2136-89-2

Basic information

• Product Name: 2-Chlorobenzotrichloride
• Synonyms: OCTC;O-CHLOROBENZOTRICHLORIDE;TIMTEC-BB SBB007588;2-CHLOROBENZOTRICHLORIDE;2-CHLOROTRICHLOROTOLUENE;2-AMINO CHLORO PHENOL;1-CHLORO-2-(TRICHLOROMETHYL)BENZENE;ALPHA,ALPHA,ALPHA,2-TETRACHLOROTOLUENE
• CAS NO: 2136-89-2
• Molecular Formula: C₇H₄Cl₄
• Molecular Weight: 229.92
• EINECS: 218-377-7
• Mol File: 2136-89-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 136-141 °C(lit.)
• Boiling Point: 260-264°C
• Flash Point: 209 °F
• Appearance: Clear colourless liquid after melting
• Density: 1.508 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0159mmHg at 25°C
• Refractive Index: 1.5836
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate (Slightly)
• Sensitive: Moisture Sensitive
• BRN: 2046639
• CAS DataBase Reference: 2-Chlorobenzotrichloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzotrichloride(2136-89-2)
• EPA Substance Registry System: 2-Chlorobenzotrichloride(2136-89-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-38-40
• Safety Statements: 26-36/37
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: SJ5700000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2136-89-2(Hazardous Substances Data)

Usage

Description

2-Chlorobenzotrichloride, also known as 2-chloro-1,3,5-trichlorobenzene, is a chlorinated aromatic compound with mutagenicity. It is characterized by its clear colorless appearance after melting and is derived from toluene through a chlorination process.

Uses

Used in Chemical Synthesis:
2-Chlorobenzotrichloride is used as an intermediate in the chemical synthesis industry for the production of various organic compounds. Its mutagenicity makes it a valuable starting material for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
In the field of research and development, 2-Chlorobenzotrichloride is utilized as a reagent for studying the effects of chlorination on aromatic compounds and their subsequent applications in various chemical reactions.
Used in Analytical Chemistry:
2-Chlorobenzotrichloride serves as a reference compound in analytical chemistry for the identification and quantification of chlorinated aromatics in environmental and industrial samples. Its clear colorless liquid form after melting makes it suitable for various analytical techniques.
Used in Material Science:
In material science, 2-Chlorobenzotrichloride can be used as a component in the development of new materials with specific properties, such as improved thermal stability or chemical resistance, due to its chlorinated nature.

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

Synthetic route

2-chlorobenzal chloride (88-66-4) → 2-chlorobenzotrichloride (2136-89-2)

Conditions	Yield
With tetrachloromethane; sodium hydroxide; trimethyldodecylammonium chloride for 1h; Heating;	91%
	91%

2-methylchlorobenzene (95-49-8) → 2-chlorobenzotrichloride (2136-89-2)

Conditions	Yield
at 130℃; durch Chlorierung;
at 160 - 190℃; Einleiten von Chlor;
at 125℃; UV-Licht;
With chlorine; copper(l) chloride at 80 - 112℃; for 20h;

(2-chlorobenzyl)sulfonyl chloride (77421-13-7) → 2-chlorobenzotrichloride (2136-89-2)

Conditions	Yield
With chlorine at 150 - 180℃;

o-chlorobenzoyl chloride (609-65-4) → 2-chlorobenzotrichloride (2136-89-2)

Conditions	Yield
With phosphorus pentachloride at 200℃; im Rohr;

salicylic acid (69-72-7) → 2-chlorobenzotrichloride (2136-89-2)

Conditions	Yield
With phosphorus pentachloride
Multi-step reaction with 2 steps 1: thionyl chloride 2: benzene; phosphorus pentachloride / 80 °C View Scheme

salicyloyl chloride (1441-87-8) → 2-chlorobenzotrichloride (2136-89-2)

Conditions	Yield
With phosphorus pentachloride; benzene at 80℃;

ortho-chlorobenzoic acid (118-91-2) → 2-chlorobenzotrichloride (2136-89-2)

Conditions	Yield
With phosphorus pentachloride at 200℃; im Rohr;

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;

sodium salicylate (54-21-7) → 2-chlorobenzotrichloride (2136-89-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride 2: benzene; phosphorus pentachloride / 80 °C View Scheme

