25186-47-4

Basic information

• Product Name: 3 5-DICHLOROTOLUENE
• Synonyms: 3 5-DICHLOROTOLUENE;1,3-Dichloro-5-methylbenzene;Toluene, 3,5-dichloro-;3,5-DICHLOROTOLUENE, 98+%
• CAS NO: 25186-47-4
• Molecular Formula: C₇H₆Cl₂
• Molecular Weight: 161.03
• EINECS: 246-722-1
• Mol File: 25186-47-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 26°C
• Boiling Point: 203℃
• Flash Point: 79℃
• Appearance: /
• Density: 1.242
• Vapor Pressure: 0.397mmHg at 25°C
• Refractive Index: 1.5442 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 3 5-DICHLOROTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3 5-DICHLOROTOLUENE(25186-47-4)
• EPA Substance Registry System: 3 5-DICHLOROTOLUENE(25186-47-4)

Safety Data

• Hazardous Substances Data: 25186-47-4(Hazardous Substances Data)

Usage

Uses

3,5-Dichlorotoluene is a common chemical reactant used in the synthesis of various pharmaceuticals and biological agents. Used in the preparation of pyrazole amide derivatives as RORγ inhibitors as well as cross coupling reactions.

InChI:InChI=1/C7H6Cl2/c1-5-2-6(8)4-7(9)3-5/h2-4H,1H3

Synthetic route

2,6-dichloro-4-methylbenzoic acid (99520-05-5) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
With silver carbonate In dimethyl sulfoxide at 120℃; for 16h; Sealed tube;	94%

2-methyl-4,6-dichloroaniline (30273-00-8) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
Stage #1: 2-methyl-4,6-dichloroaniline With sulfuric acid In ethanol at 0 - 20℃; Stage #2: With sodium nitrite In ethanol at 20 - 75℃; for 3h;	84%

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + benzaldehyde (100-52-7) → 3,5-dichlorotoluene (25186-47-4) + 2-(3,5-Dichloro-phenyl)-1-phenyl-ethanol (82106-06-7)

Conditions	Yield
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given;	A n/a B 70%

1-bromo-3,5-dichlorobenzene (19752-55-7) + methyllithium (917-54-4) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
Stage #1: 1-bromo-3,5-dichlorobenzene With bis(tri-t-butylphosphine)palladium(0); oxygen In toluene at 20℃; for 0.0166667h; Schlenk technique; Stage #2: methyllithium In toluene at 20℃; for 0.0333333h; Schlenk technique;	64%

ethyl 1-bromo-3,5-dichlorobenzene + zinc methyl bromide (18815-74-2) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
With lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at -78 - 60℃; Inert atmosphere;	56%

2,4-dichloro-6-methylbenzenediazonium tetrafluoroborate → 3,5-dichlorotoluene (25186-47-4) + 2,4-dichloro-6-methylnitrobenzene (118665-00-2)

Conditions	Yield
With copper; sodium nitrite In diethyl ether; water at 20℃; for 0.25h;	A 5.6 g B 54%

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + benzyl bromide (100-39-0) → 3,5-dichlorotoluene (25186-47-4) + 1,3-Dichloro-5-phenethyl-benzene (82106-07-8)

Conditions	Yield
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given;	A n/a B 50%

2,6-dichloro-4-methylaniline (56461-98-4) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
With ethyl nitrite; ethanol; sulfuric acid

4-bromo-3,5-dichloro-toluene (19393-93-2) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide; tert-butyl alcohol

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + potassium tert-butylate (865-47-4) → tert-butoxytrimethylsilane (13058-24-7) + 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
In tert-butyl alcohol at 50℃; Rate constant;

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + sodium methylate (124-41-4) → Methoxytrimethylsilane (1825-61-2) + 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
In methanol at 50℃; Rate constant;

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + sodium 2,2,2-trifluoroethanolate (420-87-1) → (2,2,2-trifluoroethoxy)trimethylsilane (56859-55-3) + 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
In dimethyl sulfoxide at 50℃; Rate constant; var. reactant concentration and solvent system;

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + trimethylene glycol monosodium salt (37480-93-6, 54481-30-0, 59571-05-0) → 3-trimethylsiloxypropanol (6880-24-6) + 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
In various solvent(s) at 50℃; Rate constant;

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + sodium 2-hydroxyethoxide (7388-28-5, 10604-71-4, 24768-69-2, 26915-75-3, 50856-01-4, 92004-30-3) → 2-(trimethylsilyloxy)ethanol (4403-13-8) + 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
In methanol at 50℃; Rate constant; var. reactant concentrations and solvent systems;

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + Monosodium salt of 1,4-butanediol (5536-05-0, 42271-23-8, 59571-04-9, 83560-32-1) → 4-(Trimethylsiloxy)-1-butanol (4435-55-6) + 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
In methanol at 50℃; Rate constant; var. reactant concentration and solvent system;

