Pivalic acid
A branched-chain saturated fatty acid
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Pivalic acid, also known as trimethylacetic acid, is a carboxylic acid with the formula (CH_3)_3CCO_2H. It is a branched-chain saturated fatty acid and is notable for its high degree of steric hindrance due to the presence of three methyl groups attached to the alpha carbon.
Chemical Properties[edit | edit source]
Pivalic acid is a white solid with a melting point of 35 to 38 °C and a boiling point of 163 °C. It has a density of 0.90 g/cm³ and is slightly soluble in water but more soluble in organic solvents such as ethanol, ether, and benzene. The pKa of pivalic acid is 5.03, indicating it is a weak acid.
Synthesis[edit | edit source]
Pivalic acid can be synthesized through the hydrolysis of tert-butyl chloride or by the oxidation of pinacolone. It is also produced as a byproduct in the Koch reaction.
Applications[edit | edit source]
Pivalic acid is used in the synthesis of esters and amides for various applications, including pharmaceuticals, perfumes, and polymers. Its esters, known as pivalates, are used as protecting groups in organic synthesis.
Safety and Handling[edit | edit source]
Pivalic acid should be handled with care, as it can cause irritation to the skin and eyes. It has a flash point of 56 °C and an autoignition temperature of 410 °C. Proper personal protective equipment (PPE) should be used when handling this chemical.
Related Pages[edit | edit source]
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| Identifiers | |
| CAS Number | |
| PubChem CID | |
| ChemSpider ID | |
| UNII | |
| ChEBI | |
| ChEMBL | |
| Properties | |
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| Hazards | |
| GHS Pictograms | [[File:|50px]] |
| GHS Signal Word | |
| GHS Hazard Statements | |
| NFPA 704 | [[File:|50px]] |
| References | |
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