Conditions | Yield |
---|---|
With N,N-dimethylthioformamide; sulfuric acid In acetone at 30℃; for 3h; | 100% |
With benzo[1,3,2]dioxaborole In benzene-d6 at 20℃; for 0.25h; | 100% |
With carbon monoxide; 1 wt% Au/TiO2; water In acetone at 60℃; under 7600.51 Torr; for 5h; Autoclave; | 99% |
Conditions | Yield |
---|---|
With sodium sulfide; N-benzyl-N,N,N-triethylammonium chloride In 1-methyl-pyrrolidin-2-one at 50 - 100℃; Solvent; Temperature; Reagent/catalyst; Concentration; | 98.8% |
With sodium sulfide; N,N-dimethyl-formamide | |
With sodium sulfide; ethylene glycol | |
With sodium sulfide; ethanol |
Conditions | Yield |
---|---|
With sodium sulfide In dimethyl sulfoxide at 150℃; for 0.333333h; | 95% |
With sodiumsulfide nonahydrate Reflux; | 78% |
With aluminum oxide; sulfide ion In toluene at 95℃; for 20h; | 44.7% |
With ethanol; alkali sulfide | |
With sodium sulfide; ethanol |
Conditions | Yield |
---|---|
With hydrogen sulfide; carbon monoxide at 370℃; for 6h; Ring cleavage; Dehydration; | 85% |
With aluminum oxide; hydrogen sulfide at 400℃; | |
With aluminium oxide-chromium oxide; hydrogen sulfide at 300℃; | |
With aluminium oxide-chromium oxide; hydrogen sulfide at 265℃; |
4-Mercapto-1-butanol
thiophene
Conditions | Yield |
---|---|
With 2,2,2-triphenyl-4,5-(2',2''-biphenyleno)-1,3,2-dioxyphospholane Ambient temperature; | 85% |
With BNTP In dichloromethane at 40℃; for 24h; | 93 % Chromat. |
With diethoxyltriphenylphosphorane In toluene at -25℃; for 6h; Yield given; | |
at 350℃; under 760.051 Torr; for 1h; Inert atmosphere; Flow reactor; |
(tetrahydrothiophene)gold(I) chloride
A
thiophene
Conditions | Yield |
---|---|
In dichloromethane byproducts: AgCl; addn. of solid Au compd. to the phosphonium salt in CH2Cl2 at room temp. and stirring for 3 h; filtn., concn. and addn. of diethyl ether; elem. anal.; | A n/a B 85% |
hydrogenchloride
Cp(CO)2W(η(2)-DHTH)
triphenylphosphine
A
thiophene
Conditions | Yield |
---|---|
In dichloromethane addn. of HCl to the metal complex; color change from yellow to red; addn. of PPh3; stirring (15 min); removing solvent; extn. with CHCl3; removing solvent in vac. from the ext.; | A n/a B 81% |
S-1-hexylthiolanium tetrafluoroborate
potassium selenocyanate
A
thiophene
B
n-hexyl selenocyanate
Conditions | Yield |
---|---|
In ethanol at 80℃; for 24h; | A n/a B 73% |
S-methylthiolanium cation
A
thiophene
B
methane
C
methane-d3
D
n-butyl methyl sulfide
Conditions | Yield |
---|---|
With diclazuril; water-d2; mercury; zinc; Ni(I)-F430 pentamethyl ester In N,N-dimethyl-formamide at 25℃; Kinetics; reductive cleavage of methyl sulphonium salts, deuterated methane formation; | A 67% B 70% C n/a D 30% |
S-methylthiolanium cation
A
thiophene
B
methane
C
n-butyl methyl sulfide
Conditions | Yield |
---|---|
With hydrogenchloride; water; mercury; zinc; Ni(I)-F430 pentamethyl ester In N,N-dimethyl-formamide at 25℃; Kinetics; reductive cleavage of methyl sulphonium salts, CH4 formation; | A 67% B 70% C 30% |
pyrrolidine
CpV(CO)3(tetrahydrothiophene)
A
thiophene
(C5H5)V(CO)3(C4H8NH)
Conditions | Yield |
---|---|
In toluene soln. concd. to a small vol., addn. of hexane and cooling the soln. to -30°C yields crystals; elem. anal.; | A n/a B 57.8% |
[2,2]bipyridinyl
CpV(CO)3(tetrahydrothiophene)
A
thiophene
tetracarbonylcyclopentadienylvanadium
cis-(η5-C5H5)V(CO)2*bipyridine
Conditions | Yield |
---|---|
In toluene soln. allowed to stand at room temp. overnight; elem. anal.; | A n/a B n/a C 48.9% |
potassium thioacyanate
A
thiophene
B
methyl thiocyanate
C
erucin
D
4-(methylthio)butyl thiocyanate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 70℃; for 7h; Yields of byproduct given; | A n/a B n/a C n/a D 45% |
