3-Isobutylglutaric acid

Base Information

• Chemical Name: 3-Isobutylglutaric acid
• CAS No.: 75143-89-4
• Molecular Formula: C9H16O4
• Molecular Weight: 188.224
• Hs Code.: 2917190090
• European Community (EC) Number: 921-663-0,844-398-1
• UNII: EMH1IVR5QH
• DSSTox Substance ID: DTXSID00450420
• Wikidata: Q72485043
• Mol file: 75143-89-4.mol

Synonyms:3-isobutylglutaric acid;75143-89-4;3-(2-methylpropyl)pentanedioic Acid;3-isobutylpentanedioic acid;Pentanedioic acid, 3-(2-methylpropyl)-;isobutylglutaric acid;EMH1IVR5QH;3-isobutyl glutaric acid;MFCD15529751;3-Isobutylglutaricacid;Pregabalin Impurity B;Pregabalin Impurity 4;UNII-EMH1IVR5QH;SCHEMBL1410027;AMY4101;DTXSID00450420;UATSLDZQNXAKMA-UHFFFAOYSA-N;BCP12370;AKOS015841726;CS-O-13756;CS-W019327;AC-25625;AS-10103;SY033309;FT-0657207;D70576;EN300-1847553;A838334;J-512713;2,3-DIHYDRO-1H-INDOLE-4-CARBONITRILEHYDROCHLORIDE;3-(2-Methylpropyl)pentanedioic Acid (3-Isobutylglutaric Acid);3-(2-Methylpropyl)pentanedioic acid;3-Isobutylglutaric acid

Chemical Property of 3-Isobutylglutaric acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 47 °C
• Refractive Index: 1.472
• Boiling Point: 326.197 °C at 760 mmHg
• PKA: 4.19±0.10(Predicted)
• Flash Point: 165.289 °C
• PSA: 74.60000
• Density: 1.126 g/cm³
• LogP: 1.59810
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 188.10485899
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

99.5% ^*data from raw suppliers

3-(2-Methylpropyl)pentanedioicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(CC(=O)O)CC(=O)O
• Uses: An impurity of Pregabalin (P704800) with anticonvulsant properties.

Technology Process of 3-Isobutylglutaric acid

There total 26 articles about 3-Isobutylglutaric 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: 99.4%

2,4-dicyano-3-isobutylglutaramide (185815-56-9) → 5-methyl-3-carboxymethylhexanoic acid (75143-89-4)

Guidance literature:

With sulfuric acid; for 12h; Reflux;

Reference yield: 91.0%

1,5-diethy 3-isobutylpentanedioate → 5-methyl-3-carboxymethylhexanoic acid (75143-89-4)

Guidance literature:

With hydrogenchloride; In water; for 4h; Time; Reflux;

Reference yield: 85.0%

2?cyano?5?methylhex?2?enoic acid methyl ester (868-52-0) + diethyl malonate (105-53-3) → 5-methyl-3-carboxymethylhexanoic acid (75143-89-4)

Guidance literature:

2?cyano?5?methylhex?2?enoic acid methyl ester; diethyl malonate; With piperidine; at 55 ℃; for 2h;

With hydrogenchloride; In water; at 100 - 120 ℃; for 72h;

DOI:10.1007/s13738-019-01759-3

upstream raw materials:

malonic acid

isovaleraldehyde

2-isobutyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester

C₁₇H₂₄O₈

Downstream raw materials:

pregabilin

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid

(R)-3-(carbamoylmethyl)-5-methylhexanoic acid (R)-(+)-α-phenylethylamine

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

Refernces

• 1、 -. "Method for synthesizing optically pure (R)-3-carbamoymethyl-5-methylhexanoic acid". Paragraph 0019; 0021; 0024; 0028; 0030. . Retrieved 2019/09/14.
• 2、 -. "Preparation method and application of high-purity dimethyl 3-isobutylglutarate". Paragraph 0124; 0127; 0133; 0135; 0171-0172. . Retrieved 2019/12/02.