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Thiophen

Thiophene

HCID 8030
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Grundinformationen

CAS
110-02-1
Standard-SMILES
c1ccsc1
InChIKey
YTPLMLYBLZKORZ-UHFFFAOYSA-N
Summenformel
C4H4S
Durchschnittliche Molmasse
84,14 g/mol
Monoisotopische Masse
84,00337113

Überblick

Thiophene appears as a colorless liquid with an unpleasant odor. Insoluble in water and slightly denser than water. Flash point 30 °F. Vapors heavier than air. Irritates the skin, eyes, and mucous membranes. Used to make pharmaceuticals and dyes.

Namen und Bezeichner

Bevorzugter Name
Thiophene
IUPAC
thiophene
Lokaler Name
Thiophen
Englischer Name
Thiophene
Summenformel
C4H4S
Molmasse
84.14

Namen und Synonyme

THIOPHENE110-02-1ThiofuranThioleThiophenThiotetroleThiacyclopentadieneThiofurfuranDivinylene sulfideThiapheneThiofuramFuran, thio-
Weitere Namen anzeigen
CYP3AthiophenoneHLPcp34THIOPHENE FOR SYNTHESIS 5 MLThiophene, benzene free, extra pure, 99.5%CP33
Huile HSOThiofenHuile H50CP 34USAF EK-1860CCRIS 2935HSDB 130NSC 405073

Datenbank-Bezeichner

CAS
110-02-1
PubChem CID
8030
DTXSID
DTXSID8026145
ChEMBL
CHEMBL278958
ChEBI
CHEBI:30856
UNII
SMB37IQ40B
EC Number
203-729-4
Nikkaji
J1.162.593B、J2.445G

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,8
Polarare Oberfläche (TPSA)
28,2 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
5
Formalladung
0
Komplexität
22,8

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Thiophenes

Flammable agents - 3rd degree

SpringerMaterials PropertiesCoriolis coupling
LogP · 4 Einträge

log Kow = 1.81

1.81

1.81

1.89

OdorSLIGHT AROMATIC ODOR RESEMBLING BENZENE
Density · 3 Einträge

1.0649 at 68 °F (NTP, 1992) - Denser than water; will sink

1.06494 @ 20 °C/4 °C

Relative density (water = 1): 1.06

Viscosity0.621 mPa.s
Color/FormCOLORLESS LIQUID
Solubility · 6 Einträge

less than 1 mg/mL at 75 °F (NTP, 1992)

MISCIBLE IN ETHANOL, ETHER, ACETONE, AND BENZENE.

SOL IN ALL PROPORTIONS IN ORDINARY ORG SOLVENTS, CARBON TETRACHLORIDE, DIOXANE, PYRIMIDINE, TOLUENE

water solubility = 3,020 mg/l @ 25 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 1.5% (6 of 391) of reports.

Danger

H225 (98.5%): 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, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 391 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H402: Harmful to aquatic life [Hazardous to the aquatic environment, acute hazard]

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Thiophene

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 07-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12099

Thiophene: HSNO Approval: HSR001226 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.)

DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire PotentialA VERY DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 3 Einträge

THIOPHEN IS METABOLIZED IN VIVO TO PREMERCAPTURIC ACID AND 2-THIENYL-MERCAPTURIC ACID.

RABBITS FED THIOPHEN 150 MG/KG EXCRETED 40% OF DOSE IN URINE IN FORM OF 2 MERCAPTURIC ACIDS, BELIEVED TO BE THIENYL 3-MERCAPTURIC ACID & THIENYL 2-MERCAPTURIC ACID.

MAJOR METABOLITE OF THIOPHENE (200-300 MG/KG, ORALLY) IN RATS & RABBITS WAS 3-HYDROXY-2,3-DIHYDRO-2-THIENYLMERCAPTURIC ACID & 2-THIENYLMERCAPTURIC ACID WAS MINOR METABOLITE. IN RAT 32% OF THIOPHENE EXCRETED UNCHANGED IN EXPIRED AIR & 40% EXCRETED IN URINE AS MERCAPTURIC ACIDS.

Absorption, Distribution and Excretion · 4 Einträge

RABBITS FED THIOPHEN 150 MG/KG EXCRETED ABOUT 35% OF DOSE UNCHANGED IN EXPIRED AIR & 0.5% IN FECES.

