2,2-Dimethoxypropane

2,2-dimethoxypropane[1]
	2,2-dimethoxypropane ball view
Names
	IUPAC name 2,2-dimethoxypropane
	Other names acetone dimethyl acetal
Identifiers
CAS Number	77-76-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3184215;
ChemSpider	21106033 ;
ECHA InfoCard	100.000.961
EC Number	201-056-0;
PubChem CID	6495;
UNII	66P41R0030;
CompTox Dashboard (EPA)	DTXSID7026441 ;
	InChI InChI=1S/C5H12O2/c1-5(2,6-3)7-4/h1-4H3 Key: HEWZVZIVELJPQZ-UHFFFAOYSA-N;
	SMILES CC(C)(OC)OC;
Properties
Chemical formula	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)
Solubility in water	15 g/L (20 °C)
Hazards
Safety data sheet	External MSDS
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H315, H319, H335
GHS precautionary statements	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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	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 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 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

2,2-Dimethoxypropane at Sigma-Aldrich
Critchfield, F. E.; Bishop, E. T. (1961). "Water determination by reaction with 2, 2-dimethoxypropane". Anal. Chem. 33 (8): 1034. doi:10.1021/ac60176a051.
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.
Christopher R. Schmid; Jerry D. Bryant (1995). "D-(R)-Glyceraldehyde Acetonide". Org. Synth. 72: 6. doi:10.15227/orgsyn.072.0006.
Christian Hubschwerlen; Jean-luc Specklin; J. Higelin (1995). "L-(S)-glyceraldehyde Acetonide". Org. Synth. 72: 1. doi:10.15227/orgsyn.072.0001.
Poul Prentø (1978). "Rapid dehydration--clearing with 2,2-dimethoxypropane for paraffin embedding". J. Histochem. Cytochem. 26 (10): 865. doi:10.1177/26.10.363931. PMID 363931.

External links

MSDS
MSDS

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[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. doi:10.1177/26.10.363931. PMID 363931.