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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 181
実験および物理化学的性質
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
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- Chloroform (Slightly, Heated)
- 外見
- 結晶、結晶性粉末または顆粒
- 比重
- 1.626 · 1.626 (20℃)
- 色
- 白い
- 水溶解度
- 激しく反応して発熱する
- BRN
- 1237247 · 1237247
- InChI
- 1S/CClNO3S/c2-7(5,6)3-1-4
- InChIKey
- WRJWRGBVPUUDLA-UHFFFAOYSA-N
- SMILES
- ClS(=O)(=O)N=C=O
- CAS データベース
- 1189 · 1189-71-5(CAS DataBase Reference)
- EPAの化学物質情報
- Sulfuryl chloride isocyanate (1189-71-5)
化学的性質
化学的特性Clear liquid, colourless
安全と法規制
GHS分類
GHS Classification
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
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
毒性情報
Treatment
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
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)
Toxicity Summary
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)
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
- risk_code
- 14-22-34-42-20/22
- 化審法
- (1)-1216
- hazard_code
- C
- safety_code
- 23-26-30-36/37/39-45
- hazard_class
- 8
- packing_group
- II
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1
- ストレージクラス
- 8A - Combustible corrosive hazardous materials
化学と産業
薬理情報
Metabolism/Metabolites
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
応用分野
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。
上流・下流製品情報
下流製品
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