(35)S-LABELED THIOPHENE APPLIED TO RABBIT SKIN OR INJECTED IP INTO RATS WAS IMMEDIATELY INCORPORATED INTO SKIN.

(35)S-LABELED THIOPHENE (250 MUCI) ADMIN ONCE SC TO RATS WAS RAPIDLY ABSORBED INTO BLOOD STREAM, DEPOSITED IN MAJOR ORGANS, & EXCRETED WITH URINE. URINE ANAL SHOWED 61.1% OF ISOTOPE WAS EXCRETED WITHIN 34 HR & 74.4% WITHIN 3 DAYS.

FOLLOWING RECTAL & ORAL ADMIN OF (14)C-LABELED THIOPHENE (33 MG/KG), PULMONARY EXCRETION WAS 40% & 5%, RESPECTIVELY.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 3 Einträge

Used as a solvent, chemical intermediate, and monomer to make copolymers; [HSDB]

ORGANIC SYNTHESIS; COPOLYMERIZES WITH MALEIC ANHYDRIDE

SOLVENT; INT FOR PHARMACEUTICALS, THIOPHENE-PHENOL/FORMALDEHYDE RESINS, AND NEMATOCIDE TETRACHLOROTHIOPHENE

U.S. Production · 2 Einträge

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) GREATER THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 2 Einträge

MADE AVAILABLE IN COMMERCIAL QUANTITIES BY PROCESS UTILIZING DEHYDROGENATION OF BUTANE WITH SULFUR AS DEHYDROGENATING AGENT, FOLLOWED BY CYCLIZATION WITH SULFUR TO FORM THIOPHENE RING. LAB PREPN BY HEATING SODIUM SUCCINATE WITH PHOSPHORUS TRISULFIDE. ALSO PREPARED BY PASSING ETHYLENE OR ACETYLENE INTO BOILING SULFUR; OR BY PASSING ACETYLENE AND HYDROGEN SULFIDE OVER HOT BAUXITE OR NICKEL HYDROXIDE.

Zugehörige Reaktionen

799
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HRID 2318als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2807
HRID 2807als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 5779
HRID 5779als Eduktuspto-grants-1993_09
Reaktionsgleichung von HRID 5844
HRID 5844als Eduktuspto-grants-1993_09
Reaktionsgleichung von HRID 23334
HRID 23334als Eduktuspto-grants-2005_02
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3.01 mg/mL at 25 °C

Solubility in water: none

Flash Point · 3 Einträge

30 °F (NTP, 1992)

30 °F (-1 °C) (CLOSED CUP)

-1 °C

Boiling Point · 4 Einträge

183.9 °F at 760 mmHg (NTP, 1992)

84.0 °C @ 760 MM HG

84.00 °C. @ 760.00 mm Hg

84 °C

Decomposition · 2 Einträge

WHEN HEATED TO DECOMPOSITION IT EMITS HIGHLY TOXIC FUMES OF SULFUR OXIDES.

May be heated to 850 °C without decomposition.

Melting Point · 4 Einträge

-36.8 °F (NTP, 1992)

-39.4 °C

-38.3 °C

-38 °C

Physikochemische Eigenschaften

Schmelzpunkt
-38 °C · -38 °C (lit.)
Siedepunkt
84 °C · 84 °C (lit.)
Dichte
1.051 g/mL · 1.051 g/mL at 25 °C (lit.)
Dampfdichte
2.9 · 2.9 (vs air)
Dampfdruck
40 mm · 40 mm Hg ( 12.5 °C)
Brechungsindex
20 · n20/D 1.529(lit.)
Flammpunkt
-9 °C · -9 °C
storage temp.
30 °C · Store below +30°C.
Löslichkeit
Miscible with carbon tetrachloride, heptane, pyrimidine, dioxane, toluene, and many organic solvents (quoted, Keith and Walters, 1992)
Aggregatzustand
powder
Farbe
Clear
Wichte
1.06 · 1.06
Geruch (Odor)
0.1 % · at 0.10 % in propylene glycol. alliaceous garlic
Geruchsart
sulfurous
Biologische Quelle
mouse
Odor Threshold
0.00056 ppm · 0.00056ppm
Explosionsgrenze
1.5 · 1.5-12.5%(V)
Wasserlöslichkeit
INSOLUBLE
Spezifische Wärmekapazität
1.47 J/ · Cp(liquid): 1.47 J/(g·K); Cp(gas): 0.87 J/(g·K), at 25℃
Merck
14 · 14,9353
BRN
103222 · 103222
Henry's Law Constant
2.33 and · 2.33 and 2.70 in distilled water and seawater, respectively (Przyjazny et al., 1983)
Dielectric constant
9.3 · 9.3(20℃)
Stabilität
Stable. Highly flammable. Incompatible with strong oxidizing agents, nitrates.
InChI
1S/C4H4S/c1-2-4-5-3-1/h1-4H
InChIKey
YTPLMLYBLZKORZ-UHFFFAOYSA-N
SMILES
c1ccsc1
LogP
1.81 · 1.81-1.86 at pH10
Oberflächenspannung
26.13 mN/m · 26.13mN/m at 298.15K
CAS Datenbank
110 · 110-02-1(CAS DataBase Reference)
NIST chemische Informationen
Thiophene(110-02-1)
EPA chemische Informationen
Thiophene (110-02-1)
Health Hazards · 2 Einträge

