Diethyl(3-methylbutylidene)malonate

Base Information

• Chemical Name: Diethyl(3-methylbutylidene)malonate
• CAS No.: 51615-30-6
• Molecular Formula: C12H20 O4
• Molecular Weight: 228.288
• Hs Code.: 2917190090
• European Community (EC) Number: 610-710-8
• NSC Number: 30048
• DSSTox Substance ID: DTXSID80283137
• Nikkaji Number: J1.196.654C
• Mol file: 51615-30-6.mol

Synonyms:diethyl(3-methylbutylidene)malonate;51615-30-6;diethyl 2-(3-methylbutylidene)propanedioate;2-(3-methyl-butylidene)-malonic acid diethyl ester;NSC30048;SCHEMBL1408810;DTXSID80283137;NSC 30048;NSC-30048;Isopentylidenemalonic acid diethyl ester;1,3-DIETHYL 2-(3-METHYLBUTYLIDENE)PROPANEDIOATE

Chemical Property of Diethyl(3-methylbutylidene)malonate

Chemical Property:

• Vapor Pressure: 0.0182mmHg at 25°C
• Boiling Point: 253.5°C at 760 mmHg
• Flash Point: 111.2°C
• PSA: 52.60000
• Density: 1.003g/cm³
• LogP: 2.08510
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 228.13615911
• Heavy Atom Count: 16
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(=CCC(C)C)C(=O)OCC
• Uses: Diethyl 2-(3-methylbutylidene)malonate used in the preparation of pregabalin (P704790) which is a GABA analogue used as an anticonvulsant. Anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia.

Technology Process of Diethyl(3-methylbutylidene)malonate

There total 2 articles about Diethyl(3-methylbutylidene)malonate 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: 96.6%

isovaleraldehyde (590-86-3) + diethyl malonate (105-53-3) → diethyl 2-(3-methylbutylidene)malonate (51615-30-6)

Guidance literature:

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

Reference yield:

→ diethyl 2-(3-methylbutylidene)malonate (51615-30-6)

Guidance literature:

DOI:10.1016/S0040-4039(01)93571-3

Reference yield: 97.97%

diethyl 2-(3-methylbutylidene)malonate (51615-30-6) + sodium cyanide (143-33-9,25596-52-5) → 2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid ethyl ester (186038-82-4)

Guidance literature:

In ethanol; at 25 - 35 ℃; for 2 - 3h;

upstream raw materials:

isovaleraldehyde

diethyl malonate

Downstream raw materials:

3-amino-5-methylhexanoic acid

diethyl isopentylmalonate

5-methylhexyl bromide

5-methyl-1-hexanol

Refernces

• 1、 -. "Preparation method of 1-cyano-3-methylbutyldiethyl malonate". Paragraph 0060-0062. . Retrieved 2021/06/12.
• 2、 -. "Synthesis method of pregabalin intermediate 2-carboxyethyl-3-nitromethylene-5-methyl ethyl hexanoate". Paragraph 0021-0025; 0029; 0030; 0032; 0033; 0035-0039. . Retrieved 2020/02/27.