3-Isopropylglutaric acid

Base Information

• Chemical Name: 3-Isopropylglutaric acid
• CAS No.: 4165-99-5
• Molecular Formula: C8H14O4
• Molecular Weight: 174.197
• Hs Code.: 2917190090
• European Community (EC) Number: 224-018-5
• DSSTox Substance ID: DTXSID50194468
• Nikkaji Number: J224.970G
• Wikidata: Q83067218
• Mol file: 4165-99-5.mol

Synonyms:3-Isopropylglutaric acid;4165-99-5;3-(propan-2-yl)pentanedioic acid;3-propan-2-ylpentanedioic acid;beta-Isopropylglutaric acid;Pentanedioic acid, 3-(1-methylethyl)-;EINECS 224-018-5;3-isopropylpentanedioic acid;SCHEMBL5960145;3-(propan-2-yl)pentanedioicacid;DTXSID50194468;AKOS006272061;CS-0235251;EN300-154382;F2148-1480

Chemical Property of 3-Isopropylglutaric acid

Chemical Property:

• Vapor Pressure: 0.000111mmHg at 25°C
• Boiling Point: 313°Cat760mmHg
• PKA: pK1:4.3;pK2:5.51 (25°C)
• Flash Point: 157.3°C
• PSA: 74.60000
• Density: 1.156g/cm³
• LogP: 1.20800
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 174.08920892
• Heavy Atom Count: 12
• Complexity: 158

Purity/Quality:

98%Min ^*data from raw suppliers

3-(propan-2-yl)pentanedioicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Isopropylglutaric acid

There total 40 articles about 3-Isopropylglutaric acid 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: 87.0%

methyl ethyl 2-carbomethoxy-4-cyano-3-isopropylglutarate (145610-10-2) → 3-isopropylglutaric acid (4165-99-5)

Guidance literature:

With hydrogen bromide; for 24h; Heating;

DOI:10.1021/jo00053a027

Reference yield: 23.0%

(E)-ethyl 2-cyano-4-methylpent-2-enoate (868-47-3,125027-35-2,93222-76-5) + malonic acid dimethyl ester (108-59-8) → 3-isopropylglutaric acid (4165-99-5)

Guidance literature:

(E)-ethyl 2-cyano-4-methylpent-2-enoate; malonic acid dimethyl ester; With sodium; In methanol; for 16h; Inert atmosphere; Reflux;

With hydrogenchloride; In methanol; water; for 48h; Inert atmosphere; Reflux;

DOI:10.1002/chem.202003280

Reference yield:

3-Isopropylglutarnitril (1023971-76-7) → 3-isopropylglutaric acid (4165-99-5)

Guidance literature:

With hydrogenchloride; for 4h; Yield given; Heating;

upstream raw materials:

dimethyl 3-isopropylglutarate

2-isopropyl-propane-1,1,3-tricarboxylic acid

3-chloro-5-isopropyl-cyclohex-2-enone

4-isopropyl-2-methyl-cyclopentanone

Downstream raw materials:

terpenylic acid

Refernces

• 1、 Kutama, Ibrahim U.,Jones, Simon. "Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol". . p. 11468 - 11479. Retrieved 2015/12/04.
• 2、 Theisen, Peter D.,Heathcock, Clayton H.. "Prochiral Recognition in the Reaction of 3-Substituted Glutaric Anhydrides with Chiral Secondary Alcohols". . p. 142 - 146. Retrieved 2007/10/02.