13014-18-1

Basic information

• Product Name: 2,4-DICHLOROBENZOTRICHLORIDE
• Synonyms: 2,4-Dichlor-1-(trichlormethyl)benzol;2,4-DICHLOROBENZOTRICHLORIDE 99+%;1-(Trichloromethyl)-2,4-dichlorobenzene;α,α,α,2,4-Pentachlorotoluene;1,3-Dichloro-4-(trichloromethyl)benzene;2,4-dichloro-1-(trichloromethyl)-benzen;2,4-Dichloro-1-(trichloromethyl)benzene;2,4-Dichlorophenyltrichloromethane
• CAS NO: 13014-18-1
• Molecular Formula: C₇H₃Cl₅
• Molecular Weight: 264.36
• EINECS: 235-868-1
• Mol File: 13014-18-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 49°C
• Boiling Point: 288°C
• Flash Point: > 112 C
• Appearance: clear liquid
• Density: 1.5935 (estimate)
• Vapor Pressure: 0.00256mmHg at 25°C
• Refractive Index: 1.5939 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 2,4-DICHLOROBENZOTRICHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLOROBENZOTRICHLORIDE(13014-18-1)
• EPA Substance Registry System: 2,4-DICHLOROBENZOTRICHLORIDE(13014-18-1)

Safety Data

• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3261
• RTECS: CZ5475020
• Hazardous Substances Data: 13014-18-1(Hazardous Substances Data)

Usage

Uses

2,4-Dichlorobenzotrichloride is used in the synthesis of aromatic acid chlorides.

General Description

White crystalline powder.

Air & Water Reactions

2,4-DICHLOROBENZOTRICHLORIDE may be sensitive to exposure to moisture. Insoluble in water.

Reactivity Profile

Simple aromatic halogenated organic compounds, such as 2,4-DICHLOROBENZOTRICHLORIDE, 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.

Fire Hazard

Flash point data for 2,4-DICHLOROBENZOTRICHLORIDE are not available. 2,4-DICHLOROBENZOTRICHLORIDE is probably combustible.

Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of Clí.

InChI:InChI=1/C7H3Cl5/c8-4-1-2-5(6(9)3-4)7(10,11)12/h1-3H

Synthetic route

2,4-dichlorotoluene (95-73-8) → 2,4-dichlorobenzotrichloride (13014-18-1)

Conditions	Yield
at 125℃; UV-Licht; Einleiten von Chlor;
With 2,2'-azobis(isobutyronitrile); chlorine at 95℃; for 7h; Temperature; Sealed tube;	489.8 g
With chlorine at 115 - 117℃; for 20h; Temperature;
With chlorine at 115 - 117℃; for 20h; Temperature;
With CuCl/Cu; chlorine at 115 - 117℃; for 24h; Temperature; Green chemistry;

3-chloro-4-methylbenzenesulfonyl chloride (42413-03-6) → 2,4-dichlorobenzotrichloride (13014-18-1)

Conditions	Yield
With chlorine at 150 - 200℃;

2,4-dichlorobenzotrichloride (13014-18-1) + triethylamine (121-44-8) → 2,4-dichloro-N,N-diethylbenzamide (24309-78-2)

Conditions	Yield
With B12 complex immobilized on rhodium(III) modified anatase TiO2; air In acetonitrile at 20℃; for 3h; Irradiation;	97%
With heptamethyl Coβ-perchlorato-cob(II)yrinate; tetrabutylammonium perchlorate In acetonitrile at 20℃; for 3h; Electrolysis;	94%

methanol (67-56-1) + 2,4-dichlorobenzotrichloride (13014-18-1) → methyl 2,4-dichlorobenzoate (35112-28-8)

Conditions	Yield
at 20℃; for 3h; UV-irradiation;	96%

2,4-dichlorobenzotrichloride (13014-18-1) → 2,4-dichlorobenzoyl chloride (89-75-8)

