2,2'-アゾビス(イソブチロニトリル)

Azobisisobutyronitrile

HCID 6547CAS 34241-39-9

基本情報

標準SMILES
CC(C)(C#N)N=NC(C)(C)C#N
InChIKey
OZAIFHULBGXAKX-UHFFFAOYSA-N
分子式
C8H12N4
平均分子量
164.21 g/mol
単同位体質量
164.10619638

概要

Insoluble in water and denser than water. Moderately toxic by ingestion. Readily ignited by sparks or flames. Burns intensely and persistently. Toxic oxides of nitrogen produced during combustion. Used as a catalyst, in vinyl polymerizations and a blowing agent for plastics.

名称と識別子

優先名称
Azobisisobutyronitrile
IUPAC
2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile
現地名
2,2'-アゾビス(イソブチロニトリル)
英語名
AIBN
分子式
C8H12N4
分子量
164.21

名称と別名

78-67-12,2'-Azobis(2-methylpropionitrile)AzobisisobutyronitrileAzdhPorofor NAceto AZIBPianofor anPorofor 57Azobis(isobutyronitrile)Chkhz 57VAZO 64AZODIISOBUTYRONITRILE
名称をさらに表示
2,2'-アゾビス(イソブチロニトリル)ポリ-ゾールAZDN1,2-ビス(1-シアノ-1-メチルエチル)ジアゼン2,2'-アゾビス(2-メチルプロパンニトリル)バゾ642,2'-アゾビス[2-メチルプロパンニトリル]アゾビスイソブチロニトリルアゾイソブチロニトリルポロホール572,2'-ジシアノ-2,2'-アゾプロパンアセトAZIB2,2'-(ジアゼン-1,2-ジイル)ビス(2-メチルプロパンニトリル)α,α'-アゾビスイソブチロニトリル2,2,2',2'-テトラメチル[2,2'-アゾビスアセトニトリル]2,2'-アゾジイソブチロニトリル2,2'-アゾビス(2-メチルプロピオノニトリル)2,2'-アゾビスイソブチロニトリル2,2'-ジメチル-2,2'-ジアゼンジイルビス(プロパンニトリル)2,2'-アゾビス(2-メチルプロピオニトリル)2,2’-アゾビスイソブチロニトリルAIBNABINAZOISOBUTYRONITRILEAIVN2,2'-Azobisisobutyronitrile2,2-AZOBIS(2-METHYLPROPIONITRILE)ALPHA,ALPHA'-AZOISOBUTYRONITRILEPropanenitrile, 2,2'-azobis[2-methyl-
2,2'-Azobis(2-methylpropanenitrile)DTXSID10264572,2'-azobis(2-cyanopropane)PERKADOX AIBNDTXCID60809637alpha,alpha'-azobis(isobutyronitrile)Azobis[isobutyronitrile]2,2'-Azobis[2-methylpropionitrile]

データベース識別子

CAS
34241-39-9、78-67-1
PubChem CID
6547
DTXSID
DTXSID1026457
ChEMBL
CHEMBL1886625
ChEBI
CHEBI:189360
UNII
FZ6PX8U5YB
EC Number
201-132-3、829-366-7
Nikkaji
J1.955K、J3.670.816F

物性

構造計算による物性

XLogP
1.3
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
12

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Nitriles

Flammable agents - 3rd degree

SpringerMaterials PropertiesBoiling point
Density1.1 g/cm³
Color/Form · 2 件

CRYSTALS FROM ETHANOL + WATER

WHITE POWDER

Solubility · 3 件

SOL IN METHANOL @ 0, 20, 40 °C: 1.8, 4.96, 16.06 G/100 ML; SOL IN ETHANOL @ 0, 20, 40 °C: 0.58, 2.04, 7.15 G/100 ML

INSOL IN WATER; SOL IN MANY ORG SOLVENTS; SOL IN VINYL MONOMERS

Solubility in water at 20 °C: none

Melting Point221 °F (105 °C)

