4-Hydroxy-4-methylpent-2-ynoic acid

Base Information

• Chemical Name: 4-Hydroxy-4-methylpent-2-ynoic acid
• CAS No.: 50624-25-4
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• Hs Code.: 2918199090
• European Community (EC) Number: 809-468-8
• DSSTox Substance ID: DTXSID60390373
• Nikkaji Number: J3.354.818D
• Wikidata: Q82187020
• Mol file: 50624-25-4.mol

Synonyms:4-hydroxy-4-methylpent-2-ynoic acid;50624-25-4;4-Hydroxy-4-methyl-pent-2-ynoic acid;4-hydroxy-4-methyl-2-pentynoic acid;SCHEMBL8163121;DTXSID60390373;SSMODACYDJLXEK-UHFFFAOYSA-N;4-hydroxy-4-methylpent-2-ynoicacid;MFCD05863690;4-hydroxy-4-methyl-2-pentinoic acid;4-methyl-4-hydroxypent-2-ynoic acid;4-Methyl-4-hydroxy-2-pentyneoic acid;AKOS005263947;BS-36617;BB 0260136;CS-0244851;FT-0724451;EN300-2956232;4-Hydroxy-4-methylpent-2-ynoic acid, AldrichCPR;Z1198166162

Chemical Property of 4-Hydroxy-4-methylpent-2-ynoic acid

Chemical Property:

• Vapor Pressure: 0.000626mmHg at 25°C
• Boiling Point: 275.8°C at 760 mmHg
• PKA: 2.26±0.10(Predicted)
• Flash Point: 134.8°C
• PSA: 57.53000
• Density: 1.243g/cm³
• LogP: -0.15470
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 179

Purity/Quality:

98%min ^*data from raw suppliers

4-Hydroxy-4-methylpent-2-ynoic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C#CC(=O)O)O

Technology Process of 4-Hydroxy-4-methylpent-2-ynoic acid

There total 8 articles about 4-Hydroxy-4-methylpent-2-ynoic 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: 53.0%

acetone (67-64-1) + Propiolic acid (471-25-0) → 4-hydroxy-4-methyl-2-pentynoic acid (50624-25-4)

Guidance literature:

With potassium hydroxide; at 20 ℃; Inert atmosphere;

DOI:10.3762/bjoc.10.36

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + 2-methyl-but-3-yn-2-ol (115-19-5) → 4-hydroxy-4-methyl-2-pentynoic acid (50624-25-4)

Guidance literature:

Multistep reaction; (i) EtMgBr, (ii) /BRN= 1900390/;

DOI:10.1007/BF00909539

Reference yield:

4-methyl-4-tert-butylperoxy-2-pentynoic acid (129913-03-7) → 4-hydroxy-4-methyl-2-pentynoic acid (50624-25-4) + 4-n-butoxy-4-methylpentanoic acid (24303-68-2)

Guidance literature:

In diethyl ether; hexane; at 60 ℃; for 3h; under 0.02 Torr;

upstream raw materials:

methyl chloroformate

carbon dioxide

2-methyl-but-3-yn-2-ol

n-butyllithium

Downstream raw materials:

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

2-methyl-4-(3-aminophenyl)-3-butyn-2-ol

3-butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl, hydrochloride

2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol

Refernces

• 1、 Caporale, Andrea,Tartaggia, Stefano,Castellin, Andrea,De Lucchi, Ottorino. "Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions". supporting information. p. 384 - 393. Retrieved 2014/03/21.