(E)-N-[(ethoxycarbonyl)imino]ethoxyformamide

• ChemBase编号: 70308
• 分子式: C6H10N2O4
• 平均质量: 174.1546
• 单一同位素质量: 174.06405681
• SMILES: N(=N\C(=O)OCC)/C(=O)OCC
• Canonical SMILES: CCOC(=O)/N=N/C(=O)OCC
• InChI: InChI=1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+
• InChIKey: FAMRKDQNMBBFBR-BQYQJAHWSA-N

名称和登记号

名称

• IUPAC标准名: (E)-N-[(ethoxycarbonyl)imino]ethoxyformamide; N-[(ethoxycarbonyl)imino]ethoxyformamide
• IUPAC传统名: diethyl azodicarboxylate; N-[(ethoxycarbonyl)imino]ethoxyformamide
• 别名: 偶氮二甲酸二乙酯 溶液; 偶氮二甲酸二乙酯; Diethyl azodicarboxylate; 1,2-Ethoxycarbonyl diazene; Diethyl diazene-1,2-dicarboxylate, 40% solution in toluene; 1,2-Ethoxycarbonyl diazene solution; DEAD; Diethoxycarbonyldiazene solution; Diethyl azodiformate solution; NSC 3474; NSC 679015; Unifoam AZ-AE 200; Diethyl azodicarboxylate solution; Diethyl azidoformate; Diazenedicarboxylic acid; Diethyl azo diformate; (E)-diethyl diazene-1,2-dicarboxylate; 1,2-Bis(ethoxycarbonyl) diazene; Diethyl diazene-1,2-dicarboxylate 97%; Diethyl azodicarboxylate; 1,2-Diazenedicarboxylic Acid 1,2-Diethyl Ester; Azodicarboxylic Acid Diethyl Ester; Diethoxycarbonyldiazene; Diethyl Azodiformate; Diethyl Diazenedicarboxylate; Diethyl Diazodicarboxylate

登记号

• CAS号: 1972-28-7
• EC号: 217-821-7
• MDL号: MFCD00009103
• Beilstein号: 908662
• PubChem SID: 162036031; 24847277; 24880080
• PubChem CID: 5462977
• Chemspider ID: 4510444
• 维基百科标题: Diethyl_azodicarboxylate

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 0.77329946
• LogD (pH = 7.4): 0.77329946
• Log P: 0.77329946
• 摩尔折射率: 38.4762 cm^3
• 极化性: 15.216925 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

• 外观: Orange to red to orange liquid
• 熔点: 6 °C
• 沸点: 104.5 °C at 12 mm Hg; 106 °C/13 mmHg(lit.); 106°C/13mm; 106°C/13mm; 116-117 °C
• 闪点: 105.8 °F; 113 °C; 235 °F; 41 °C; 41°C; 85 °C; 85°C; 85°C(185°F)
• 密度: 0.956 g/mL at 25 °C; 0.96; 1.106; 1.106 g/mL at 25 °C(lit.); 1.11 g/cm^3
• 折射率: 1.420 (20 °C); 1.421; 1.4210; n20/D 1.43(lit.); n20/D 1.4690; n20/D 1.47

安全信息

• 保存注意事项: Air Sensitive; Highly Flammable/Harmful/Irritant/Teratogenic/Keep Cold; IRRITANT; Toxic/Harmful/Irritant/Air Sensitive/Store under Argon/Keep Cold
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 3379; UN2810
• 德国WGK号: 3
• 联合国危险货物等级: 3; 6.1
• 联合国危险货物包装类别(PG): 1; III
• 危险公开号: 5-20-36/37/38; 5-21/22-36/37/38; 63-10-20-36/37/38-48/20-65; 63-5-10-20-36/37/38-48/20-65; R20 R21 R22 R36 R37 R38 R40 R44
• 安全公开号: 26-36/37-60; 26-36/37-62; 26-47; S15 S23 S26 S36
• TSCA收录: false; 否
• GHS危险品标识: GHS02; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H226-H242-H304-H315-H319-H335 + H336-H361d-H373; H226-H304-H315-H319-H335-H336-H361d-H373; H302-H312-H315-H319-H335-H227
• GHS警示性声明: P210-P305+P351+P338-P302+P352-P321-P405-P501A; P261-P281-P301 + P310-P305 + P351 + P338-P331
• 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 3379 3/PG 1; UN REST
• 保存温度: 2-8°C

