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메틸 싸이오사이아네이트

Methyl thiocyanate

HCID 11168
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
556-64-9
표준 SMILES
CSC#N
InChIKey
VYHVQEYOFIYNJP-UHFFFAOYSA-N
분자식
C2H3NS
평균 분자량
73.12 g/mol
단동위원소 질량
72.9986201

개요

Methyl thiocyanate is a colorless liquid and an odor of onions. Used as an agricultural insecticide, a fumigant and as a research chemical. No evidence of commercial production in the U.S. (EPA, 1998)

이름 및 식별자

우선 이름
Methyl thiocyanate
IUPAC
methyl thiocyanate
현지명
메틸 싸이오사이아네이트
영어명
Methyl thiocyanate
분자식
C2H3NS
분자량
73.12

이름 및 동의어

METHYL THIOCYANATE556-64-9Methyl sulfocyanateMethylrhodanidThiocyanic acid, methyl esterMethyl rhodanateMethylthiokyanatMethane, thiocyanato-CH3SCNMeSCN(methylsulfanyl)carbonitrile55I23VY6IE
이름 더 보기
메틸싸이오사이아네이트메틸 싸이오사이아네이트methylrhodanateThiocyanomethaneMETHYL RHODANIDEMethylsalfocyanateMethylethiocyanatemethylsulfocyanate
NSC-9368DTXSID5060304CHEBI:61112RefChem:158037DTXCID2041915209-134-6thiocyanatomethaneThiocyanic Acid Methyl Ester

데이터베이스 식별자

CAS
556-64-9
PubChem CID
11168
DTXSID
DTXSID5060304
ChEBI
CHEBI:61112
UNII
55I23VY6IE
EC Number
209-134-6
Nikkaji
J3.296D

물성

구조 계산 물성

XLogP
0.9
극성 표면적
49.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
4
형식 전하
0
복잡도
41.2

실험 및 물리화학적 성질

Chemical ClassesFlammable agents - 2nd degree
SpringerMaterials PropertiesCoriolis coupling
PesticidesPesticides -> Other Insecticides
OdorONION ODOR
Density · 3건

1.068 at 77 °F (EPA, 1998) - Denser than water; will sink

1.068 g/cu cm at 25 °C

1.068 @25 °C

Color/FormCOLORLESS LIQUID
Solubility · 2건

VERY SLIGHTLY SOL IN WATER; MISCIBLE WITH ALC, ETHER

Soluble in carbon tetrachloride.

Boiling Point · 2건

266 to 271 °F at 760 mmHg (EPA, 1998)

130-133 °C

DecompositionWhen heated to decomposition it emits very toxic fumes of NOx and SOx.
Melting Point · 3건

-60 °F (EPA, 1998)

-51 °C

-51 °C

Vapor Pressure

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Danger

H226 (98%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 3건

Chemical: Thiocyanic acid, methyl ester

Methyl thiocyanate: Does not have an individual approval but may be used under an appropriate group standard

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 LabelPoison Flammable Liquid
Fire Hazards · 1건

When heated to decomposition, it emits very toxic fumes of oxides of nitrogen and sulfur. (Non-Specific -- Thiocyanates) Incompatible with nitric acid. Violent reactions have occurred when mixed with chlorates, nitrates, nitric acid, organic peroxides, peroxides, potassium chlorate, and sodium chlorate. This material is volatile. (EPA, 1998)

Health HazardsThis material is highly toxic if ingested. It is a rapidly acting poison. (EPA, 1998)
Hazards Summary · 1건

Releases cyanide after absorption into the body; Onset of symptoms may be delayed; [HSDB] Causes somnolence and convulsions in lethal dose studies of animals; [RTECS] A fast acting poison; [CAMEO] An irritant and lachrymator; Toxic by ingestion, inhalation, or skin absorption; May cause burns after skin contact and lung edema after inhalation; [Aldrich MSDS]

화학 및 산업

약리 정보

Metabolism/Metabolites · 3건

ENZYMES IN THE LIVER AND PERHAPS OTHER ORGANS ARE KNOWN TO LIBERATE CYANIDE ION FROM METHYL...THIOCYANATE... GLUTATHIONE S-TRANSFERASE CATALYZES THE ATTACK OF REDUCED GLUTATHIONE @ THIOCYANATE SULFUR, RESULTING IN LIBERATION OF HYDROGEN CYANIDE, OXIDIZED GLUTATHIONE & THE MERCAPTAN MOIETY OF THE ORGANOTHIOCYANATE.

METHYL THIOCYANATE UP TO 5 MMOL REDUCED THE HYDROGEN ION SECRETION OF BULLFROG, RANA CATESBEIANA, GASTRIC MUCOSA WITHOUT EXHIBITING ANY APPRECIABLE INHIBITORY EFFECT ON MICROSOMAL ATPASE ACTIVITY. NO CONVERSION OF METHYL THIOCYANATE TO THIOCYANATE ION, A POTENT INHIBITOR OF GASTRIC ACID SECRETION, WAS DEMONSTRATED IN THE GASTRIC MUCOSA.

