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MedKoo Cat#: 581607 | Name: Diethyl azodicarboxylate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH3CH2O2CN=NCO2CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating.

Chemical Structure

Diethyl azodicarboxylate
CAS#4143-61-7

Theoretical Analysis

MedKoo Cat#: 581607

Name: Diethyl azodicarboxylate

CAS#: 4143-61-7

Chemical Formula: C6H10N2O4

Exact Mass: 174.0641

Molecular Weight: 174.16

Elemental Analysis: C, 41.38; H, 5.79; N, 16.09; O, 36.75

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Diethyl azodicarboxylate; DEAD; Azodiformic acid diethyl ester; Diethyl diazenedicarboxylate; Ethyl azodicarboxylate; Diethyl azodicarboxylate.
IUPAC/Chemical Name
1,2-Diazenedicarboxylic acid 1,2-diethyl ester
InChi Key
FAMRKDQNMBBFBR-BQYQJAHWSA-N
InChi Code
InChI=1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+
SMILES Code
O=C(/N=N/C(OCC)=O)OCC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 174.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Aly AA, Hassan AA, Mohamed NK, Ramadan M, Brown AB, Abd El-Aal AS, Bräse S, Nieger M. Regioselective formation of 1,2,4-triazoles by the reaction of amidrazones in the presence of diethyl azodicarboxylate and catalyzed by triethylamine. Mol Divers. 2018 Aug 13. doi: 10.1007/s11030-018-9868-6. [Epub ahead of print] PubMed PMID: 30105556. 2: Hirose D, Gazvoda M, Košmrlj J, Taniguchi T. Systematic Evaluation of 2-Arylazocarboxylates and 2-Arylazocarboxamides as Mitsunobu Reagents. J Org Chem. 2018 Apr 20;83(8):4712-4729. doi: 10.1021/acs.joc.8b00486. Epub 2018 Apr 5. PubMed PMID: 29570289. 3: Bain RM, Sathyamoorthi S, Zare RN. "On-Droplet" Chemistry: The Cycloaddition of Diethyl Azodicarboxylate and Quadricyclane. Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15083-15087. doi: 10.1002/anie.201708413. Epub 2017 Oct 24. PubMed PMID: 28992393. 4: Wang M, Nudelman F, Matthes RR, Shaver MP. Frustrated Lewis Pair Polymers as Responsive Self-Healing Gels. J Am Chem Soc. 2017 Oct 11;139(40):14232-14236. doi: 10.1021/jacs.7b07725. Epub 2017 Sep 27. PubMed PMID: 28915038. 5: Sugiura M, Kashiwagi T, Ito M, Kotani S, Nakajima M. Stereoselective Synthesis of Nitrogen-Containing Compounds from Enamines. J Org Chem. 2017 Oct 20;82(20):10968-10979. doi: 10.1021/acs.joc.7b01923. Epub 2017 Oct 6. PubMed PMID: 28915033. 6: Xu ZL, Xing P, Jiang B. Intramolecular Aza-Piancatelli Rearrangement of Alkyl- or Arylamines Promoted by PPh(3)/Diethyl Azodicarboxylate. Org Lett. 2017 Mar 3;19(5):1028-1031. doi: 10.1021/acs.orglett.6b03853. Epub 2017 Feb 16. PubMed PMID: 28205440. 7: Hirose D, Gazvoda M, Košmrlj J, Taniguchi T. Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents. Chem Sci. 2016 Aug 1;7(8):5148-5159. doi: 10.1039/c6sc00308g. Epub 2016 Apr 13. PubMed PMID: 30155165; PubMed Central PMCID: PMC6020523. 8: Lau YF, Chan CM, Zhou Z, Yu WY. Cp*Rh(iii)-catalyzed electrophilic amination of arylboronic acids with azo compounds for synthesis of arylhydrazides. Org Biomol Chem. 2016 Jul 12;14(28):6821-5. doi: 10.1039/c6ob00719h. PubMed PMID: 27339710. 