180-59-1 2-fluoro-6-(thiophen-2-ylmethoxy)benzonitrile 
• 1015445-61-0 4-[4-(4-fluorophenyl)-2-methylsulfanyl-1H-imidazol-5-yl]-2-(thiophen-2-ylmethoxy)pyridine 
• 140-19-2 2-<(2-thienylmethyl)amino>pyridine 
• 869099-20-7 C₂₆H₂₁F₆NO₃S₂ 
• 1107692-63-6 thien-2-ylmethyl 3-benzoylbenzoate 
• 545358-50-7 4-methyl-N-(thiophen-2-ylmethyl)benzenesulfonamide 
• 23259-98-5 2-thienylmethyltriphenylphosphonium bromide 
• 1003-31-2 thiophene-2-carbonitrile 
• 5813-89-8 2-thiophenylcarboxamide 

Relevant articles and documents

Redox-active ligand based Mn(i)-catalyst for hydrosilylative ester reduction

Herein a Mn(i) catalyst bearing a redox-active phenalenyl (PLY) based ligand is reported for the efficient hydrosilylation of esters to alcohols using the inexpensive silane source polymethylhydrosiloxane (PMHS) under mild conditions. Mechanistic investigations suggest a strong ligand-metal cooperation where a ligand-based single electron transfer (SET) process initiates the reaction through Si-H bond activation.

A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.

Potassium Fluoride-Catalyzed Hydroboration of Aldehydes and Ketones: Facile Reduction to Primary and Secondary Alcohols

A catalytic hydroboration of various ketones and aldehydes can be achieved in the presence of inexpensive and commercially available inorganic salts containing fluoride anion. As a result, the reduction of carbonyl moieties to the corresponding primary and secondary alcohols can be achieved at room temperature under mild conditions.