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2,2-Dimethoxypropane

From Wikipedia, the free encyclopedia
(Redirected from Dimethoxypropane)
2,2-Dimethoxypropane[1]
2,2-dimethoxypropane ball view
2,2-dimethoxypropane ball view
Names
Preferred IUPAC name
2,2-Dimethoxypropane
Other names
acetone dimethyl acetal
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.961 Edit this at Wikidata
EC Number
  • 201-056-0
UNII
  • InChI=1S/C5H12O2/c1-5(2,6-3)7-4/h1-4H3
    Key: HEWZVZIVELJPQZ-UHFFFAOYSA-N
  • CC(C)(OC)OC
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
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Safety data sheet (SDS) 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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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. This property can be used to accurately determine the amount of water in a sample, alternatively to the Karl Fischer method.[2][3]

DMP is used to prepare acetonides from diols, where it is both a synthon for acetone and a scavenger for the water byproduct:[4][5]

RCHOHCHOHCH2 + (CH3O)2C(CH3)2 → RCHCHCH2O2C(CH3)2 + 2 CH3OH

It can also be used to prepare methyl esters from carboxylic acids, where it acts as a water scavenger and source of methanol:[6]

RCOOH + CH3OH → RCOOCH3 + H2O
H2O + (CH3)2C(OCH3)2 —> 2CH3OH + (CH3)2C(O)

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

In histology, DMP is used for the dehydration of animal tissue.[7]

References

[edit]
  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. ↑ Lorette, N.; Brown, Jr., J. (1959). "Notes- Use of Acetone Dimethyl Acetal in Preparation of Methyl Esters". The Journal of Organic Chemistry. 24 (2): 261–262. doi:10.1021/jo01084a633.
  7. ↑ 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.
[edit]
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