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

· May cause toxic effects if inhaled or absorbed through skin.

Hazards SummaryContact can cause redness of the eyes and skin; Inhalation can cause sore throat, cough and dizziness; [ICSC] May be toxic to the liver; [NJ-HSFS] A skin and eye irritant; May cause liver injury; [MSDSonline]
DOT ID and Guide2414 130
Reactive GroupHydrocarbons, Aromatic
UN ClassificationUN Hazard Class: 3; UN Pack Group: II
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 Eintrag

THIOPHENE reacts violently with strong oxidizing agents and concentrated nitric acid causing fire and explosion hazards [Handling Chemicals Safely 1980. p. 899]. A mixture of thiophene and N-nitrosoacetanilide exploded at 0 °C [Ber., 1887, 30, 367].

Chemical DangersDecomposes on heating and on burning. This produces toxic and irritating fumes (sulfur oxides). Reacts violently with oxidizing materials, including fuming nitric acid.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Use foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. 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 · 2 Einträge

· 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 · 2 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Safe StorageFireproof. Separated from oxidizing materials.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresFOAM, CARBON DIOXIDE, DRY CHEMICAL.
Nonfire Spill ResponseExcerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 Eintrag

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 · 2 Einträge

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Immediate precautionary measure

Eye PreventionWear safety goggles or eye protection in combination with breathing protection.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 230(SRC), determined from an experimental log Kow of 1.81(2) and a recommended regression-derived equation(3), indicates that thiophene is expected to have moderate mobility in soil(SRC). Volatilization of thiophene is expected from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mole(SRC), determined from an experimental vapor pressure of 79.7 mm Hg at 25 °C(4) and water solubility of 3,020 mg/l at 25 °C(5). Volatilization from dry soil surfaces is expected based upon the vapor pressure of this compound(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 230, determined from an experimental log Kow of 1.81(2) and a recommended regression-derived equation(3), indicates that thiophene may adsorb to suspended solids and sediment in water(SRC). Thiophene is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mole(SRC),determined from an experimental vapor pressure of 79.7 mm Hg at 25 °C(4) and water solubility of 3,020 mg/l at 25 °C(5). Estimated half-lives for a model river and model lake are 3 and 89, hours respectively(6,SRC). According to a classification scheme(7), experimental BCF values in the range of 2-7 measured for carp(8), suggests that bioconcentration in aquatic organisms is low(SRC). Biodegradation is not expected to be an important fate process for this compound(SRC). Using a standard BOD dilution technique and an activated sludge inoculum, a theoretical BOD of 0% was observed during a 2 week incubation period(8). No biodegradation was observed when thiophene was incubated in an aquifer slurry for a period of 1 year(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiophene, which has an experimental vapor pressure of 79.7 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase thiophene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and nitrate radicals with experimental atmospheric half-life of about 40 hours and 2.5 nighttime hours, respectively(SRC).

Food Survey ValuesThiophene was detected in the volatiles of Idaho Russet baked potatoes(1) and meat volatiles(2).
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour.
Signs and Symptoms · 3 Einträge

Cough. Dizziness. Sore throat.

Redness.

Redness. Pain.

Ongoing Test Status · 1 Eintrag

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=110-02-1]

Effluent Concentrations · 1 Eintrag

Thiophene was detected, not quantified, in the gas emissions of a Norwegian waste incinerator(1). Thiophene was detected at concentrations of 20-620 ppb in the leachate of a shale oil processing facility(2). Thiophene was detected in air samples above wastewater from shale oil processing facilities in Colorado and Utah at concentrations of 1-10 ng/l(3).

