2,2-Dimethoxypropane

2,2-dimethoxypropane[1]
Names
IUPAC name
2,2-dimethoxypropane
Other names
acetone dimethyl acetal
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.961
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2,2-Dimethoxypropane (DMP) is an organic compound with the formula (CH3)2C(OCH3)2. A colorless liquid, it is the product of the reaction of acetone and methanol, according to the equation below:[2]

DMP is commonly used as a water scavenger in water-sensitive reactions. Upon acid-catalyzed reaction, DMP reacts quantitatively with water to form acetone and methanol[3]. This property can be used to accurately determine the amount of water in a sample, alternatively to Karl Fischer method[4].

DMP is specifically used to prepare acetonides:[5][6]

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 [7].

References

  1. ↑ 2,2-Dimethoxypropane at Sigma-Aldrich
  2. ↑ CN103772167A, 顾金林, "Preparation method of 2, 2-dimethoxypropane", published 1981-02-26, assigned to 浙江胡涂硅有限公司
  3. ↑ Critchfield, F. E., Bishop, E. T. (1961). "Water determination by reaction with 2, 2-dimethoxypropane". Anal. Chem. 33: 1034. doi:10.1021/ac60176a051.
  4. ↑ Martin, J. H., Knevel, A. M. (1965). "Gas chromatographic method of moisture determination". J. Pharm. Sci. 54: 1464. doi:10.1002/jps.2600541013.
  5. ↑ Christopher R. Schmid, Jerry D. Bryant (1995). "D-(R)-Glyceraldehyde Acetonide". Org. Synth. 72: 6. doi:10.15227/orgsyn.072.0006.
  6. ↑ Christian Hubschwerlen, Jean-luc Specklin, J. Higelin (1995). "L-(S)-glyceraldehyde Acetonide". Org. Synth. 72: 1. doi:10.15227/orgsyn.072.0001.
  7. ↑ Poul Prentø (1978). "Rapid dehydration--clearing with 2,2-dimethoxypropane for paraffin embedding". J. Histochem. Cytochem. 26: 865. doi:10.1177/26.10.363931.


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