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + monosodium salt of 1,5-pentanediol → 3,5-dichlorotoluene (25186-47-4) + 5-trimethylsiloxy-1-pentanol

Conditions	Yield
In various solvent(s) at 50℃; Rate constant;

1-((trimethylsilyl)methyl)-3,5-dichlorobenzene (69380-94-5) + 6-hydroxy-hexan-1-ol; monosodium salt → 3,5-dichlorotoluene (25186-47-4) + 6-trimethylsiloxy-1-hexanol (5665-79-2)

Conditions	Yield
In various solvent(s) at 50℃; Rate constant;

3.5-dibromo-toluene-2-diazonium chloride → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
With hydrogenchloride; ethanol Faellen mit Wasser;

3.5-dibromo-toluene-4-diazonium chloride → 3,5-dichlorotoluene (25186-47-4)

2-methyl-4,6-dichloroaniline (30273-00-8) + hydrogen → 3,5-dichlorotoluene (25186-47-4)

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + 3,5-dibromo-toluene-2-diazonium ; chloride → 3,5-dichlorotoluene (25186-47-4)

N-(2-chloro-4-methylphenyl)acetamide (18931-78-7) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: glacial acetic acid; chlorine 2: concentrated hydrochloric acid / 100 - 120 °C 3: concentrated sulfuric acid; ethyl nitrite; alcohol View Scheme

acetic acid-(2,6-dichloro-4-methyl-anilide) (99520-03-3) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated hydrochloric acid / 100 - 120 °C 2: concentrated sulfuric acid; ethyl nitrite; alcohol View Scheme

N-(2-methylphenyl)acetamide (120-66-1) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; chlorine 2: aq.-ethanolic sulfuric acid 3: NaNO2; aq.-ethanolic HCl / anschliessendes Erwaermen auf 60grad View Scheme

2,4-dichloro-6-methylacetanilide (61655-97-8) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq.-ethanolic sulfuric acid 2: NaNO2; aq.-ethanolic HCl / anschliessendes Erwaermen auf 60grad View Scheme

ethyl 2-chloro-4-methylbenzoate (99500-35-3) → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-chloro-succinimide; palladium diacetate; sodium persulfate; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 6 h / 60 °C / Sealed tube 2: potassium hydroxide / methanol / 12 h / Sealed tube; Reflux 3: silver carbonate / dimethyl sulfoxide / 16 h / 120 °C / Sealed tube View Scheme

4-methylbenzoic acid ethyl ester (94-08-6) → 3,5-dichlorotoluene (25186-47-4)

Conditions

Yield

Multi-step reaction with 4 steps 1: N-chloro-succinimide; palladium diacetate; sodium persulfate; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 4 h / 70 °C / Sealed tube 2: N-chloro-succinimide; palladium diacetate; sodium persulfate; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 6 h / 60 °C / Sealed tube 3: potassium hydroxide / methanol / 12 h / Sealed tube; Reflux 4: silver carbonate / dimethyl sulfoxide / 16 h / 120 °C / Sealed tube View Scheme

ethyl 2, 6-dichloro-4-methylbenzoate → 3,5-dichlorotoluene (25186-47-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 12 h / Sealed tube; Reflux 2: silver carbonate / dimethyl sulfoxide / 16 h / 120 °C / Sealed tube View Scheme

3,5-dichlorotoluene (25186-47-4) + 2,6-dichlorobenzenediazonium tetrafluoroborate → (Z)-1-(2,6-dichloro-4-methylphenyl)-2-(2,6-dichlorophenyl)diazene

Conditions	Yield
Stage #1: 3,5-dichlorotoluene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 2,6-dichlorobenzenediazonium tetrafluoroborate In tetrahydrofuran at -78 - 20℃; for 1.5h;	75%

carbon dioxide (124-38-9) + 3,5-dichlorotoluene (25186-47-4) → 2,6-dichloro-4-methylbenzoic acid (99520-05-5)

Conditions	Yield
Stage #1: 3,5-dichlorotoluene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 - 20℃;	44%
With n-butyllithium 1.) THF, hexane, -50 deg C, 1.5 h, 2.) Et2O, from -50 deg C to RT; Yield given. Multistep reaction;

3,5-dichlorotoluene (25186-47-4) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With sodium molybdate; dihydrogen peroxide; cobalt(II) acetate; acetic acid; sodium bromide at 105℃; for 0.166667h; Temperature;	39.2%

3,5-dichlorotoluene (25186-47-4) → 2,4-dichloro-6-methylnitrobenzene (118665-00-2)

Conditions	Yield
With nitric acid In 1,2-dichloro-ethane at 40 - 45℃; for 2h;	32%
bei der Nitrierung;
durch Nitrierung;

3,5-dichlorotoluene (25186-47-4) + 1-phenylethynyl-1-phenyl-trifluoromethylcarbinol (117710-90-4) → 1-(2,6-dichloro-4-methylphenyl)-1,3-diphenyl-4,4,4-trifluoro-1,2-butadiene

