Ethyl malonyl chloride

Base Information

• Chemical Name: Ethyl malonyl chloride
• CAS No.: 36239-09-5
• Molecular Formula: C5H7ClO3
• Molecular Weight: 150.562
• Hs Code.: 29171900
• European Community (EC) Number: 252-934-5
• UNII: 6TYB4UU3RU
• DSSTox Substance ID: DTXSID80189786
• Nikkaji Number: J148.007C
• Wikidata: Q72475660
• Mol file: 36239-09-5.mol

Synonyms:ethyl malonyl chloride

Chemical Property of Ethyl malonyl chloride

Chemical Property:

• Appearance/Colour: clear yellow to brown liquid
• Vapor Pressure: 1.003mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Boiling Point: 172.4 °C at 760 mmHg
• PKA: 9.35±0.46(Predicted)
• Flash Point: 65 °C
• PSA: 34.14000
• Density: 1.223 g/cm³
• LogP: 1.54340
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: REACTS
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 150.0083718
• Heavy Atom Count: 9
• Complexity: 121

Purity/Quality:

99% ^*data from raw suppliers

Ethyl Malonyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 7-26-36/37/39-45-36/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)Cl
• Uses: Employed in the synthesis of 3-pyrrolin-2-ones via amidation with propargylamines and subsequent base catalyzed 5-exo-dig cyclization.1 Ethyl malonyl chloride is used in the syntheses of methanofullerodendimers and 3-pyrrolin-2-ones. It plays a vital role in the preparation of 3,5-disubstituted 1,2,4-oxadiazole derivatives, which are potential peptidomimetic building blocks. It is a versatile acylating agent for propargyl alcohols, hydrazines and amines.

Technology Process of Ethyl malonyl chloride

There total 10 articles about Ethyl malonyl chloride 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: 91.0%

hydrogen ethyl malonate (1071-46-1) → ethyl chlorocarbonylacetate (36239-09-5)

Guidance literature:

With thionyl chloride;

DOI:10.1016/j.bmcl.2006.10.030

Reference yield: 90.0%

ethyl potassium malonate (6148-64-7) → ethyl chlorocarbonylacetate (36239-09-5)

Guidance literature:

With oxalyl dichloride; In benzene; for 1h; Ambient temperature;

Reference yield:

diethyl malonate (105-53-3) → ethyl chlorocarbonylacetate (36239-09-5)

Guidance literature:

Multistep reaction; (i) (hydrolysis), (ii) SOCl₂, PhNMe₂;

DOI:10.1021/ja01039a029

upstream raw materials:

hydrogen ethyl malonate

diethyl malonate

ethyl potassium malonate

Phthaloyl dichloride

Downstream raw materials:

2-Amino-1,3,4-thiadiazolyl-5-acetic acid ethyl ester

(amino-anilino-[1,3,5]triazin-2-yl)-acetic acid ethyl ester

N²,N^2'-diphenyl-6,6'-methanediyl-bis-[1,3,5]triazine-2,4-diyldiamine

tert-Butyl ethyl malonate

Refernces

• 1、 -. "Double-[...] compound and its method and use thereof". Paragraph 0342; 0343; 0413; 0414. . Retrieved 2018/10/11.
• 2、 -. "ANTIBACTERIAL COMPOUNDS". Page/Page column 110; 111. . Retrieved 2017/04/11.