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티오펜

Thiophene

HCID 8030
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
110-02-1
표준 SMILES
c1ccsc1
InChIKey
YTPLMLYBLZKORZ-UHFFFAOYSA-N
분자식
C4H4S
평균 분자량
84.14 g/mol
단동위원소 질량
84.00337113

개요

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.

이름 및 식별자

우선 이름
Thiophene
IUPAC
thiophene
현지명
티오펜
영어명
Thiophene
분자식
C4H4S
분자량
84.14

이름 및 동의어

THIOPHENE110-02-1ThiofuranThioleThiophenThiotetroleThiacyclopentadieneThiofurfuranDivinylene sulfideThiapheneThiofuramFuran, thio-
이름 더 보기
티오펜CYP3AthiophenoneHLPcp34THIOPHENE FOR SYNTHESIS 5 MLThiophene, benzene free, extra pure, 99.5%CP33
Huile HSOThiofenHuile H50CP 34USAF EK-1860CCRIS 2935HSDB 130NSC 405073

데이터베이스 식별자

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

물성

구조 계산 물성보충 중

XLogP
1.8
극성 표면적
28.2 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
0
무거운 원자 수
5
형식 전하
0
복잡도
22.8

실험 및 물리화학적 성질

Chemical Classes · 2건

Other Classes -> Thiophenes

Flammable agents - 3rd degree

SpringerMaterials PropertiesCoriolis coupling
LogP · 4건

log Kow = 1.81

1.81

1.81

1.89

OdorSLIGHT AROMATIC ODOR RESEMBLING BENZENE
Density · 3건

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 · 6건

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

3.01 mg/mL at 25 °C

Solubility in water: none

Flash Point · 3건

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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]

유해성 정보

Regulatory Information · 5건

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 · 3건

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.
Health Hazards · 2건

화학 및 산업

약리 정보

Metabolism/Metabolites · 3건

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 · 4건

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

용도 및 제조

Uses · 3건

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 · 2건

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) GREATER THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 2건

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.

관련 반응

799건
반응 기록 만들기
HRID 1369 반응식
HRID 1369반응물로uspto-grants-1998_03
HRID 1385 반응식
HRID 1385반응물로uspto-grants-1998_03
HRID 1391 반응식
HRID 1391반응물로uspto-grants-1998_03
HRID 2318 반응식
HRID 2318반응물로uspto-grants-1998_03
HRID 2807 반응식
HRID 2807반응물로uspto-grants-1998_03
HRID 5779 반응식
HRID 5779반응물로uspto-grants-1993_09
HRID 5844 반응식
HRID 5844반응물로uspto-grants-1993_09
HRID 23334 반응식
HRID 23334반응물로uspto-grants-2005_02
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30 °F (NTP, 1992)

30 °F (-1 °C) (CLOSED CUP)

-1 °C

Boiling Point · 4건

183.9 °F at 760 mmHg (NTP, 1992)

84.0 °C @ 760 MM HG

84.00 °C. @ 760.00 mm Hg

84 °C

Decomposition · 2건

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

May be heated to 850 °C without decomposition.

Melting Point · 4건

-36.8 °F (NTP, 1992)

-39.4 °C

-38.3 °C

-38 °C

물리화학적 성질

녹는점
-38 °C · -38 °C (lit.)
끓는 점
84 °C · 84 °C (lit.)
밀도
1.051 g/mL · 1.051 g/mL at 25 °C (lit.)
증기 밀도
2.9 · 2.9 (vs air)
증기압
40 mm · 40 mm Hg ( 12.5 °C)
굴절률
20 · n20/D 1.529(lit.)
인화점
-9 °C · -9 °C
저장 조건
30 °C · Store below +30°C.
용해도
Miscible with carbon tetrachloride, heptane, pyrimidine, dioxane, toluene, and many organic solvents (quoted, Keith and Walters, 1992)
물리적 상태
가루
색상
투명한
Specific Gravity
1.06 · 1.06
냄새
0.1 % · 프로필렌 글리콜 중 0.10%. 부추 마늘
냄새 유형
유황의
생물학적 소스
mouse
Odor Threshold
0.00056 ppm · 0.00056ppm
폭발한계
1.5 · 1.5-12.5%(V)
수용성
불용성
비열
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℃)
안정성
안정적인. 가연성이 높습니다. 강한 산화제, 질산염과 호환되지 않습니다.
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
표면장력
26.13 mN/m · 26.13mN/m at 298.15K
NIST
Thiophene(110-02-1)
EPA
Thiophene (110-02-1)
화학적 성질 · 1건

Thiophene is a colourless to pale yellow liquid that has an odor similar to benzene. It is a heterocyclic compound with a five-membered ring containing four carbon atoms and one sulfur atom. The ring system is also known as a thienyl ring. It occurs as an impurity in commercial benzene and is used as a solvent and in organic syntheses.

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 · 1건

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.

안전 및 보호

Fire Fighting · 2건

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 · 4건

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 · 2건

· 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 · 2건

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 · 1건

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 · 1건

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 · 2건

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.

독성 정보

Environmental Fate · 3건

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 · 3건

Cough. Dizziness. Sore throat.

Redness.

Redness. Pain.

Ongoing Test Status · 1건

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 · 1건

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 · 1건

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 · 1건

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).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
XM7350000
ridadr
UN 2414
독성
LD50 orally in Rabbit: 1400 mg/kg
HS 번호
29349990
risk_code
45-46-11-20/21/22-41-52/53-36-20/22-37/38-22-48/20/21/22
hazard_code
F,Xn,Xi,T
safety_code
53-26-39-45-61-36/37/39-16-36
포장분류
II
위험 등급
3
기존화학 물질
KE-33795
위험 참고 사항
Irritant/Highly Flammable
자연 발화 온도
743 °F
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 2
스토리지 클래스
3 - Flammable liquids
유해 물질 데이터
110-02-1(Hazardous Substances Data)

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

General Manufacturing Information · 6건

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.

응용 분야 · 2건

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

일반 설명Thiophene 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.

제조 방법 · 1건

생산 방법Thiophene is present in coal tar and is recovered in the benzene distillation fraction (up to about 0.5% of the benzene present). Its removal from benzene is accomplished by mixing with concentrated sulfuric acid, soluble thiophene sulfonic acid being formed. Thiophene gives a characteristic blue coloration with isatin in concentrated sulfuric acid. The basic nomenclature of the thiophene ring system and its derivatives is indicated by the following: the sulfur atom is number 1, positions 2 and 5 are equivalent in the parent ring, as are the 3 and 4 positions.

상·하류 제품 정보

상류 원료

Motor benzolSolid sodium hydroxideMethylthiophene콜타르 증류액부탄삼이황화인

하류 제품

5-Oxo-5-(2-thienyl)valeric acidBis(2-thienyl) ketone4-(2-Thienyl)butyric acid2-(트리메틸아세틸)티오펜pyrante요오드티펜(2-)NOCODAZOLE3-티오펜-2-YL-벤잘데하이드2-(N-Heptanoyl)thiophene2-Thiophenesulfonyl chloride4-옥소-4-(2-티에닐)부티르산2-Thiophenemethylamine(4-Amino-3-nitrophenyl)-(2-thienyl)methanone2-Benzoylthiophene2-(트리플루오로아세틸)티오펜2-Thiopheneacetic acid2-(4-브로모페닐)티오펜5-(2-티에닐)펜타노산2-(5-브로모-2-티에닐)피리딘(4-메톡시-3-니트로페닐)-(티오펜-2-일)메탄온2-(4-메톡시벤졸일)티오펜
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정의ChEBI: 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.