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Merck
CN

225541

Sigma-Aldrich

偶氮二甲酸二异丙酯

98%

别名:

DIAD, 偶氮二甲酸二异丙酯

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About This Item

线性分子式:
(CH3)2CHOOCN=NCOOCH(CH3)2
CAS号:
分子量:
202.21
Beilstein:
1912326
MDL编号:
UNSPSC代码:
12352302
PubChem化学物质编号:
NACRES:
NA.22

质量水平

方案

98%

表单

liquid

杂质

≤2% dichloromethane

折射率

n20/D 1.420 (lit.)

沸点

75 °C/0.25 mmHg (lit.)

密度

1.027 g/mL at 25 °C (lit.)

官能团

azo

储存温度

2-8°C

SMILES字符串

CC(C)OC(=O)\N=N\C(=O)OC(C)C

InChI

1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+

InChI key

VVWRJUBEIPHGQF-MDZDMXLPSA-N

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一般描述

与二氧磷杂环己烷和铁催化剂反应,生成重排的鏻叶立德产物。

应用

作为反应物用于制备:
  • 苯并哌喃,类似于传统的大麻素
  • 丙型肝炎病毒NS5B聚合酶的MK-3281抑制剂
  • 降冰片烯类富含胍聚合物,作为细胞穿透肽(CPP)的模拟物
  • 铜绿假单胞菌群体感应分子N-(3-氧化十二烷酰基)-L-同型丝氨酸内酯的类似物,具有免疫抑制作用,但无LasR诱导特性
  • 染料敏化太阳能电池的受体-供体-受体有机染料
  • 1,3-二恶烷-2-羧酸衍生物,作为PPARα/γ双重激动剂
  • 通过Morrison-Brunn-Huisgen甜菜碱的Mitsunobu和Arbuzov型多组分反应制备肼基膦酸盐和肼基二膦酸盐
偶氮二甲酸二异丙酯(DIAD)在有机合成中常用于制备有用的化学中间体。常用于光延(Mitsunobu)和氮杂Baylis-Hillman反应。DIAD也可用作N-苯甲基的选择性脱保护剂。

警示用语:

Warning

危险分类

Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

10 - Combustible liquids

WGK

WGK 2

闪点(°F)

222.8 °F

闪点(°C)

106 °C

个人防护装备

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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访问文档库

J Miles Blackburn et al.
Organic letters, 19(21), 6012-6015 (2017-10-20)
A general approach to access sulfamate esters through preparation of sulfamic acid salts, subsequent activation with triphenylphosphine ditriflate, and nucleophilic trapping is disclosed. The method proceeds in modest to excellent yields to incorporate nucleophiles derived from aliphatic alcohols and phenols.
Petia Atanasova et al.
Nanomaterials (Basel, Switzerland), 9(5) (2019-05-30)
The robust, anisotropic tobacco mosaic virus (TMV) provides a monodisperse particle size and defined surface chemistry. Owing to these properties, it became an excellent bio-template for the synthesis of diverse nanostructured organic/inorganic functional materials. For selective mineralization of the bio-template
Jorge J Llibre-Guerra et al.
JAMA network open, 2(12), e1917126-e1917126 (2019-12-12)
The amyloid/tau/neurodegeneration (A/T/N) framework uses cerebrospinal fluid (CSF) levels of total tau (tTau) as a marker of neurodegeneration and CSF levels of phosphorylated tau 181 (pTau181) as a marker of tau tangles. However, it is unclear whether CSF levels of
Eun-Hye Kim et al.
International journal of molecular sciences, 21(10) (2020-05-28)
Cancer immunotherapy has been revolutionized by the development of monoclonal antibodies (mAbs) that inhibit interactions between immune checkpoint molecules, such as programmed cell-death 1 (PD-1), and its ligand PD-L1. However, mAb-based drugs have some drawbacks, including poor tumor penetration and
Aza-Baylis-Hillman reactions of diisopropyl azodicarboxylate or diethyl azodicarboxylate with acrylates and acrylonitrile
Shi M and Zhao G-L
Tetrahedron, 60(9), 2083-2089 (2004)

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