Diethyl azodicarboxylate - ≥97% , CAS No.1972-28-7

CAS: 1972-28-7 Cat. No.: D111047 Peso molecular: 174.15 Beilstein Registry Number: 908662 Número EC: 217-821-7

GRADE & PURITY ≥97%

Synonyms

Diethoxycarbonyldiazene | ethyl (NE)-N-ethoxycarbonyliminocarbamate | 1,2-Ethoxycarbonyl diazene | diethyl (E)-diazene-1,2-dicarboxylate | Diethyl azodicarboxylate, E-isomer | Unifoam AZ-AE 200 | Diethyl 1,2-diazenedicarboxylate | NSC 679015 | SCHEMBL9077

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Descripción general

Diethyl azodicarboxylate acts as a dienophile used in Diels-Alder reactions. It is used as a reagent in alfa-thiocyanation of enolizable ketones with ammonium thiocyanate and annulation of N-protected imines. It acts as a reactant for the preparation of immunostimulants alfa-Galactosylceramides, bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase and aza-beta-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes. It finds application in Mitsunobu reaction and used in the synthesis of pharmaceuticals like zidovudine and procarbazine. The presence of azo group in it is a Michael acceptor and used for the conversion of beta-ketoesters to the corresponding hydrazine derivatives in presence of copper(II) catalyst. Further, it is an efficient dehydrogenating agent, which is involved in the preparation of aldehydes, disulfides from alcohols and thiols respectively.

Specifications

Sinónimos

Diethoxycarbonyldiazene | ethyl (NE)-N-ethoxycarbonyliminocarbamate | 1, 2-Ethoxycarbonyl diazene | diethyl (E)-diazene-1, 2-dicarboxylate | Diethyl azodicarboxylate, E-isomer | Unifoam AZ-AE 200 | Diethyl 1, 2-diazenedicarboxylate | NSC 679015 | SCHEMBL9077

Especificaciones y pureza

≥97%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Protected from light, Argon charged

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥97%

Nombres e identificadores

• Pubchem Sid: 504763840
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763840
• Sonrisas canónicas: CCOC(=O)N=NC(=O)OCC
• IUPAC Name: ethyl (NE)-N-ethoxycarbonyliminocarbamate
• InChIKey: FAMRKDQNMBBFBR-BQYQJAHWSA-N
• INCHI: 1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+
• Isómeros SMILES: CCOC(=O)/N=N/C(=O)OCC
• WGK Alemania: 3
• Número ONU: 1993
• Peso molecular: 174.15
• Beilstein: 908662
• Reaxy-Rn: 908662
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=908662&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Organic carbonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Organic carbonic acids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Organic carbonic acids and derivatives
• Alternative Parents: Azo compounds Propargyl-type 1,3-dipolar organic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Carbonic acid derivative - Azo compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as organic carbonic acids and derivatives. These are compounds comprising the organic carbonic acid or a derivative thereof.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Solubilidad: Miscible with dichloromethane, diethyl ether and toluene.
• Sensibilidad: Air,Light,Heat sensitive.
• Índice de refracción: 1.421
• Punto de inflamación (°F): 85℃
• Punto de inflamación (°C): 85℃
• Punto de ebullición (°C): 106°C
• Peso molecular: 174.150 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 174.064 Da
• Monoisotopic Mass: 174.064 Da
• Topological Polar Surface Area: 77.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 170.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Referencias

1. Yanan Wang, Huichao Wei, Keyang Li, Liru Liu, Yingfei Zhu, Xinyuan Wang, Jiahui Yan, Liangmin Yu, Xuefeng Yan, Zhiyu He.  (2023)  Ros-responsive dextran-phenylboronic acid-silibinin nanoparticles for targeting delivery of BAPTA-AM to effectively eliminate calcium overload-mediated inflammatory cascades and mitochondrial apoptosis: Alleviating acute liver injury.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.148283]

2. Peng Zeng, Wei-De Zhang.  (2021)  Photocatalytic hydrogen evolution over a nickel complex anchoring to thiophene embedded g-C3N4.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:33838327] [10.1016/j.jcis.2021.03.080]

3. Jun Zhang, Runtian Wang, Xiaojian Ou, Xiaoyan Zhang, Pu Liu, Zhengcan Chen, Boyuan Zhang, Chunli Liu, Shengyuan Zhao, Zhenbin Chen, Jinian Zhu, Sujun Lu, Peng Zhang.  (2020)  Bio-inspired synthesis of thermo-responsive imprinted composite membranes for selective recognition and separation of ReO4−.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2020.118165]

4. Yun-Xiao Zhang, Peng Zeng, Yu-Xiang Yu, Wei-De Zhang.  (2019)  Integration of nickel complex as a cocatalyst onto in-plane benzene ring-incorporated graphitic carbon nitride nanosheets for efficient photocatalytic hydrogen evolution.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2019.122635]

5. Hong Yang, Ming-Xia Liu, Yue-Wei Yao, Ping-Yang Tao, Bao-Ping Lin, Patrick Keller, Xue-Qin Zhang, Ying Sun, Ling-Xiang Guo.  (2013)  Polysiloxane-Based Liquid Crystalline Polymers and Elastomers Prepared by Thiol–Ene Chemistry.  MACROMOLECULES,      [PMID:] [10.1021/ma400462e]

6. Hong Yang, Fei Zhang, Bao-Ping Lin, Patrick Keller, Xue-Qin Zhang, Ying Sun, Ling-Xiang Guo.  (2012)  Mesogen-jacketed liquid crystalline polymers and elastomers bearing polynorbornene backbone.  Journal of Materials Chemistry C,  1  (7): (1482-1490).  [PMID:] [10.1039/C2TC00879C]

7. Xiaoya Li, Shirong Sun, Qian Zhang, Weidong Wu, Yingchun Liu, Liheng Chen, Xueqing Qiu.  (2024)  Porphyrin-conjugated lignin p-n heterojunction as an effective and biocompatible photosensitizer for antibacterial applications.  EUROPEAN POLYMER JOURNAL,      [PMID:] [10.1016/j.eurpolymj.2024.112970]

8. Haolin Song, Hongyi Chen, Qinjun Chen, Hongrui Fan, Chufeng Li, Yu Wang, Shilin Zhang, Xuwen Li, Boyu Su, Tao Sun, Chen Jiang.  (2024)  Size and Charge Dual-Switchable Nanoparticles for Achieving Chemosensitization and Immune Infiltration against Pancreatic Ductal Adenocarcinoma.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202411643]