偶氮二甲酸二异丙酯

• 产品号: L10386
• CAS号: 2446-83-5
• 分子式: C8H14N2O4
• 分子量: 202.20776
• 纯 度: 94%

产品别名

• 标题: Diisopropyl azodicarboxylate
• IUPAC标准名: N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide
• IUPAC传统名: diisopropyl azodicarboxylate
• 别名: Azodicarboxylic acid diisopropyl ester; DIAD

产品登记号

• EC号: 219-502-8
• MDL号: MFCD00008875
• Beilstein号: 1912326
• CAS号: 2446-83-5

产品性质

• 纯度: 94%
• 沸点: 74-75°C/0.3mm
• 密度: 1.027
• 闪点: 160°C(320°F)
• 熔点: 3-5°C
• 折射率: 1.4200
• GHS危险声明: H315-H319-H335-H411-H401
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N)
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 危险公开号: 36/37/38-51/53
• 安全公开号: 26-37-61
• 保存注意事项: Light Sensitive
• TSCA收录: 否
• 联合国危险货物等级: 9
• 联合国危险货物编号: UN3082
• 联合国危险货物包装类别(PG): III

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).