1,1'-Azobis(cyclohexanecarbonitrile)

HCID 74978CAS 2094-98-6

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

2094-98-61,1'-Azobis(cyclohexanecarbonitrile)1,1'-Azobis(cyanocyclohexane)1,1'-Azobiscyclohexanecarbonitrile9Y0B93KKUS1,1'-Azobis(1-cyclohexanecarbonitrile)azobiscyclohexylnitrileCyclohexanecarbonitrile, 1,1'-azobis-V-40 (INITIATOR)1,1'-azobis(cyclohexane-1-carbonitrile)Azo-bis(cyclohexanecarbonitrile)EINECS 218-254-8
名称をさらに表示
1.1'-アゾビス(シクロヘキサン-1-カルボニトリル)1,1'-アゾビスー(シクロヘキサンー1-カルボニトリル)1,1’アゾビス(シクロヘキサンカルボニトリル)1,1’-アゾビス(シクロヘキサン-カルボニトリル)1,1'-アゾビス(シクロヘキサン-1-カルボニトリル)1,1′-アゾビス(シクロヘキサンカルボニトリル)1,1'-アゾビス(シクロヘキサンカルボニトリル)ACCNV-40MDEGBNAC1ASIC2LABOTEST-BB LT00160148AZO-1-CYANOCYCLOHEXANEAzodicyclohexanonitrile1-Azo-1-cyanocyclohexane
N,N-AZOBIS(CYCLOHEXANECARBONITRILE)1,1'-AZOBIS(CYCLOHEXANECARBONITRILE) [MI]Cyclohexanecarbonitrile, 1,1'-(1,2-diazenediyl)bis-1-[2-(1-cyanocyclohexyl)diazen-1-yl]cyclohexane-1-carbonitrile1,1'-azobis[cyclohexane-1-carbonitrile]1-(2-(1-cyanocyclohexyl)diazen-1-yl)cyclohexane-1-carbonitrile1,1'-AZODICYCLOHEXANE CARBONITRILERefChem:409162

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

実験および物理化学的性質

Physical Description · 2 件

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

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 · 4 件

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 · 5 件

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

Other Safety InformationIMAP assessments - Cyclohexanecarbonitrile, 1,1'-azobis-: Human health tier I assessment
DOT LabelFlammable Solid
Fire HazardsExcerpt from ERG Guide 133 [Flammable Solids]:
Health HazardsExcerpt from ERG Guide 133 [Flammable Solids]:
Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds

安全と保護具

Fire FightingExcerpt from ERG Guide 133 [Flammable Solids]:
First AidExcerpt from ERG Guide 133 [Flammable Solids]:
Nonfire Spill ResponseExcerpt from ERG Guide 133 [Flammable Solids]:
Isolation and EvacuationExcerpt from ERG Guide 133 [Flammable Solids]:
Personal Protective Equipment (PPE)Excerpt from ERG Guide 133 [Flammable Solids]:

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

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)

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
4.9
wgk
3
tsca
TSCA listed
ridadr
UN 3226 4.1
risk_code
11-36/37/38
hazard_code
F,Xi

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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

U.S. Production2023: 50,000 - <250,000 lb
Industry UsesChain transfer agent
General Manufacturing Information · 2 件

Plastics Material and Resin Manufacturing

Cyclohexanecarbonitrile, 1,1'-(1,2-diazenediyl)bis-: ACTIVE

応用分野 · 3 件

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 · 1 件

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.]

上流・下流製品情報

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
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上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]

関連反応

95 件

関連ノート

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