物理化学的性質

融点
102 · 102-104 °C (dec.)(lit.)
沸点
281.68 °C · 281.68°C (rough estimate)
比重(密度)
1.11 · 1.11
蒸気圧
0.81 Pa · 0.81Pa at 24.85℃
屈折率
20 · n20/D1.495
闪点
4 ℃ · 4℃

化学的性質

化学性质白色結晶,分解温度 106℃,水・アルコー ルに微溶

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H242: Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]

P210, P234, P235, P240, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P317, P330, P370+P378, P403, P410, P411, P420, and P501 (click each P-code to see the statement)

Danger

H242 (100%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]

P210, P234, P235, P240, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P317, P330, P370+P378, P403, P410, P411, P420, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: Propanenitrile, 2,2'-azobis[2-methyl-

Propanenitrile, 2,2'-(1,2-diazenediyl)bis[2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanenitrile, 2,2'-(1,2-diazenediyl)bis[2-methyl- 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)

Status: Active Update: 28-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14322

Propanenitrile, 2,2'-azobis(2-methyl)-: HSNO Approval: HSR001429 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Propanenitrile, 2,2'-azobis[2-methyl-: Human health tier I assessment
DOT LabelFlammable Solid
Fire Hazards · 2 件

Excerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:

Highly flammable. Finely dispersed particles form explosive mixtures in air. Risk of fire and explosion when dissolving in organic solvents. Explosive.

Health HazardsExcerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Hazards Summary · 1 件

Forms hydrogen cyanide in the body; [Merck Index] Decomposed by warming forming toxic fumes such as tetramethylsuccinonitrile and cyanide; May decompose explosively from heating, shock, friction, or concussion; May cause CNS and liver effects; [ICSC] May form explosive mixture of dust in air; May self-decompose or self-ignite from heat, chemical reaction, or impact; [CAMEO] Effects in high-dose animal studies include toxicity to liver and kidneys; [eChemPortal: SIDSUNEP] Highly flammable; May explode from shock, friction, fire, or other source of ignition; May cause irritation; Targets the CNS, liver, and kidneys; [MSDSonline] See NITRILES.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:

Use water in large amounts, water spray. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give a slurry of activated charcoal in water to drink. Refer for medical attention .

First AidExcerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Safe StorageFireproof. Cool. Separated from strong oxidants and incompatible materials. See Chemical Dangers.
Nonfire Spill ResponseExcerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Spillage Disposal · 1 件

Consult an expert! Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Remove all ignition sources. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

毒性情報

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by ingestion.
Signs and SymptomsHeadache. Nausea. Weakness. Convulsions.
ICSC Environmental DataThe substance is harmful to aquatic organisms. The substance may cause long-term effects in the aquatic environment.
Human Toxicity ExcerptsMAY BE TOXIC BY INGESTION.
Probable Routes of Human Exposure...IS TOXIC, & RELEASES NITROGEN GAS & RESIDUE OF TETRAMETHYL SUCCINIC DINITRILE, WHICH PERSISTS IN FOAM. THIS COMPD...HAS BEEN BELIEVED TO BE CAUSE OF HEADACHE, NAUSEA, & OTHER ILL-DEFINED SYSTEMIC COMPLAINTS IN WORKERS.

安全データ

F
4.4
wgk
2
tsca
TSCA listed
rtecs
UG0800000
ridadr
UN 3234 4.1
毒性
LDLo orl-rat: 670 mg/kg 34ZIAG 0,117,69

化学と産業

薬理情報

Metabolism/MetabolitesIN ORGANISM, FORMS HCN WHICH IS FOUND IN BLOOD, LIVER & BRAIN.

用途と製造

Uses · 5 件

Used as blowing agent (elastomers and plastics), catalyst (vinyl polymerizations), curing agent (unsaturated polyester resins), and fumigant (when heated); [HSDB]

Plastic Composites Manufacturing [Category: Industry]

BLOWING AGENT FOR ELASTOMERS & PLASTICS; INITIATOR FOR FREE RADICAL REACTIONS

CATALYST FOR VINYL POLYMERIZATIONS & FOR CURING UNSATURATED POLYESTER RESINS

AZOBISNITRILES ARE CARRIER GASES FOR FUMIGANTS. COMPOUND CONTAINING PERMETHRIN 10, 2,2'-AZOBISISOBUTYRONITRILE 80, & MOLDING AGENT 10 PARTS WAS GRANULATED. WHEN HEATED 92% OF PERMETHRIN GASIFIED.

