2-Hydroxyisobutyric acid

Base Information

• Chemical Name: 2-Hydroxyisobutyric acid
• CAS No.: 594-61-6
• Deprecated CAS: 27909-95-1
• Molecular Formula: C4H8O3
• Molecular Weight: 104.106
• Hs Code.: 29181980
• European Community (EC) Number: 209-848-8
• NSC Number: 402158,4505
• UNII: DMW250U2HF
• DSSTox Substance ID: DTXSID4032954
• Nikkaji Number: J2.707C
• Wikipedia: 2-Hydroxyisobutyric_acid
• Wikidata: Q2735617
• Metabolomics Workbench ID: 1522
• ChEMBL ID: CHEMBL1345148
• Mol file: 594-61-6.mol

Synonyms:Isobutyricacid, a-hydroxy- (3CI);Lactic acid, 2-methyl-(8CI);2-Hydroxy-2-methylpropanoic acid;2-Hydroxyisobutyricacid;2-Methyllactic acid;Acetonic acid;Hydroxydimethylacetic acid;NSC402158;NSC 4505;a-HIB;a-Hydroxy-a-methylpropanoicacid;a-Hydroxyisobutanoic acid;

Chemical Property of 2-Hydroxyisobutyric acid

Chemical Property:

• Appearance/Colour: white to off-white needle-like crystals
• Vapor Pressure: 0.0398mmHg at 25°C
• Melting Point: 76-80 °C(lit.)
• Refractive Index: 1.4761 (estimate)
• Boiling Point: 84 °C 1.5 mm Hg(lit.)
• PKA: pK1:3.717 (25°C,μ=0.1)
• Flash Point: 114 °C/12mm
• PSA: 57.53000
• Density: 11412
• LogP: -0.15810
• Storage Temp.: Store below +30°C.
• Solubility.: water: soluble10%, clear to very slightly hazy, colorless
• Water Solubility.: Soluble in water, ether, alcohol, methanol and hot benzene.
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 104.047344113
• Heavy Atom Count: 7
• Complexity: 84.9

Purity/Quality:

99% ^*data from raw suppliers

2-Hydroxyisobutyric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-39-25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(C)(C(=O)O)O
• Uses: 2-Hydroxyisobutyric acid is used as background electrolyte for separation and detection of the metal ions by on-line cyclic voltammetry. 2-Hydroxyisobutyric acid is used as an electrolyte in the separation of the metal ions by on-line cyclic voltammetry. It is also used as a building block for the synthesis of polymers. Its conjugate base, 2-hydroxybutyrate is utilized to catabolize L-threonine as well as synthesize glutathione. Further, it is used as an indicator for the early detection insulin resistance in non-diabetic subjects. α-Hydroxyisobutyric acid was used as background electrolyte for separation and detection of the metal ions by on-line cyclic voltammetry.

Technology Process of 2-Hydroxyisobutyric acid

There total 171 articles about 2-Hydroxyisobutyric 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: 89.0%

ethyl 2-hydroxy-2,2-dimethylethanoate (80-55-7) → 2-methyllactic acid (594-61-6)

Guidance literature:

With potassium hydroxide; In methanol; water; at 20 ℃;

DOI:10.1246/cl.2010.698

Reference yield: 85.0%

cyanohydrin + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 2-methyllactic acid (594-61-6)

Guidance literature:

With hydrogenchloride; In diethyl ether;

Reference yield: 50.0%

2-methylenesuccinic acid (97-65-4,25119-64-6) → propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) + 2-methyllactic acid (594-61-6) + carbon dioxide (124-38-9,18923-20-1) + 2-oxo-propionic acid (127-17-3) + acetone (67-64-1)

Guidance literature:

With barium hexa-aluminate; In water; at 250 ℃; for 3h; under 15001.5 Torr; Reagent/catalyst; Autoclave; Inert atmosphere;

DOI:10.1016/j.mcat.2019.110520

upstream raw materials:

tetrachloromethane

α-(α-hydroxy-isobutyryloxy)-isobutyric acid amide

2-Methyl-1,2-propanediol

4-methyl-pent-3-en-2-one

Downstream raw materials:

sulfurous acid dibutyl ester

2-phenylethyl 2-hydroxy-2-methylpropionate

6-hydroxy-2,4-diphenyl-nicotinonitrile

3,3,8,8-tetramethyl-5-phenyl-1,4,6,9-tetraoxa-5λ⁵-arsa-spiro[4.4]nonane-2,7-dione

Refernces

• 1、 Windaus. "". . p. 2558,2562, 2564, 2566. Retrieved 1908.
• 2、 Bohre, Ashish,Novak, Uro?,Grilc, Miha,Likozar, Bla?. "Synthesis of bio-based methacrylic acid from biomass-derived itaconic acid over barium hexa-aluminate catalyst by selective decarboxylation reaction". . . Retrieved 2019/07/31.
• 3、 Verduyckt, Jasper,De Vos, Dirk E.. "Highly selective one-step dehydration, decarboxylation and hydrogenation of citric acid to methylsuccinic acid". . p. 2616 - 2620. Retrieved 2017/04/06.