5216-25-1

Basic information

• Product Name: 4-Chlorobenzotrichloride
• Synonyms: 4-CHLOROBENZOTRICHLORIDE;A,A,A,P-TETRACHLOROTOLUENE;ALPHA,ALPHA,ALPHA,4-TETRACHLOROTOLUENE;P-CHLORO-A,A,A-TRICHLOROTOLUENE;P-CHLOROBENZOTRICHLORIDE;PCTC;P-CHLORO(TRICHLOROMETHYL)BENZENE;1-chloro-4-(trichloromethyl)-benzen
• CAS NO: 5216-25-1
• Molecular Formula: C₇H₄Cl₄
• Molecular Weight: 229.92
• EINECS: 226-009-1
• Mol File: 5216-25-1.mol

Chemical Properties

• Melting Point: 5.8 °C
• Boiling Point: 245 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless liquid
• Density: 1.495 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.046mmHg at 25°C
• Refractive Index: n20/D 1.572(lit.)
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1866549
• CAS DataBase Reference: 4-Chlorobenzotrichloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorobenzotrichloride(5216-25-1)
• EPA Substance Registry System: 4-Chlorobenzotrichloride(5216-25-1)

Safety Data

• Hazard Codes: T
• Statements: 45-21/22-37/38-48/23-62
• Safety Statements: 53-45
• RIDADR: UN 1760 8/PG 2
• WGK Germany: 3
• RTECS: XT8580000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5216-25-1(Hazardous Substances Data)

Usage

Uses

4-Chlorobenzotrichloride is used as a reactant in the field of organic synthesis for its versatile chemical properties, which allow it to participate in a range of reactions and contribute to the formation of different compounds.
Used in Chemical Synthesis:
4-Chlorobenzotrichloride is used as a building block in the chemical synthesis industry for the production of various organic compounds. Its reactivity and stability make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Chlorobenzotrichloride is used as an intermediate in the synthesis of various drugs. Its unique structure allows for the development of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
4-Chlorobenzotrichloride is also utilized in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its chemical properties enable the creation of compounds that can effectively control pests and diseases in agriculture.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Simple aromatic halogenated organic compounds, such as 4-Chlorobenzotrichloride , are very unreactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Health Hazard

ACUTE/CHRONIC HAZARDS: Corrosive; Lachrymator.

Fire Hazard

Flash point data for 4-Chlorobenzotrichloride are not available, however, 4-Chlorobenzotrichloride is probably combustible.

Flammability and Explosibility

Notclassified

Safety Profile

Suspected carcinogen. A poison by inhalation. Moderately toxic by ingestion and skin contact. When heated to decomposition it emits toxic vapors of Cl-.

Potential Exposure

Used in agrochemicals manufacture as an intermediate; reaction with HF yields chlorobenzotrifluoride as a major intermediate for several pesticides; for making pharmaceuticals; UV absorbers, and dyestuffs. This chemical is manufactured in high volume (exceeds 1 million pounds per annum) in the United States.

Incompatibilities

A halogenated aromatic compound. Hydrolyzes to hydrochloric acid and benzoic acid in all forms of moisture. Incompatible with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from reducing agents, alkaline materials, strong acids, strong bases, amines, nitrides, azo/ diazo compounds, alkali metals, and epoxides.

InChI:InChI=1/C7H4Cl4/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H

Synthetic route

C7H4Cl6P(1+)*Cl(1-) → 4-chlorotrichloromethylbenzene (5216-25-1) + (4-trichloromethylphenyl)phosphonic dichloride (98555-85-2)

Conditions	Yield
With sulfur dioxide for 1h;	A n/a B 87%

dichlorine monoxide + para-chlorotoluene (106-43-4) → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
In tetrachloromethane	83.9%

4-hydroxy-benzoic acid (99-96-7) → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride at 160℃; for 5h;	64.9%
With phosphorus pentachloride

Ethyl 4-hydroxybenzoate (120-47-8) → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride at 160℃; for 5h;	54.6%

para-chlorotoluene (106-43-4) → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
With phosphorus pentachloride at 108 - 112℃;

benzyl chloride (100-44-7) → 4-chlorotrichloromethylbenzene (5216-25-1) + 1,2,3,4,5,6-hexachloro-1-dichloromethyl-cyclohexane (855753-65-0) + Benzotrichlorid (98-07-7)

Conditions	Yield
Chlorierung im Sonnenlicht;

