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Thiophen
Thiophen · CYP3A · THIOFURAN · thiophenone · HLP · cp34 · Thiacyclopentadiene · THIOPHENE FOR SYNTHESIS 5 ML
Identifikatoren & physikalische Daten
| CAS No. | 110-02-1 |
|---|---|
| Summenformel | C4H4S |
| Durchschnittliche Molmasse | 84,14 g/mol |
| Monoisotopische Masse | 84,00337113 g/mol |
| SMILES | c1ccsc1 |
| InChIKey | YTPLMLYBLZKORZ-UHFFFAOYSA-N |
| PubChem CID | 8030 |
| ChEMBL | CHEMBL278958 |
| ChEBI | CHEBI:30856 |
| EC No. | 203-729-4 |
| DTXSID | DTXSID8026145 |
| Lokaler Name | Thiophen |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 28,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 22,8 |
| Stoffklassen | Other Classes -> ThiophenesFlammable agents - 3rd degree |
| SpringerMaterials Properties | Coriolis coupling |
| LogP (Verteilungskoeffizient) | log Kow = 1.811.89 |
| Geruch | SLIGHT AROMATIC ODOR RESEMBLING BENZENE |
| Dichte | 1.0649 at 68 °F (NTP, 1992) - Denser than waterwill sink1.06494 @ 20 °C/4 °CRelative density (water = 1): 1.061.051 g/mL at 25 °C (lit.) |
| Viscosity | 0.621 mPa.s |
| Color/Form | COLORLESS LIQUID |
| Löslichkeit | 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, TOLUENEwater solubility = 3,020 mg/l @ 25 °C3.01 mg/mL at 25 °CSolubility in water: noneMiscible with carbon tetrachloride, heptane, pyrimidine, dioxane, toluene, and many organic solvents (quoted, Keith and Walters, 1992)INSOLUBLE |
| Flammpunkt | 30 °F (NTP, 1992)30 °F (-1 °C) (CLOSED CUP)-9 °C |
| Siedepunkt | 183.9 °F at 760 mmHg (NTP, 1992)84.0 °C @ 760 MM HG84.00 °C. @ 760.00 mm Hg84 °C84 °C (lit.) |
| Decomposition | WHEN HEATED TO DECOMPOSITION IT EMITS HIGHLY TOXIC FUMES OF SULFUR OXIDES.May be heated to 850 °C without decomposition. |
| Schmelzpunkt | -36.8 °F (NTP, 1992)-39.4 °C-38.3 °C-38 °C-38 °C (lit.) |
| Dampfdichte | 2.9 (vs air) |
| Dampfdruck | 40 mm Hg ( 12.5 °C) |
| Brechungsindex | n20/D 1.529(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | powder |
| Farbe | Clear |
| Wichte | 1.06 |
| Geruch | at 0.10 % in propylene glycol. alliaceous garlic |
| Geruchsart | sulfurous |
| Biologische Quelle | mouse |
| Geruchsschwelle | 0.00056ppm |
| Explosionsgrenze | 1.5-12.5%(V) |
| Spezifische Wärmekapazität | Cp(liquid): 1.47 J/(g·K)Cp(gas): 0.87 J/(g·K), at 25℃ |
| Merck | 14,9353 |
| BRN | 103222 |
| Henry-Konstante | 2.33 and 2.70 in distilled water and seawater, respectively (Przyjazny et al., 1983) |
| Dielektrizitätskonstante | 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 (Verteilungskoeffizient) | 1.81-1.86 at pH10 |
| Oberflächenspannung | 26.13mN/m at 298.15K |
| CAS Datenbank | 110-02-1(CAS DataBase Reference) |
| NIST chemische Informationen | Thiophene(110-02-1) |
| EPA chemische Informationen | Thiophene (110-02-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.5% (6 of 391) of reports.DangerH225 (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] |
|---|---|
| Regulatorische Informationen | Chemical: ThiopheneCommission 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/12099Thiophene: HSNO Approval: HSR001226 Approved with controlsThe 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-Kennzeichnung | Flammable Liquid |
| Brandgefahren | 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. |
| Brandpotenzial | A VERY DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME. |
| Gesundheitsgefahren | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:· May cause toxic effects if inhaled or absorbed through skin. |
| Gefahrenübersicht | Contact can cause redness of the eyes and skinInhalation can cause sore throat, cough and dizziness[ICSC] May be toxic to the liver[NJ-HSFS] A skin and eye irritantMay cause liver injury[MSDSonline] |
| DOT-Nummer und Handbuch | 2414 130 |
| Reaktive Gruppe | Hydrocarbons, Aromatic |
| UN-Einstufung | UN Hazard Class: 3UN Pack Group: II |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | 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 Dangers | Decomposes on heating and on burning. This produces toxic and irritating fumes (sulfur oxides). Reacts violently with oxidizing materials, including fuming nitric acid. |
| Brandbekämpfung | 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. |
| Erste-Hilfe-Maßnahmen | 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. |
| Freisetungsmaßnahmen | · 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. |
| Erste Hilfe | 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: |
| Sichere Lagerung | Fireproof. Separated from oxidizing materials. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | FOAM, CARBON DIOXIDE, DRY CHEMICAL. |
| Freisetung ohne Brand | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: |
| Entsorgungsverfahren | 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. |
| Verschüttetes entsorgen | 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 |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection. |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | Thiophene was detected in the volatiles of Idaho Russet baked potatoes(1) and meat volatiles(2). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour. |
| Signs and Symptoms | Cough. Dizziness. Sore throat.Redness.Redness. Pain. |
| Ongoing Test Status | 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 | 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 | 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 Sources | Naturally occurring source of thiophene is petroleum(1,2). |
| Human Toxicity Excerpts | In 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 Sources | Thiophenes'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 | 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). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2414 |
| Zollcode | 29349990 |
| RTECS-Nr. | XM7350000 |
| R-Sätze (R) | 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 |
| Gefahrensymbole | F,Xn,Xi,T |
| hazard_note | Irritant/Highly Flammable |
| Sicherheitshinweise (S) | 53-26-39-45-61-36/37/39-16-36 |
| Gefahrenklasse | 3Acute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 2 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 110-02-1(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 743 °F |
Anwendungen & Verwendung
Verwenden
Thiophene is used as a building block of various organic molecules and pharmaceuticals providing functional properties.