6575-05-9

Basic information

• Product Name: 2,4,6-Trichlorobenzonitrile
• Synonyms: 2,4,6-TRICHLOROBENZONITRILE;Benzonitrile,2,4,6-trichloro-;2,4,6-Trichlorobenzonitrile, 97+%
• CAS NO: 6575-05-9
• Molecular Formula: C₇H₂Cl₃N
• Molecular Weight: 206.46
• Product Categories: Benzene series;Nitrile
• Mol File: 6575-05-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 80-82°C
• Boiling Point: 303.1 °C at 760 mmHg
• Flash Point: 136.4 °C
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 0.000951mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• CAS DataBase Reference: 2,4,6-Trichlorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trichlorobenzonitrile(6575-05-9)
• EPA Substance Registry System: 2,4,6-Trichlorobenzonitrile(6575-05-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6575-05-9(Hazardous Substances Data)

Usage

Chemical Properties

White crystals

InChI:InChI=1/C7H2Cl3N/c8-4-1-6(9)5(3-11)7(10)2-4/h1-2H

Synthetic route

1,3,5-trichloro-2-(chloromethyl)benzene (17293-03-7) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

Conditions	Yield
With ammonia at 638℃; for 8h; Reagent/catalyst;	94.6%

1,3,5-trichloro-2-iodobenzene (6324-50-1) + dicyanozinc (557-21-1) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 85℃;	84%

2,4,6-trichloro-benzaldehyde-oxime (22241-21-0) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

Conditions	Yield
With melamine-formaldehyde supported H2SO4 for 0.0666667h; Microwave irradiation;	80%

2,4,6-trichloro-benzoic acid amide (23400-04-6) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

Conditions	Yield
With aluminium trichloride; sodium chloride

2,4,6-trichloroaniline (634-93-5) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

Conditions	Yield
With hydrogenchloride Behandlung der Diazoniumchloridloesung mit Kaliumkupfercyanuerloesung;

diazotized 2.4.6-trichloro-aniline + potassium cyanocuprate(I) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

2,4,6-trichloro-benzenediazonium; chloride (27093-67-0) + potassium cyanocuprate(I) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

aniline (62-53-3) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: CHCl3; chlorine 2: hydrochloric acid / Behandlung der Diazoniumchloridloesung mit Kaliumkupfercyanuerloesung View Scheme

ethyl bromide (74-96-4) + propyl bromide (106-94-5) → 2,4,6-Trichlorobenzonitrile (6575-05-9)

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichlorobenzaldehyde (24473-00-5)

Conditions	Yield
With formic acid; nickel-aluminum alloy; water at 100℃; for 4h;	93%

2,4,6-Trichlorobenzonitrile (6575-05-9) → (2,4,6-trichlorophenyl)methanamine (101084-06-4)

Conditions	Yield
With ammonium hydroxide; hydrogen In water; isopropyl alcohol at 60 - 80℃; under 7500.75 Torr;	75%
With potassium hydroxide; chromium(II) acetate
With borane-THF In tetrahydrofuran at 40℃; for 2h;
Stage #1: 2,4,6-Trichlorobenzonitrile With diborane In tetrahydrofuran at 40℃; for 2h; Stage #2: With methanol In tetrahydrofuran at 20℃; for 0.5h;

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
With hydrogenchloride at 200℃; im Druckrohr;
With sulfuric acid; water; acetic acid

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichloro-benzoic acid amide (23400-04-6)

Conditions	Yield
With sulfuric acid

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2-Chlorobenzonitrile (873-32-5) + 2,6-dichloro-benzonitrile (1194-65-6) + benzonitrile (100-47-0) + 2,4-dichlorobenzylnitrile (6574-98-7)

Conditions	Yield
With (C2H5)3NH2CO2; palladium on activated charcoal In acetonitrile at 80℃; Yield given;

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichloro-N-hydroxy-benzamidine

Conditions	Yield
With hydroxylamine In methanol Addition; Heating;

hydrogenchloride (7647-01-0) + 2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichlorobenzoic acid (50-43-1)

Conditions	Yield
at 200℃;

2,4,6-Trichlorobenzonitrile (6575-05-9) → C18H11Cl3N2O2

Conditions	Yield
Multi-step reaction with 2 steps 1: NH2OH / methanol / Heating 2: Et3N / tetrahydrofuran / 24 h / 25 °C View Scheme

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,4,6-trichlorobenzoyl chloride (4136-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid; water 2: phosphorus (V)-chloride View Scheme

2,4,6-Trichlorobenzonitrile (6575-05-9) → 1,3-bis-(2,4,6-trichloro-phenyl)-propane-1,3-dione (65305-79-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; sulfuric acid; water 2: phosphorus (V)-chloride 3: methyl magnesium halide; diethyl ether View Scheme

2,4,6-Trichlorobenzonitrile (6575-05-9) → 2,2-dichloro-1,3-bis-(2,4,6-trichloro-phenyl)-propane-1,3-dione