Soil Adsorption/Mobility · 1 Eintrag

The Koc of thiophene is estimated as approximately 230(SRC), using a measured log Kow of 1.81(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that thiophene is expected to have moderate mobility in soil(SRC).

Natural Pollution SourcesNaturally occurring source of thiophene is petroleum(1,2).
Human Toxicity ExcerptsIn man, tiophene has caused skin irritation and may induce sensitization responses. Nausea, itching and jaundice were seen in a woman repeatedly taking thiophene in suppositories.
Artificial Pollution SourcesThiophenes's production and use as an organic synthesis reagent and solvent(1,2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

Biodegradation is not expected to be an important environmental fate process for thiophene(SRC). No biodegradation was observed when thiophene was incubated in an anoxic aquifer slurry for a period of 3 months(1). Using a standard BOD dilution technique and an activated sludge inoculum, a theoretical BOD of 0% was observed during a 2 week incubation period(2). No biodegradation was observed when thiophene was incubated in an aquifer slurry for a period of 1 year(3).

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 2414
hs_code
29349990
RTECS-Nr.
XM7350000
risk_code
45-46-11-20/21/22-41-52/53-36-20/22-37/38-22-48/20/21/22
Toxizität
LD50 orally in Rabbit: 1400 mg/kg
hazard_code
F,Xn,Xi,T
hazard_note
Irritant/Highly Flammable
safety_code
53-26-39-45-61-36/37/39-16-36
hazard_class
3
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
110-02-1(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 2
Selbstentzündungstemperatur
743 °F

FROM...PETROLEUM; SYNTHETICALLY FROM HEATING SODIUM SUCCINATE WITH PHOSPHORUS TRISULFIDE.

General Manufacturing Information · 6 Einträge

Thiophene: ACTIVE

THIOPHENE IS A SULFUR-CONTAINING FLAVOR COMPOUND FORMED BY MAILLARD REACTIONS IN HEAT-PROCESSED COFFEE AND BEEF. /FROM TABLE/

/THIOPHENE IS A/ SOLVENT SIMILAR TO BENZENE, BUT SUITABLE FOR LOWER & HIGHER TEMPERATURES...

STUDIES WERE CONDUCTED ON DEODORIZATION CATALYSTS. THIOPHENE WAS USED AS MODEL IN LOW CONCN RANGE.

MILK XANTHINE OXIDASE CATALYZED THE OXIDATION OF CROTONALDEHYDE WHEN PRESENT AS A SUSPENSION IN THIOPHENE OR IN OTHER NONPOLAR SOLVENTS.

FOUND IN COAL TAR, IN COAL GAS & TECHNICAL BENZENE.

Anwendungen

VerwendenThiophene is used as a building block of various organic molecules and pharmaceuticals providing functional properties.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Motor benzolSolid sodium hydroxideMethylthiopheneDestillate (Kohlenteer)ButanDiphosphortrisulfid

Nachgelagerte Produkte

5-Oxo-5-(2-thienyl)valeric acidBis(2-thienyl) ketone2-Thiophenbuttersaeure2-(Trimethylacetyl)thiophene1,4,5,6-Tetrahydro-1-methyl-2-(2-(2-thienyl)-ethenyl)pyrimidin,(E)-2-IodthiophenNocodazol3-Thiophen-2-yl-benzaldehyde2-(N-Heptanoyl)thiophene2-Thiophenesulfonyl chloride3-(2-Thenoyl)propionsaeure(2-Thienylmethyl)amin(4-Amino-3-nitrophenyl)-(2-thienyl)methanonePhenyl-2-thienylketon2-(Trifluoroacetyl)thiophene2-Thienylessigsaeure2-(4-Bromophenyl)thiophene5-(2-Thienyl)pentanoic acid2-(5-Bromo-2-thienyl)pyridine(4-Methoxy-3-nitrophenyl)-(thiophen-2-yl)methanone ,98%p-Anisylthiophen-2-ylketon
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Thiophene is a monocyclic heteroarene that is furan in which the oxygen atom is replaced by a sulfur. It has a role as a non-polar solvent. It is a mancude organic heteromonocyclic parent, a member of thiophenes, a monocyclic heteroarene and a volatile organic compound.