Conditions	Yield
With iron(III) chloride In water at 110℃; for 2h; Temperature;	93.05%

2,4-dichlorobenzotrichloride (13014-18-1) + cyanogen chloride (506-77-4) → 2,4-dichloro-6-(2,4-dichloro-phenyl)-[1,3,5]triazine (14943-69-2)

Conditions	Yield
In aluminium trichloride	64%

p-cresol (106-44-5) + 2,4-dichlorobenzotrichloride (13014-18-1) → 6-chloro-2-methyl-9H-xanthen-9-one (37884-02-9)

Conditions	Yield
With carbon disulfide; aluminium trichloride

2,4-dichlorobenzotrichloride (13014-18-1) → 2,4 dichlorobenzoic acid (50-84-0)

Conditions	Yield
beim Verseifen;

2,4-dichlorobenzotrichloride (13014-18-1) + trichloroacetonitrile (545-06-2) → N-Pentachlorethyl-2,4-dichlorbenzimidoylchlorid (65934-92-1)

Conditions	Yield
With aluminium trichloride

2,4-dichlorobenzotrichloride (13014-18-1) → 2,4-Dichlor-5-nitrophenylchloroform (717-43-1)

Conditions	Yield
With sulfuric acid; nitric acid

2,4-dichlorobenzotrichloride (13014-18-1) → C14H6Cl6 + C14H6Cl6

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;

2,4-dichlorobenzotrichloride (13014-18-1) + cyanogen chloride (506-77-4) → 2,4-Dichlor-N-dichlormethylen-N'-trichlormethylbenzamidin (65866-99-1)

hydrogen fluoride (7664-39-3) + 2,4-dichlorobenzotrichloride (13014-18-1) → 2,4-dichloro-benzotrifluoride (320-60-5)

Conditions	Yield
at 140 - 150℃;
at 140 - 150℃;

sulfuric acid (7664-93-9) + 2,4-dichlorobenzotrichloride (13014-18-1) → 2,4-dichloro-5-nitrobenzoic acid (19861-62-2)

Conditions	Yield
folgend Behandeln mit Nitriersaeure bei 10grad;

p-cresol (106-44-5) + 2,4-dichlorobenzotrichloride (13014-18-1) → 2,4-dichloro-2'-hydroxy-5'-methyl-benzophenone (92153-14-5) + 6,12-bis-<2,4-dichloro-phenyl>-2,8-dimethyl-6H,12H-6,12-epoxido-dibenzodioxocin

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

2,4-dichlorobenzotrichloride (13014-18-1) → 6-chloro-2-methyl-9H-xanthen-9-one (37884-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3; CS2 / Behandeln des erhaltenen Reaktionsprodukts mit H2O 2: potassium hydroxide; ethylene glycol View Scheme

2,4-dichlorobenzotrichloride (13014-18-1) → 2,4-dichloro-5-nitro benzoyl chloride (713-28-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3, H2SO4 2: aq. FeCl3 View Scheme

1,3-dimethylpyrazol-5-one (3201-29-4) + 1,1-dichloroethane (75-34-3) + 2,4-dichlorobenzotrichloride (13014-18-1) → 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-hydroxypyrazole (58010-98-3)

Conditions	Yield
With potassium hydroxide; aluminium trichloride In water

1,3-dimethylpyrazol-5-one (3201-29-4) + 6 N-HCl + 1,1-dichloroethane (75-34-3) + 2,4-dichlorobenzotrichloride (13014-18-1) → 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-hydroxypyrazole (58010-98-3)

Conditions	Yield
With sodium hydrogencarbonate; aluminium trichloride

1,2-dihydro-5-methyl-3H-pyrazol-3-one (4344-87-0) + 2,4-dichlorobenzotrichloride (13014-18-1) → 3-methyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole

Conditions	Yield
With hydrogenchloride; aluminium trichloride In 1,1-dichloroethane