Conditions	Yield
With iron(III) chloride at 80℃; for 24h;	23%

3,5-dichlorotoluene (25186-47-4) + 1-phenylethynyl-1-phenyl-trifluoromethylcarbinol (117710-90-4) → 1-(2,4-dichloro-5-methylphenyl)-1,3-diphenyl-4,4,4-trifluoro-1,2-butadiene

Conditions	Yield
With iron(III) chloride at 80℃; for 24h;	10%

3,5-dichlorotoluene (25186-47-4) + copper(I) thiophenolate (1192-40-1) → 3,5-bis-phenylsulfanyl-toluene (101894-49-9)

Conditions	Yield
With pyridine; quinoline at 200 - 210℃;

3,5-dichlorotoluene (25186-47-4) → 3,5-dichlorobenzoic acid (51-36-5)

Conditions	Yield
With nitric acid at 170℃;
With chlorine at 185 - 190℃; Irradiation.anschliessendes Behandeln mit H2SO4 <8prozent SO3 enthaltend>;

3,5-dichlorotoluene (25186-47-4) → 2,3,5-trichloro-toluene (56961-86-5)

Conditions	Yield
With aluminium; mercury durch Chlorierung;

3,5-dichlorotoluene (25186-47-4) → 2-bromo-3,5-dichloro-toluene (876493-68-4)

Conditions	Yield
With bromine; iron

3,5-dichlorotoluene (25186-47-4) → 1-dibromomethyl-3,5-dichloro-benzene

Conditions	Yield
With bromine at 170 - 180℃; Irradiation;
With bromine at 180℃;

3,5-dichlorotoluene (25186-47-4) → 3,5-dichloro-toluene-2-sulfonic acid

Conditions	Yield
durch Sulfurierung;

3,5-dichlorotoluene (25186-47-4) → 3,5-dichloro-2,6-dinitro-toluene

Conditions	Yield
With sulfuric acid; nitric acid

3,5-dichlorotoluene (25186-47-4) → 3,5-dichlorobenzyl bromide (7778-01-0)

Conditions	Yield
With bromine at 130℃;
With N-Bromosuccinimide; dibenzoyl peroxide In benzene for 4h; Heating;

1-Methylpyrrolidine (120-94-5) + 3,5-dichlorotoluene (25186-47-4) → 2-methyl-1,3-benzenedicarbocylic acid (15120-47-5)

Conditions	Yield
With potassium hydroxide; copper(l) cyanide 1) reflux, 2 d; 2) EtOH; Multistep reaction;

3,5-dichlorobenzoyl chloride (2905-62-6) + 3,5-dichlorotoluene (25186-47-4) → (2,6-Dichloro-4-methyl-phenyl)-(3,5-dichloro-phenyl)-methanone (135340-47-5)

Conditions	Yield
With n-butyllithium 1.) THF, hexane, -40 deg C, 30 min, 2.) THF, -40 deg C, 1 h; Yield given. Multistep reaction;

Upstream product

• 30273-00-8 2-methyl-4,6-dichloroaniline 
• 99520-05-5 2,6-dichloro-4-methylbenzoic acid 
• 99500-35-3 ethyl 2-chloro-4-methylbenzoate 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 19752-55-7 1-bromo-3,5-dichlorobenzene 
• 917-54-4 methyllithium 
• 18815-74-2 zinc methyl bromide 
• 61655-97-8 2,4-dichloro-6-methylacetanilide 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 99520-03-3 acetic acid-(2,6-dichloro-4-methyl-anilide) 
• 18931-78-7 N-(2-chloro-4-methylphenyl)acetamide 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 69380-94-5 1-((trimethylsilyl)methyl)-3,5-dichlorobenzene 

Downstream Products

• 99508-23-3 2',6',4''-trichloro-4'-methylbenzophenone 
• 135340-41-9 (2,6-Dichloro-4-methyl-phenyl)-(4-iodo-phenyl)-methanone 
• 86241-47-6 α,α,α-Trichlor-3,5-dichlor-toluol 
• 51-36-5 3,5-dichlorobenzoic acid 
• 133992-55-9 3,5-dichlorobenzyl azide 
• 133992-52-6 5-amino-1-(3,5-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxamide 
• 99508-26-6 (4-(azidomethyl)-2,6-dichlorophenyl)(4-chlorophenyl)methanone 
• 99519-84-3 carboxyamidotriazole 
• 99508-22-2 2,6-dichloro-4-methylbenzoyl chloride 
• 99508-46-0 2,6-dichloro-4-methylbenzophenone 
• 135340-39-5 (2,6-Dichloro-4-methyl-phenyl)-(4-fluoro-phenyl)-methanone 
• 99508-47-1 4-benzoyl-3,5-dichlorobenzyl bromide 
• 135340-43-1 2',6'-dichloro-4'-methyl-4''-cyanobenzophenone 
• 135340-45-3 (2,6-Dichloro-4-methyl-phenyl)-(3,4-dichloro-phenyl)-methanone 

Relevant articles and documents

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