hydroxypivaldehyde

{{Chembox

| ImageFile = Hydroxypivaldehyde.png

| ImageSize =

| ImageAlt =

| IUPACName =

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 597-31-9

| CASNo_Ref = {{cascite|correct|CAS}}

| ChemSpiderID = 11207

| EC_number = 209-895-4

| PubChem = 11699

| UNII = 6DK0IR9LLR

| StdInChI=1S/C5H10O2/c1-5(2,3-6)4-7/h3,7H,4H2,1-2H3

| StdInChIKey = JJMOMMLADQPZNY-UHFFFAOYSA-N

| SMILES = CC(C)(CO)C=O

}}

|Section2={{Chembox Properties

| C = 5|O = 2|H=10

| MolarMass =

| Appearance = colorless liquid

| Density =

| MeltingPt =

| BoilingPtC = 141

| Solubility = }}

|Section3={{Chembox Hazards

| GHS_ref={{cite web |title=3-Hydroxy-2,2-dimethylpropanal |url=https://pubchem.ncbi.nlm.nih.gov/compound/11699#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=31 December 2021 |language=en}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|319}}

| PPhrases = {{P-phrases|264|280|305+351+338|337+313}}

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Hydroxypivaldehyde is the organic compound with the formula HOCH₂(CH₃)₂CCHO. A colorless liquid, it is produced by condensation of formaldehyde and isobutyraldehyde:{{Ullmann|doi=10.1002/14356007.a01_321.pub3|title=Aldehydes, Aliphatic|year=2013|last1=Kohlpaintner|first1=Christian|last2=Schulte|first2=Markus|last3=Falbe|first3=Jürgen|last4=Lappe|first4=Peter|last5=Weber|first5=Jürgen|last6=Frey|first6=Guido D.|isbn=978-3527306732}}

: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.