2,2-Dimethoxypropane

2,2-Dimethoxypropane^[1]
	2,2-dimethoxypropane ball view
Names
	Preferred 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
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H315, H319, H335
Precautionary statements	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). verify (what is ?) 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 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

^ 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): 865–867. doi:10.1177/26.10.363931. PMID 363931.

External links

MSDS
MSDS

[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.

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