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

용도 및 제조

Uses · 6건

Used as an agricultural insecticide, fumigant, pharmaceutical intermediate, and research chemical; [HSDB]

Farming (Pesticides) [Category: Industry]

AGRICULTURAL INSECTICIDE

FUMIGANT

RESEARCH CHEMICAL

Chemical and pharmaceutical intermediate.

U.S. Exports · 2건

(1979) No Data

(1981) No Data

U.S. Imports · 2건

(1979) No Data

(1981) No Data

U.S. Production · 2건

(1979) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

Methods of Manufacturing...FROM DIMETHYL SULFATE AND AQ BARIUM THIOCYANATE.
Formulations/Preparations99% Colorless liquid grade

관련 반응

41건
반응 기록 만들기
HRID 8915 반응식
HRID 8915반응물로uspto-grants-2006_08
HRID 101198 반응식
HRID 101198반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 106524 반응식
HRID 106524반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 131156 반응식
HRID 131156반응물로uspto-grants-2008_06
HRID 131159 반응식
HRID 131159반응물로uspto-grants-2008_06
HRID 131162 반응식
HRID 131162반응물로uspto-grants-2008_06
HRID 144624 반응식
HRID 144624반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 165795 반응식
HRID 165795반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
· 3건

10 mmHg at 70.88 °F (EPA, 1998)

12.1 [mmHg]

12.1 mm Hg at 25 °C

Refractive Index · 2건

INDEX OF REFRACTION: 1.4669 @ 25 °C/D

INDEX OF REFRACTION: 1.4697 @ 20 °C/D

물리화학적 성질

녹는점
-5 °C · -5 °C
끓는 점
131 °C · 131 °C
밀도
1.08 · 1.08
굴절률
1.467 · 1.467-1.469
인화점
38 °C · 38 °C
저장 조건
Poison room
수용성
물에 거의 녹지 않음
용해도
클로로포름, 메탄올(약간)에 용해됨
물리적 상태
액체
색상
무색투명~연황색
냄새
0.01 · 0.01?%?in?프로필렌 글리콜에서. 황 양파
Merck
14 · 14,6127
Henry's Law Constant
2.2 · 2.2×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
Dielectric constant
4.3 · 4.3(19℃)
InChI
1S/C2H3NS/c1-4-2-3/h1H3
InChIKey
VYHVQEYOFIYNJP-UHFFFAOYSA-N
SMILES
CSC#N
LogP
0.502 · 0.502 (est)
NIST
Thiocyanic acid, methyl ester(556-64-9)
EPA
Methyl thiocyanate (556-64-9)

화학적 성질

Methyl thiocyanate is a colorless liquid. Onion-like odor

Reactive GroupIsocyanates and Isothiocyanates
Reactivity Profile · 1건

METHYL THIOCYANATE is a moderately toxic liquid, flammable. Violent, possibly explosive oxidation reaction when mixed with chlorates, nitrates, nitric acid, organic or inorganic peroxides, perchlorates. On contact with mineral acids or acid fumes deadly toxic hydrogen cyanide gas is produced. When heated to decomposition or on contact with mineral acids it emits highly toxic fumes of nitriles, oxides of sulfur and nitrogen [Lewis, 3rd ed., 1993, p. 879, 1234].

Air and Water ReactionsVery slightly soluble in water [Merck].
CERCLA Reportable Quantities · 1건

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Methyl thiocyanate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10,000 lbs.

Hazard Classes and Categories · 2건

Flam. Liq. 3 (98%)

Flammable agents - 2nd degree, Reactive agents - 1st degree

DHS Chemicals of Interest (COI) · 4건

Methyl thiocyanate

1

20000

Toxic chemical that can be released at a facility.

Skin, Eye, and Respiratory Irritations... irritant to skin & eyes. ... /Aliphatic thiocyanates/

안전 및 보호

Fire Fighting · 1건

(Non-Specific -- Pesticide, Liquid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. If water pollution occurs, notify appropriate authorities.

First AidNote: Methyl thiocyanate is very readily absorbed through the skin.
Nonfire Spill Response · 1건

Avoid inhalation and skin contact. (Non-Specific -- Pesticide, Liquid, n.o.s.) Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors. For small spills, absorb with sand or other noncombustible absorbent material and place into containers for later disposal. For large spills, dike far ahead of spill for later disposal. (EPA, 1998)

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.

