基本情報
- 標準SMILES
N#CC1(N=NC2(C#N)CCCCC2)CCCCC1- InChIKey
KYIKRXIYLAGAKQ-UHFFFAOYSA-N- 分子式
- C14H20N4
- 平均分子量
- 244.34 g/mol
- 単同位体質量
- 244.16879664
概要
1,1'-azodi-(hexahydrobenzonitrile) appears as a white to light colored solid substance. Insoluble in water and more dense that water. May cause irritation to skin, eyes, and mucous membranes. May be toxic by ingestion. If exposed to high temperatures or flames this material may ignite and burn with an intense flame. Dust may form an explosive mixture in air.
名称と識別子
- 優先名称
- 1,1'-Azobis(cyclohexanecarbonitrile)
- IUPAC
- 1-[(1-cyanocyclohexyl)diazenyl]cyclohexane-1-carbonitrile
- 現地名
- 1,1'-アゾビスー(シクロヘキサンー1-カルボニトリル)
- 英語名
- 1,1'-Azobis(cyanocyclohexane)
- 分子式
- C14H20N4
- 分子量
- 244.34
名称と別名
名称をさらに表示
データベース識別子
- CAS
2094-98-6、25551-14-8- PubChem CID
- 74978
- DTXSID
DTXSID9044613- ChEMBL
CHEMBL3183745- UNII
- 9Y0B93KKUS
- EC Number
- 218-254-8
- Nikkaji
- J36.141K
物性
構造計算による物性
- XLogP
- 3.4
- 極性表面積
- 72.3 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
- 2
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 368
実験および物理化学的性質
Physical Description
1,1'-azodi-(hexahydrobenzonitrile) appears as a white to light colored solid substance. Insoluble in water and more dense that water. May cause irritation to skin, eyes, and mucous membranes. May be toxic by ingestion. If exposed to high temperatures or flames this material may ignite and burn with an intense flame. Dust may form an explosive mixture in air.
Large Crystals
物理化学的性質
- 融点
- 114 · 114-118 °C(lit.)
- 沸点
- 423.9 · 423.9±38.0 °C(Predicted)
- 比重(密度)
- 1.13 · 1.13±0.1 g/cm3(Predicted)
- 蒸気圧
- 0 · 0-0.001Pa at 20-25℃
- 貯蔵温度
- 2 · 2-8°C
- 外見
- Solid:crystalline
- BRN
- 960744 · 960744
- 安定性
- 114 C · 安定ですが、約 114 C 以上で発熱分解します
- InChI
- 1S/C14H20N4/c15-11-13(7-3-1-4-8-13)17-18-14(12-16)9-5-2-6-10-14/h1-10H2/b18-17+
- InChIKey
- KYIKRXIYLAGAKQ-ISLYRVAYSA-N
- SMILES
- N#CC1(CCCCC1)\N=N\C2(CCCCC2)C#N
- LogP
- 3.256 at · 3.256 at 25℃ and pH5-6
- CAS データベース
- 2094 · 2094-98-6(CAS DataBase Reference)
- EPAの化学物質情報
- 1 · 1,1'-Azobiscyclohexanecarbonitrile (2094-98-6)
化学的性質
化学的特性faintly beige crystalline powder
安全と法規制
GHS分類
GHS Classification
Danger
H242 (98.8%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]
P210, P234, P235, P240, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403, P403+P233, P405, P410, P411, P420, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 83 reports by companies from 7 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: Cyclohexanecarbonitrile, 1,1'-azobis-
Cyclohexanecarbonitrile, 1,1'-(1,2-diazenediyl)bis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanecarbonitrile, 1,1'-(1,2-diazenediyl)bis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
Status: Active Update: 03-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/27517
Cyclohexanecarbonitrile, 1,1'-azobis-: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
Self-decomposition or self-ignition may be triggered by heat, chemical reaction, friction or impact. May be ignited by heat, sparks or flames. 1,1'-AZODI-(HEXAHYDROBENZONITRILE) is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.
安全と保護具
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
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)
安全データ
- F
- 4.9
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3226 4.1
- risk_code
- 11-36/37/38
- hazard_code
- F,Xi
- safety_code
- 26
- hazard_class
- 4.1
- packing_group
- II
- Hazard Classifications
- Eye Irrit. 2Self-react. DSkin Irrit. 2STOT SE 3
- ストレージクラス
- 5.2 - Organic peroxides and self-reacting hazardous materials
化学と産業
薬理情報
Metabolism/Metabolites
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)
用途と製造
General Manufacturing Information
Plastics Material and Resin Manufacturing
Cyclohexanecarbonitrile, 1,1'-(1,2-diazenediyl)bis-: ACTIVE
応用分野
用途合成樹脂原料。
使用A more efficient radical initiator than AIBN has been employed to initiate primary radical reactions.
一般的な説明A white to light colored solid substance. Insoluble in water and more dense that water. May cause irritation to skin, eyes, and mucous membranes. May be toxic by ingestion. If exposed to high temperatures or flames 1,1'-Azobis(cyanocyclohexane) may ignite and burn with an intense flame. Dust may form an explosive mixture in air.
調製方法
純化方法Purify the nitrile by dissolving it in boiling 95%EOH as rapidly as possible, cool overnight at 0o, filter, wash with a little EtOH and dry it in a vacuum desiccator over CaCl2. Note that prolonged heating >80o causes decomposition. Recrystallise it from EtOH. It should be regarded as potentially explosive. It is a radical initiator. [Overberger et al. Org Synth Coll Vol IV 66 1963, Beilstein 16 II 97.]
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