基本情報
- CAS
36635-61-7- 標準SMILES
[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1- InChIKey
CFOAUYCPAUGDFF-UHFFFAOYSA-N- 分子式
- C9H9NO2S
- 平均分子量
- 195.24 g/mol
- 単同位体質量
- 195.03539953
概要
Toluenesulfonylmethyl isocyanide is a chemical compound of cyanide.
名称と識別子
- 優先名称
- Tosylmethyl isocyanide
- IUPAC
- 1-(isocyanomethylsulfonyl)-4-methylbenzene
- 現地名
- p-トルエンスルホニルメチル イソシアニド
- 英語名
- Tosylmethyl isocyanide
- 分子式
- C9H9NO2S
- 分子量
- 195.24
名称と別名
名称をさらに表示
データベース識別子
- CAS
36635-61-7- PubChem CID
- 161915
- DTXSID
DTXSID90190101- UNII
- C35FD6OLH8
- EC Number
- 253-140-1
- Nikkaji
- J2.201.925B、J209.011B
物性
構造計算による物性
- XLogP
- 1.3
- 極性表面積
- 46.9 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 2
- 重原子数
- 13
- 形式電荷
- 0
- 複雑度
- 298
実験および物理化学的性質
物理化学的性質
- 融点
- 109 · 109-113 °C(lit.)
- 比重(密度)
- 1.2721 · 1.2721 (rough estimate)
- 屈折率
- 1.527 · 1.5270 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 水: わずかに溶ける
- 外見
- 液体
- 色
- クリア
- 水溶解度
- 不溶性
- Merck
- 14 · 14,9556
- BRN
- 3592382 · 3592382
- InChI
- InChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
- InChIKey
- BBNNLJMGPASZPD-UHFFFAOYSA-N
- SMILES
- S(C1C=CC(C)=CC=1)(=O)(=O)C[N+]#[C-]
- CAS データベース
- 36635 · 36635-61-7(CAS DataBase Reference)
化学的性質
化学的特性Pale yellow to light brown crystalline powder
安全と法規制
GHS分類
GHS Classification
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.
危険有害性情報
Regulatory Information
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
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
- 21
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29299000
- risk_code
- 23/24/25
- hazard_code
- T,Xi
- hazard_note
- Irritant
- safety_code
- 36/37-45-38-36/37/39-28A
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard Classifications
- Acute Tox. 2 DermalAcute Tox. 2 InhalationAcute Tox. 2 Oral
- ストレージクラス
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic 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
解説特性基-NCをもつ有機化合物の一般名.ニトリルの異性体.イソニトリルといわれることもあり,また古くはカルビルアミンという別名も使われた.
用途トルエンスルホニルメチルイソシアニド(toluenesulfonylmethyl isocyanide, TOSMIC)は、フローニンゲン大学のオランダ人化学者 van Leusenらによって開発された非常に用途の広いシントンである。
説明Tosylmethyl 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.
使用Tosylmethyl 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.
調製方法
製造方法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.
純化方法Use an efficient fume cupboard. Purify TOSMIC by dissolving (50g) in CH2Cl2 (150mL) and passing it through a column (40x3cm) containing neutral alumina (100g) in CH2Cl2 and eluting with CH2Cl2. A nearly colourless solution (700mL) is collected, evaporated in vacuo and the residue (42-47g) of TOSMIC (m 113-114o dec) is recrystallised once from MeOH (m 116-117o dec). [Hoogenboom et al. Org Synth 57 102 1977, Lensen Tetrahedron Lett 2367 1972.] It also crystallises from EtOH (charcoal) [Saito & Itano, J Chem Soc, Perkin Trans 1 1 1986].
上流・下流製品情報
上流原料
下流製品
サプライヤー100 社
補足説明
定義Tosylmethyl isocyanide is a chemical compound of cyanide that Versatile synthon in organic chemistry, especially in the synthesis of heterocyclic Compounds.
関連反応
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