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    2,2-Dimethoxypropane

    Topic: Chemistry

     From Handwiki - Reading time: 2 min
    2,2-Dimethoxypropane[1]
    2,2-Dimethoxypropane Structural Formula V1.svg
    2,2-dimethoxypropane ball view
    Names
    Preferred IUPAC name
    2,2-Dimethoxypropane
    Other names
    acetone dimethyl acetal
    Identifiers
    3D model (JSmol)
    ChEMBL
    ChemSpider
    EC Number
    • 201-056-0
    UNII
    Properties
    C5H12O2
    Molar mass 104.15 g/mol
    Appearance Colorless liquid
    Density 0.85 g/cm3
    Melting point −47 °C (−53 °F; 226 K)
    Boiling point 83 °C (181 °F; 356 K)
    15 g/L (20 °C)
    Hazards
    Safety data sheet External MSDS
    GHS pictograms GHS02: FlammableGHS07: Harmful
    GHS Signal word Danger
    H225, H315, H319, H335
    P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, P403+235, P405, P501
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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    2,2-Dimethoxypropane (DMP) is an organic compound with the formula (CH3)2C(OCH3)2. 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.[2] This property can be used to accurately determine the amount of water in a sample, alternatively to the Karl Fischer method.[3]

    DMP is specifically used to prepare acetonides:[4][5]

    RCHOHCHOHCH2 + (MeO)2CMe2 → RCHCHCH2O2CMe2 + 2 MeOH

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

    In histology, DMP is used for the dehydration of animal tissue.[6]

    References

    1. ↑ 2,2-Dimethoxypropane at Sigma-Aldrich
    2. ↑ Critchfield, F. E.; Bishop, E. T. (1961). "Water determination by reaction with 2, 2-dimethoxypropane". Anal. Chem. 33 (8): 1034. doi:10.1021/ac60176a051. 
    3. ↑ Martin, J. H.; Knevel, A. M. (1965). "Gas chromatographic method of moisture determination". J. Pharm. Sci. 54 (10): 1464–7. doi:10.1002/jps.2600541013. PMID 5883217. 
    4. ↑ Christopher R. Schmid; Jerry D. Bryant (1995). "D-(R)-Glyceraldehyde Acetonide". Org. Synth. 72: 6. doi:10.15227/orgsyn.072.0006. 
    5. ↑ Christian Hubschwerlen; Jean-luc Specklin; J. Higelin (1995). "L-(S)-glyceraldehyde Acetonide". Org. Synth. 72: 1. doi:10.15227/orgsyn.072.0001. 
    6. ↑ Poul Prentø (1978). "Rapid dehydration--clearing with 2,2-dimethoxypropane for paraffin embedding". J. Histochem. Cytochem. 26 (10): 865–867. doi:10.1177/26.10.363931. PMID 363931. 

    External links



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