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sulfuric acid; water 2: phosphorus (V)-chloride 3: methyl magnesium halide; diethyl ether 4: aqueous NaOCl solution View Scheme

2,4,6-Trichlorobenzonitrile (6575-05-9) + 4-(1,1-dimethylethyl)-benzenemethanamine (39895-55-1) → C18H19Cl3N2 (1039766-00-1)

Conditions	Yield
With dimethylaluminum chloride In hexane; toluene at 20 - 150℃; for 0.533333h; Microwave irradiation;

2,4,6-Trichlorobenzonitrile (6575-05-9) → 3-{[4-(1,1-dimethylethyl)phenyl]methyl}-6-hydroxy-2-(2,4,6-trichlorophenyl)-4(3H)-pyrimidinone

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylaluminum chloride / hexane; toluene / 0.53 h / 20 - 150 °C / Microwave irradiation 2: sodium methylate / methanol; 2-methoxy-ethanol / 8 h / Heating / reflux View Scheme

2,4,6-Trichlorobenzonitrile (6575-05-9) → C26H26Cl3N3O5

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethylaluminum chloride / hexane; toluene / 0.53 h / 20 - 150 °C / Microwave irradiation 2: sodium methylate / methanol; 2-methoxy-ethanol / 8 h / Heating / reflux 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 130 °C / Microwave irradiation View Scheme

2,4,6-Trichlorobenzonitrile (6575-05-9) → N-{[1-{[4-(1,1-dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-2-(2,4,6-trichlorophenyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine disodium salt

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylaluminum chloride / hexane; toluene / 0.53 h / 20 - 150 °C / Microwave irradiation 2: sodium methylate / methanol; 2-methoxy-ethanol / 8 h / Heating / reflux 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 130 °C / Microwave irradiation 4: ethanol; water / 2 h / 20 °C View Scheme

Upstream product

• 634-93-5 2,4,6-trichloroaniline 
• 19393-96-5 2-bromo-1,3,5-trichlorobenzene 
• 17293-03-7 1,3,5-trichloro-2-(chloromethyl)benzene 
• 22241-21-0 2,4,6-trichloro-benzaldehyde-oxime 
• 74-96-4 ethyl bromide 
• 106-94-5 propyl bromide 
• 6324-50-1 1,3,5-trichloro-2-iodobenzene 
• 557-21-1 dicyanozinc 
• 62-53-3 aniline 
• 27093-67-0 2,4,6-trichloro-benzenediazonium; chloride 
• 23400-04-6 2,4,6-trichloro-benzoic acid amide 

Downstream Products

• 873-32-5 2-Chlorobenzonitrile 
• 1194-65-6 2,6-dichloro-benzonitrile 
• 100-47-0 benzonitrile 
• 6574-98-7 2,4-dichlorobenzylnitrile 
• 50-43-1 2,4,6-trichlorobenzoic acid 
• 24473-00-5 2,4,6-trichlorobenzaldehyde 
• 65305-79-5 1,3-bis-(2,4,6-trichloro-phenyl)-propane-1,3-dione 
• 4136-95-2 2,4,6-trichlorobenzoyl chloride 
• 101084-06-4 (2,4,6-trichlorophenyl)methanamine 
• 23400-04-6 2,4,6-trichloro-benzoic acid amide 
• 1039766-00-1 C₁₈H₁₉Cl₃N₂ 

Relevant articles and documents

Method for preparing 2, 4, 6-trichlorobenzonitrile by ammonia oxidation method, special catalyst and preparation method

The invention discloses a method for preparing 2, 4, 6-trichlorobenzonitrile by an ammonia oxidation method. According to the method, 1, 3, 5-trichlorobenzene is taken as a raw material, 2, 4, 6-trichlorobenzyl chloride is obtained under the action of a special chloromethylation catalyst, and then 2, 4, 6-trichlorobenzonitrile is obtained under the action of a special ammoxidation catalyst. The invention further discloses a special catalyst for preparing 2, 4, 6-trichlorobenzonitrile and a preparation method. The special chloromethylation catalyst disclosed by the invention can be used for better catalyzing the reaction of 1, 3, 5-trichlorobenzene chloride and formaldehyde or paraformaldehyde and a chlorine atom donor to efficiently obtain 2, 4, 6-trichlorobenzyl chloride; and the specialammoxidation catalyst can well catalyze the reaction of 2, 4, 6-trichlorobenzyl chloride to obtain 2, 4, 6-trichlorobenzonitrile. The special catalyst disclosed by the invention has the advantages ofhigh activity, high product yield, good selectivity, high product purity, long service life and simple process; the preparation method has the advantages of short reaction route, low reaction temperature, high yield and high selectivity.

1-(HETERO)ARYL-3-AMINO-PYROLLIDINE DERIVATIVES FOR USE AS MGLUR3 RECEPTOR ANTAGONISTS

The present invention relates to compounds of the Formula (I) which are useful for treating conditions associated with mGluR3 receptors, such as depression, schizophrenia and migraine, pharmaceutical compositions thereof, and methods of using the same.