CAS 2446-83-5 Diisopropyl azodicarboxylate (HCID 5363146)

基本情報

CAS: 2446-83-5
標準SMILES: CC(C)OC(=O)/N=N/C(=O)OC(C)C
InChIKey: VVWRJUBEIPHGQF-MDZDMXLPSA-N
分子式: C8H14N2O4
平均分子量: 202.21 g/mol
単同位体質量: 202.09535693

名称と識別子

優先名称: Diisopropyl azodicarboxylate
IUPAC: propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate
現地名: アゾジカルボン酸ジイソプロピル (約1.9mol/L トルエン溶液)
英語名: Diisopropyl azodicarboxylate
分子式: C8H14N2O4
分子量: 202.21

名称と別名

Diisopropyl azodicarboxylate2446-83-5Diisopropyl azodiformate939987-56-1Diisopropyl azodicarboxylate [MI]Formic acid, azodi-, diisopropyl ester7W701BXX4KEINECS 219-502-81,2-Diazenedicarboxylic acid 1,2-bis(1-methylethyl) esterDTXSID50894754Diazenedicarboxylic acid, bis(1-methylethyl) esterRefChem:587897

名称をさらに表示

アゾジカルボン酸ジイソプロピル (約1.9mol/L トルエン溶液)アゾジぎ酸ジイソプロピルアゾビス(ぎ酸イソプロピル)ジイソプロピルアゾジカルボキシレートジアゼンビスカルボン酸ジイソプロピルジアゼンジカルボン酸ビス(1-メチルエチル)1,2-ジアゼンジカルボン酸ジイソプロピルジアゼン-1,2-ジカルボン酸ジイソプロピルジアゼンジカルボン酸ジイソプロピルアゾビスぎ酸ジイソプロピルジイソプロピルアゾジカルボキシレ-トアゾジカルボン酸ジイソプロピルアゾジカルボン酸ジイソプロピル (40%トルエン溶液, 約1.9mol/L)ジイソプロピル=アゾジカルボキシレートジイソプロピル=アゾジカルボキシレート, 95%1,2-ビス(イソプロポキシカルボニル)ジアゼン2,3-ジアザフマル酸ジイソプロピルN-{[(プロパン-2-イルオキシ)カルボニル]イミノ}(プロパン-2-イルオキシ)ホルムアミドN-[(イソプロポキシカルボニル)イミノ]カルバミド酸イソプロピルダイアッドdiisopropyl (E)-diazene-1,2-dicarboxylateDisopropyl AzodicarboxylateAZODICARBONIC ACID DIISOPROPYL ESTER(E)-diisopropyl diazene-1,2-dicarboxylateDiisopropyl azodicarboxylate [DIAD]

データベース識別子

CAS: 2446-83-5、939987-56-1
PubChem CID: 5363146
DTXSID: DTXSID50894754
UNII: 7W701BXX4K
EC Number: 219-502-8
Nikkaji: J3.771.302C、J56.134G

物性

構造計算による物性

XLogP: 2.6
極性表面積: 77.3 Å²
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: 4
重原子数: 14
形式電荷: 0
複雑度: 211

実験および物理化学的性質

Physical DescriptionOrange liquid; [Merck Index] Pungent odor; [Alfa Aesar MSDS]

物理化学的性質

融点: 3 · 3-5 °C
沸点: 75 °C/0.25 · 75 °C/0.25 mmHg (lit.)
比重(密度): 1.027 g/mL · 1.027 g/mL at 25 °C (lit.)
蒸気圧: 1.04 hPa · 1.04 hPa (20 °C)
屈折率: 20 · n20/D 1.420(lit.)
闪点: 223 °F · 223 °F
貯蔵温度: 30 °C · Store below +30°C.
溶解性: クロロホルム（微量）、酢酸エチル（微量）
外見: 液体
色: 透明～やや濁った黄橙色～赤色
水溶解度: 不溶性
BRN: 1912326 · 1912326
InChI: InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3
InChIKey: VVWRJUBEIPHGQF-UHFFFAOYSA-N
SMILES: N(C(OC(C)C)=O)=NC(OC(C)C)=O
CAS データベース: 2446 · 2446-83-5(CAS DataBase Reference)

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 35.9% (52 of 145) of reports.

Warning

H315 (62.8%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (62.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (61.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H373 (54.5%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H411 (61.4%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P260, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 145 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 52 of 145 reports by companies.；There are 20 notifications provided by 93 of 145 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 2 件

Status: Active Update: 02-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23916

Diisopropylazodicarboxylate: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin, respiratory tract, and strong eye irritant; [Alfa Aesar MSDS] See Diethyl azodicarboxylate.

Hazard Classes and CategoriesSkin Irrit. 2 (62.8%)；Eye Irrit. 2 (62.8%)；STOT SE 3 (61.4%)；STOT RE 2 (54.5%)；Aquatic Chronic 2 (61.4%)

化学と産業

用途と製造

UsesUsed as a reagent; [Merck Index]

応用分野 · 5 件

解説高分子内で2個のモノマー単位が連続して結合した部分(連鎖)をダイアッドまたは二連子とよぶ．二つの側鎖が異なるビニルポリマーでは，立体異性を生じ，メソ構造とラセモ構造のダイアッドがある．

用途有機合成中間体

用途有機合成原料。

使用Diisopropyl Azodicarboxylate is an azodicarboxylic acid derivative used as a reagent in the production of many organic compounds. Diisopropyl Azodicarboxylate is commonly used as an oxidizer in Mitsun obu reactions and can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.

一般的な説明Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.

調製方法 · 1 件

純化方法Purify the azo compound by distillation at as high a vacuum as possible. Since it is likely to explode, use an oil bath for heating the still, and all operations should be carried out behind an adequate shield. [Kauer Org Synth Coll Vol IV 412 1963, Beilstein 3 III 233]. This reagent is useful in the Mitsunobu reaction [Mitsunobu Synthesis 1 1981, Gennari et al. J Am Chem Soc 108 6394 1986, Evans et al. J Am Chem Soc 108 6394 1986, Hughes Org React 42 335 1992, Dodge et al. Org Synth 73 110 1996, Hughes Org Prep Proc Int 28 127 1996, Ferguson & Marcelle J Am Chem Soc 128 4576 2006; see also di-tert-butyl azodicarboxylate and DEAD above].