9: Guo D, Zhu D, Zhou X, Zheng B. Accelerating the "On Water" Reaction: By Organic-Water Interface or By Hydrodynamic Effects? Langmuir. 2015 Dec 29;31(51):13759-63. doi: 10.1021/acs.langmuir.5b04031. Epub 2015 Dec 16. PubMed PMID: 26624935. 10: Xu N, Li D, Zhang Y, Wang L. Palladium-catalyzed direct ortho-ethoxycarbonylation of azobenzenes and azoxybenzenes with diethyl azodicarboxylate. Org Biomol Chem. 2015 Sep 14;13(34):9083-92. doi: 10.1039/c5ob01264c. Epub 2015 Jul 29. PubMed PMID: 26220693. 11: Wang Y, Frett B, McConnell N, Li HY. Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media. Org Biomol Chem. 2015 Mar 14;13(10):2958-64. doi: 10.1039/c4ob02284j. PubMed PMID: 25611884; PubMed Central PMCID: PMC4675458. 12: Liu JY, Niu HY, Wu S, Qu GR, Guo HM. Metal catalyzed C(sp3)-H bond amination of 2-alkyl azaarenes with diethyl azodicarboxylate. Chem Commun (Camb). 2012 Oct 9;48(78):9723-5. doi: 10.1039/c2cc35309a. PubMed PMID: 22914742. 13: Camp D, Campitelli M, Hanson GR, Jenkins ID. Formation of an unusual four-membered nitrogen ring (tetrazetidine) radical cation. J Am Chem Soc. 2012 Oct 3;134(39):16188-96. doi: 10.1021/ja303019y. Epub 2012 Jul 10. PubMed PMID: 22708894. 14: Xu X, Du P, Cheng D, Wang H, Li X. Highly stereoselective synthesis of cis-β-enaminones mediated by diethyl azodicarboxylate. Chem Commun (Camb). 2012 Feb 7;48(12):1811-3. doi: 10.1039/c2cc16997e. Epub 2012 Jan 5. PubMed PMID: 22218457. 15: Figlus M, Wellaway N, Cooper AW, Sollis SL, Hartley RC. Synthesis of arrays using low molecular weight MPEG-assisted Mitsunobu reaction. ACS Comb Sci. 2011 May 9;13(3):280-5. doi: 10.1021/co100091n. Epub 2011 Mar 25. PubMed PMID: 21438502. 16: Kurach E, Djurado D, Rimarčik J, Kornet A, Wlostowski M, Lukeš V, Pécaut J, Zagorska M, Pron A. Effect of substituents on redox, spectroscopic and structural properties of conjugated diaryltetrazines--a combined experimental and theoretical study. Phys Chem Chem Phys. 2011 Feb 21;13(7):2690-700. doi: 10.1039/c0cp01553a. Epub 2010 Dec 9. PubMed PMID: 21152517. 17: Suchý M, Li AX, Bartha R, Hudson RH. Synthesis of MRI contrast agents derived from DOTAM-Gly-L-Phe-OH incorporating a disulfide bridge: conjugation to a cell penetrating peptide and preparation of a dimeric agent. Bioorg Med Chem Lett. 2010 Sep 15;20(18):5521-6. doi: 10.1016/j.bmcl.2010.07.070. Epub 2010 Jul 23. PubMed PMID: 20705462. 18: Jana A, Sen SS, Roesky HW, Schulzke C, Dutta S, Pati SK. End-on nitrogen insertion of a diazo compound into a germanium(II) hydrogen bond and a comparable reaction with diethyl azodicarboxylate. Angew Chem Int Ed Engl. 2009;48(23):4246-8. doi: 10.1002/anie.200900617. PubMed PMID: 19425043. 19: Xu X, Li X. Copper/diethyl azodicarboxylate mediated regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne. Org Lett. 2009 Feb 19;11(4):1027-9. doi: 10.1021/ol802974b. PubMed PMID: 19159324. 20: Xu X, Li X, Ma L, Ye N, Weng B. An unexpected diethyl azodicarboxylate-promoted dehydrogenation of tertiaryamine and tandem reaction with sulfonyl azide. J Am Chem Soc. 2008 Oct 29;130(43):14048-9. doi: 10.1021/ja8047514. Epub 2008 Oct 1. PubMed PMID: 18826314.

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