Hydroxypivaldehyde

Hydroxypivaldehyde
Identifiers
CAS Number	597-31-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	11207;
ECHA InfoCard	100.008.998
EC Number	209-895-4;
PubChem CID	11699;
UNII	6DK0IR9LLR;
CompTox Dashboard (EPA)	DTXSID9027231 ;
	InChI InChI=1S/C5H10O2/c1-5(2,3-6)4-7/h3,7H,4H2,1-2H3 Key: JJMOMMLADQPZNY-UHFFFAOYSA-N;
	SMILES CC(C)(CO)C=O;
Properties
Chemical formula	C5H10O2
Molar mass	102.133 g·mol−1
Appearance	colorless liquid
Boiling point	141 °C (286 °F; 414 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264, P280, P305+P351+P338, P337+P313
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hydroxypivaldehyde is the organic compound with the formula HOCH₂(CH₃)₂CCHO. A colorless liquid, it is produced by condensation of formaldehyde and isobutyraldehyde:^[2]

CH₂O + (CH₃)₂CHCHO → HOCH₂(CH₃)₂CCHO

The compound is a rare example of a distillable aldol (3-hydroxyaldehyde). Upon standing, it dimerizes reversibly to the dioxane derivative.

Applications

Hydroxypivaldehyde is a precursor to vitamin B5 as is practiced commercially.^[3]

Hydroxypivaldehyde is also a precursor to neopentyl glycol by hydrogenation:

HOCH₂(CH₃)₂CCHO + H₂ → (CH₃)₂C(CH₂OH)₂

^ "3-Hydroxy-2,2-dimethylpropanal". pubchem.ncbi.nlm.nih.gov. Retrieved 31 December 2021.
^ Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen; Frey, Guido D. (2013). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub3. ISBN 978-3527306732.
^ Eggersdorfer, Manfred; Laudert, Dietmar; Létinois, Ulla; McClymont, Tom; Medlock, Jonathan; Netscher, Thomas; Bonrath, Werner (2012). "One Hundred Years of Vitamins-A Success Story of the Natural Sciences". Angewandte Chemie International Edition. 51 (52): 12975. doi:10.1002/anie.201205886. PMID 23208776.