Benzotrichlorid (98-07-7) → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
With iodine durch Chlorieren;

p-toluenesulfonyl chloride (98-59-9) → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
With chlorine at 150 - 200℃;

(4-chlorophenyl)dichloromethane (13940-94-8) → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
With hypochlorous anhydride In tetrachloromethane at 25℃; Rate constant;

antimonypentachloride (7647-18-9) + Benzotrichlorid (98-07-7) → 4-chlorotrichloromethylbenzene (5216-25-1) + 3-chlorobenzotrichloride (2136-81-4) + 2-chlorobenzotrichloride (2136-89-2) + dichloro-trichloromethyl-benzene

Conditions	Yield
at 0 - 50℃; Einleiten von Chlor;

iodine (7553-56-2) + Benzotrichlorid (98-07-7) → 4-chlorotrichloromethylbenzene (5216-25-1) + 3-chlorobenzotrichloride (2136-81-4) + 2,3,4-trichloro-1-(trichloromethyl)benzene (20020-72-8) + dichloro-trichloromethyl-benzene

Conditions	Yield
at 25 - 30℃; Einleiten von Chlor;

p-oxy-benzide → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
With phosphorus pentachloride at 290 - 300℃;

p-tolyldichlorophosphine (1005-32-9) → 4-chlorotrichloromethylbenzene (5216-25-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Cl2 / CCl4 / 8 h / Heating; Irradiation 2: SO2 / 1 h View Scheme

4-chlorotrichloromethylbenzene (5216-25-1) + chlorobenzene (108-90-7) + para-chlorobenzoic acid (74-11-3) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With iron(III) oxide at 145℃; under 4500.45 Torr; for 7h;	95.7%

ortho-mercaptophenol (1121-24-0) + 4-chlorotrichloromethylbenzene (5216-25-1) → 2-(4-Chlorophenyl)-1,3-benzoxathiolium tetrafluoroborate (58948-38-2)

Conditions	Yield
With tetrafluoroboric acid diethyl ether for 2h; Ambient temperature;	95%

3-chlorophthalic anhydride (117-21-5) + 4-chlorotrichloromethylbenzene (5216-25-1) → 3-chloro-phthaloyl dichloride (113770-84-6) + 4-chloro-benzoyl chloride (122-01-0)

Conditions	Yield
zirconium(IV) chloride at 160℃; for 16h;	A 61% B 95%

4-chlorotrichloromethylbenzene (5216-25-1) + para-chlorobenzoic acid (74-11-3) + benzene (71-43-2) → 4-chlorobenzophenone (134-85-0)

Conditions	Yield
With iron(III) oxide at 120℃; under 1500.15 Torr; for 8h;	94.1%

4-chlorotrichloromethylbenzene (5216-25-1) + triethylamine (121-44-8) → 4-chloro-N,N-diethyl-benzamide (7461-38-3)

Conditions	Yield
With B12 complex immobilized on rhodium(III) modified anatase TiO2; air In acetonitrile at 20℃; for 3h; Irradiation;	94%
With heptamethyl Coβ-perchlorato-cob(II)yrinate; tetrabutylammonium perchlorate In acetonitrile at 20℃; for 3h; Electrolysis;	89%

phthalic anhydride (85-44-9) + 4-chlorotrichloromethylbenzene (5216-25-1) → 4-chloro-benzoyl chloride (122-01-0) + Phthaloyl dichloride (88-95-9)

Conditions	Yield
zirconium(IV) chloride at 160℃; for 6h;	A 93% B 70%

methanol (67-56-1) + 4-chlorotrichloromethylbenzene (5216-25-1) → Methyl 4-chlorobenzoate (1126-46-1)

Conditions	Yield
at 20℃; for 3h; UV-irradiation;	93%

4-chlorotrichloromethylbenzene (5216-25-1) + C13H11NO3S → O-(4-hydroxyphenyl) (4-(4-(trichloromethyl)phenoxy)phenyl)carbamothioate

Conditions	Yield
With sodium carbonate In toluene for 12h; Reflux;	92.3%

4-chlorotrichloromethylbenzene (5216-25-1) + C15H14N2O3S → O-(4-acetamidophenyl) (4-(4-(trichloromethyl)phenoxy)phenyl)carbamothioate

Conditions	Yield
With sodium carbonate In toluene for 12h; Reflux;	92.3%

4-chlorotrichloromethylbenzene (5216-25-1) + C13H12N2O2S → O-(4-hydroxyphenyl) (4-((4-(trichloromethyl)phenyl)amino)phenyl)carbamothioate

