イソシアン酸クロロスルホニル

Chlorosulfonyl isocyanate

HCID 70918CAS 1189-71-5

基本情報

標準SMILES
O=C=NS(=O)(=O)Cl
InChIKey
WRJWRGBVPUUDLA-UHFFFAOYSA-N
分子式
CClNO3S
平均分子量
141.53 g/mol
単同位体質量
140.92874154

概要

Chlorosulfonyl isocyanate, also known as CSI, is a chemical compound of cyanide. It is used in organic synthesis for purposes such as the preparation of medically important preparation of beta-lactams. (L573)

名称と識別子

優先名称
Chlorosulfonyl isocyanate
IUPAC
N-(oxomethylidene)sulfamoyl chloride
現地名
イソシアン酸クロロスルホニル
英語名
Chlorosulfonyl isocyanate
分子式
CClNO3S
分子量
141.53

名称と別名

Chlorosulfonyl isocyanate1189-71-5Sulfuryl chloride isocyanateChlorosulfonylisocyanateChlorosulphonyl isocyanate[(CHLOROSULFONYL)IMINO]METHANONEDTXSID0061585((chlorosulfonyl)imino)methanoneRefChem:125518DTXCID1033458214-715-2sulfurisocyanatidic chloride
名称をさらに表示
イソシアン酸クロロスルホニル[(クロロスルホニル)イミノ]メタノンクロロスルホニルイソシアナート(クロロスルホニル)イソシアナートクロロスルホニルイソシアネトクロロスルホニル=イソシアナートクロロスルホニルイソシアネート2-[3-[(E)-2-[4-(4-ヒドロキシ-2-オキソ-2H-1-ベンゾピラン-3-イル)-2-モルホリノチアゾール-5-イル]ビニル]-5,5-ジメチルシクロヘキサ-2-エン-1-イリデン]マロノニトリル2-{3-[(1E)-2-[4-(4-ヒドロキシ-2-オキソ-2H-クロメン-3-イル)-2-(モルホリン-4-イル)-1,3-チアゾール-5-イル]エテニル]-5,5-ジメチルシクロヘキサ-2-エン-1-イリデン}プロパンジニトリルCSIchloroSulfonylN-Carbonylsulfamyl chloride, CSIChlorosulfonyl isocyCefuroxim Impurity 17
N-Carbonylsulfamyl chloridechlorsulfonyl isocyanateN-(oxomethylidene)sulfamoyl chlorideN-Chlorosulfonyl isocyanatesulfurisocyanatidoyl chlorideN-(oxomethylene)sulfamoyl chlorideMFCD000116082903Y990SM

データベース識別子

CAS
1189-71-5
PubChem CID
70918
DTXSID
DTXSID0061585
UNII
2903Y990SM
EC Number
214-715-2
Nikkaji
J111.247C

物性

構造計算による物性

XLogP
1.5
極性表面積
72 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
1
重原子数
7

実験および物理化学的性質

SpringerMaterials PropertiesSchoenflies notation

物理化学的性質

融点
-44 °C · -44 °C (lit.)
沸点
107 °C · 107 °C (lit.)
比重(密度)
1.626 g/mL · 1.626 g/mL at 25 °C (lit.)
蒸気圧
5.57 psi · 5.57 psi ( 20 °C)
屈折率
20 · n20/D 1.447(lit.)
闪点
110 °C · >110°C

化学的性質

化学的特性Clear liquid, colourless

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P342+P316, P362+P364, P363, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 88 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 3 件

Chemical: Sulfuryl chloride isocyanate

Status: Active Update: 28-11-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10803

Chlorosulphonyl isocyanate: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Treatment · 1 件

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 · 1 件

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 · 1 件

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).

安全データ

F
10-21-19
wgk
3
tsca
TSCA listed
ridadr
UN 3265 8/PG 2
毒性
LD50 orally in Rabbit: 640 mg/kg
hs_code
28510080

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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)

用途と製造

UsesChlorosulfonyl isocyanate is used in organic synthesis for purposes such as the preparation of medically important preparation of beta-lactams. (L573)
General Manufacturing InformationSulfuryl chloride isocyanate: ACTIVE
応用分野 · 4 件

用途有機合成用。a) Burgess試薬の合成b) ヒドロキシル基のスルファミン酸エステルへの変換c) ヘテロ環のシアノ化

使用Chlorosulfonyl isocyanate, a highly reactive chemical for chemical synthesis, is used as an intermediate used for production of antibiotics (Cefuroxime, penems), polymers as well as agrochemicals. Product Data Sheet

一般的な説明Chlorosulfonyl isocyanate reacts with hydrocarbon alkenes via stepwise dipolar pathway to give N-chlorosulfonyl-β-lactams.

用途a) Burgess試薬の合成b) ヒドロキシル基のスルファミン酸エステルへの変換c) ヘテロ環のシアノ化

調製方法

合成方法無水硫酸(三酸化硫黄)とクロロシアンを反応させることで合成される。工業的な方法として、生成物であるイソシアン酸クロロスルホニルを溶媒として利用する方法が開示されている。

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