Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 3-Hydroxybutanal: Difference between pages

{{short description|Organic compound with the formula CH3CH(OH)CH2CHO}}

| Verifiedfields = changed

| verifiedrevid = 477218700

| PIN = 3-Hydroxybutanal<ref>{{Cite web|title = 3-hydroxybutanal – Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7897|work = PubChem Compound|publisher = National Center for Biotechnology Information|access-date = 13 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref>

| OtherNames = {{bulletedlist|Acetaldol|3-Hydroxybutyraldehyde|beta-Hydroxybutyraldehyde|β-Hydroxybutyraldehyde}}

|Section1={{Chembox Identifiers

| CASNo = 107-89-1

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

| CASNo_Comment = <small>(''R''/''S'')</small>

| CASNo1 = 117706-97-5

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo1_Comment = <small>(''R'')</small>

| CASNo2 = 117706-98-6

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2_Comment = <small>(''S'')</small>

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 8C6G962B53

| PubChem = 7897

| PubChem_Comment = <small>(''R''/''S'')</small>

| PubChem1 = 13061653

| PubChem1_Comment = <small>(''R'')</small>

| ChemSpiderID = 7609

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID_Comment = <small>(''R''/''S'')</small>

| ChemSpiderID1 = 18915429

| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID1_Comment = <small>(''R'')</small>

| EINECS = 203-530-2

| MeSHName = 3-hydroxybutanal

| SMILES = CC(O)CC=O

| StdInChI = 1S/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| InChI = 1/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3

| StdInChIKey = HSJKGGMUJITCBW-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey = HSJKGGMUJITCBW-UHFFFAOYAI

|Section2={{Chembox Properties

| MolarMass =

| Appearance = colorless liquid

| C=4 | H=8 | O=2

| Density = 0.98 g/mL

| BoilingPtC = 162

|Section3={{Chembox Related

| OtherFunction_label = aldehydes

| OtherFunction = [[Glycolaldehyde]]<br />

In [[organic chemistry]], '''3-hydroxybutanal''' ('''acetaldol''', '''aldol''') is an [[organic compound]] with the formula {{chem2|CH3CH(OH)CH2CHO}} and the structure {{chem2|[[Methyl group|H3C]]\sCH([[Hydroxy group|OH]])\s[[Methylene bridge|CH2]]\s[[Aldehyde|CH\dO]]}}. It is classified as an [[aldol]] ({{chem2|R\sCH(OH)\sCHR'\sC(\dO)\sR"}}) and the word "aldol" can refer specifically to 3-hydroxybutanal. It is formally the product of the [[dimer (chemistry)|dimerization]] of [[acetaldehyde]] ({{chem2|CH3CHO}}). A thick colorless or pale-yellow liquid, it is a versatile and valuable [[Reaction intermediate|intermediate]] with diverse impacts.<ref name=Ullmann/> The compound is [[chiral]] although this aspect is not often exploited.

==Production==

Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide:<ref name=Ullmann/>

:{{chem2|2 CH3CHO -> CH3CH(OH)CH2CHO + H2O}}

This is the prototypical [[aldol reaction]].

==Reactions and uses==

Dehydration of 3-hydroxybutanal gives [[crotonaldehyde]]. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion:<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a01_321.pub2|chapter=Aldehydes, Aliphatic|year=2008|last1=Kohlpaintner|first1=Christian|last2=Schulte|first2=Markus|last3=Falbe|first3=Jürgen|last4=Lappe|first4=Peter|last5=Weber|first5=Jürgen|isbn=978-3527306732}}</ref>

:{{chem2|CH3CH(OH)CH2CHO -> CH3CH\dCHCHO + H2O}}

Hydrogenation of 3-hydroxybutanal gives [[1,3-butanediol]]:

:{{chem2|CH3CH(OH)CH2CHO + H2 -> CH3CH(OH)CH2CH2OH}}

This diol is a precursor to 1,3-[[butadiene]], precursor to diverse polymers.

Polymerization of 3-hydroxybutanal is also spontaneous, but can be stopped with the addition of water.

Aldol has been used in making [[perfume]]s and in ore [[froth flotation|flotation]].<ref>[[American Heritage Dictionary]], 1973.</ref>

==Former or niche uses==

It was formerly used in medicine as a [[hypnotic]] and [[sedative]].<ref>{{Cite book | author = Hans Brandenberger, Robert A. A. Maes. | title = Analytical Toxicology: For Clinical, Forensic, and Pharmaceutical Chemists | location = New York | publisher = de Gruyter | date = 1997}}</ref>

==See also==

* [[4-Hydroxybutanal]]

==References==

{{reflist|30em}}

{{Sedatives}}

{{Authority control}}

{{DEFAULTSORT:Hydroxybutanal, 3-}}

[[Category:Hydroxy aldehydes]]

[[Category:GABA analogues]]

[[Category:Hypnotics]]

[[Category:Sedatives]]

[[Category:Aldols]]