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2,2-Dichloropropane
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2,2-Dichloropropane DimethyldichloromethanePubChem 2,2-Dichloropropane https://pubchem.ncbi.nlm.nih.gov/compound/2,2-Dichloropropane 2026-02-15 pubchem.ncbi.nlm.nih.gov en Dichlorodimethylmethane Isopropylidene dichloride 2,2-dichloropropane.svg 150px 594-20-7 209-832-0 1S/C3H6Cl2/c1-3(2,4)5/h1-2H3 ZEOVXNVKXIPWMS-UHFFFAOYSA-N 11660 11170 CC(C)(Cl)Cl C5V432N6XB DTXSID7030060
3 6 2 Colorless liquidSigma-Aldrich 2,2-Dichloropropane https://www.sigmaaldrich.com/GB/en/sds/aldrich/258571 2026-02-15 www.sigmaaldrich.com en Chloroform-like 68 - 69 1.082 g/mL (CH3)2CCl2 -35 Slightly solublehttps://gestis.dguv.de/data?name=032040 Soluble in ethanol, benzene and chloroform 180 hPa 1.41https://www.tcichemicals.com/OP/en/p/D0400#docomentsSectionPDP
Tetrahedral at C
-5.0 C F Danger 02 07 Highly flammable, toxic H225 H302 H312 H319 H332 P210 P233 P240 P241 P242 P243 P261 P271 P280 P303+P361+P353 P304+P340 P317 P370+P378 P403+P235 P501
Dimethyldichlorosilane Dimethyltin dichloride 1,2-Dichloropropane 1,3-Dichloropropane
2,2-Dichloropropane is an organic compound with the chemical formula (CH3)2CCl2 1. It is a colorless liquid.
Synthesis
2,2-Dichloropropane can be synthesized by reaction between acetone and phosphorus pentachloride at low temperatures.Preparation of 2,2-dichloropropane https://www.prepchem.com/synthesis-of-2-2-dichloropropane/
CH3\sCO\sCH3 + PCl5 → CH3\sCCl2\sCH3 + POCl3
Another method involves the reaction between 2-chloropropylene (CH3\sCCl\dCH2) with hydrogen chloride.https://patents.google.com/patent/EP0665202A2/en
CH3\sCCl\dCH2 + HCl → CH3\sCCl2\sCH3
Structure
The distances and angles between atoms in 2,2-dichloropropane molecule are as follows:Hirota Masashi Iijima Takao Kimura Masao Molecular Structure of 2,2-Dichloropropane as Determined by a Combined Use of the Electron-diffraction Data and the Spectroscopic Moments of Inertia Bulletin of the Chemical Society of Japan 1 June 1978 51 6 1589–1593 10.1246/bcsj.51.1589 https://academic.oup.com/bcsj/article-abstract/51/6/1589/7356872 subscription
d(C-H) = 111 pm
d(C-Cl) = 179.9 pm
d(C-C) = 152.3 pm
∠(Cl-C-Cl) = 108.3°
∠(C-C-C) = 113.0°
The C-Cl and C-C distances are shorter than the corresponding distances in 2-chloropropane.
Polymorphism of 2,2-dichloropropane
The polymorphism of 2,2-dichloropropane has been investigated by thermal and X-ray powder diffraction experiments. From the former the phase transitions between the different phases have been characterized at normal and high pressures (up to 200 MPa). The existence of two low-temperature stable ordered phases (II and III), one high-temperature orientationally disordered phase (rhombohedral, Ib) and one additional monotropic orientationally disordered phase Ia, has been confirmed. The structure of the low-temperature ordered phase II has been determined by X-ray powder diffraction and Rietveld refinement as monoclinic C2/c, with lattice parameters a = 10.6402(3) Å, b = 5.4074(2) Å, c = 10.7295(3) Å, and β = 116.274(3)° at 175.2 K C F.Negrier P. Pardo L. C. Salud J. Tamarit J. Ll. Barrio M. López D. O. Würflinger A. Mondieig D. Polymorphism of 2,2-Dichloropropane: Crystallographic Characterization of the Ordered and Disordered Phases Chemistry of Materials 2002 14 5 1921–1929 10.1021/cm011000g https://pubs.acs.org/doi/10.1021/cm011000g subscription
Uses
2,2-Dichloropropane is used as a solvent for pesticides.Analytes - 2,2-dichloropropane :: Chromatography Online http://chromatography-online.org/content.php?id=233&ext=.php https://web.archive.org/web/20191122123941/http://chromatography-online.org/content.php?id=233&ext=.php 22 November 2019
Safety
Vapor of 2,2-dichloropropane is heavier than air (relative density = 3.9, air = 1), so it can spread along floors. It is highly flammable. Its vapors form explosive mixtures with air. While burning, it releases toxic gases including carbon monoxide, carbon dioxide, and hydrogen chloride. It should not be allowed to enter drains due to the risk of explosion. This chemical poses acute and chronic health hazards. It is harmful if inhaled. Can cause serious eye irritation. It is a neurotoxin and hepatotoxin.
References
Category:Organochlorides