U.S. Production2023: 1,000,000 - <2,500,000 lb
Consumer UsesOther
Industry UsesChain transfer agent
Methods of Manufacturing · 2 件

...BY OXIDATION OF ALPHA,ALPHA'-HYDRAZOBUTYRIC ACID DINITRILE: OVERBERGER ET AL, J AM CHEM SOC 71, 2661 (1949); HORNER, SCHWENK, ANN 566, 69 (1950); FROM 2-AMINOISOBUTYRONITRILE + NAOCL: BRITISH PATENT 672,106 (1952 TO DU PONT)...

...FROM 2,2'-DICHLORO-2,2'-AZOPROPANE: BENZING, ANN 631, 1 (1960); BRITISH PATENT 929,182 (1963 TO MONSANTO).

General Manufacturing Information · 2 件

Plastics Material and Resin Manufacturing

Propanenitrile, 2,2'-(1,2-diazenediyl)bis[2-methyl-: ACTIVE

応用分野 · 7 件

解説無色の結晶.融点107 ℃(分解).エーテル,エタノールに可溶,水に不溶.約80 ℃ 以上に加熱すると窒素を発生し,テトラメチルスクシノニトリルC6H12(CN)2になる.この分解反応過程で生成する1-シアノ-1-メチルエチルラジカルを利用して,ラジカル反応開始剤として広く用いられている.そのほか,スポンジなどの製造用発泡剤として,ゴム,エポキシ,および塩化ビニル樹脂の発泡体製造に用いられる.生体内ではシアン化水素を発生する.LD50 0.7 g/kg(マウス,経口).森北出版「化学辞典(第2版)

用途それを応用する発泡剤、ラジカル重合誘発剤、ハロゲネーション用触媒。

用途合成樹脂ゴムの発泡剤、重合酸化触媒

用途合成樹脂原料(発泡剤、重合開始剤)。

使用Used as an initiator in the synthesis of highly cross-linked Poly(divinylbenzene) (PDVB) polymers. 1 Used as an initiator in the polymerization process of 2-hydroxyethyl methacrylate (HEMA). 2

一般的な説明Insoluble in water and denser than water. Moderately toxic by ingestion. Readily ignited by sparks or flames. Burns intensely and persistently. Toxic oxides of nitrogen produced during combustion. Used as a catalyst, in vinyl polymerizations and a blowing agent for plastics.

使用用途アゾビスイソブチロニトリルは、容易に分解して、窒素ガスの放出とともに2-シアノ-2-プロピルラジカルを与えます。この性質を利用して、各種ラジカル反応のラジカル開始剤として広く利用されています。 代表的な反応は、ビニル化合物やなどの汎用ポリマーを合成する重合反応や、 (HBr) を用いたアルケンのヒドロ臭素化反応などです。を溶媒とするとの混合溶液にアゾビスイソブチロニトリルを加えて穏やかに加熱すると、ポリスチレンを得ることができます。また、有機合成における中間体、ゴムやプラスチックなどの発泡剤などの利用用途もあります。

上流・下流製品情報

下流製品

4-[4-(ブロモメチル)フェニル]-1,2,3-チアジアゾールジクロロアセチル クロリドsuper absorbent resin synthesized by microwave cation ion radiation4-(ピペリジン-1-カルボニル)フェニルボロン酸2,1,3-ベンゾチアジアゾール-5-イルメタノール4-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID2',3'-ジデオキシイノシン2,1,3-ベンゾチアジアゾール-5-カルバルデヒド3-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACIDgraft copolymer PAA-G-PIPA microsphere2-(ブロモメチル)安息香酸2,6-ジクロロベンズアルデヒド

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補足説明

定義ChEBI: (E)-Azobis(isobutyronitrile) is an azo compound.

関連反応

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