产品相关信息

• 纯度: 85%; 95+%; 97%
• 浓度: ~40% in toluene (H-NMR); 40 wt. % in toluene
• 级别: purum; technical grade
• 线性分子式: C2H5OCON=NCOOC2H5

详细说明

Sigma Aldrich - 563110

Application
常用于 Mitsunobo 反应的活化试剂。9
Reactant for preparation of:
• Immunostimulants α-Galactosylceramides1
• Cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases2
• Bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase3
• Derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities4
• Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes5Reagent for:
• Annulation of N-protected imines6
• α-thiocyanation of enolizable ketones with ammonium thiocyanate7
• Diels-Alder reactions8
General description
DOT Special Approval Submission is Under Review. Availability is Estimated as March 2012.
包装
25, 100 g in glass bottle
每 100g 约含 40g DEAD 溶质
每 25g 约含 10g DEAD 溶质
Warning
有毒性、刺激性、易燃

Sigma Aldrich - 11627

Other Notes
用于 Mitsunobu 反应的试剂，综述9,10,11
Application
Reactant for preparation of:
• Immunostimulants α-Galactosylceramides1
• Cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases2
• Bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase3
• Derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities4
• Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes5Reagent for:
• Annulation of N-protected imines6
• α-thiocyanation of enolizable ketones with ammonium thiocyanate7
• Diels-Alder reactions8

Toronto Research Chemicals - D443765

A fluorescent CDK inhibitor for treatment of cancer.

参考文献

• Wilton, D., et al.: Biochem. J., 266, 435 (1990)
• Suzuki, K., et al.: J. Biol. Chem., 266, 18498 (1990)
• Wilson, W., et al.: Curr. Med. Chem., 7, 73 (1990)
• Details for esterification of (-)-menthol with 4-nitrobenzoic acid with stereoinversion: Org. Synth. Coll., 9, 607 (1998). For an example of its use to convert a secondary alcohol to an amine by reaction with phthalimide followed by hydrazinolysis, see: Org. Synth. Coll., 7, 501 (1990). For dehydration of Boc-L-serine to the cyclic anhydride (2-oxetanone), see: Org. Synth. Coll., 9, 24 (1998).
• ɑ-Amination of aldehydes can be effected in the presence of L-proline as an enantioselective catalyst, affording chiral ɑ-amino alcohols and ɑ-amino acids with good ee: Angew. Chem. Int. Ed., 41, 1790 (2002); for a similar reaction with scheme, see Dibenzyl azodicarboxylate, L19347.
• See also Di-tert-butyl azodicarboxylate, L00294, and Diisopropyl azodicarboxylate, L10386.
• Dehydrogenating agent and aza-dienophile. Oxidizes alcohols to aldehydes, thiols to disulfides and hydrazo to azo groups: J. Am. Chem. Soc., 88, 2328 (1966). Arylhydroxylamines are converted in high yield to nitroso compounds: Chem. Commun., 199 (1967).
• Undergoes pericyclic reactions with alkenes and dienes via both ene and Diels-Alder processes. For further details and references, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 3, p. 1790.
• In combination with Triphenylphosphine, L02502, is widely used in the Mitsunobu reaction for activation of primary and secondary alcohols by formation of the alkoxyphosphonium salts, which behave as versatile alkylating agents under mild S_N2 conditions: reactions normally proceed with inversion of configuration. For reviews, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996); Synlett, 1221 (2003); Eur. J. Org. Chem., 2763 (2004):
  
• For study of the mechanism, see: J. Org. Chem., 67, 1751 (2002).
• Explosion risk by heating undiluted material.
• Secondary and tertiary amines have been dealkylated by reaction with DEAD under mild conditions, followed by acid hydrolysis: J. Org. Chem., 38, 1652 (1973).