1-oxothiolane
1-ethenyl-4-methylbenzene
Ethyl bromodifluoroacetate
A
thiophene
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III) at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; | A n/a B 33% |
Conditions | Yield |
---|---|
With biphenyl; tetraethylammonium perchlorate In water; N,N-dimethyl-formamide electrolysis in a separated cell, the operating electrode was mercury, the reference electrode was the saturated calomel electrode, initial current was 150 mA; | A 19.7% B 24% |
With biphenyl; tetraethylammonium perchlorate In water; N,N-dimethyl-formamide electrolysis in a separated cell, the operating electrode was mercury, the reference electrode was the saturated calomel electrode, initial current was 150 mA; | A 19.7% B 24% |
With biphenyl; tetraethylammonium perchlorate In water; N,N-dimethyl-formamide Product distribution; electrolysis in a separated cell, the operating electrode was mercury, the reference electrode was the saturated calomel electrode, initial current 150 mA; other solvent; | A 19.7% B 24% |
1,1,2,3,4,5-hexahydro-1-<<(4-methylphenyl)sulfonyl>imino>tiophene
thiophene
Conditions | Yield |
---|---|
With 1,4-dibromo-butane; zinc at 150℃; for 2h; | 20% |
With dimethylsilicon dichloride; zinc Ambient temperature; |
thiophene
thiophene
Conditions | Yield |
---|---|
With 10% Ru/MgO; hydrogen at 200℃; under 38002.6 Torr; for 24h; | 11% |
With rhenium heptasulfide at 250℃; under 220652 Torr; Hydrogenation; | |
With methanol; palladium on activated charcoal; sulfuric acid Hydrogenation; |
Conditions | Yield |
---|---|
With palladium on activated charcoal; ethanol Hydrogenation; |
Conditions | Yield |
---|---|
With ethanol; alkali sulfide |
Conditions | Yield |
---|---|
With aluminum oxide; hydrogen sulfide at 400℃; | |
With hydrogen sulfide at 230 - 250℃; for 0.00138889h; Reagent/catalyst; Temperature; Flow reactor; |
thiophene
Conditions | Yield |
---|---|
beim Erhitzen; |
thiophene
A
thiophene
B
trans-2-Butene
C
Isobutane
D
Dibutyl sulfide
E
2-methylpropan-2-thiol
F
isobutene
Conditions | Yield |
---|---|
aluminum oxide; cobalt molybdenum In n-heptane at 290℃; under 21280 Torr; Product distribution; Mechanism; effect of temperature, pressure and contact time; |
thiophene
A
thiophene
B
1-butylene
C
(Z)-2-Butene
D
trans-2-Butene
E
buta-1,3-diene
F
n-butane
Conditions | Yield |
---|---|
With hydrogen sulfide; hydrogen; aluminum oxide; molybdenum at 399.9℃; Product distribution; other catalysts; conversion of thiophene, product selectivities; |
thiophene
A
thiophene
B
1-butylene
C
butene-2
D
n-butane
Conditions | Yield |
---|---|
With aluminum oxide; cobalt molybdenum; hydrogen sulfide; hydrogen at 300℃; rate of thiophene disappearance as a function of the actual H2S at various temperatures; |
Conditions | Yield |
---|---|
Al(III)-montmorillonite at 175℃; for 1h; | 66 % Chromat. |
With hydrogen at 350℃; under 760.051 Torr; for 1h; Flow reactor; |
4-Mercapto-1-butanol
diethoxyltriphenylphosphorane
A
thiophene
B
4-(ethylthio)-1-butanol
Conditions | Yield |
---|---|
In toluene at 25℃; | A 65 % Spectr. B 35 % Spectr. |
Conditions | Yield |
---|---|
In cyclohexane at 80℃; Yield given. Yields of byproduct given; |
thiophene
thiophene
Conditions | Yield |
---|---|
MTB-4A catalyst at 230℃; under 413.729 Torr; Product distribution / selectivity; Inert atmosphere; | 100% |
at 500℃; Product distribution; gas phase pyrolysis; | 10% |
beim Durchleiten durch ein dunkelrotgluehendes Glasrohr; |
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; tetrabutylammomium bromide In dichloromethane; water for 0.25h; Ambient temperature; | 100% |
