View source for 2,2-Dimethoxypropane

{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|Reference=<ref>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=D136808|SIAL&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 2,2-Dimethoxypropane] at [[Sigma-Aldrich]]</ref>
|verifiedrevid = 477190426
|Name = 2,2-Dimethoxypropane
|ImageFileL1=2,2-Dimethoxypropane Structural Formula V1.svg
|ImageSizeL1 = 150px 
|ImageFileR1 = 2,2-dimethoxypropane-3D-balls.png
|ImageSizeR1 = 120px 
|ImageNameR1 = 2,2-dimethoxypropane ball view
|PIN = 2,2-Dimethoxypropane
|OtherNames = acetone dimethyl acetal
|Section1={{Chembox Identifiers
|SMILES = CC(C)(OC)OC
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 21106033
|PubChem = 6495
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 77-76-9
|EC_number = 201-056-0
|UNII = 66P41R0030
|ChEMBL = 3184215
|StdInChI=1S/C5H12O2/c1-5(2,6-3)7-4/h1-4H3
|StdInChIKey = HEWZVZIVELJPQZ-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
|Formula = C<sub>5</sub>H<sub>12</sub>O<sub>2</sub>
|MolarMass = 104.15 g/mol
|Appearance = Colorless liquid
|Density = 0.85 g/cm<sup>3</sup>
|Solubility = 15 g/L (20 °C)
|MeltingPtC = -47
|BoilingPtC = 83
}}
|Section7={{Chembox Hazards
|ExternalSDS = [[2,2-Dimethoxypropane#External links|External MSDS]]
|GHSPictograms = {{GHS02}}{{GHS07}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|225|315|319|335}}
|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|302+352|303+361+353|304+340|305+351+338|312|321|332+313|337+313|362|370+378|403+233|403+235|405|501}}
}}
}}

'''2,2-Dimethoxypropane''' ('''DMP''') is an [[organic compound]] with the formula (CH<sub>3</sub>)<sub>2</sub>C(OCH<sub>3</sub>)<sub>2</sub>. A colorless liquid, it is the product of the condensation of [[acetone]] and [[methanol]]. DMP is used as a water scavenger in water-sensitive reactions. Upon acid-catalyzed reaction, DMP reacts quantitatively with water to form acetone and methanol.<ref>{{cite journal|title=Water determination by reaction with 2, 2-dimethoxypropane|author1=Critchfield, F. E. |author2=Bishop, E. T.|journal=Anal. Chem.|year=1961|volume=33|issue=8|page=1034|doi=10.1021/ac60176a051}}</ref> This property can be used to accurately determine the amount of water in a sample, alternatively to the [[Karl Fischer titration|Karl Fischer]] method.<ref>{{cite journal|title=Gas chromatographic method of moisture determination|author1=Martin, J. H. |author2=Knevel, A. M.|journal=J. Pharm. Sci.|year=1965|volume=54|issue=10|pages=1464–7|doi=10.1002/jps.2600541013|pmid=5883217}}</ref>

DMP is specifically used to prepare [[acetonide]]s:<ref>{{cite journal|title=D-(R)-Glyceraldehyde Acetonide|author1=Christopher R. Schmid |author2=Jerry D. Bryant|journal=Org. Synth.|year=1995|volume=72|page=6|doi=10.15227/orgsyn.072.0006}}</ref><ref>{{cite journal|title=L-(S)-glyceraldehyde Acetonide|author1=Christian Hubschwerlen |author2=Jean-luc Specklin |author3=J. Higelin|journal=Org. Synth.|year=1995|volume=72|page=1|doi=10.15227/orgsyn.072.0001}}</ref>
:RCHOHCHOHCH<sub>2</sub> + (MeO)<sub>2</sub>CMe<sub>2</sub> → RCHCHCH<sub>2</sub>O<sub>2</sub>CMe<sub>2</sub> + 2 MeOH

Dimethoxypropane is an intermediate for the synthesis of [[2-methoxypropene]].

In histology, DMP is used for the dehydration of animal tissue.<ref>{{cite journal|title=Rapid dehydration--clearing with 2,2-dimethoxypropane for paraffin embedding|author1=Poul Prentø|journal=J. Histochem. Cytochem.|year=1978|volume=26|issue=10|pages=865–867 |doi=10.1177/26.10.363931|pmid=363931|doi-access=free}}</ref>

==References==
{{reflist}}

==External links==
* [https://web.archive.org/web/20060301061015/http://ptcl.chem.ox.ac.uk/MSDS/DI/2,2-dimethoxypropane.html MSDS]
* [http://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/33053 MSDS]

{{DEFAULTSORT:Dimethoxypropane, 2,2-}}
[[Category:Methylating agents]]
[[Category:Ethers]]
[[Category:Ketals]]
[[Category:Reagents for organic chemistry]]