Isolation and EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Protective Action Criteria (PAC) · 3건

0.18 [mg/m3]

2.0 [mg/m3]

12 [mg/m3]

Personal Protective Equipment (PPE) · 1건

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Acute Exposure Guideline Levels (AEGLs)The compound is currently at the Holding Status AEGLs which have been reviewed by the NAC/AEGL Committee and are on hold due to insufficient data to develop AEGL values.
AEGLs NotesAEGLs Status: Holding

독성 정보

Treatment · 1건

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Health Effects · 1건

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 8.3(SRC), determined from a structure estimation method(2), indicates that methyl thiocyanate is expected to have very high mobility in soil(SRC). Volatilization of methyl thiocyanate from moist soil surfaces is expected (SRC) based upon an estimated Henry's Law constant of 4.4X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of methyl thiocyanate from dry soil surfaces is expected to exist(SRC) based on a measured vapor pressure of 12 mm Hg(4). Based upon a group contribution method for predicting the probability and rate of aerobic biodegradation(5), methyl thiocyanate has been estimated to biodegrade fast with primary biodegradation occurring over a period of days to weeks(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 8.3(SRC), determined from a structure estimation method(2), indicates that methyl thiocyanate is not expected to adsorb to suspended solids and sediment in water(SRC). Methyl thiocyanate is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.4X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 20 hours and 8.6 days, respectively(3,SRC). According to a classification scheme(5), an estimated BCF value of 2.1(3,SRC), from an estimated log Kow(6,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Based upon a group contribution method for predicting the probability and rate of aerobic biodegradation(7), methyl thiocyanate has been estimated to be highly biodegraded with ultimate biodegradation occurring over a period of weeks(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl thiocyanate, which has an measured vapor pressure of 12 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl thiocyanate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 15 days(3,SRC).

Adverse EffectsOther Poison - Chemical Asphyxiant
Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1건

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl thiocyanate can be estimated to be about 8.3(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that methyl thiocyanate is expected to have very high mobility in soil(SRC).

Natural Pollution SourcesMethyl thiocyanate is of anthropogenic origin, and is not known to be produced by natural sources. (SRC)
Human Toxicity Excerpts · 4건

SYMPTOMATOLOGY (LARGELY INFERRED FROM ANIMAL TESTS): 1. INGESTION OF CONCN SOLN MAY LEAD TO VOMITING BECAUSE OF MUCOSAL IRRITATION. ... 5. MASSIVE SKIN CONTAMINATION WITH ORGANIC THIOCYANATE SOLN MAY PRODUCE SYSTEMIC POISONING...&...LOCAL IRRITATION & DERMATITIS. /ALIPHATIC THIOCYANATES/

SYMPTOMATOLOGY (LARGELY INFERRED FROM ANIMAL TESTS): 6. IN NONFATAL CASES EVIDENCE OF INJURIES TO THE LIVER & KIDNEYS MAY APPEAR. /ALIPHATIC THIOCYANATES/

...METHYL.../THIOCYANATE IS/ RAPIDLY ACTING /POISON/...OF HIGH POTENCY...

THE SIGNS AND SYMPTOMS OF KEROSENE POISONING ARE OFTEN DOMINANT AFTER EXPOSURES TO DILUTE SOLN OF THIOCYANATE INSECTICIDES. /ALIPHATIC THIOCYANATES/

Artificial Pollution SourcesMethyl thiocyanate's production and use as a chemical and pharmaceutical intermediate(1) may result in its release to the environment(SRC).
Environmental BiodegradationBased upon a group contribution method for predicting the probability and rate of aerobic biodegradation(1), methyl thiocyanate has been estimated to biodegrade fast with primary biodegradation occurring over a period of days to weeks(SRC).

규제 정보

CERCLA Reportable Quantities · 1건

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Methyl thiocyanate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10,000 lbs.

DHS Chemicals of Interest (COI) · 4건

Methyl thiocyanate

1

20000

Toxic chemical that can be released at a facility.

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
XL1575000
ridadr
UN1992
독성
LD50 i.p. in mice: 315 nmoles/g (Ohkawa)
HS 번호
29309099
risk_code
23/24/25-10-36/37
hazard_code
T
safety_code
28A-27-26-16-45-36/37/39
포장분류
III
위험 등급
3
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Flam. Liq. 3STOT SE 3
스토리지 클래스
3 - Flammable liquids
유해 물질 데이터
556-64-9(Hazardous Substances Data)
General Manufacturing InformationThiocyanic acid, methyl ester: ACTIVE

응용 분야

일반 설명Colorless liquid and an odor of onions. Used as an agricultural insecticide, a fumigant and as a research chemical. No evidence of commercial production in the U.S.

상·하류 제품 정보

상류 원료

싸이오사이안산 칼륨4-Fluorothioanisole

하류 제품

메탄술폰산시아누릭 염부틸티오시아네이트2-아미노-5-(메틸티오)-1,3,4-티아디아졸과염소메틸 머캡탄(과염소메틸 메르캅탄)Isoquinoline, 3,4-dihydro-3,3,6-trimethyl-1-(methylthio)-O,O-디에틸S-메틸디티오포스페이트2-[(1-methylpiperidin-4-yl)amino]benzonitrile

추가 설명

정의ChEBI: Methyl thiocyanate is a member of the class of thiocyanates, being the methyl ester of thiocyanic acid.