Diethyl 2-acetylsuccinate

Base Information

• Chemical Name: Diethyl 2-acetylsuccinate
• CAS No.: 1115-30-6
• Molecular Formula: C10H16O5
• Molecular Weight: 216.234
• Hs Code.: 29183000
• European Community (EC) Number: 214-223-8
• NSC Number: 233
• DSSTox Substance ID: DTXSID60870842
• Nikkaji Number: J134.660A
• Mol file: 1115-30-6.mol

Synonyms:Diethyl 2-acetylsuccinate;Diethyl acetylsuccinate;1115-30-6;Butanedioic acid, acetyl-, diethyl ester;diethyl 2-acetylbutanedioate;Ethyl acetylsuccinate;Diethyl acetosuccinate;Acetylsuccinic acid diethyl ester;DIETHYLACETYLSUCCINATE;Succinic acid, acetyl-, diethyl ester;NSC 233;Butanedioic acid, 2-acetyl-, 1,4-diethyl ester;EINECS 214-223-8;MFCD00009157;AI3-05620;Diethyl acetylsuccinates;1,4-diethyl 2-acetylbutanedioate;DEAS;Diethyl-2-acetylsuccinate;CBDivE_005241;Diethyl acetylsuccinate, 95%;Diethylacetylsuccinate (DEAS);SCHEMBL460011;Diethyl acetylsuccinate, 97+%;NSC233;DTXSID60870842;NSC-233;2-Acetylsuccinic acid diethyl ester;2-acetyl-succinic acid diethyl ester;AC2238;STL199189;(2S)-2-acetyl-2,3-diethylsuccinate;AKOS000120634;AC-12479;AS-10128;SY033184;(2s,1s,2s)-2-(carboxycyclopropyl)glycine;A2212;CS-0067336;FT-0621811;Q-102038;F0001-0251

Chemical Property of Diethyl 2-acetylsuccinate

Chemical Property:

• Appearance/Colour: clear slightly yellow liquid
• Vapor Pressure: 0.0167mmHg at 25°C
• Melting Point: -8 °C
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 255 °C at 760 mmHg
• PKA: 10.63±0.59(Predicted)
• Flash Point: 126.1 °C
• PSA: 69.67000
• Density: 1.091 g/cm³
• LogP: 0.70790
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: 15g/L at 20℃
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 216.09977361
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

99.9% ^*data from raw suppliers

Diethyl 2-Acetylsuccinate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(C(=O)C)C(=O)OCC
• Uses: Diethyl 2-Acetylsuccinate functions as a reagent in the synthesis of Coumarin and Coumarin-3-acetic acid derivatives that exhibites antimicrobial activities against variety of gram positive and gram negative bacteria.

Technology Process of Diethyl 2-acetylsuccinate

There total 16 articles about Diethyl 2-acetylsuccinate 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: 75.0%

ethyl acetoacetate (141-97-9) + chloroacetic acid ethyl ester (105-39-5) → diethyl acetylsuccinate (1115-30-6)

Guidance literature:

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; at 45 - 50 ℃; 1.5-2h, other bases;

DOI:10.1007/BF00960683

Reference yield: 72.0%

ethyl acetoacetate (141-97-9) + ethyl bromoacetate (105-36-2) → diethyl acetylsuccinate (1115-30-6)

Guidance literature:

With aluminum oxide; potassium tert-butylate; for 6h;

Reference yield: 40.0%

acetaldehyde (75-07-0,9002-91-9) + diethyl Fumarate (623-91-6) → diethyl acetylsuccinate (1115-30-6)

Guidance literature:

With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; caesium carbonate; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c0ob01178a

upstream raw materials:

acetaldehyde

Diethyl maleate

dibenzoyl peroxide

sodium ethyl acetylacetate enolate

Downstream raw materials:

5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester

ethyl (4Z)-4-(2-phenylhydrazono)-4,5-dihydro-5-oxo-1-phenyl-1H-pyrazole-3-carboxylate

bis-phenylhydrazono-succinic acid diethyl ester

1-p-tolyl-3-carbethoxy-4-(p-tolylhydrazono)-5-pyrazolone

Refernces

• 1、 Dong, Wenyue,Yao, Peiyuan,Wang, Yingang,Wu, Qiaqing,Zhu, Dunming. "Chemoenzymatic Stereoselective Synthesis of Substituted γ- or δ-lactams with Two Chiral Centers via Transaminase-catalysed Dynamic Kinetic Resolution". . p. 6311 - 6316. Retrieved 2020.
• 2、 Adkins,Isbell,Wojcik. "-". . p. 38. Retrieved 1934.
• 3、 Sun, Mingna,Hu, Jinfeng,Song, Xiuyun,Wu, Donghui,Kong, Linglei,Sun, Yupeng,Wang, Dongmei,Wang, Yan,Chen, Naihong,Liu, Gang. "Coumarin derivatives protect against ischemic brain injury in rats". . p. 39 - 53. Retrieved 2013/10/01.