2,2-Dichloropropane

2,2-Dichloropropane
Names
IUPAC name
2,2-Dichloropropane[1]
Other names
  • Dimethyldichloromethane[1]
  • Dichlorodimethylmethane[1]
  • Isopropylidene dichloride[2]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.940
EC Number
  • 209-832-0
UNII
  • InChI=1S/C3H6Cl2/c1-3(2,4)5/h1-2H3
    Key: ZEOVXNVKXIPWMS-UHFFFAOYSA-N
  • CC(C)(Cl)Cl
Properties
(CH3)2CCl2
Molar mass 112.98 g·mol−1
Appearance Colorless liquid[1][2]
Odor Chloroform-like[3]
Density 1.082 g/mL[2]
Melting point −35 °C (−31 °F; 238 K)[2]
Boiling point 68–69 °C (154–156 °F; 341–342 K)[2]
Slightly soluble[4]
Solubility Soluble in ethanol, benzene and chloroform
Vapor pressure 180 hPa[2]
1.41[5]
Structure
Tetrahedral at C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly flammable, toxic
GHS labelling:
Danger
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
Flash point −5.0 °C (23.0 °F)[2]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2,2-Dichloropropane is an organic compound with the chemical formula (CH3)2CCl2. It is a colorless liquid.

Synthesis

2,2-Dichloropropane can be synthesized by reaction between acetone and phosphorus pentachloride at low temperatures.[3]

CH3−CO−CH3 + PCl5 → CH3−CCl2−CH3 + POCl3

Another method involves the reaction between 2-chloropropylene (CH3−CCl=CH2) with hydrogen chloride.[6]

CH3−CCl=CH2 + HCl → CH3−CCl2−CH3

Structure

The distances and angles between atoms in 2,2-dichloropropane molecule are as follows:[7]

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.[7]

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 (−98.0 °C; −144.3 °F).[8]

Uses

2,2-Dichloropropane is used as a solvent for pesticides.[9]

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 like carbon monoxide, carbon dioxide and hydrogen chloride. Do not let product enter drains because of risk of explosion. This chemical poses acute and chronic health hazards.[4][2] It is harmful if inhaled. Can cause serious eye irritation. It is a neurotoxin and hepatotoxin.[1]

References

  1. ^ a b c d e PubChem. "2,2-Dichloropropane". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-15.
  2. ^ a b c d e f g h Sigma-Aldrich. "2,2-Dichloropropane". www.sigmaaldrich.com. Retrieved 2026-02-15.
  3. ^ a b "Preparation of 2,2-dichloropropane".
  4. ^ a b https://gestis.dguv.de/data?name=032040
  5. ^ https://www.tcichemicals.com/OP/en/p/D0400#docomentsSectionPDP
  6. ^ https://patents.google.com/patent/EP0665202A2/en
  7. ^ a b Hirota, Masashi; Iijima, Takao; Kimura, Masao (1 June 1978). "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. 51 (6): 1589–1593. doi:10.1246/bcsj.51.1589.
  8. ^ Negrier, P.; Pardo, L. C.; Salud, J.; Tamarit, J. Ll.; Barrio, M.; López, D. O.; Würflinger, A.; Mondieig, D. (2002). "Polymorphism of 2,2-Dichloropropane: Crystallographic Characterization of the Ordered and Disordered Phases". Chemistry of Materials. 14 (5): 1921–1929. doi:10.1021/cm011000g.
  9. ^ "Analytes - 2,2-dichloropropane :: Chromatography Online". Archived from the original on 22 November 2019.
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