1,3-dimethylpyrazol-5-one (3201-29-4) + 2,4-dichlorobenzotrichloride (13014-18-1) → 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-hydroxypyrazole (58010-98-3)

Conditions	Yield
With pyridine; potassium hydroxide In ethanol; dichloromethane; water
With hydrogenchloride; aluminium trichloride In 1,1-dichloroethane

2,4-dichlorobenzotrichloride (13014-18-1) → 2,4-dichloro-5-nitrobenzotrifluoride (400-70-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 140 - 150 °C 2: Nitrierung View Scheme

2,4-dichlorobenzotrichloride (13014-18-1) + diethylamine (109-89-7) → 2,4-dichloro-N,N-diethylbenzamide (24309-78-2)

Conditions	Yield
With heptamethyl Coβ-perchlorato-cob(II)yrinate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h; Irradiation;	98 %Chromat.

2,4-dichlorobenzotrichloride (13014-18-1) → 2,4-dichloro-benzotrifluoride (320-60-5)

Conditions	Yield
With hydrogen fluoride at 110℃; under 11251.1 - 12751.3 Torr; Pressure; Temperature;
With hydrogen fluoride at 110℃; under 11251.1 - 12751.3 Torr; Temperature; Pressure;
With hydrogen fluoride at 110℃; under 11251.1 - 12751.3 Torr; Temperature; Pressure; Green chemistry;

Upstream product

• 95-73-8 2,4-dichlorotoluene 
• 42413-03-6 3-chloro-4-methylbenzenesulfonyl chloride 

Downstream Products

• 65934-92-1 N-Pentachlorethyl-2,4-dichlorbenzimidoylchlorid 
• 320-60-5 2,4-dichloro-benzotrifluoride 
• 19861-62-2 2,4-dichloro-5-nitrobenzoic acid 
• 92153-14-5 2,4-dichloro-2'-hydroxy-5'-methyl-benzophenone 
• 58010-98-3 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-hydroxypyrazole 
• 35112-28-8 methyl 2,4-dichlorobenzoate 
• 400-70-4 2,4-dichloro-5-nitrobenzotrifluoride 
• 24309-78-2 2,4-dichloro-N,N-diethylbenzamide 
• 89-75-8 2,4-dichlorobenzoyl chloride 
• 713-28-0 2,4-dichloro-5-nitro benzoyl chloride 
• 37884-02-9 6-chloro-2-methyl-9H-xanthen-9-one 
• 65866-99-1 2,4-Dichlor-N-dichlormethylen-N'-trichlormethylbenzamidin 
• 50-84-0 2,4 dichlorobenzoic acid 
• 14943-69-2 2,4-dichloro-6-(2,4-dichloro-phenyl)-[1,3,5]triazine 

Relevant articles and documents

2,4-dichlorobenzotrifluoride preparation method

The invention discloses a 2,4-dichlorobenzotrifluoridepreparation method, wherein the target compound is obtained by using 2,4-dichlorotoluene as a raw material and using a mixture of cuprous chlorideand copper powder as a catalyst through a two-step reaction of chlorination and fluorination. Compared with the method in the prior art, the method of the invention has the following advantages thatthe chlorination side reactions are less, the isomer of 2,4-dichlorobenzotrifluoride cannot be generated in the reaction process, the product purity is high, the raw material sources are wide, the catalyst is low in price and convenient to recover, the production cost of the target compound is reduced, the economic benefit is increased, and environment pollution cannot be generated.

Efficient chlorination process of 2,4-dichlorobenzotrifluoride

The invention discloses an efficient chlorination process of 2,4-dichlorobenzotrifluoride, and belongs to the field of organic synthesis. According to the method, 2, 4-dichlorotoluene is used as a rawmaterial, a mixture catalyst of cuprous chloride and copper powder is added, a target compound is obtained through two-step reaction of chlorination and fluorination, the raw materials applied in thereaction process are convenient to purchase, the production cost is low, after-treatment is simple, reaction conditions are mild, and good economic benefits and social benefits are achieved.