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MedKoo Cat#: 581148 | Name: Diazoacetic ester
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Description:

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

Diazoacetic ester is also known as Ethyl Diazoacetate. Ethyl Diazoacetate is used in the synthesis of Arteludovicinolide A as well as pyrimidoazepine analogs as seritonin 5-HT2A/C receptor ligands for treatment of obesity. This compound contains solvent for added stability.

Chemical Structure

Diazoacetic ester
CAS#623-73-4

Theoretical Analysis

MedKoo Cat#: 581148

Name: Diazoacetic ester

CAS#: 623-73-4

Chemical Formula: C4H6N2O2

Exact Mass: 114.0429

Molecular Weight: 114.10

Elemental Analysis: C, 42.11; H, 5.30; N, 24.55; O, 28.04

Price and Availability

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5g USD 250.00 2 Weeks
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Synonym
Diazoacetic ester; AI3-52121; CCRIS 1403; EINECS 210-810-8; Ethoxycarbonyldiazomethane; Ethyl diazoacetate;
IUPAC/Chemical Name
ethyl 2-diazoacetate
InChi Key
YVPJCJLMRRTDMQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3
SMILES Code
C(C=[N+]=[N-])(OCC)=O
Appearance
Liquid
Purity
≥13 wt. % dichloromethane
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 114.10 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: Delville MM, van Hest JC, Rutjes FP. Ethyl diazoacetate synthesis in flow. Beilstein J Org Chem. 2013 Sep 5;9:1813-8. doi: 10.3762/bjoc.9.211. eCollection 2013. PubMed PMID: 24062847; PubMed Central PMCID: PMC3778378. 2: Ma C, Xing D, Zhai C, Che J, Liu S, Wang J, Hu W. Iron porphyrin-catalyzed three-component reaction of ethyl diazoacetate with aliphatic amines and β,γ-unsaturated α-keto esters. Org Lett. 2013 Dec 20;15(24):6140-3. doi: 10.1021/ol403011r. Epub 2013 Nov 19. PubMed PMID: 24251920. 3: Fructos MR, Urbano J, Díaz-Requejo MM, Pérez PJ. Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate. Beilstein J Org Chem. 2015 Nov 20;11:2254-60. doi: 10.3762/bjoc.11.245. eCollection 2015. PubMed PMID: 26664649; PubMed Central PMCID: PMC4660976. 4: Li J, Qin G, Huang H. Silver-catalyzed nucleophilic substitution of aminals with ethyl diazoacetate: a new pathway to β-amino-α-diazoesters. Org Biomol Chem. 2016 Dec 7;14(45):10572-10575. Epub 2016 Oct 26. PubMed PMID: 27782284. 5: Trost BM, Malhotra S, Koschker P, Ellerbrock P. Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols. J Am Chem Soc. 2012 Feb 1;134(4):2075-84. doi: 10.1021/ja206995s. Epub 2012 Jan 18. PubMed PMID: 22088096; PubMed Central PMCID: PMC3271135. 6: Pagar VV, Liu RS. Gold-catalyzed cycloaddition reactions of ethyl diazoacetate, nitrosoarenes, and vinyldiazo carbonyl compounds: synthesis of isoxazolidine and benzo[b]azepine derivatives. Angew Chem Int Ed Engl. 2015 Apr 13;54(16):4923-6. doi: 10.1002/anie.201500340. Epub 2015 Feb 20. PubMed PMID: 25702833. 7: Zhou L, Haorah J, Chen SC, Wang X, Kolar C, Lawson TA, Mirvish SS. Nitrosation of glycine ethyl ester and ethyl diazoacetate to give the alkylating agent and mutagen ethyl chloro(hydroximino)acetate. Chem Res Toxicol. 2004 Mar;17(3):416-23. PubMed PMID: 15025513. 8: Fructos MR, Díaz-Requejo MM, Pérez PJ. Highly active gold-based catalyst for the reaction of benzaldehyde with ethyl diazoacetate. Chem Commun (Camb). 2009 Sep 14;(34):5153-5. doi: 10.1039/b908233f. Epub 2009 Jul 16. PubMed PMID: 20448977. 