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Revision as of 17:51, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 471789183 of page 3-Hydroxybutanal for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 14:12, 5 June 2024 edit LiClO (talk | contribs)5 editsm add linksTags: Visual edit Mobile edit Mobile web edit 
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{{short description|Organic compound with the formula CH3CH(OH)CH2CHO}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 455349876 | verifiedrevid = 477218700
| ImageFile = 3-hydroxybutanal.png | ImageFile = 3-hydroxybutanal.png
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 100 | ImageSize = 100
| ImageName = Skeletal formula of 3-hydroxybutanal | ImageName = Skeletal formula of 3-hydroxybutanal
| IUPACName = 3-Hydroxybutanal<ref>{{Cite web|title = 3-hydroxybutanal - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7897|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 13 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref> | 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 |Section1={{Chembox Identifiers
| CASNo = <!-- blanked - oldvalue: 107-89-1 -->
| CASNo_Ref = {{cascite|correct|??}} | CASNo = 107-89-1
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo_Comment = <small>(''R''/''S'')</small>
⚫ | PubChem = 7897
| CASNo1 = 117706-97-5
| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
| CASNo1_Ref = {{cascite|correct|CAS}}
⚫ | PubChem1 = 13061653
⚫ | CASNo1_Comment = <small>(''R'')</small>
| PubChem1_Ref = {{Pubchemcite|correct|Pubchem}}
| CASNo2 = 117706-98-6
⚫ | PubChem1_Comment = <small>(''R'')</small>
| CASNo2_Ref = {{cascite|correct|CAS}}
⚫ | ChemSpiderID = 7609
| CASNo2_Comment = <small>(''S'')</small>
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII_Ref = {{fdacite|changed|FDA}}
⚫ | ChemSpiderID1 = 18915429
| UNII = 8C6G962B53
⚫ | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
⚫ | PubChem = 7897
⚫ | ChemSpiderID1_Comment = <small>(''R'')</small>
| PubChem_Comment = <small>(''R''/''S'')</small>
⚫ | EINECS = 203-530-2
⚫ | PubChem1 = 13061653
⚫ | MeSHName = 3-hydroxybutanal
| PubChem1_Comment = <small>(''R'')</small>
⚫ | SMILES = CC(O)CC=O
⚫ | ChemSpiderID = 7609
⚫ | StdInChI = 1S/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Comment = <small>(''R''/''S'')</small>
⚫ | InChI = 1/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3
⚫ | ChemSpiderID1 = 18915429
⚫ | StdInChIKey = HSJKGGMUJITCBW-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1_Comment = <small>(''R'')</small>
⚫ | InChIKey = HSJKGGMUJITCBW-UHFFFAOYAI
⚫ | 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 |Section2={{Chembox Properties
| C = 4 | MolarMass =
| Appearance = colorless liquid
| H = 8
| O = 2 | C=4 | H=8 | O=2
| Density = 0.98 g/mL
| ExactMass = 88.052429500 g mol<sup>-1</sup>
| BoilingPtC = 162
}} }}
| Section3 = {{Chembox Related |Section3={{Chembox Related
| Function = aldehydes | OtherFunction_label = aldehydes
| OtherFunctn = ]<br /> | OtherFunction = ]<br />
] ]
}} }}
}} }}

In ], '''3-hydroxybutanal''' ('''acetaldol''', '''aldol''') is an ] with the formula {{chem2|CH3CH(OH)CH2CHO}} and the structure {{chem2|]\sCH(])\s]\s]}}. It is classified as an ] ({{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 ] of ] ({{chem2|CH3CHO}}). A thick colorless or pale-yellow liquid, it is a versatile and valuable ] with diverse impacts.<ref name=Ullmann/> The compound is ] although this aspect is not often exploited.

==Production==
] ] upon treatment with aqueous ]:<ref name=Ullmann/>
:{{chem2|2 CH3CHO -> CH3CH(OH)CH2CHO + H2O}}

This is the prototypical ].

==Reactions and uses==
Dehydration of 3-hydroxybutanal gives ]. 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 ]:
:{{chem2|CH3CH(OH)CH2CHO + H2 -> CH3CH(OH)CH2CH2OH}}
This diol is a precursor to 1,3-], 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 ]s and in ore ].<ref>], 1973.</ref>

==Former or niche uses==
It was formerly used in medicine as a ] and ].<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==
* ]

==References==
{{reflist|30em}}

{{Sedatives}}
{{Authority control}}

{{DEFAULTSORT:Hydroxybutanal, 3-}}
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