34888-05-6

Basic information

• Product Name: (trichloromethoxy)benzene
• Synonyms: TRICHLOROMETYOXYBENZOLE;(Trichloromethyl)phenyl ether
• CAS NO: 34888-05-6
• Molecular Formula: C₇H₅Cl₃O
• Molecular Weight: 211.47
• EINECS: 252-271-1
• Mol File: 34888-05-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 237°Cat760mmHg
• Flash Point: 90.6°C
• Appearance: /
• Density: 1.432g/cm³
• Vapor Pressure: 0.0705mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (trichloromethoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (trichloromethoxy)benzene(34888-05-6)
• EPA Substance Registry System: (trichloromethoxy)benzene(34888-05-6)

Safety Data

• Hazardous Substances Data: 34888-05-6(Hazardous Substances Data)

Usage

General Description

(trichloromethoxy)benzene is a chemical compound with the formula C7H5Cl3O. It is a colorless liquid with a sweet aromatic odor and is used in the production of pesticides and other chemical compounds. (Trichloromethoxy)benzene is highly flammable and can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. It is important to handle this chemical with care and use proper safety precautions when working with it.

InChI:InChI=1/C7H5Cl3O/c8-7(9,10)11-6-4-2-1-3-5-6/h1-5H

Synthetic route

1-trifluoromethoxybenzene (456-55-3) → (trichloromethoxy)benzene (34888-05-6) + α,α,α-dichlorofluoromethoxybenzene (1544-69-0)

Conditions	Yield
With aluminium trichloride In dichloromethane at 0 - 10℃; for 0.5h;	A 98.2% B 1.8%

1-trifluoromethoxybenzene (456-55-3) + acetyl chloride (75-36-5) → (trichloromethoxy)benzene (34888-05-6) + 1-[4-(trifluoromethoxy)phenyl]ethan-1-one (85013-98-5)

Conditions	Yield
With aluminium trichloride In tetrachloromethane for 2h; Product distribution; Further Variations:; Solvents;	A 80% B 20%

dichloro-phenoxy-methanesulfenyl chloride (98273-25-7) → (trichloromethoxy)benzene (34888-05-6)

Conditions	Yield
With chlorine

phenyl cyanate (1122-85-6) + perchloro-2-aza-1-propene (29164-55-4) → (trichloromethoxy)benzene (34888-05-6)

tetrachloromethane (56-23-5) + phenol (108-95-2) → (trichloromethoxy)benzene (34888-05-6) + Phenyl 4-hydroxybenzoate (17696-62-7) + phenyl Salicylate (118-55-8) + salicyloyl chloride (1441-87-8)

Conditions	Yield
for 5h; Irradiation; Yield given. Yields of byproduct given;

phenylcarbonochloridothioate (1005-56-7) → (trichloromethoxy)benzene (34888-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine 2: chlorine View Scheme

1-trifluoromethoxybenzene (456-55-3) → (trichloromethoxy)benzene (34888-05-6)

Conditions	Yield
With aluminum (III) chloride In benzene-d6; chlorobenzene at 80℃; for 42h;

methoxybenzene (100-66-3) → (trichloromethoxy)benzene (34888-05-6)

Conditions	Yield
With chlorine; 4-chlorobenzotrifluoride at 90 - 100℃; UV-irradiation;
With 2,2'-azobis(isobutyronitrile); chlorine at 139 - 140℃; for 12h; Temperature;

(trichloromethoxy)benzene (34888-05-6) → 1-trifluoromethoxybenzene (456-55-3)

Conditions	Yield
With hydrogen fluoride at 95℃; under 21002.1 Torr; Temperature; Pressure; Autoclave;	95.46%
	90%
With antimonypentachloride; antimony(III) fluoride

(trichloromethoxy)benzene (34888-05-6) → difluorochloromethoxybenzene (770-11-6)

Conditions	Yield
With perfluorooctyl sulfofluorure; hydrogen fluoride at 5 - 110℃; under 18751.9 - 21002.1 Torr; for 4h; Autoclave;	74.9%
With antimony(III) fluoride
With (HF)10-pyridine at 20℃; for 6h;	97 % Spectr.
With hydrogen fluoride at 50℃; under 7500.75 Torr; for 1h; Autoclave;
With hydrogen fluoride at 50℃; under 7500.75 Torr; Inert atmosphere; Autoclave;

(trichloromethoxy)benzene (34888-05-6) + cyanogen chloride (506-77-4) → 2,4-dichloro-6-phenoxy-1,3,5-triazine (4682-78-4)

Conditions	Yield
Zinc chloride	57%

(trichloromethoxy)benzene (34888-05-6) + triethyl phosphite (122-52-1) → (Dichloro-phenoxy-methyl)-phosphonic acid diethyl ester (28975-76-0)

Conditions	Yield
In benzene

(trichloromethoxy)benzene (34888-05-6) + triethyl phosphite (122-52-1) → [Chloro-(diethoxy-phosphoryl)-phenoxy-methyl]-phosphonic acid diethyl ester (28975-77-1)

(trichloromethoxy)benzene (34888-05-6) → 1-trifluoromethoxybenzene (456-55-3) + difluorochloromethoxybenzene (770-11-6)

Conditions	Yield
With hydrogen fluoride; antimonypentachloride at 50℃; under 7500.6 Torr; for 1h; Product distribution; Further Variations:; Reagents; Temperatures; time;
With hydrogen fluoride; antimonypentachloride at 50℃; under 7500.75 Torr; for 1h; Inert atmosphere; Autoclave;

(trichloromethoxy)benzene (34888-05-6) → α,α,α-dichlorofluoromethoxybenzene (1544-69-0)

Conditions	Yield
With triethylamine tris(hydrogen fluoride) at 50℃; for 25h;	93 % Spectr.