2-chlorobenzotrichloride (2136-89-2) → 1-chloro-4-nitro-2-(trichloromethyl)benzene (831-50-5)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 10℃; for 2h;	99.1%
With sulfuric acid; nitric acid

2-chlorobenzotrichloride (2136-89-2) + triethylamine (121-44-8) → N,N-Diethyl-2-chlorobenzamide (10345-79-6)

Conditions	Yield
With B12 complex immobilized on rhodium(III) modified anatase TiO2; air In acetonitrile at 20℃; for 3h; Irradiation;	98%
With heptamethyl Coβ-perchlorato-cob(II)yrinate; tetrabutylammonium perchlorate In acetonitrile at 20℃; for 3h; Electrolysis;	94%

2-chlorobenzotrichloride (2136-89-2) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
Stage #1: 2-chlorobenzotrichloride With ferric(III) bromide; ferrocenyl methyl trimethyl ammonium bromide; copper(I) bromide; iron(II) bromide at 20℃; for 15h; Stage #2: With aminosulfonic acid In water at 80℃; for 8h;	92.5%
Stage #1: 2-chlorobenzotrichloride With bromine; iron for 6h; Stage #2: With sulfuric acid at 100℃; for 5h;	90%
Stage #1: 2-chlorobenzotrichloride With ferric(III) bromide; bromine In dichloromethane at 25 - 30℃; for 6h; Stage #2: With acetic acid at 110℃; for 15h; Reagent/catalyst; Temperature;

2-chlorobenzotrichloride (2136-89-2) + 2-AMINOBENZENESULFONAMIDE (3306-62-5) → 3-(2-chlorophenyl)-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide (73676-89-8)

Conditions	Yield
With Sodium borate In water at 100℃; for 16h;	76%

methanol (67-56-1) + 2-chlorobenzotrichloride (2136-89-2) → methyl chlorobenzoate (610-96-8)

Conditions	Yield
at 20℃; for 3h; UV-irradiation;	75%

2-chlorobenzotrichloride (2136-89-2) + anthranilic acid amide (28144-70-9) → 2-(2-chlorophenyl)quinazolin-4(3H)-one (4765-50-8)

Conditions	Yield
With Sodium borate In water at 100℃; for 16h;	60%

2-chlorobenzotrichloride (2136-89-2) → (Z)-1,2-dichloro-1,2-bis(2-chlorophenyl)ethylene (856162-07-7) + C14H8Cl6

Conditions	Yield
With iron(II) chloride In acetonitrile at 25℃; for 7h;	A 39% B 38%

2-chlorobenzotrichloride (2136-89-2) + benzene (71-43-2) → 2-chlorotrityl chloride (42074-68-0)

Conditions	Yield
With aluminium trichloride for 14h; Friedel-Crafts alkylation; Heating;	36%

p-cresol (106-44-5) + 2-chlorobenzotrichloride (2136-89-2) → 2-methyl-9H-xanthen-9-one (6280-45-1)

Conditions	Yield
With carbon disulfide; aluminium trichloride

p-cresol (106-44-5) + 2-chlorobenzotrichloride (2136-89-2) → (2-chlorophenyl)(2-hydroxy-5-methylphenyl)methanone (6280-52-0)

Conditions	Yield
With carbon disulfide; aluminium trichloride Behandeln des erhaltenen Reaktionsprodukts mit H2O;

2-chlorobenzotrichloride (2136-89-2) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With hydrogen fluoride; antimonypentachloride
With antimony(III) fluoride
With hydrogen fluoride at 50℃; under 7500.75 Torr; for 1h; Autoclave;
With antimony (V)-fluoride chloride; phosphorus pentachloride; hydrogen fluoride
With hydrogen fluoride at 82℃; under 1500.15 - 13501.4 Torr; for 0.5h; Pressure; Temperature;

2-chlorobenzotrichloride (2136-89-2) → (Z)-1,2-dichloro-1,2-bis(2-chlorophenyl)ethylene (856162-07-7) + (E)-1,2-dichloro-1,2-bis(2-chlorophenyl)ethylene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,1,1,2,2,2-hexamethyldisilane In 1,3,5-trimethyl-benzene at 130℃; for 2h; Yield given. Yields of byproduct given;
With F2Cl2*4H2O In acetonitrile at 45 - 50℃; for 7h;

ethanol (64-17-5) + 2-chlorobenzotrichloride (2136-89-2) → ethyl 2-chlorobenzoate (7335-25-3)

Conditions	Yield
With hydrazine hydrate Heating;
With heptamethyl cobyrinate perchlorate; tetrabutylammonium perchlorate at 20℃; Electrolysis;	48 %Chromat.