With water; silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane for 1h; Ambient temperature; | 100% |
With bromine; silica gel In dichloromethane for 0.833333h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane for 0.833333h; Heating; | 100% |
With sodium tungstate (VI) dihydrate; dihydrogen peroxide In methanol; water at 40℃; | 100% |
With selenium(IV) oxide; dihydrogen peroxide In water; ethyl acetate chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With silver tetrafluoroborate In acetonitrile for 72h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With silver tetrafluoroborate In acetonitrile for 72h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With silver tetrafluoroborate In acetonitrile for 72h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With silver tetrafluoroborate In acetonitrile for 72h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With silver tetrafluoroborate In acetonitrile for 72h; Ambient temperature; | 100% |
thiophene
12-iodododecan-1-oic acid
Conditions | Yield |
---|---|
With silver perchlorate In acetonitrile for 72h; Ambient temperature; | 100% |
With silver perchlorate In acetonitrile |
thiophene
(2E,4E)-1-bromo-2,4-pentadecadiene-6,9-diyne
(E,E)-2,4-pentadecadien-6,9-diyn-1-yl tetrahydrothiophenium bromide
Conditions | Yield |
---|---|
In methanol; water for 1h; Ambient temperature; | 100% |
In methanol; water for 0.666667h; Ambient temperature; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 25℃; for 3h; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; Green chemistry; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; Green chemistry; | 100% |
Conditions | Yield |
---|---|
In toluene at 20℃; for 0.0833333h; Inert atmosphere; | 100% |
thiophene
(η6-toluene)bis(η1-pentafluorophenyl)cobalt(II)
bis(pentafluorophenyl)bis(tetrahydrothiophene)cobalt(II)
Conditions | Yield |
---|---|
In dichloromethane tetrahydrothiophene was added to a soln. of Co complex under N2; evapn.; washing with pentane, drying in vac. for 5 min; elem. anal.; | 99% |
thiophene
(η(5)-C5H4C(O)CH2OCH3)Mn(CO)3
(η(5)-C5H4C(O)CH2OCH3)Mn(CO)2(tetrahydrothiophene)
Conditions | Yield |
---|---|
In cyclohexane byproducts: CO; Irradiation (UV/VIS); irradiation of mixt. of Mn-complex and tetrathiophene soln. (350 nm light source, 46 min, IR monitoring); filtration (Celite), solvent removal (vac.), chromy. (SiO2, 8% EtOAc-C6H6), evapn.; elem. anal.; | 99% |
In n-heptane Kinetics; Ar-atmosphere; at least 10 times excess of C4H8S; not isolated; detd. by UV-VIS spectroscopy; |
thiophene
fac-[Re(CO)3(THF)((Ph2C4HN)2N)]
fac-[Re(CO)3(tetrahydrothiophene)((Ph2C4HN)2N)]
Conditions | Yield |
---|---|
In thiophene dissolving of Re(CO)3(THF)(N(C4HNPh2)2) in THT; pentane vapor diffusion; crystn.; | 99% |
thiophene
trifluoromethanesulfonic acid 2-fluoroethyl ester
Conditions | Yield |
---|---|
In neat (no solvent) at 60℃; for 15h; Inert atmosphere; Sealed tube; | 99% |
thiophene
trichloro(tetrahydrothiophene)gold(III)
(tetrahydrothiophene)gold(I) chloride
Conditions | Yield |
---|---|
In ethanol; water | 98.9% |
Conditions | Yield |
---|---|
In methanol at 25℃; for 22h; | 98.5% |
In methanol at 20℃; for 16h; | 95% |
In dichloromethane at 20℃; for 168h; | 86% |
Conditions | Yield |
---|---|
With p-methylbenzenesulfenyl chloride; lithium perchlorate In nitromethane at 20℃; for 10h; | A n/a B 98% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 90h; Inert atmosphere; | 98% |
In methanol for 60h; Ambient temperature; | 91% |
In methanol Heating; | 80% |
Conditions | Yield |
---|---|
In thiophene Ar; stirring (room temp., 1 h); crystn. on cooling (-20°C, 2 d), drying (vac., 20 min); elem. anal.; | 98% |
