3-HYDROXY-3-METHYL-2-BUTANONE

Base Information

• Chemical Name: 3-HYDROXY-3-METHYL-2-BUTANONE
• CAS No.: 115-22-0
• Deprecated CAS: 109916-60-1
• Molecular Formula: C5H10O2
• Molecular Weight: 102.133
• Hs Code.: 29144000
• European Community (EC) Number: 204-073-1
• NSC Number: 5576
• DSSTox Substance ID: DTXSID60870468
• Nikkaji Number: J95.395D
• Wikidata: Q72485146
• Metabolomics Workbench ID: 5469
• Mol file: 115-22-0.mol

Synonyms:1-Hydroxy-1-methylethylmethyl ketone;2-Hydroxy-2-methyl-3-butanone;2-Methyl-2-hydroxy-3-butanone;3-Hydroxy-3-methylbutanone;3-Methyl-3-hydroxy-2-butanone;3-Methylacetoin;Acetyldimethylcarbinol;Dimethylacetylcarbinol;Methylacetoin;NSC 5576;

Chemical Property of 3-HYDROXY-3-METHYL-2-BUTANONE

Chemical Property:

• Appearance/Colour: clear colourless to light yellow liquid
• Vapor Pressure: 1.03mmHg at 25°C
• Melting Point: 84-85 °C
• Refractive Index: n20/D 1.415(lit.)
• Boiling Point: 145.214 °C at 760 mmHg
• PKA: 13.28±0.29(Predicted)
• Flash Point: 42.222 °C
• PSA: 37.30000
• Density: 0.966 g/cm³
• LogP: 0.34630
• Storage Temp.: Flammables area
• Solubility.: Soluble in chloroform.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 102.068079557
• Heavy Atom Count: 7
• Complexity: 84.1

Purity/Quality:

99.9% ^*data from raw suppliers

3-Hydroxy-3-methyl-2-butanone >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 23-24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Other Solvents
• Canonical SMILES: CC(=O)C(C)(C)O
• Uses: 3-Hydroxy-3-methyl-2-butanone used to produce 2,5-dihydroxy-2-methyl-heptan-3-one, laboratory chemicals.

Technology Process of 3-HYDROXY-3-METHYL-2-BUTANONE

There total 107 articles about 3-HYDROXY-3-METHYL-2-BUTANONE 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: 98.0%

Hexane-1,2-diol (6920-22-5) + carbon dioxide (124-38-9,18923-20-1) + 2-methyl-but-3-yn-2-ol (115-19-5) → 3-Hydroxy-3-methyl-2-butanone (115-22-0) + 4-butyl-1,3-dioxolan-2-one (66675-43-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In acetonitrile; at 80 ℃; for 24h; under 7500.75 Torr; chemoselective reaction; Autoclave; Sealed tube;

DOI:10.1055/s-0037-1611058

Reference yield: 98.0%

phenylethane 1,2-diol (93-56-1) + carbon dioxide (124-38-9,18923-20-1) + 2-methyl-but-3-yn-2-ol (115-19-5) → 4-Phenyl-1,3-dioxolan-2-one (4427-92-3) + 3-Hydroxy-3-methyl-2-butanone (115-22-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In acetonitrile; at 80 ℃; for 24h; under 15001.5 Torr; chemoselective reaction; Autoclave; Sealed tube;

DOI:10.1055/s-0037-1611058

Reference yield: 97.0%

carbon dioxide (124-38-9,18923-20-1) + 2-methyl-but-3-yn-2-ol (115-19-5) → 4,4-dimethyl-5-methylene-1,3-dioxolan-2-one (4437-80-3) + 3-Hydroxy-3-methyl-2-butanone (115-22-0)

Guidance literature:

With copper(l) chloride; 1-butyl-3-methylimidazolium benzenesulfonate; at 120 ℃; for 8h; under 7600 Torr;

DOI:10.1021/jo0351365

upstream raw materials:

methanol

3-bromo-3-methyl-2-butanone

potassium formate

methyl magnesium iodide

Downstream raw materials:

Trimethylacetic acid

4,5,5-Trimethyl-2-oxazolidinon-4-carboxamid

3-Methyl-3-buten-2-one

3-amino-2-methylbutan-2-ol

Refernces

• 1、 Wang, Haoran,Liu, Fenggang,Yang, Yuhui,Zhang, Maolin,Peng, Chengcheng,Bo, Shuhui,Liu, Xinhou,Qiu, Ling,Zhen, Zhen. "A study of two thermostable NLO chromophores with different π-electron bridges using fluorene as the donor". . p. 1038 - 1044. Retrieved 2015.
• 2、 Villemin, Didier,Jaffres, Paul-Alain,Hachemi, Messaoud. "An abnormal reaction of esters of 3-hydroxy-3-methylbutan-2-one. A rapid synthesis of bullatenone and geiparvarin". . p. 537 - 538. Retrieved 1997.
• 3、 Gu, Yanlong,Shi, Feng,Deng, Youquan. "Ionic Liquid as an Efficient Promoting Medium for Fixation of CO 2: Clean Synthesis of α-Methylene Cyclic Carbonates from CO2 and Propargyl Alcohols Catalyzed by Metal Salts under Mild Conditions". . p. 391 - 394. Retrieved 2004.
• 4、 Nabeta, K.,Nishimori, I.,Sato, S.,Sugisawa, H.. "VOLATILE CONSTITUENTS OF PLUS AND MINUS STRAINS OF BLAKESLEA TRISPORA". . p. 1133 - 1136. Retrieved 1980.
• 5、 van de Sande,Kopesky. "". . p. 163. Retrieved 1969.
• 6、 Chen, Cheng,Chen, Yiyun,Hu, Jia,Huang, Leilei,Verpoort, Francis,Wang, Yu,Yuan, Ye,Zhao, Yufeng,Zheng, Jiayun. "A green and recyclable CuSO4·5H2O/ionic liquid catalytic system for the CO2-promoted hydration of propargyl alcohols: an efficient assembly of α-hydroxy ketones". . . Retrieved 2021/12/03.
• 7、 Bu, Chao,Chaemchuen, Somboon,Chen, Cheng,Du, Minchen,Gong, Yanyan,Hu, Jia,Verpoort, Francis,Yuan, Ye,Zhang, Yongxing. "An efficient and recyclable AgNO3/ionic liquid system catalyzed atmospheric CO2 utilization: Simultaneous synthesis of 2-oxazolidinones and α-hydroxyl ketones". . p. 70 - 82. Retrieved 2020/12/21.