Conditions	Yield
With sodium carbonate In toluene for 12h; Reflux;	91.3%

4-chlorotrichloromethylbenzene (5216-25-1) + C15H15N3O2S → O-(4-acetamidophenyl) (4-((4-(trichloromethyl)phenyl)amino)phenyl)carbamothioate

Conditions	Yield
With sodium carbonate In toluene for 12h; Reflux;	91.3%

4-Cyanochlorobenzene (623-03-0) + 4-chlorotrichloromethylbenzene (5216-25-1) → 1,3-dichloro-1,3-bis(4-chlorophenyl)-2-azoniaallene hexachloroantimonate

Conditions	Yield
With antimonypentachloride In dichloromethane -30 deg C 15 min, reflux 30 min;	88%

4-chlorotrichloromethylbenzene (5216-25-1) + C13H11NO2S2 → O-(4-hydroxyphenyl) (4-((4-(trichloromethyl)phenyl)thio)phenyl)carbamothioate

Conditions	Yield
With sodium carbonate In toluene for 12h; Reflux;	84.1%

4-chlorotrichloromethylbenzene (5216-25-1) → 2,5-bis(4-chlorophenyl)-1,3,4-oxadiazole (2491-90-9)

Conditions	Yield
With hydrazine hydrate In ethanol for 0.666667h; Heating;	81%

4-chlorotrichloromethylbenzene (5216-25-1) + iron (7439-89-6) → 3-bromo-4-chlorobenzotrifluoride (454-78-4)

Conditions	Yield
With hydrogen fluoride; bromine	81%

4-chlorotrichloromethylbenzene (5216-25-1) + C15H14N2O2S2 → O-(4-acetamidophenyl) (4-((4-(trichloromethyl)phenyl)thio)phenyl)carbamothioate

Conditions	Yield
With sodium carbonate In toluene for 12h; Reflux;	80.1%

4-chlorotrichloromethylbenzene (5216-25-1) → 4,α,α,4',α',α'-hexachloro-bibenzyl (4137-78-4)

Conditions	Yield
With iron(II) chloride In acetonitrile at 25℃; for 7h;	80%
With copper(l) chloride; triethyl phosphite

1,2-dimethoxybenzene (91-16-7) + 4-chlorotrichloromethylbenzene (5216-25-1) + 1,1,2,2-tetrachloroethane (79-34-5) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
graphite In water	79.5%

4-chlorotrichloromethylbenzene (5216-25-1) + dimethyl methane phosphonate (756-79-6) → Methyl 4-chlorobenzoate (1126-46-1) + methylene chloride (74-87-3) + methylphosphonic acid anhydride

Conditions	Yield
at 180℃; for 53h;	A 79% B n/a C n/a

4-chlorotrichloromethylbenzene (5216-25-1) + 2-amino-phenol (95-55-6) → 2-(4-chlorophenyl)benzoxazole (1141-35-1)

Conditions	Yield
With Sodium borate In water at 100℃; for 10h;	78%
With PPA at 100 - 120℃; for 12h; Addition;	60%

4-chlorotrichloromethylbenzene (5216-25-1) + copper (12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8) → 4,α,α,4',α',α'-hexachloro-bibenzyl (4137-78-4)

Conditions	Yield
With pyridine; hydrogenchloride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate	75%

4-chlorotrichloromethylbenzene (5216-25-1) + Isopropyl isocyanate (1795-48-8) → 3,6-dichloro-2-isopropyl-1-oxoisoindolium hexachloroantimonate

Conditions	Yield
With antimonypentachloride In dichloromethane 1.) -30 deg C, 10 min, 2.) 23 deg C, 4 h;	73%

4-chlorotrichloromethylbenzene (5216-25-1) + p-Tolylisocyanate (622-58-2) → 3-chloro-1-(4-chlorophenyl)-7-methylbenzo-2,4-oxazinium hexachloroantimonate

Conditions	Yield
With antimonypentachloride In dichloromethane 1.) -30 deg C, 2.) 23 deg C, 3 h;	71%

4-chlorotrichloromethylbenzene (5216-25-1) + 4-(5-amino-1,3,4-thiadiazol-2-ylsulfanyl)benzenesulfonyl chloride (1076689-72-9) → 4-[5-(4-trichloromethylphenylamino)-[1,3,4]thiadiazol-2-ylsulfanyl]-benzenesulfonylchloride (1076689-67-2)

