1,1'-Azobis(cyclohexanecarbonitrile)

HCID 74978

Basic information

CAS
2094-98-6
Standard SMILES
N#CC1(N=NC2(C#N)CCCCC2)CCCCC1
InChIKey
KYIKRXIYLAGAKQ-UHFFFAOYSA-N
Molecular formula
C14H20N4
Average molar mass
244.34 g/mol
Monoisotopic mass
244.16879664

Overview

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.

Names & identifiers

Preferred name
1,1'-Azobis(cyclohexanecarbonitrile)
IUPAC
1-[(1-cyanocyclohexyl)diazenyl]cyclohexane-1-carbonitrile
English name
1,1'-Azobis(cyanocyclohexane)
Molecular formula
C14H20N4
Molecular weight
244.34

Names & synonyms

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
Show more names
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

Database identifiers

CAS
2094-98-6、25551-14-8
PubChem CID
74978
DTXSID
DTXSID9044613
ChEMBL
CHEMBL3183745
UNII
9Y0B93KKUS
EC Number
218-254-8
Nikkaji
J36.141K

Properties

Computed structural properties

XLogP
3.4
Topological polar surface area
72.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
18

Experimental & physicochemical properties

Physical Description · 2 items

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

Physicochemical properties

Melting point
114 · 114-118 °C(lit.)
Boiling point
423.9 · 423.9±38.0 °C(Predicted)
Density
1.13 · 1.13±0.1 g/cm3(Predicted)
vapor pressure
0 · 0-0.001Pa at 20-25℃
storage temp.
2 · 2-8°C
form
Solid:crystalline

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 5 items

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

Safety & protection

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]:

Toxicology

Treatment · 1 item

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 item

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 item

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).

Safety data

F
4.9
PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
ridadr
UN 3226 4.1
risk_code
11-36/37/38

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)

Uses & manufacturing

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

Plastics Material and Resin Manufacturing

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

Applications · 2 items

UsesA more efficient radical initiator than AIBN has been employed to initiate primary radical reactions.

General DescriptionA 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.

Upstream & downstream products

Suppliers50 total

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]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
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]

Related reactions

95 records

Compound notes

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