9: Caballero A, Despagnet-Ayoub E, Díaz-Requejo MM, Díaz-Rodríguez A, González-Núñez ME, Mello R, Muñoz BK, Ojo WS, Asensio G, Etienne M, Pérez PJ. Silver-catalyzed C-C bond formation between methane and ethyl diazoacetate in supercritical CO₂. Science. 2011 May 13;332(6031):835-8. doi: 10.1126/science.1204131. PubMed PMID: 21566191. 10: Reingruber EM, Chojnacka A, Jellema E, de Bruin B, Buchberger W, Schoenmakers PJ. Chromatographic examination of the chemical composition and sequence distribution of copolymers from ethyl and benzyl diazoacetate. J Chromatogr A. 2012 Sep 14;1255:259-66. doi: 10.1016/j.chroma.2012.02.059. Epub 2012 Mar 3. PubMed PMID: 22458967. 11: Alcaide B, Almendros P, Aragoncillo C, Callejo R, Ruiz MP, Torres MR. Rhodium-catalyzed synthesis of 3-hydroxy-beta-lactams via oxonium ylide generation: three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols. J Org Chem. 2009 Nov 6;74(21):8421-4. doi: 10.1021/jo9019013. PubMed PMID: 19831381. 12: Martín C, Molina F, Alvarez E, Belderrain TR. Stable N-heterocyclic carbene (NHC)-palladium(0) complexes as active catalysts for olefin cyclopropanation reactions with ethyl diazoacetate. Chemistry. 2011 Dec 23;17(52):14885-95. doi: 10.1002/chem.201102900. Epub 2011 Dec 2. PubMed PMID: 22139750. 13: Rosenberg ML, Krivokapic A, Tilset M. Highly cis-selective cyclopropanations with ethyl diazoacetate using a novel Rh(I) catalyst with a chelating N-heterocyclic iminocarbene ligand. Org Lett. 2009 Feb 5;11(3):547-50. doi: 10.1021/ol802591j. PubMed PMID: 19108673. 14: Shishilov ON, Stromnova TA, Cámpora J, Palma P, Cartes MA, Martínez-Prieto LM. Palladium(II) carboxylates and palladium(I) carbonyl carboxylate complexes as catalysts for olefin cyclopropanation with ethyl diazoacetate. Dalton Trans. 2009 Sep 7;(33):6626-33. doi: 10.1039/b904891j. Epub 2009 Jul 8. PubMed PMID: 19672507. 15: Kadina AP, Khlebnikov AF, Novikov MS, Pérez PJ, Yufit DS. Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to ester carbonyl--experimental and DFT computational study. Org Biomol Chem. 2012 Aug 7;10(29):5582-91. doi: 10.1039/c2ob25676b. Epub 2012 Jun 21. PubMed PMID: 22722405. 16: Liu G, Hu J, Wen J, Dai H, Li Y, Yan H. Cobalt-mediated selective B-H activation and formation of a Co-B bond in the reaction of the 16-electron CpCo half-sandwich complex containing an o-carborane-1,2-dithiolate ligand with ethyl diazoacetate. Inorg Chem. 2011 May 2;50(9):4187-94. doi: 10.1021/ic200333q. Epub 2011 Mar 28. PubMed PMID: 21443176. 17: Axe BP. Trace level detection and quantitation of ethyl diazoacetate by reversed-phase high performance liquid chromatography and UV detection. J Pharm Biomed Anal. 2006 Jun 7;41(3):804-10. Epub 2006 Feb 21. PubMed PMID: 16495031. 18: Trost BM, Malhotra S, Fried BA. Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes. J Am Chem Soc. 2009 Feb 11;131(5):1674-5. doi: 10.1021/ja809181m. PubMed PMID: 19191696; PubMed Central PMCID: PMC2652472. 19: Dudley ME, Morshed MM, Brennan CL, Islam MS, Ahmad MS, Atuu MR, Branstetter B, Hossain MM. Acid-catalyzed reactions of aromatic aldehydes with ethyl diazoacetate: an investigation on the synthesis of 3-hydroxy-2-arylacrylic acid ethyl esters. J Org Chem. 2004 Oct 29;69(22):7599-608. PubMed PMID: 15497987. 20: Xie JW, Wang Z, Yang WJ, Kong LC, Xu DC. Efficient method for the synthesis of functionalized pyrazoles by catalyst-free one-pot tandem reaction of nitroalkenes with ethyl diazoacetate. Org Biomol Chem. 2009 Nov 7;7(21):4352-4. doi: 10.1039/b915231h. Epub 2009 Aug 28. PubMed PMID: 19830281.

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SR57227A

SR57227A