ETHYL DIAZOACETOACETATE

Base Information

• Chemical Name: ETHYL DIAZOACETOACETATE
• CAS No.: 2009-97-4
• Molecular Formula: C6H8 N2 O3
• Molecular Weight: 156.141
• Hs Code.: 29270000
• Mol file: 2009-97-4.mol

Synonyms:Acetoaceticacid, 2-diazo-, ethyl ester (7CI,8CI); 2-Diazo-3-oxobutanoic acid ethyl ester;Ethyl 2-diazo-3-oxobutanoate; Ethyl 2-diazo-3-oxobutyrate; Ethyl2-diazoacetoacetate; Ethyl a-diazoacetoacetate

Chemical Property of ETHYL DIAZOACETOACETATE

Chemical Property:

• Vapor Pressure: 0.36 psi ( 20 °C)
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 102-103 °C(Press: 12 Torr)
• Flash Point: 185 °F
• PSA: 80.76000
• Density: 1.131 g/mL at 25 °C(lit.)
• LogP: -0.10964

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl diazoacetoacetate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ETHYL DIAZOACETOACETATE

There total 14 articles about ETHYL DIAZOACETOACETATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

ethyl acetoacetate (141-97-9) → ethyl 2-diazo-3-oxobutanoate (2009-97-4)

Guidance literature:

With 4-toluenesulfonyl azide; tetrabutyl-ammonium chloride; potassium carbonate; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201600952

Reference yield: 92.0%

4-toluenesulfonyl azide (941-55-9) + ethyl acetoacetate (141-97-9) → ethyl 2-diazo-3-oxobutanoate (2009-97-4)

Guidance literature:

With caesium carbonate; In tetrahydrofuran; at 25 ℃; for 3h;

DOI:10.1002/anie.201812925

Reference yield: 92.0%

ethyl acetoacetate (141-97-9) + Methanesulfonyl azide (624-90-8,1516-70-7) → ethyl 2-diazo-3-oxobutanoate (2009-97-4)

Guidance literature:

With sodium hydroxide; In 1,2-dichloro-ethane; for 8h; Ambient temperature;

DOI:10.1080/00397919108055444

upstream raw materials:

diazoacetic acid ethyl ester

acetyl chloride

ethyl 2-hydroxyimino-3-oxobutanoate

ethyl acetoacetate

Downstream raw materials:

ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate

5-methyl-1-ureido-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

3-oxo-2-(triphenylphosphoranylidene-hydrazono)-butyric acid ethyl ester

ethyl 2-acetyl-4-oxopentanoate

Refernces

• 1、 Yan, Ziqiang,Li, Yuanheng,Ma, Mingming. "Solvent-Directed Click Reaction between Active Methylene Compounds and Azido-1,3,5-triazines". . p. 7204 - 7208. Retrieved 2019.
• 2、 Jaszay, Zsuzsa M.,Pham, Truong Son,Goenczi, Katalin,Petnehazy, Imre,Toke, Laszlo. "Efficient solid/liquid phase-transfer catalytic diazo transfer synthesis". . p. 1574 - 1579. Retrieved 2010.
• 3、 Li, Fengxi,Li, Zhengqiang,Tang, Xuyong,Wang, Chunyu,Wang, Lei,Wang, Zhi,Xu, Yaning. "A dual-protein cascade reaction for the regioselective synthesis of quinoxalines". . p. 3900 - 3904. Retrieved 2020.
• 4、 Nagarajan, Rajendran,Jayashankaran, Jayadevan,Emmanuvel, Lourdusamy. "Transition metal-free steric controlled one-pot synthesis of highly substituted N-amino 1,2,3-triazole derivatives via diazo transfer reaction from β-keto esters". . p. 2612 - 2615. Retrieved 2016.
• 5、 Fantinel, Mariane,Valiati, Nayara,Moro, Pedro A.M.,Sá, Marcus M.. "Amino-modified Merrifield resins as recyclable catalysts for the safe and sustainable preparation of functionalized α-diazo carbonyl compounds". . . Retrieved 2021/03/30.
• 6、 Kim, Jiyoung,Yoo, Eun Jeong. "Catalytic Ring Expansion of Activated Heteroarenes Enabled by Regioselective Dearomatization". supporting information. p. 4256 - 4260. Retrieved 2021/06/28.