2-chlorobenzotrichloride (2136-89-2) + water (7732-18-5) → ortho-chlorobenzoic acid (118-91-2)

Conditions	Yield
at 150℃;

2-chlorobenzotrichloride (2136-89-2) + benzene (71-43-2) + copper powder → a-o.o'-dichloro-tolan dichloride + β-o.o'-dichloro-tolan dichloride

2-chlorobenzotrichloride (2136-89-2) → UCL-1880

Conditions	Yield
Multi-step reaction with 2 steps 1: 36 percent / AlCl3 / 14 h / Heating 2: 18 percent / Et3N / acetonitrile / 4 h / Heating View Scheme

2-chlorobenzotrichloride (2136-89-2) → 2-trifluoromethyl-phenetole (2366-91-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: SbCl5; HF 2: NaOH; ethanol / 160 °C View Scheme

2-chlorobenzotrichloride (2136-89-2) → salicylic acid (69-72-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: SbCl5; HF 2: NaOH; ethanol / 160 °C View Scheme

2-chlorobenzotrichloride (2136-89-2) → 2-Chlor-5-amino-benzotrichlorid (71195-69-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3, H2SO4 2: aq. HCl, SnCl2 / ethanol; acetone View Scheme

2-chlorobenzal chloride (88-66-4) + 2-chlorobenzotrichloride (2136-89-2) → 2-chloro-benzaldehyde (89-98-5)

Upstream product

• 118-91-2 ortho-chlorobenzoic acid 
• 7647-18-9 antimonypentachloride 
• 98-07-7 Benzotrichlorid 
• 54-21-7 sodium salicylate 
• 1441-87-8 salicyloyl chloride 
• 69-72-7 salicylic acid 
• 609-65-4 o-chlorobenzoyl chloride 
• 95-49-8 2-methylchlorobenzene 
• 77421-13-7 (2-chlorobenzyl)sulfonyl chloride 
• 88-66-4 2-chlorobenzal chloride 

Downstream Products

• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 
• 856162-07-7 (Z)-1,2-dichloro-1,2-bis(2-chlorophenyl)ethylene 
• 7335-25-3 ethyl 2-chlorobenzoate 
• 118-91-2 ortho-chlorobenzoic acid 
• 73676-89-8 3-(2-chlorophenyl)-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 4765-50-8 2-(2-chlorophenyl)quinazolin-4(3H)-one 
• 10345-79-6 N,N-Diethyl-2-chlorobenzamide 
• 5814-05-1 2-chlorobenzoylhydrazide 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 610-96-8 methyl chlorobenzoate 
• 115345-92-1 1-Chloro-2-(chloro-difluoro-methyl)-benzene 
• 1258790-97-4 C₇H₄Cl₃F 
• 127442-07-3 N,N'-Bis(4-ethoxycarbonylphenyl)-2-chlorobenzamidine 
• 89-98-5 2-chloro-benzaldehyde 

Relevant articles and documents

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Novel synthesis method of chlorobenzotrifluoride

The invention discloses a novel synthesis method of chlorobenzotrifluoride, wherein o-chlorotoluene is used as a raw material, copper chloride or cuprous chloride is used as a catalyst, and o-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 the dehydration kettle, so that the chlorination side reactions are few, the product purity is high, the graded chlorination device does not need to be additionally arranged, the technological process is simple, and the operation is convenient. According to the chlorination process of the invention, the catalyst is added in batches to increase the efficiency of the catalyst, so that the by-product generated by thechlorination reaction and the emission of waste gas in the production are greatly reduced, and the emission of pollutants in the production process is reduced.

Process for preparing substituted benzotrichloride compounds

This invention pertains to a process for preparing substituted and unsubstituted benzotrichlorides. The process generally involves reacting the starting compound with a perchloroalkane with presence of base and a phase transfer catalyst.