Basic information
- Standard SMILES
C1CCSC1- InChIKey
RAOIDOHSFRTOEL-UHFFFAOYSA-N- Molecular formula
- C4H8S
- Average molar mass
- 88.17 g/mol
- Monoisotopic mass
- 88.03467126
Overview
Tetrahydrothiophene appears as a water-white liquid. About the same density as water and insoluble in water. Vapors heavier than air. Used as a solvent and to make other chemicals.
Names & identifiers
- Preferred name
- Tetrahydrothiophene
- IUPAC
- thiolane
- English name
- Tetrahydrothiophene
- Molecular formula
- C4H8S
- Molecular weight
- 88.17
Names & synonyms
Show more names
Database identifiers
- CAS
110-01-0- PubChem CID
- 1127
- DTXSID
DTXSID3047760- ChEMBL
CHEMBL1379- ChEBI
CHEBI:48458- UNII
- 744EHT13FM
- EC Number
- 203-728-9
- Nikkaji
- J2.444I
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 25.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 22.8
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Thiophenes
Flammable agents - 3rd degree
LogP
1.8 (estimated by method of Leo et al, 1971).
1.8
Density
0.9987 @ 20 °C/4 °C
Relative density (water = 1): 1.0
Solubility
INSOLUBLE IN WATER; SOL IN ALL PROPORTIONS IN ALCOHOL, ETHER, ACETONE, BENZENE, IN ORGANIC SOLVENTS
Solubility in water: none
Flash Point
55 °F (12 °C)
12 °C
Boiling Point
121.12 °C @ 760 MM HG
119-121 °C
Melting Point
-96.16 °C
-96.2 °C
Physicochemical properties
- Melting point
- -96 °C · -96 °C (lit.)
- Boiling point
- 119 °C · 119 °C (lit.)
- Density
- 1 g/mL · 1 g/mL at 25 °C (lit.)
- vapor pressure
- 18 mm · 18 mm Hg ( 25 °C)
- refractive index
- 20 · n20/D 1.504(lit.)
- Flash point
- 55 °F · 55 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- immiscible
- form
- liquid
- Specific Gravity
- 1.002 · 1.002 (20/4℃)
- color
- Colorless to Almost colorless
- Odor
- Smells of rotting eggs
- PH
- 7 · 7 (H2O, 20℃)
- explosive limit
- 1.1 · 1.1-12.1%(V)
- Odor Threshold
- 0.00062 ppm · 0.00062ppm
- Odor Type
- sulfurous
- Water Solubility
- immiscible
- Specific Heat Capacity
- 1.05 J/ · Cp(gas): 1.05 J/(g·K), at 25℃
- Merck
- 14 · 14,9218
- BRN
- 102392 · 102392
- Henry's Law Constant
- 2.2 · 2.2×10-3 mol/(m3Pa) at 25℃, Yaws et al. (2003)
- Dielectric constant
- 8.61 · 8.6099999999999994
- 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.
- InChI
- 1S/C4H8S/c1-2-4-5-3-1/h1-4H2
- InChIKey
- RAOIDOHSFRTOEL-UHFFFAOYSA-N
- SMILES
- C1CCSC1
- LogP
- 1.8 at · 1.8 at 20℃
- CAS DataBase Reference
- 110 · 110-01-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-2
- FDA UNII
- 744 EHT13FM · 744EHT13FM
- NIST Chemistry Reference
- Thiophene, tetrahydro-(110-01-0)
- EPA Substance Registry System
- Tetrahydrothiophene (110-01-0)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302+H312+H332-H315-H319-H412-H225
- Precautionary statements
- 501 · P501-P261-P273-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P301+P312+P330-P304+P340+P312-P403+P235
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xn
- Risk Statements
- 11 · 11-20/21/22-36/38-52/53
- Safety Statements
- 16 · 16-23-36/37-61
- RIDADR
- 2412 · UN 2412
- WGK Germany
- 2 · 2
- RTECS
- 370000 · XN0370000
- Autoignition Temperature
- 202 °C · 202 °C
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29349990 · 29349990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2
- Hazardous Substances Data
- 110 · 110-01-0(Hazardous Substances Data)
- Toxicity
- 50 by · LD50 by inhalation in mice: 26.7 mg/l (Carlucci)
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 11.5% (36 of 314) of reports.
Danger
H225 (88.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]
Hazard information
Regulatory Information
Chemical: Thiophene, tetrahydro-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Thiophene, tetrahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Thiophene, tetrahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 29-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/2145
Thiophene, tetrahydro-: HSNO Approval: HSR001225 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Highly flammable. Heating will cause rise in pressure with risk of bursting. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.
Health Hazards
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
· May cause toxic effects if inhaled or absorbed through skin.
