27683-61-0

Basic information

• Product Name: 1,1-BIS(4-CHLOROPHENYL)2,2-DICHLOROETHANOL
• Synonyms: 1,1-BIS(4-CHLOROPHENYL)2,2-DICHLOROETHANOL;m-Chloro-α-(dichloromethyl)benzenemethanol;1-(3-CHLOROPHENYL)-2,2-DICHLOROETHANOL
• CAS NO: 27683-61-0
• Molecular Formula: C₈H₇Cl₃O
• Molecular Weight: 225.5
• Mol File: 27683-61-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 310.2°Cat760mmHg
• Flash Point: 141.4°C
• Appearance: /
• Density: 1.449g/cm³
• Vapor Pressure: 0.000262mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 1,1-BIS(4-CHLOROPHENYL)2,2-DICHLOROETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-BIS(4-CHLOROPHENYL)2,2-DICHLOROETHANOL(27683-61-0)
• EPA Substance Registry System: 1,1-BIS(4-CHLOROPHENYL)2,2-DICHLOROETHANOL(27683-61-0)

Safety Data

• Hazardous Substances Data: 27683-61-0(Hazardous Substances Data)

Usage

Usage

Acaricide and insecticide in agriculture

Application

Control pests on crops such as cotton, tea, and fruits

Toxicity

Highly toxic to aquatic organisms

Environmental Impact

Known to bioaccumulate in the environment

Health Concerns

Potential endocrine disruptor, may affect hormone function in humans and wildlife

Regulatory Status

Restricted use in some countries due to potential harm to human health and the environment

Chemical Structure

Contains two 4-chlorophenyl groups and a dichloroethanol group

Physical State

Likely a solid or viscous liquid at room temperature (based on molecular weight and structure)

Solubility

Likely soluble in organic solvents, such as acetone or ethanol (based on the presence of aromatic rings and chlorine atoms)

Stability

May be sensitive to light, heat, or moisture (based on the presence of chlorine atoms and aromatic rings)

Persistence

Potential for long-term environmental persistence due to bioaccumulation and low degradation rates

Ecological Risks

Negative impact on aquatic ecosystems, including harm to non-target species and disruption of food chains

Human Exposure

Risk of exposure through ingestion of contaminated food, drinking water, or occupational exposure in agriculture

Alternatives

Development and use of safer, less toxic alternatives for pest control in agriculture

Monitoring and Mitigation

Regular monitoring of dicofol levels in the environment and implementation of strategies to reduce its use and impact

Public Awareness

Education and communication about the risks associated with dicofol and the importance of adopting safer alternatives

Research

Ongoing research into the effects of dicofol on human health and the environment, as well as the development of safer alternatives

International Cooperation

Collaboration between countries to regulate the use of dicofol and promote the adoption of safer pest control methods.

InChI:InChI=1/C8H7Cl3O/c9-6-3-1-2-5(4-6)7(12)8(10)11/h1-4,7-8,12H

Upstream product

• 84553-20-8 α,α-dichloro-m-chloroacetophenone 
• 6963-38-8 2,2,2-trichloro-1-(3-chlorophenyl)ethan-1-ol 
• 75-09-2 dichloromethane 
• 587-04-2 m-Chlorobenzaldehyde 
• 99-02-5 3'-Chloroacetophenone 

Downstream Products

• 16608-70-1 1,1-Dichlor-2-(m-chlorphenyl)-2-(p-iodphenyl)ethan 
• 73805-21-7 trans-β-chloro-m-chlorostyrene oxide 
• 4329-12-8 1,1-Dichloro-2,2-bis(p-chlorophenyl)ethane 

Relevant articles and documents

Expanding the scope of alcohol dehydrogenases towards bulkier substrates: Stereo- and enantiopreference for α,α-dihalogenated ketones

Alcohol dehydrogenases (ADHs) were identified as suitable enzymes for the reduction of the corresponding α,α-dihalogenated ketones, obtaining optically pure β,β-dichloro- or β,β-dibromohydrins with excellent conversions and enantiomeric excess. Among the different biocatalysts tested, ADHs from Rhodococcus ruber (ADH-A), Ralstonia sp. (RasADH), Lactobacillus brevis (LBADH), and PR2ADH proved to be the most efficient ones in terms of activity and stereoselectivity. In a further study, two racemic α-substituted ketones, namely α-bromo- α-chloro- and α-chloro-α-fluoroacetophenone were investigated to obtain one of the four possible diastereoisomers through a dynamic kinetic process. In the case of the brominated derivative, only the (1R)-enantiomer was obtained by using ADH-A, although with moderate diastereomeric excess (>99 % ee, 63 % de), whereas the fluorinated ketone exhibited a lower stereoselectivity (up to 45 % de). Bulking up: A series of β,β-dihalohydrins are obtained through alcohol dehydrogenase (ADH) catalyzed bioreduction of the synthesized α,α-dihalogenated ketones. Two racemic acetophenone derivatives are also subjected to this protocol to obtain stereoenriched alcohols through dynamic kinetic resolution (DKR).

Molecular Rearrangements. 13. Kinetics and Mechanism of Rearrangements of Some Ring-Substituted α-Chlorostyrene Oxides and trans-β-Chlorostyrene Oxides.

The synthesis of certain phenyl-substituted derivatives of the isomeric trans-β-chlorostyrene oxides (6) and α-chlorostyrene oxides (7) are reported.The kinetics of rearrangement of 6 (X = p-CH3, H, p-Br, m-Cl, p-NO2) to phenylchloroacetaldehydes (12) in CCl4 buffered by Na2HPO4 and 7 (X = p-CH3, H, p-NO2) to ω-chloroacetophenones in CCl4 were determined by following the rates of disappearance of the α-chloro epoxide and formation of the α-chloro carbonyl product.These substituent effects at 130 deg C were correlated with ?+ constants, yielding ρ values of-3.5 and -0.57 for the rearrangements of 6 and 7, respectively.In nitrobenzene solvent, the kC6H5NO2/kCCl4 for 6 was 180 and for 7 was 1740, the latter solvent effect attributed to nucleophilic solvent participation.It was concluded that these thermal rearrangements of 6 and 7 occur by disrotatory Cβ-O bond heterolysis to yield the corresponding α-keto carbonium-chloride ion pairs.