(trichloromethoxy)benzene (34888-05-6) → 4-(trifluoromethoxy)aniline (461-82-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen fluoride / 80 °C / 22502.3 - 26252.6 Torr / Inert atmosphere; Autoclave 2: sulfuric acid; nitric acid / dichloromethane / 2 h / 0 - 30 °C 3: iron; hydrogenchloride / methanol / 2 h / 60 - 65 °C View Scheme

(trichloromethoxy)benzene (34888-05-6) → 4-Trifluoromethoxyphenol (828-27-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen fluoride / 80 °C / 22502.3 - 26252.6 Torr / Inert atmosphere; Autoclave 2: sulfuric acid; nitric acid / dichloromethane / 2 h / 0 - 30 °C 3: iron; hydrogenchloride / methanol / 2 h / 60 - 65 °C 4: sodium nitrite; sulfuric acid / water / 2 h / 5 - 110 °C View Scheme

(trichloromethoxy)benzene (34888-05-6) → 4-nitrophenyl trifluoromethyl ether (713-65-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen fluoride / 80 °C / 22502.3 - 26252.6 Torr / Inert atmosphere; Autoclave 2: sulfuric acid; nitric acid / dichloromethane / 2 h / 0 - 30 °C View Scheme

(trichloromethoxy)benzene (34888-05-6) → 1-(chlorodifluoromethoxy)-4-nitrobenzene (40750-71-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen fluoride; perfluorooctyl sulfofluorure / 4 h / 5 - 110 °C / 18751.9 - 21002.1 Torr / Autoclave 2: sulfuric acid; nitric acid / water / 15 - 20 °C View Scheme

(trichloromethoxy)benzene (34888-05-6) → 4-[chloro(difluoro)methoxy]aniline (39065-95-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen fluoride; perfluorooctyl sulfofluorure / 4 h / 5 - 110 °C / 18751.9 - 21002.1 Torr / Autoclave 2: sulfuric acid; nitric acid / water / 15 - 20 °C 3: hydrogen / ethyl acetate / 1 h / 30 - 40 °C / 15001.5 - 22502.3 Torr / Autoclave View Scheme

Upstream product

• 456-55-3 1-trifluoromethoxybenzene 
• 100-66-3 methoxybenzene 
• 1005-56-7 phenylcarbonochloridothioate 
• 75-36-5 acetyl chloride 
• 56-23-5 tetrachloromethane 
• 108-95-2 phenol 
• 1122-85-6 phenyl cyanate 
• 29164-55-4 perchloro-2-aza-1-propene 
• 98273-25-7 dichloro-phenoxy-methanesulfenyl chloride 

Downstream Products

• 1544-69-0 α,α,α-dichlorofluoromethoxybenzene 
• 461-82-5 4-(trifluoromethoxy)aniline 
• 828-27-3 4-Trifluoromethoxyphenol 
• 713-65-5 4-nitrophenyl trifluoromethyl ether 
• 39065-95-7 4-[chloro(difluoro)methoxy]aniline 
• 40750-71-8 1-(chlorodifluoromethoxy)-4-nitrobenzene 
• 4682-78-4 2,4-dichloro-6-phenoxy-1,3,5-triazine 
• 456-55-3 1-trifluoromethoxybenzene 
• 770-11-6 difluorochloromethoxybenzene 
• 28975-77-1 [Chloro-(diethoxy-phosphoryl)-phenoxy-methyl]-phosphonic acid diethyl ester 
• 28975-76-0 (Dichloro-phenoxy-methyl)-phosphonic acid diethyl ester 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF 4-SUBSTITUTED-1-(TRIFLUOROMETHOXY)BENZENE COMPOUNDS

The present invention provides the process for the preparation of 4-substituted-1- (trifluoromethoxy) benzene compounds..

Catalytic halodefluorination of aliphatic carbon-fluorine bonds

A variety of halosilanes, in conjunction with aluminum catalysts, convert fluorocarbons into higher halocarbons. Bromination and iodination of fluorocarbons are more effective than chlorination in terms of yield and activity. The mechanism for the reaction is investigated utilizing experimental and computational evidence and preliminary results suggest an alternate mechanism to that reported for the related hydrodefluorination reaction.

Method of making trichloromethoxybenzene

Disclosed is a method of making trichloromethoxybenzene. A mixture is prepared of anisole and a source of chlorine free radicals, such as chlorine or sulfuryl chloride. The reaction is performed in a solvent, which can be either benzotrifluoride, orthochlorobenzotrifluoride, metachlorobenzotrifluoride, parachlorobenzotrifluoride, or dichlorobenzotrifluoride. The mixture is exposed to actinic radiation, such as ultraviolet light, which generates the chlorine free radicals.