4-Methylpentanoic acid

Base Information

• Chemical Name: 4-Methylpentanoic acid
• CAS No.: 646-07-1
• Deprecated CAS: 1331-16-4,1866-94-0,38784-67-7,1866-94-0,38784-67-7
• Molecular Formula: C6H12 O2
• Molecular Weight: 116.16
• Hs Code.: 29159080
• European Community (EC) Number: 211-464-0
• NSC Number: 4126
• UNII: 4G4U8JA28T
• DSSTox Substance ID: DTXSID8060951
• Nikkaji Number: J1.720E
• Wikipedia: 4-Methylpentanoic_acid
• Wikidata: Q19597905
• Metabolomics Workbench ID: 146
• ChEMBL ID: CHEMBL1230308
• Mol file: 646-07-1.mol

Synonyms:4-methylpentanoic acid;isocaproic acid;isocaproic acid, sodium salt;isohexanoic acid

Chemical Property of 4-Methylpentanoic acid

Chemical Property:

• Appearance/Colour: slightly brown liquid
• Vapor Pressure: 0.131mmHg at 25°C
• Melting Point: -35 ºC
• Refractive Index: n20/D 1.414(lit.)
• Boiling Point: 200 ºC
• PKA: 4.84(at 18℃)
• Flash Point: 97 ºC
• PSA: 37.30000
• Density: 0.922
• LogP: 1.50720
• Storage Temp.: Store below +30°C.
• Water Solubility.: INSOLUBLE
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 116.083729621
• Heavy Atom Count: 8
• Complexity: 76.6

Purity/Quality:

99% ^*data from raw suppliers

4-Methylvaleric Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,C
• Statements: 21-38-34
• Safety Statements: 36/37-45-36/37/39-25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(C)CCC(=O)O
• Description: 4-Methylpentanoic acid has an unpleasant sour and penetrating odor.
• Uses: 4-Methylvaleric acid has been used in asymmetric synthesis of (4S)-4-isopropyl-3-[(2?S)-2?,4?-dimethyl-valeryl)]-2-oxazolidinone. It is a versatile building block used in the synthesis of various pharmaceutical and biologically active compounds, including inhibitors and antagonists. It is involved in the synthesis of novel series of high affinity, functionally potent antagonists of the CCR1 receptor. 4-Methylvaleric acid has been used in asymmetric synthesis of (4S)-4-isopropyl-3-[(2′S)-2′,4′-dimethyl-valeryl)]-2-oxazolidinone. Intermediate for plasticizers, pharmaceuticalsand perfumes.

Technology Process of 4-Methylpentanoic acid

There total 83 articles about 4-Methylpentanoic 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: 97.0%

dihydro-5,5-dimethyl-2(3H)-furanone (3123-97-5) → 4-Methylpentanoic acid (646-07-1)

Guidance literature:

With hafnium tetrakis(trifluoromethanesulfonate); palladium on activated carbon; hydrogen; In neat (no solvent); at 135 ℃; for 12h; under 760.051 Torr; Schlenk technique; Glovebox;

DOI:10.1021/acs.orglett.9b02673

Reference yield: 86.0%

2,2-Dimethyl-5-(2-methylpropyl)-1,3-dioxane-4,6-dione (74965-92-7) → 4-Methylpentanoic acid (646-07-1)

Guidance literature:

With hydrogenchloride; for 24h; Heating;

DOI:10.1021/jo01311a011

Reference yield: 82.0%

β-Propiolactone (57-57-8) + isopropylmagnesium chloride (1068-55-9) → 4-Methylpentanoic acid (646-07-1)

Guidance literature:

With copper(I) bromide; In tetrahydrofuran; at -5 ℃; for 1h;

DOI:10.1016/S0040-4039(00)77743-4

upstream raw materials:

4-(1-methylethyl)oxetan-2-one

dihydro-5,5-dimethyl-2(3H)-furanone

diethyl ether

ethene

Downstream raw materials:

5-methyl-1-phenylhexan-2-one

isomyristic acid

2,8-dimethylnonan-5-one

2-Bromo-4-methylpentanoic Acid

Refernces

• 1、 Jung, Hoi-Yun,Chang, Sukbok,Hong, Sungwoo. "Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation". supporting information. p. 7099 - 7103. Retrieved 2019/09/07.
• 2、 Zhu, Rui,Jiang, Ju-Long,Li, Xing-Long,Deng, Jin,Fu, Yao. "A Comprehensive Study on Metal Triflate-Promoted Hydrogenolysis of Lactones to Carboxylic Acids: From Synthetic and Mechanistic Perspectives". . p. 7520 - 7528. Retrieved 2017/11/10.