3474-12-2

Basic information

• Product Name: dichloromethyl
• Synonyms: Dichloromethyl radical; Methyl radical, dichloro-
• CAS NO: 3474-12-2
• Molecular Formula: CHCl₂
• Molecular Weight: 83.9246
• Mol File: 3474-12-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: dichloromethyl(CAS DataBase Reference)
• NIST Chemistry Reference: dichloromethyl(3474-12-2)
• EPA Substance Registry System: dichloromethyl(3474-12-2)

Safety Data

• Hazardous Substances Data: 3474-12-2(Hazardous Substances Data)

Usage

General Description

Dichloromethyl is a chemical compound with the molecular formula CH2Cl2. It is commonly used in the synthesis of various organic compounds and is also used as a solvent for paints, varnishes, and adhesives. Dichloromethyl is a colorless liquid with a sweet, chloroform-like odor, and is considered to be moderately toxic and potentially carcinogenic. It is also known to have harmful effects on the environment, particularly aquatic life. Despite its potential hazards, dichloromethyl is still widely used in various industrial applications due to its versatile properties and ability to dissolve a wide range of substances.

Upstream product

• 127-18-4 1,1,2,2-tetrachloroethylene 
• 2074-87-5 carbon nitride 
• 75-09-2 dichloromethane 
• 67-66-3 chloroform 
• 3141-58-0 tert-butoxy radical 
• 3369-48-0 pentafluoroethyl radical 
• 87191-88-6 2-oxo-ethen-1-id-1-yl 
• 1828-89-3 o-benzyne radical anion 
• 14552-67-1 (Ph₃P)2Pd(N₃)2 

Downstream Products

• 75-09-2 dichloromethane 
• 2108-20-5 chlorocarbene 
• 3170-80-7 trichloromethyl radical 
• 67-66-3 chloroform 
• 76-01-7 pentachloroethane 
• 75-27-4 bromodichloromethane 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 93245-39-7 C₂₄H₄₀Cl₂NO₃ 

Relevant articles and documents

Kinetics of reactions of CN with chlorinated methanes

The kinetics of reactions of CN with the chlorinated methanes CH3Cl, CH2Cl2, CHCl3 and CCl4 were investigated over the temperature range 298-573 K, using laser induced fluorescence (LIF) spectroscopy. At 298 K, rate constants of 9.0 ± 0.3 × 10-13, 8.8 ± 0.4 × 10-13, 9.0 ± 0.5 × 10-13 and 4.3 ± 0.6 × 10-13 cm3 molecule-1 s-1 were measured, respectively. A small positive temperature dependence was observed, as well as kinetic isotope effects of kH/kD ～ 2.14-2.25. These data along with product detection experiments strongly suggest that hydrogen abstraction dominates these reactions.

FTIR and computational studies of gas-phase hydrogen atom abstraction kinetics by t-butoxy radical

By using Fourier-Transform Infrared (FTIR) absorption spectroscopy, rate coefficients in the range of 10-16 to 10-14 cm3 molecule-1 s-1 have been determined for the hydrogen atom abstraction reactions of several substrates including halogenated organic compounds and amines by t-butoxy radical generated from the uv photolysis of t-butyl nitrite in the gas phase. Arrhenius parameters for selected reactions have been measured in the temperature range 299-318 K. Transition states and activation barriers for such reactions have been computed with the help of Gaussian 03 software and found to match very well with the experimental values.

Reactivity of the radical anion OCC-

The characteristic reactivity of the radical anion OCC- has been investigated in the gas phase at 298 K through determination of rate coefficients, products, and branching fractions for each of 29 ion-molecule reactions. A wide variety of reactions is observed including abstraction of H, H+, and H2+, nucleophilic displacement, charge transfer, and reactions involving electron detachment. Many of the reactions involve cleavage of the C--CO bond, consistent with the relatively small C--CO bond energy and the proposed1 electronic structure of the ground state anion in which both radical and charge are centered on the terminal carbon. Similarities are noted between the chemistry of OCC- and its neutral analogue OCC and between the chemistry of OCC- and the radical anions O- and o-C6H4-. Most reaction products observed are consistent with reaction mechanisms involving initial attack of the terminal carbon in OCC- on the neutral reaction partner. The gas-phase acidity of HCCO is bracketed between those of CH3NO2 and CH3CHO, yielding 1502 ± 8 > ΔGoacid(HCCO) ≥ 1463 ± 8 kJ mol-1 and 1531 ± 12 > ΔHoacid(HCCO) ≥ 1491 ± 12 kJ mol-1. Observation of H atom transfer from CH2Cl2 to OCC- indicates that ΔHof(OCC-) ≥ 148 ± 12 kJ mol-1 and gives a larger lower limit of ΔHoacid ≥ 1507 ± 15 kJ mol-1. These and related thermochemical values, including the hydrogen bond dissociation energy in HCCO, are compared with literature values.