Ethyl 5-methyl-3-(nitromethyl)hexanoate

Base Information

• Chemical Name: Ethyl 5-methyl-3-(nitromethyl)hexanoate
• CAS No.: 128013-65-0
• Molecular Formula: C10H19NO4
• Molecular Weight: 217.265
• DSSTox Substance ID: DTXSID30560647
• Mol file: 128013-65-0.mol

Synonyms:128013-65-0;ethyl 5-methyl-3-(nitromethyl)hexanoate;5-METHYL-3-(NITROMETHYL)HEXANOIC ACID ETHYL ESTER;Hexanoic acid, 5-methyl-3-(nitromethyl)-, ethyl ester;Ethyl 5-methyl-3-nitromethyl-hexanoate;starbld0010817;SCHEMBL1228652;DTXSID30560647;LOHHVAYLSGONPS-UHFFFAOYSA-N;AKOS030255437;Ethyl (+/-)-3-nitromethyl-5-methylhexanoate;(+/-) Ethyl 5-methyl-3-nitromethyl-hexanoate;5-methyl-3-nitromethyl-hexanoic acid ethyl ester;J-005562

Chemical Property of Ethyl 5-methyl-3-(nitromethyl)hexanoate

Chemical Property:

• Vapor Pressure: 0.00139mmHg at 25°C
• Boiling Point: 297oC at 760 mmHg
• PKA: 8.41±0.50(Predicted)
• Flash Point: 112.6oC
• PSA: 72.12000
• Density: 1.031g/cm3
• LogP: 2.40180
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 217.13140809
• Heavy Atom Count: 15
• Complexity: 210

Purity/Quality:

98%Min ^*data from raw suppliers

5-Methyl-3-(nitromethyl)hexanoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(CC(C)C)C[N+](=O)[O-]
• Uses: 5-Methyl-3-nitromethyl-hexanoic Acid, Ethyl Ester is a useful synthetic intermediate Pregabalin Pregabalin intermediate.

Technology Process of Ethyl 5-methyl-3-(nitromethyl)hexanoate

There total 5 articles about Ethyl 5-methyl-3-(nitromethyl)hexanoate 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: 97.0%

nitromethane (75-52-5) + 5-methyl-2-hexenoic acid ethyl ester (34993-63-0,79918-80-2,2351-89-5) → 3-nitromethyl-5-methyl-hexanoic acid ethyl ester (128013-65-0)

Guidance literature:

With choline chloride; urea; at 80 ℃; Temperature;

Reference yield: 96.0%

nitromethane (75-52-5) + (+/-) ethyl 5-methyl-3-bromo-hexanoate (1166864-51-2) → 3-nitromethyl-5-methyl-hexanoic acid ethyl ester (128013-65-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 0 - 30 ℃; for 2.5h;

Reference yield: 75.0%

nitromethane (75-52-5) + ethyl (E)-5-methylhex-2-enoate (34993-63-0) → 3-nitromethyl-5-methyl-hexanoic acid ethyl ester (128013-65-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 20 ℃;

DOI:10.1016/j.tetasy.2008.03.014

upstream raw materials:

nitromethane

5-methyl-2-hexenoic acid ethyl ester

ethyl (E)-5-methylhex-2-enoate

(+/-) ethyl 5-methyl-3-bromo-hexanoate

Downstream raw materials:

4-(2-methylpropyl)pyrrolidin-2-one

pregabilin

(R,S)-3-iso-butyl-4-aminobutyric acid

Refernces

• 1、 -. "Synthesis method of pregabalin intermediate 3-nitromethylene-5-methyl-ethyl hexanoate". Paragraph 0022; 0029; 0031; 0032-0037. . Retrieved 2020/02/27.
• 2、 -. "PROCESS FOR PREPARING PREGABALIN". Page/Page column 6. . Retrieved 2012/06/16.