2-Hydroxy-3,3-dimethylbutanoic acid

Base Information

• Chemical Name: 2-Hydroxy-3,3-dimethylbutanoic acid
• CAS No.: 4026-20-4
• Deprecated CAS: 22146-54-9
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• European Community (EC) Number: 223-698-0
• UNII: TS4J3KZN8P
• DSSTox Substance ID: DTXSID1027554
• Nikkaji Number: J217.840K
• Wikidata: Q27290234
• Mol file: 4026-20-4.mol

Synonyms:2-Hydroxy-3,3-dimethylbutanoic acid;4026-20-4;Butanoic acid, 2-hydroxy-3,3-dimethyl-;2-Hydroxy-3,3-dimethylbutyric acid;3,3-Dimethyl-2-hydroxybutyric acid;UNII-TS4J3KZN8P;TS4J3KZN8P;EINECS 223-698-0;Butyric acid, 2-hydroxy-3,3-dimethyl-;2-hydroxy-3,3-dimethyl-butanoic acid;(R)-TRIMETHYLLACTIC ACID;H-PRO-PRO-OHHCL;SCHEMBL194255;DTXSID1027554;2-Hydroxy-3,3-dimethylbutanoicacid;3,3-Dimethyl-1-hydroxybutyric acid;MFCD00029993;AKOS010579955;SB44394;SB44967;2-Hydroxy-3,3-dimethylbutanoic acid #;BS-12239;J217.840K;CS-0378432;FT-0649057;FT-0649060;FT-0773053;EN300-75503;F79763;(RS)-2-HYDROXY-3,3-DIMETHYLBUTANOIC ACID;A858171;(+/-)-2-HYDROXY-3,3-DIMETHYLBUTANOIC ACID;(+/-)-2-HYDROXY-3,3-DIMETHYLBUTYRIC ACID;Q27290234;Z803056544

Chemical Property of 2-Hydroxy-3,3-dimethylbutanoic acid

Chemical Property:

• Vapor Pressure: 0.00583mmHg at 25°C
• Melting Point: 191-191.5℃
• Boiling Point: 118℃ (9 Torr)
• PKA: 3.91±0.27(Predicted)
• Flash Point: 114.6°C
• PSA: 57.53000
• Density: 1.1g/cm³
• LogP: 0.47800
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 112

Purity/Quality:

98%Min ^*data from raw suppliers

2-hydroxy-3,3-dimethylbutanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Hydroxy-3,3-dimethylbutanoic acid

There total 31 articles about 2-Hydroxy-3,3-dimethylbutanoic 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%

2-hydroxy-3,3-dimethylbutyronitrile (33350-17-3) → 2-hydroxy-3,3-dimethylbutanoic acid (4026-20-4,851866-86-9)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 20h; Reflux;

DOI:10.1016/j.tet.2009.01.117

Reference yield: 95.0%

1,1-dichloro-3,3-dimethylbutan-2-one (22591-21-5) → 2-hydroxy-3,3-dimethylbutanoic acid (4026-20-4,851866-86-9)

Guidance literature:

With sodium hydroxide; at 50 - 70 ℃; for 1h;

Reference yield: 93.0%

phosphoric acid 1,1-dicyano-2,2-dimethyl-propyl ester diethyl ester → 2-hydroxy-3,3-dimethylbutanoic acid (4026-20-4,851866-86-9)

Guidance literature:

With hydrogenchloride; for 24h; Heating;

DOI:10.1016/S0040-4039(98)02099-1

upstream raw materials:

3,3-dimethyl-butan-2-one

1-hydroxy-3,3-dimethylbutan-2-one

2-bromo-2-tert-butyl acetic acid

1,1-dibromo-3,3-dimethylbutan-2-one

Downstream raw materials:

3-methyl-butan-2-one

2,4,6-tris(tert-butyl)-1,3,5-trioxane

(+/-)-methyl (2-hydroxy-3,3-dimethyl)butyrate

Trimethylacetic acid

Refernces

• 1、 Enholm, Eric J.,Lavieri, Sophie,Cordóva, Tanya,Ghiviriga, Ion. "1,3-Diastereocontrol in acyclic radical allylations". . p. 531 - 534. Retrieved 2003.
• 2、 -. "Preparation method of 3, 3-dimethyl-2-oxobutyric acid and triazinone". Paragraph 0055-0056; 0058-0059; 0061-0062; 0064-0065; 0067. . Retrieved 2021/06/23.
• 3、 Van Der Heijden, Gydo,Kraakman, Jasper,Biemolt, Jasper,Ruijter, Eelco,Orru, Romano V. A.. "Metal-free one-pot α-carboxylation of primary alcohols". supporting information. p. 9716 - 9719. Retrieved 2016/10/31.