토실메틸이소시아나이드

Tosylmethyl isocyanide

HCID 161915

기본 정보

CAS
36635-61-7
표준 SMILES
[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1
InChIKey
CFOAUYCPAUGDFF-UHFFFAOYSA-N
분자식
C9H9NO2S
평균 분자량
195.24 g/mol
단동위원소 질량
195.03539953

개요

Toluenesulfonylmethyl isocyanide is a chemical compound of cyanide.

이름 및 식별자

우선 이름
Tosylmethyl isocyanide
IUPAC
1-(isocyanomethylsulfonyl)-4-methylbenzene
현지명
토실메틸이소시아나이드
영어명
Tosylmethyl isocyanide
분자식
C9H9NO2S
분자량
195.24

이름 및 동의어

Tosylmethyl isocyanide36635-61-7TosMICp-Toluenesulfonylmethyl isocyanide4-Toluenesulfonylmethyl isocyanide(p-Tolylsulfonyl)methyl isocyanideTMIC isocyanideC35FD6OLH8p-toluenesulphonylmethyl isocyanideNSC-631633DTXSID90190101RefChem:190488
이름 더 보기
토실메틸이소시아나이드isocyanideToluenesulfonyl Methyl isocyanideTosylmethyl isocyaniTosylmethy isocyanide ,98%TOLUENE-4-SULFONYLMETHYL ISOCYANIDE
DTXCID60112592253-140-11-((Isocyanomethyl)sulfonyl)-4-methylbenzene1-(isocyanomethylsulfonyl)-4-methylbenzene4-Toluenesulphonylmethyl IsocyanideTosylmethylisocyanide1-isocyanomethanesulfonyl-4-methylbenzeneMFCD00000005

데이터베이스 식별자

CAS
36635-61-7
PubChem CID
161915
DTXSID
DTXSID90190101
UNII
C35FD6OLH8
EC Number
253-140-1
Nikkaji
J2.201.925B、J209.011B

물성

구조 계산 물성

XLogP
1.3
극성 표면적
46.9 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
2
무거운 원자 수
13

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
Physical DescriptionSolid; [Merck Index] Light brown powder; [Alfa Aesar MSDS]

물리화학적 성질

녹는점
109 · 109-113 °C(lit.)
밀도
1.2721 · 1.2721 (rough estimate)
굴절률
1.527 · 1.5270 (estimate)
저장 조건
2 · 2-8°C
용해도
물: 약간 용해됨
물리적 상태
액체

화학적 성질

Pale yellow to light brown crystalline powder

안전 및 규제

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 1.1% (1 of 93) of reports.

Danger

H301+H311+H331 (31.2%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P233, P260, P261, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P342+P316, P361+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 93 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 3건

Chemical: Benzene, 1-[(isocyanomethyl)sulfonyl]-4-methyl-

Status: Active Update: 08-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/22098

4-Toluenesulphonylmethyl isocyanide: HSNO Approval: HSR004315 Approved with controls

Hazards SummaryMay cause irritation; Toxic by ingestion, inhalation, and skin absorption; [Alfa Aesar MSDS] See Ethyl isocyanide and Phenylisocyanide.
Hazard Classes and CategoriesAcute Tox. 3 (91.4%)

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)

Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1건

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)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

안전 데이터

wgk
3
ridadr
UN 2811 6.1/PG 3
HS 번호
29299000
risk_code
23/24/25
hazard_code
T,Xi
safety_code
36/37-45-38-36/37/39-28A

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes 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

UsesUsed in organic synthesis; [Merck Index]
응용 분야 · 2건

개요Tosylmethyl isocyanide is a versatile synthon in organic chemistry, widely used as a reagent for the preparation of biologically active pyrroles and imidazoles. Tosylmethyl isocyanide undergoes a base-promoted 1,3-dipolar cycloaddition reaction with immobilised imines under microwave irradiation to give 1,5-disubstituted imidazoles.

용도Tosylmethyl Isocyanide is used as a synthetic reagent in the preparation of variety or biologically active heterocycles such as pyrroles and imidazoles. Tosylmethyl Isocyanide is reported to inhibit [ Fe]-hydrogenase with very high affinity.

제조 방법 · 1건

N-(p-Tolylsulfonylmethyl)formamide 1609: A 3-L, three-necked, round-bottomed flask, equipped with a mechanical stirrer, a condenser, and a thermometer, was charged with sodium p-toluenesulfinate 1606 (267 g, 1.5 mol). After the addition of water (750 mL), a 34–37% solution of formaldehyde 1607 (350 mL, 378 g, ca. 4.4 mol), formamide 1608 (600 mL, 680 g, 15 mol), and formic acid (200 mL, 244 g, 5.3 mol), the stirred reaction mixture was heated at 90 C°. The sodium p-toluenesulfinate dissolved during the heating, and the clear solution was kept at 90–95 C° for 2 h. It was then cooled in an ice/salt bath with continued stirring and further cooled overnight in a freezer at 20 C°. The white solid produced was collected by suction filtration. It was washed thoroughly in a beaker by stirring with three 250 mL portions of iced water. The product was dried under reduced pressure over phosphorus pentoxide at 70 C° to provide 134–150 g (42–47%) of crude N-(p-tolylsulfonylmethyl)formamide 1609; mp 106–110 C°. This product was sufficiently pure to be used directly in the following reaction.

공급사100 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
宁波君龙新材料有限公司0574 88552216 19032109277 · [email protected]

추가 설명

정의Tosylmethyl isocyanide is a chemical compound of cyanide that Versatile synthon in organic chemistry, especially in the synthesis of heterocyclic Compounds.

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761건

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