N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide

• ChemBase编号: 74363
• 分子式: C8H14N2O4
• 平均质量: 202.20776
• 单一同位素质量: 202.09535694
• SMILES: N(=N\C(=O)OC(C)C)/C(=O)OC(C)C
• Canonical SMILES: CC(OC(=O)/N=N/C(=O)OC(C)C)C
• 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

名称和登记号

名称

• IUPAC标准名: N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide; (E)-N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide
• IUPAC传统名: diisopropyl azodicarboxylate; N-[(isopropoxycarbonyl)imino]isopropoxyformamide
• 别名: 偶氮二甲酸二异丙酯; Azodicarboxylic acid diisopropyl ester; Diisopropyl azodicarboxylate; Diisopropyl azodiformate; Diisopropyl azodicarboxylate; DIAD; Diprop-2-yl diazene-1,2-dicarboxylate; Bis(isopropyl) azodicarboxylate 96%; Diisopropyl diazene-1,2-dicarboxylate

登记号

• CAS号: 2446-83-5
• EC号: 219-502-8
• MDL号: MFCD00008875
• Beilstein号: 1912326
• PubChem SID: 24847276; 24853505; 162039282
• PubChem CID: 5363146
• Chemspider ID: 4515532
• 维基百科标题: Diisopropyl_azodicarboxylate

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 1.6064495
• LogD (pH = 7.4): 1.6064495
• Log P: 1.6064495
• 摩尔折射率: 47.3138 cm^3
• 极化性: 18.836767 Å^3
• 极化表面积: 77.32 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: insoluble in water
• 熔点: 3-5 °C; 3-5°C; 3-5°C
• 沸点: 74-75°C/0.3mm; 74-75°C/0.3mm; 75 °C at 0.25 mmHg; 75 °C/0.25 mmHg(lit.)
• 闪点: 106 °C; 106°C; 106°C; 160°C(320°F); 222.8 °F; 223 °F
• 密度: 1.027; 1.027 g/cm^3; 1.027 g/mL at 25 °C(lit.)
• 折射率: 1.42; 1.4200; n20/D 1.420; n20/D 1.420(lit.)

安全信息

• 保存注意事项: Harmful/Irritant/Keep Cold/Store under Argon; Light Sensitive
• 欧盟危险性物质标志: Env. Danger (N); Flammable (F); Irritant (Xi); 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 3082; UN3082
• 德国WGK号: 1; 2
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 36/37/38-40-48/20/22-51/53; 36/37/38-51/53; 36/38-51/53; R5, R11, R36, R37, R38, R43, R51, R53
• 安全公开号: 26-36/37-61; 26-37-61; 26-60; S16, S26, S29, S36, S37, S39, S47, S61
• TSCA收录: 否
• GHS危险品标识: GHS07; GHS08; GHS09
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335-H351-H373-H411; H315-H319-H335-H411-H401
• GHS警示性声明: P261-P273-P281-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3082 9/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥94% (GC); 94%; 95+%; 98%
• 级别: technical
• 杂质: ≤2% dichloromethane
• 线性分子式: (CH3)2CHOOCN=NCOOCH(CH3)2

详细说明

Apollo Scientific Ltd - OR0923

Alternative to DEAD

Sigma Aldrich - 225541

General description
在铁催化剂催化下与二氧磷杂环己烷反应生成重排膦叶立德产物。8
包装
25, 100 g in poly bottle
5 g in glass bottle
Application
Reactant for preparation of:
• Chromenes resembling classical cannabinoids1
• MK-3281 inhibitor of the hepatitis C virus NS5B polymerase2
• Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)3
• Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties4
• Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells5
• 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists6
• Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine7

Sigma Aldrich - 11626

Other Notes
用于 Mitsunobu 反应的试剂，综述8,9
Application
Reactant for preparation of:
• Chromenes resembling classical cannabinoids1
• MK-3281 inhibitor of the hepatitis C virus NS5B polymerase2
• Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)3
• Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties4
• Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells5
• 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists6
• Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine7

参考文献

• Alternative to 'DEAD' (Diethyl azodicarboxylate, L19348), more stable at elevated temperatures. DIAD has been used in combination with Triphenylphosphine, L02502, in Mitsunobu-type reactions of alcohols with acids, amides, etc. In the Mitsunobu esterification reaction yields improve with increasing acid strength. For a discussion, see: J. Org. Chem., 61, 2967 (1996).
• For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethylsilyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).
• An extremely mild route to isocyanates involves treatment of an aliphtic primary amine with CO₂ to form the carbamate salt which reacts at low temperature with the Mitsunobu reagent from DIAD and PPh₃, giving the isocyanate in high yield. 2,6-Dialkylanilines also undergo the reaction if Bu₃P is used; the reaction failed with other anilines: Tetrahedron Lett., 40, 363 (1999).
• For reviews of the Mitsunobu reaction, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996). For a brief feature on synthetic uses of Mitsunobu reagents, see: Synlett, 1221 (2003).