3,3-Dimethyl-2-oxobutyric acid Chemical Properties

Melting point:

90.5°C

Boiling point:

80 °C / 15mmHg

Density 

1.06

refractive index 

1.4270-1.4320

Flash point:

13 °C

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Soluble in water

form 

powder to lump to clear liquid

pka

2.65±0.54(Predicted)

color 

White or Colorless to Almost white or Almost colorless

InChI

InChI=1S/C6H10O3/c1-6(2,3)4(7)5(8)9/h1-3H3,(H,8,9)

InChIKey

IAWVHZJZHDSEOC-UHFFFAOYSA-N

SMILES

C(O)(=O)C(=O)C(C)(C)C

CAS DataBase Reference

815-17-8(CAS DataBase Reference)

NIST Chemistry Reference

Butanoic acid, 3,3-dimethyl-2-oxo-(815-17-8)

EPA Substance Registry System

3,3-Dimethyl-2-oxobutyric acid (815-17-8)

Safety Information

Hazard Codes 

C

Risk Statements 

36/37/38-34

Safety Statements 

26-37/39-45-36/37/39

RIDADR 

3261

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

2918300090

Hazardous Substances Data

815-17-8(Hazardous Substances Data)

MSDS

• Language:English Provider:ALFA

3,3-Dimethyl-2-oxobutyric acid Usage And Synthesis

Uses

3,?3-?Dimethyl-?2-?oxobutyric acid was used as an inhibitor in a study for tuberculosis,as it was analyzed for its binding affinity to pantothenate synthetase (PS)?, an essential metabolic enzyme in the pantothenate biosynthetic.

Definition

ChEBI: 3,3-dimethyl-2-oxobutanoic acid is a 2-oxo monocarboxylic acid that is 3,3-dimethylbutyric acid substituted by an oxo group at position 2. It is functionally related to a 3,3-dimethylbutyric acid.

Synthesis

The general procedure for the synthesis of trimethylpyruvic acid (DOBA) from 2-hydroxy-3,3-dimethylbutyric acid (DHBA) is as follows: 1. dissolve 0.1 mol (13.2 g) of 3,3-dimethyl-2-hydroxybutyric acid (DHBA) in 100 mL of 5 N sodium hydroxide solution (containing 5 mol NaOH/mol DHBA). 2. 5 x 10^-4 mol Bi(NO3)3/mol DHBA was added as an additive and the reaction mixture was heated to about 100 °C at atmospheric pressure in the presence of 1 g of activated carbon containing 5 wt. % palladium (pharmaceutical charcoal) until about 1,300 mL of oxygen (about 0.535 mol O2/mol DHBA) was absorbed. 3. The reaction times and results of 3,3-dimethyl-2-oxobutyric acid (DOBA) yields determined by polarography are summarized in Table 2. Following the procedure of Example 1, 0.1 mol (13.2 g) of 3,3-dimethyl-2-hydroxybutyric acid (DHBA) was dissolved in 100 mL of sodium hydroxide solution at various concentrations, 5 x 10^-4 mol Bi(NO3)3/mol DHBA was added as an activator, and the reaction was carried out in the presence of 1 g of activated charcoal containing 5 wt. % palladium at 95 °C and atmospheric pressure until about 1,300 mL of oxygen (about 0.535 mol O2/mol DHBA) was absorbed. The reaction time and DOBA yield results are summarized in Table 3. Example 16 is a control experiment in which no super stoichiometric base was used.

References

[1] Patent: US2004/30186, 2004, A1. Location in patent: Page 4
[2] Patent: US2004/30186, 2004, A1. Location in patent: Page 3-4
[3] Patent: US2004/30186, 2004, A1. Location in patent: Page 3-4
[4] Patent: US2004/30186, 2004, A1. Location in patent: Page 3-4
[5] Patent: US5091568, 1992, A

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