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Isobutyric acid

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Title: Isobutyric acid  
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Subject: Isobutyrate, Mukaiyama Taxol total synthesis, C4H8O2, Asparagusic acid, List of UN numbers 2501 to 2600
Collection: Alkanoic Acids, Carboxylic Acids, Glycine Receptor Antagonists
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Isobutyric acid

Isobutyric acid[1]
Skeletal formula of isobutyric acid
Ball-and-stick model of the isobutyric acid molecule
Names
IUPAC name
2-Methylpropanoic acid
Other names
Isobutyric acid
2-Methylpropionic acid
Isobutanoic acid
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
DrugBank  N
Jmol-3D images Image
KEGG  Y
UNII  Y
Properties
C4H8O2
Molar mass 88.11 g/mol
Density 0.9697 g/cm3 at 0 °C
Melting point −47 °C (−53 °F; 226 K)
Boiling point 155 °C (311 °F; 428 K)
Acidity (pKa) 4.86[2]
Hazards
NFPA 704
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Isobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acid with structural formula (CH3)2-CH-COOH.

It is found in the free state in carobs (Ceratonia siliqua), in vanilla and in the root of Arnica dulcis, and as an ethyl ester in croton oil.

Isobutyric acid is an isomer of n-butyric acid; they have the same chemical formula C4H8O2 but a different structure.

Production

Isobutyric acid may be artificially prepared by the hydrolysis of isobutyronitrile with alkalis, by the oxidation of isobutanol with potassium dichromate and sulfuric acid,[4] or by the action of sodium amalgam on methacrylic acid. Isobutyric acid is a liquid under common conditions with a somewhat unpleasant smell. It boils at 155 °C and has a specific gravity is 0.9697 (0 °C). When heated with a chromic acid solution to 140 °C, it decomposes to form carbon dioxide and acetone. Alkaline potassium permanganate oxidizes it to α-hydroxyisobutyric acid, (CH3)2-C(OH)-COOH. Its salts are more soluble in water than those of butyric acid.

Biological production

Isobutyric acid can also be manufactured commercially using engineered bacteria using a sugar feedstock.[5]

Isobutyric acid is a retained trivial name under the IUPAC rules.[6]

References

  1. ^ Merck Index, 11th Edition, 5039
  2. ^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
  3. ^ http://www.ehs.neu.edu/laboratory_safety/general_information/nfpa_hazard_rating/documents/NFPAratingDI.htm
  4. ^ I. Pierre and E. Puchot (1873). "New Studies on Valerianic Acid and its Preparation on a Large Scale". Ann. de chim. et de phys. 28: 366. 
  5. ^ "Biological pathways to produce methacrylate". 
  6. ^ Panico R, Powell WH, Richer JC, eds. (1993). "Recommendation R-9.1".  


 

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