Conditions	Yield
In diethyl ether at 0 - 5℃; for 0.5h;	71%

[(Ir(η5-C5Me5))2(μ-CH2)2(μ-S2-S:S')] + 4-chlorotrichloromethylbenzene (5216-25-1) → cis-[(Ir(C5(CH3)5)2(μ-CH2)2(μ-S2C-C6H4-Cl-p)]Cl

Conditions	Yield
In methanol (N2); standard Schlenk technique; MeOH and soln. of ClC6H4CCl3 in methanol were added to Ir complex;	70%

4-chlorotrichloromethylbenzene (5216-25-1) + anthranilic acid amide (28144-70-9) → 2-(4-chlorophenyl)-4(3H)-quinazolinone (7455-77-8)

Conditions	Yield
With Sodium borate In water at 100℃; for 14h;	69%

4-chlorotrichloromethylbenzene (5216-25-1) + 3-phenyl-4-amino-5-mercapto-1,2,4-triazole (22706-11-2) → C15H11Cl3N4S (1149378-80-2)

Conditions	Yield
Stage #1: 3-phenyl-4-amino-5-mercapto-1,2,4-triazole With potassium hydroxide In water at 20℃; Stage #2: 4-chlorotrichloromethylbenzene In water at 0℃;	68%

4-chlorotrichloromethylbenzene (5216-25-1) + 2-amino-1-benzylamine (4403-69-4) → 2-(4-chloro-phenyl)-quinazoline

Conditions	Yield
With oxygen; sodium hydroxide In water at 100℃; Sealed tube; Green chemistry;	68%

Upstream product

• 106-43-4 para-chlorotoluene 
• 100-44-7 benzyl chloride 
• 98-07-7 Benzotrichlorid 
• 98-59-9 p-toluenesulfonyl chloride 
• 99-96-7 4-hydroxy-benzoic acid 
• 13940-94-8 (4-chlorophenyl)dichloromethane 
• 7647-18-9 antimonypentachloride 
• 7553-56-2 iodine 
• 1005-32-9 p-tolyldichlorophosphine 
• 120-47-8 Ethyl 4-hydroxybenzoate 

Downstream Products

• 6279-05-6 4'-chloro-2-hydroxy-5-methylbenzophenone 
• 98-56-6 4-chlorobenzotrifluoride 
• 94880-40-7 4-(4'-chloro-4-hydroxy-3-methyl-benzhydrylidene)-2-methyl-cyclohexa-2,5-dienone 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 1871-38-1 phenyl 4-chlorobenzoate 
• 713-29-1 4-Chlor-5-nitrophenylchloroform 
• 38204-36-3 p-chlorothiobenzoylthioacetic acid 
• 58948-38-2 2-(4-Chlorophenyl)-1,3-benzoxathiolium tetrafluoroborate 
• 129427-58-3 1,3-Bis-(4-methoxy-phenyl)-5-phenyl-5,6-dihydro-[1,2,4,5]tetrazin-1-ium; chloride 
• 5216-26-2 trans-1,2-Dichlor-1,2-bis-(4-chlorphenyl)-ethylen 
• 5216-27-3 cis-1,2-Dichlor-1,2-bis-(4-chlorphenyl)-ethylen 
• 2494-79-3 4-chloro-3-(chlorosulfonyl)benzoic acid 
• 68340-48-7 sodium 4-chlorodithiobenzoate 
• 53119-90-7 α,β,4-trichlorobenzyltrimethylsilane 

Relevant articles and documents

Novel synthetic method of halogenated aromatic hydrocarbon

The invention discloses a novel synthetic method of halogenated aromatic hydrocarbon, wherein p-chlorotoluene is used as a raw material, copper chloride or cuprous chloride is used as a catalyst, andp-chlorobenzotrifluoride is synthesized through two steps of chlorination and fluorination. Compared with the method in the prior art, the method of the invention has the following characteristics that raw materials are subjected to heating dehydration treatment in a dehydration kettle, so that the chlorination side reactions are few, the product purity is high, the grading chlorination device does not need to be additionally arranged, the technological process is simple, and the operation is convenient; and by adding the catalyst in batches in the chlorination process, the use efficiency of the catalyst is improved, so that the emission of the byproducts and the waste gas generated by the chlorination reaction in production is greatly reduced, and the emission of pollutants in the production process is reduced.

