Ethyl 7-chloro-2-oxoheptanoate

Base Information

• Chemical Name: Ethyl 7-chloro-2-oxoheptanoate
• CAS No.: 78834-75-0
• Molecular Formula: C9H15ClO3
• Molecular Weight: 206.669
• Hs Code.: 2918300090
• European Community (EC) Number: 278-992-1
• DSSTox Substance ID: DTXSID0057833
• Nikkaji Number: J319.186I
• Wikidata: Q72473736
• Mol file: 78834-75-0.mol

Synonyms:Ethyl 7-chloro-2-oxoheptanoate;78834-75-0;MFCD07698675;DTXSID0057833;Heptanoic acid, 7-chloro-2-oxo-, ethyl ester;EINECS 278-992-1;7-Chloro-2-oxoheptanoic Acid Ethyl Ester;ethyl 7-chloro-2-oxo heptanoate;Ethyl7-chloro-2-oxoheptanoate;SCHEMBL183581;DTXCID1031622;Ethyl 7-Chloro-2-Otoheptanoate;YJJLIIMRHGRCFM-UHFFFAOYSA-N;BCP13706;Tox21_113807;AC2328;AKOS015850587;AC-8476;CS-W015296;SB67322;NCGC00253683-01;DS-17736;SY036348;CAS-78834-75-0;E0827;FT-0641696;A22406;SR-01000944899;Q-201083;SR-01000944899-1

Chemical Property of Ethyl 7-chloro-2-oxoheptanoate

Chemical Property:

• Appearance/Colour: Slight green or slight yellow, clear Liquid
• Vapor Pressure: 0.00361mmHg at 25°C
• Refractive Index: 1.445
• Boiling Point: 281.2 °C at 760 mmHg
• Flash Point: 111.3 °C
• PSA: 43.37000
• Density: 1.093 g/cm³
• LogP: 1.91780
• Storage Temp.: -70°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 206.0709720
• Heavy Atom Count: 13
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 7-Chloro-2-oxoheptanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=O)CCCCCCl
• Uses: Ethyl 7-Chloro-2-oxoheptanoate is a reagent used in the synthesis of selective BCL-XL inhibitor A1155463 used in the treatment of cancer. Ethyl 7-chloro-2-oxoheptanoate is a product of the Grignard reaction that can be used to synthesize organic compounds. It has been used in the preparation of pharmaceuticals such as cilastatin, which is used to inhibit cytochrome P450 enzymes in order to prolong the effectiveness of other drugs. This reagent also reacts with hydrochloric acid to form ethyl chloride and heptanoic acid, which can be used for chlorination reactions.

Technology Process of Ethyl 7-chloro-2-oxoheptanoate

There total 11 articles about Ethyl 7-chloro-2-oxoheptanoate 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: 99.1%

1-bromo-5-chloropentane (54512-75-3) + oxalic acid diethyl ester (95-92-1) → ethyl-7-Chloro-2-oxoheptanoate (78834-75-0)

Guidance literature:

1-bromo-5-chloropentane; oxalic acid diethyl ester; In tetrahydrofuran; at -25 - -10 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 0 ℃; Reagent/catalyst; Inert atmosphere;

Reference yield: 97.0%

ethyl 7-chloro-α-hydroxyheptylate (1174680-07-9) → ethyl-7-Chloro-2-oxoheptanoate (78834-75-0)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide; In dichloromethane; water; at -2 - 8 ℃; for 3h;

Reference yield: 86.5%

C9H16ClO6S(1-)*Na(1+) → ethyl-7-Chloro-2-oxoheptanoate (78834-75-0)

Guidance literature:

With hydrogenchloride; In water; toluene; at 50 - 55 ℃; for 2h; Temperature; Solvent;

upstream raw materials:

1-bromo-5-chloropentane

oxalic acid diethyl ester

ethyl (E)-7-chloro-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate

5-chloro-n-pentylmagnesium bromide

Downstream raw materials:

7-chloro(1-oxoethyl)heptanoic acid ethyl ester

7-chloro-2-[[(1S)-2,2-dimethylcyclopropane]carboxamide]-2-heptenoic acid

(Z)-7-chloro-2 ((2s)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid

cilastatine

Refernces

• 1、 -. "Synthesis method of ethyl 7-chloro-2-oxohepanoate". Paragraph 0008; 0010-0018; 0029. . Retrieved 2018/11/22.
• 2、 -. "Purification method of ethyl 7-chloro-2-oxoheptanoate". Paragraph 0083; 0087. . Retrieved 2017/01/19.