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
• Article Data: 11

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

Chemical Properties

p-Chlorobenzotrichloride, an organochloride, is a flammable, water-white liquid.

Uses

Different sources of media describe the Uses of 5216-25-1 differently. You can refer to the following data:
1. Same as o-chlorobenzotrichloride.
2. 4-Chlorobenzotrichloride is a useful reactant in organic synthesis.

General Description

Clear colorless liquid.

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

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

Downstream Products

• 94880-40-7 4-(4'-chloro-4-hydroxy-3-methyl-benzhydrylidene)-2-methyl-cyclohexa-2,5-dienone 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 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 
• 74-11-3 para-chlorobenzoic acid 
• 27023-37-6 4-chlorotrityl chloride 
• 116412-83-0 4-chloro-3',4'-dimethoxy benzophenone 
• 122-01-0 4-chloro-benzoyl chloride 
• 147715-58-0 4'-chloro-2-isocyanato-5-methylbenzophenone diethyl acetal 
• 1194131-65-1 4-(2-chlorobenzyloxy)-4-(4-chlorophenyl)-6-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one 
• 775348-40-8 4'-chloro-2-isocyanato-5-methylbenzophenone-diallylketal 

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.

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.

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.