Novel fluorination process of p-chlorobenzotrifluoride

The invention discloses a novel fluorination process of p-chlorobenzotrifluoride. P-chlorotoluene is used as a raw material, and 4-chlorobenzotrifluoride is synthesized through two steps of chlorination and fluorination. Compared with the prior art, the fluorination process has the advantages of no catalyst, lower cost than other organic catalysts or noble metal catalysts, convenience in recoveryand no pollution to the environment; a solvent-free fluorination process is adopted, so that the emission of by-products and waste gas of a solvation reaction is greatly reduced, and the emission of pollutants in the production process is reduced.

Synthesis method of 4-chlorobenzotrifluoride

The invention discloses a synthetic method of 4-chlorobenzotrifluoride. P-chlorotoluene is used as a raw material, and 4-chlorobenzotrifluoride is synthesized through two steps of chlorination and fluorination. Compared with the prior art, the raw materials are subjected to heating dehydration treatment in the dehydration kettle, chlorination side reactions are few, the product purity is high, a graded chlorination device does not need to be added, the technological process is simple, and operation is convenient; according to the chlorination process, a mode of adding the catalyst in batches is adopted, so that the use efficiency of the catalyst is improved, the emission of byproducts and waste gas generated by chlorination reaction in production is greatly reduced, and the emission of pollutants in the production process is reduced.

CLEAN PROCESS FOR PREPARING CHLOROFORMYL-SUBSTITUTED BENZENE

Clean process for preparing a chloroformyl-substituted benzene by oxidation of a tail gas hydrogen chloride from a chlorination reaction and a chloroacylation reaction and recycling of the resulting oxidation product chlorine gas into the chlorination reaction. The present invention provides a clean process for preparing a polymer-grade chloroformyl-substituted benzene.

METHOD FOR THE PREPARATION OF TRICHLOROMETHYL-GROUP-SUBSTITUTED BENZENE

The present application relates to a method for photochlorination, and specifically to photochlorination by a photochemical reaction of an aromatic compound with gaseous chlorine so as to prepare a trichloromethyl-substituted benzene, and to a method using bis-(trichloromethyl)-benzene as the trichloromethyl-substituted benzene to prepare by further reaction bis-(chloroformyl)-benzene. Through the control of temperature, illuminance and consumption of gaseous chlorine, the method of this application can greatly improve the purity of trichloromethyl-substituted benzene and further prepare polymer-grade bis-(chloroformyl)-benzene with low cost. The present application also relates to a method for purifying trichloromethyl-substituted benzene, and specifically to a method for purifying trichloromethyl-substituted benzene via molecular distillation. The present application further relates to a photochlorination reactor for use in photochlorination reactions (such as those of the present application).

PhPOCl2as a potent catalyst for chlorination reaction of phenols with PCl5

Phenols are easily converted to the corresponding aryl chlorides by using phosphorus pentachloride (PCl5) and a catalytic amount of phenylphosphonic dichloride (PhPOCl2), which is a new efficient method for synthesis of aryl chloride in good yields.

PROCESS FOR THE PREPARATION OF 2,6-DIHALO-PARA-TRIFLUOROMETHYL- ANILINES AS INTERMEDIATES OF PYRAZOLES

The present invention provides a process for the preparation of 2,6-dihalo-para-trifluoromethylanilines as intermediates for pyrazoles comprising the halogenation of para-trifluoromethylaniniline with dihalogen.

Process for the preparation of nuclear-halogenated benzotrichlorides from the corresponding benzotrifluorides

Nuclear-halogenated benzotrichlorides are prepared in a particularly advantageous manner from the corresponding nuclear-halogenated benzotrifluorides by reacting nuclear-halogenated benzotrifluorides with silicon tetrachloride in the presence of catalytic amounts of aluminium trichloride.

Phosporylation of 1,3-di(N-alkyl)azoles by phosphorus(V) acid chlorides - A route to potential haptens derived from phosphinic acids

Phosphorylation of N-alkylated imidazoles and benzimidazoles at C-2 by CH3POCl2, PhPOCl2, POCl3 in pyridine-triethylamine solution is described. The formed heteroaryl-substituted phosphinic or phosphonic acid chlorides were transformed without isolation into the corresponding phosphinic (phosphinic) acids, their salts or amides with moderate yields. This reaction opens a simple way to potential haptens derived from phosphinic acids. These haptens mimic tetrahedral transition state of many reactions and can be used to obtain catalytic antibodies. The functionalized heteroarylsubstituted phosphinic acids which have been used as hapten precursors were obtained by phosphorylation of 1-alkyl-5-nitrobenzimidazole or by usage of a new phosphorylating reagent - (4-trichloromethylphenyl)phosphonic dichloride.