Safety & protection
Fire Fighting
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
Use water spray, alcohol-resistant foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest.
Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Rest.
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
General First Aid:
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
50.0 [ppm]
Spillage Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
Isolation and Evacuation
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
Immediate precautionary measure
Toxicology
Environmental Fate
Atmospheric: Expected to rapidly oxidize by hydroxyl radicals in the atmosphere.
Terrestrial: Little tendency to sorb to soil.
Human Toxicity Excerpts
Workers at a factory producing tetrahydrothiophene complained of headache, palpitations, giddiness, nausea or a general feeling of being unwell, after a short (unspecified) exposure.
...APPEARS TO BE SLIGHTLY LESS TOXIC THAN THIOPHENE. HOWEVER, LITTLE INFORMATION IS AVAILABLE.
Non-Human Toxicity Excerpts
In studies conducted according to FHSA using the patch test technique on albino rabbit skin, the substance did not produce visible destruction or irreversible alterations in the tissue at the site of contact; not a skin irritant.
In studies conducted according to FHSA using the standard eye irritation test in albino rabbits, the noncorrosive substance did not induce local inflammatory reaction; not an eye irritant.
American Cyanamid (1982) tested tetrahydrothiophene in Salmonella Ames assay. The compound did not show mutagenicity to strains TA98, TA100, TA1535, and TA1537 at a concentration of 1000 ul/plate. Information on metabolic activation was not given. The compound was also non-mutagenic to strain WP-2 uvrA- of E. coli.
EPA Provisional Peer-Reviewed Toxicity Values
Tetrahydrothiophene
PDF Document
Inadequate information to assess carcinogenic potential
2007
Regulatory information
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- XN0370000
- ridadr
- UN 2412
- hs_code
- 29349990
- Toxicity
- LD50 by inhalation in mice: 26.7 mg/l (Carlucci)
- risk_code
- 11-20/21/22-36/38-52/53
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xn
- safety_code
- 16-23-36/37-61
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H302+H312+H332-H315-H319-H412-H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2
- Autoignition Temperature
- 202 °C
- Precautionary statements
- P501-P261-P273-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P301+P312+P330-P304+P340+P312-P403+P235
- Hazardous Substances Data
- 110-01-0(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used as a solvent, chemical intermediate, and odorant for fuel gas and other gases and liquids; [HSDB]
SOLVENT; INTERMEDIATE; FUEL GAS ODORANT
A HERBICIDAL COMPOSITION BASED ON BIPYRIDYLIUM COMPD CONTAIN TETRAHYDROTHIOPHENE AS THE OLFACTORY ALERTING AGENT IN ORDER TO AVERT INADVERTENT POISONING
THIOLANE IS USED AS A GROWTH REGULATOR
Used in odorization operations of natural gas.
For more Uses (Complete) data for TETRAHYDROTHIOPHENE (8 total), please visit the HSDB record page.
U.S. Production
2023: 75,000 - <500,000 lb
200,000 to 2,000,000 lb
Methods of Manufacturing
Vapor-phase reaction of tetrahydrofuran and hydrogen sulfide over a heteropolyacid-promoted metal oxide catalyst followed by separation and distillation of tetrahydrothiophene.
Thiophene is reduced to tetrahydrothiophene by sodium in alcohol or ammonia, or with palladium, cobalt, molybdenum or rhenium catalysts under carefully controlled conditions.
General Manufacturing Information
Utilities
Thiophene, tetrahydro-: ACTIVE
A DISCUSSION IS GIVEN ON WASTEWATER FORMED IN NATURAL GAS UNDERGROUND STORAGE RESERVOIRS; ON AIR POLLUTION & WASTEWATERS; ON METHODS FOR TREATMENTS OF WASTEWATERS AND THE PREVENTION & CONTROL OF AIR POLLUTION IN THE ODORIZATION OF NATURAL GAS WITH TETRAHYDROTHIOPHENE.
Applications
UsesTetrahydrothiophene is a solvent and a fuel gas odorant used in fire safety stench warning systems in underground mines. Tetrahydrothiophene was also used as an organocatalyst for the reaction between enynediones and benzoic acid to afford highly substituted furfuryl alcohol benzoates.
UsesTetrahydrothiophene is used as pharmaceutical and agrochemical intermediates.
General DescriptionA water-white liquid. About the same density as water and insoluble in water. Flash point near 20°F. Vapors heavier than air. Used as a solvent and to make other chemicals.
Preparation methods
PreparationTetrahydrothiophene is prepared by the reaction of hydrogen sulfide and furan in the vapor phase at 400°C. This vapor-phase reaction is catalyzed by alumina(Al2O3) and other heterogenous acid catalysts.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Tetrahydrothiophene is a saturated organic heteromonocyclic parent and a member of tetrahydrothiophenes.
Related reactions
Linked notes
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