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110-01-0

Basic Information
CAS No.: 110-01-0
Name: Tetrahydrothiophene
Article Data: 153
Molecular Structure:
Molecular Structure of 110-01-0 (Tetrahydrothiophene)
Formula: C4H8S
Molecular Weight: 88.1735
Synonyms: NSC 5272;THT;Tetrahydrothiophen;Tetrahydrothiophene;Tetramethylene sulfide;Thiacyclopentane;Thilane;Thiolane;Thiophane;
EINECS: 203-728-9
Density: 0.999 g/cm3
Melting Point: -96 °C
Boiling Point: 121.5 °C at 760 mmHg
Flash Point: 12.8 °C
Solubility: immiscible in water
Appearance: volatile, clear, colorless liquid with a strong unpleasant odor
Hazard Symbols: FlammableF; HarmfulXn
Risk Codes: 11-20/21/22-36/38-52/53
Safety: 16-23-36/37-61
Transport Information: UN 2412
PSA: 25.30000
LogP: 1.51340
Synthetic route
1600-44-8

1-oxothiolane

110-01-0

thiophene

Conditions
ConditionsYield
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%
110-56-5

1,4-dichlorobutane

110-01-0

thiophene

Conditions
ConditionsYield
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
110-52-1

1,4-dibromo-butane

110-01-0

thiophene

Conditions
ConditionsYield
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
109-99-9

tetrahydrofuran

110-01-0

thiophene

Conditions
ConditionsYield
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℃;
14970-83-3

4-Mercapto-1-butanol

110-01-0

thiophene

Conditions
ConditionsYield
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;
39929-21-0

(tetrahydrothiophene)gold(I) chloride

{silver(I)2(μ-((CHPPh3)2)CO)2} diperchlorate*n acetone

A

110-01-0

thiophene

B

{gold(I)2(μ-((CHPPh3)2)CO)2} diperchlorate*n acetone

Conditions
ConditionsYield
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%
7647-01-0

hydrogenchloride

121268-49-3

Cp(CO)2W(η(2)-DHTH)

603-35-0

triphenylphosphine

A

110-01-0

thiophene

B

CpW(CO)2(PPh3)Cl

Conditions
ConditionsYield
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%
918945-49-0

S-1-hexylthiolanium tetrafluoroborate

3425-46-5

potassium selenocyanate

A

110-01-0

thiophene

B

60669-47-8

n-hexyl selenocyanate

Conditions
ConditionsYield
In ethanol at 80℃; for 24h;A n/a
B 73%
45377-03-5

S-methylthiolanium cation

A

110-01-0

thiophene

B

34557-54-5

methane

C

676-80-2

methane-d3

D

628-29-5

n-butyl methyl sulfide

Conditions
ConditionsYield
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%
45377-03-5

S-methylthiolanium cation

A

110-01-0

thiophene

B

34557-54-5

methane

C

628-29-5

n-butyl methyl sulfide

Conditions
ConditionsYield
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%
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Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

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,