Dimethyl 3,3-dimethylpentanedioate

Base Information

• Chemical Name: Dimethyl 3,3-dimethylpentanedioate
• CAS No.: 19184-67-9
• Molecular Formula: C9H16O4
• Molecular Weight: 188.224
• European Community (EC) Number: 621-346-4
• NSC Number: 99223
• DSSTox Substance ID: DTXSID10172722
• Nikkaji Number: J663G
• Wikidata: Q63398076
• Mol file: 19184-67-9.mol

Synonyms:19184-67-9;Dimethyl 3,3-dimethylpentanedioate;3,3-DIMETHYL-PENTANEDIOIC ACID DIMETHYL ESTER;Pentanedioic acid, 3,3-dimethyl-, dimethyl ester;Methyl 3,3-dimethylglutarate;Glutaric acid, 3,3-dimethyl-, dimethyl ester;NSC99223;SCHEMBL667630;Dimethyl3,3-dimethylpentanedioate;DTXSID10172722;3,3-Dimethylglutaric acid dimethyl;MFCD00182435;NSC 99223;NSC-99223;Dimethyl 3,3-dimethylpentanedioate #;AKOS024332258;AM806128;BS-21978;Glutaric acid,3-dimethyl-, dimethyl ester;CS-0205140;FT-0749670;Pentanedioic acid,3-dimethyl-, dimethyl ester;3,3-DIMETHYLGLUTARIC ACID DIMETHYL ESTER;Q63398076

Chemical Property of Dimethyl 3,3-dimethylpentanedioate

Chemical Property:

• Vapor Pressure: 0.301mmHg at 25°C
• Refractive Index: 1.4199 (estimate)
• Boiling Point: 201.9°Cat760mmHg
• Flash Point: 86.2°C
• PSA: 52.60000
• Density: 1.022g/cm³
• LogP: 1.13880
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 188.10485899
• Heavy Atom Count: 13
• Complexity: 176

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,3-DIMETHYL-PENTANEDIOIC ACID DIMETHYL ESTER Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(CC(=O)OC)CC(=O)OC

Technology Process of Dimethyl 3,3-dimethylpentanedioate

There total 7 articles about Dimethyl 3,3-dimethylpentanedioate 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: 99.0%

methanol (67-56-1) + 3,3-Dimethylglutaric acid (4839-46-7) → methyl 3,3-dimethylglutarate (19184-67-9)

Guidance literature:

With thionyl chloride; for 2h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.9b03078

Reference yield:

N-(1-Methoxy-3-oxo-1-cyclopenten-2-yl)benzamid (41893-60-1) → methyl 3,3-dimethylglutarate (19184-67-9) + benzamide (55-21-0,27208-38-4)

Guidance literature:

With hydrogenchloride; ozone; Yield given. Multistep reaction. Yields of byproduct given; 1.) methylenechlorid, -60 deg C; 2.) methanol, reflux, 60 min.;

DOI:10.1016/S0040-4020(01)97722-1

Reference yield:

methyldimedone (1125-11-7) → methyl 3,3-dimethylglutarate (19184-67-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O₂, aq. NaOH / methanol

With sodium hydroxide; dihydrogen peroxide; In methanol;

upstream raw materials:

methanol

3,3-Dimethylglutaric acid

diazomethane

N-(1-Methoxy-3-oxo-1-cyclopenten-2-yl)benzamid

Downstream raw materials:

3,3-Dimethyl-1,1,5,5-tetraphenyl-1,5-pentanediol

2-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-3,3-dimethyl-pentanedioic acid 1-methyl ester

2-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-3,3-dimethyl-pentanedioic acid 1-methyl ester

2-[1-(3,4-Dichloro-phenyl)-meth-(E)-ylidene]-3,3-dimethyl-pentanedioic acid 1-methyl ester

Refernces

• 1、 -. "BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS". Page/Page column 62. . Retrieved 2018/03/09.
• 2、 Heard, Kathryn R.,Wu, Wengen,Li, Youhua,Zhao, Peng,Woznica, Iwona,Lai, Jack H.,Beinborn, Martin,Sanford, David G.,Dimare, Matthew T.,Chiluwal, Amrita K.,Peters, Diane E.,Whicher, Danielle,Sudmeier, James L.,Bachovchin, William W.. "A general method for making peptide therapeutics resistant to serine protease degradation: Application to dipeptidyl peptidase IV substrates". supporting information. p. 8339 - 8351. Retrieved 2013/12/04.