Conditions | Yield |
---|---|
With diiron nonacarbonyl; di-tert-butyl peroxide for 1h; Reflux; | 98% |
thiophene
[Pt(7,8-benzo[h]quinolinyl)(pentafluorophenyl)(acetone)]
[Pt(C6F5)(bzq)(tht)]
Conditions | Yield |
---|---|
In acetone at 0℃; for 0.0333333h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; Green chemistry; | 98% |
thiophene
(tetrahydrothiophene)gold(I) chloride
Conditions | Yield |
---|---|
In ethanol; water at 20℃; for 0.5h; | 98% |
In ethanol at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 98% |
In ethanol; water | 65% |
Conditions | Yield |
---|---|
With iron(III) acetylacetonate In dichloromethane at 20℃; under 2100.21 Torr; for 0.833333h; Flow reactor; UV-irradiation; | 98% |
The Tetrahydrothiophene, with the CAS registry number 110-01-0 and EINECS registry number 203-728-9, is also known as Thiophane. And the molecular formula of this chemical is C4H8S. It is the saturated analog of thiophene. Besides, it is a volatile, clear, colorless liquid with a strong unpleasant odor,and stability Highly flammable,vapour-air mixtures explosive in some proportions; note low flash point and fairly wide explosion limit range. Heavier than air, so potentially explosive mixtures may travel considerable distances to source of ignition .It is used as a solvent and to make other chemicals.
The physical properties of Tetrahydrothiophene are as following:
(1)ACD/LogP: 1.34; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.34; (4)ACD/LogD (pH 7.4): 1.34; (5)ACD/BCF (pH 5.5): 6.1; (6)ACD/BCF (pH 7.4): 6.1; (7)ACD/KOC (pH 5.5): 127.03; (8)ACD/KOC (pH 7.4): 127.03; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 25.3 Å2; (13)Index of Refraction: 1.515; (14)Molar Refractivity: 26.6 cm3; (15)Molar Volume: 88.1 cm3; (16)Polarizability: 10.54×10-24cm3; (17)Surface Tension: 35.7 dyne/cm; (18)Density: 0.999 g/cm3; (19)Flash Point: 12.8 °C; (20)Enthalpy of Vaporization: 34.66 kJ/mol; (21)Boiling Point: 121.5 °C at 760 mmHg; (22)Vapour Pressure: 17.5 mmHg at 25°C.
Preparation and uses of Tetrahydrothiophene:
It can be prepared by 1,4-dibromobutane and sodium sulfide in the solvent alcohol. It is occasionally used as an odorant in natural gas because of its smell. It is also used as a solvent, as an insecticide, and as a moth repellant. It is an intermediate in the preparation of the solvent sulfolane, which is produced by the oxidation of tetrahydrothiophene. In addition, it is also used as an electrolyte for lithium batteries.
Safety information of Tetrahydrothiophene:
You should be cautious while dealing with this chemical. It is a kind of highly flammable chemical which irritates eyes and skin. It is also harmful by inhalation, in contact with skin and if swallowed. Besides, it is harmful to aquatic organisms, and may cause long-term adverse effects in the aquatic environment. Therefore, you had better take the following instructions: Wear suitable protective clothing and gloves; Keep away from food, drink and animal feeding stuffs; Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer); Avoid release to the environment. Refer to special instructions safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: S1CCCC1
(2)InChI: InChI=1/C4H8S/c1-2-4-5-3-1/h1-4H2
(3)InChIKey: RAOIDOHSFRTOEL-UHFFFAOYAY
The toxicity data of Tetrahydrothiophene is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 27gm/m3/2H (27000mg/m3) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1088, 1986. | |
rat | LD50 | oral | 1750mg/kg (1750mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0555157, |
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