95-75-0

Basic information

• Product Name: 3,4-Dichlorotoluene
• Synonyms: 1,2-dichloro-4-methyl-benzen;Benzene,1,2-dichloro-4-methyl-;Toluene, 3,4-dichloro-;toluene,3,4-dichloro-;1,2-DICHLORO-4-METHYLBENZENE;3,4-DCT;3,4-DICHLOROTOLUENE;3,4-DICHLOROTOLUENE OEKANAL, 250 MG
• CAS NO: 95-75-0
• Molecular Formula: C₇H₆Cl₂
• Molecular Weight: 161.03
• EINECS: 202-447-9
• Product Categories: Organics;Aryl;C7;Halogenated Hydrocarbons;Alpha Sort;Analytical Standards;AromaticsChemical Class;Chemical Class;ChloroVolatiles/ Semivolatiles;D;DAlphabetic;DIA - DIC;Halogenated
• Mol File: 95-75-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: -15.2 °C
• Boiling Point: 200.5 °C741 mm Hg(lit.)
• Flash Point: 186 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 1.251 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.301mmHg at 25°C
• Refractive Index: n20/D 1.547(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• Water Solubility: insoluble
• BRN: 1931687
• CAS DataBase Reference: 3,4-Dichlorotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dichlorotoluene(95-75-0)
• EPA Substance Registry System: 3,4-Dichlorotoluene(95-75-0)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 23-24/25
• RIDADR: UN 2810
• WGK Germany: 2
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 95-75-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

3,4-Dichlorotoluene was used in determination of enthalpy of formation for molecular complexes of I2 with chloromethylbenzene molecules in CCl4.

General Description

3,4-Dichlorotoluene is added as growth supplement in culture medium of Ralstonia sp. strain PS12.

Purification Methods

Recrystallise it from EtOH at very low temperature or fractionally distil it. [Beilstein 5 IV 815.]

Synthetic route

3,4-dichlorobenzaldehyde (6287-38-3) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol for 6h; Wolff-Kishner reduction; Heating;	89%
Multi-step reaction with 2 steps 1: methanol / 60 °C / Inert atmosphere 2: potassium carbonate; methanol; hydrogen; palladium 10% on activated carbon / 24 h / 65 °C / 760.05 Torr View Scheme

1-chloro-3-methylbenzene (108-41-8) → 2,5-dichlorotoluene (19398-61-9) + 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
With aluminium; mercury durch Chlorierung;
bei der Chlorierung;
With aluminium; mercury durch Chlorieren;

para-chlorotoluene (106-43-4) → 3,4-Dichlorotoluene (95-75-0) + 2,4-dichlorotoluene (95-73-8)

Conditions	Yield
bei der Chlorierung;
With aluminium; mercury durch Chlorieren;
With iodine; chlorine

2-chloro-p-cresol (6640-27-3) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
With phosphorus pentachloride

4-methyl-1,2-diaminobenzene (496-72-0) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl;

toluene (108-88-3) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
With iodine durch Chlorieren;
With molybdenum(V) chloride durch Chlorieren;

2-chloro-4-methyl-benzenamine (615-65-6) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
Diazotization.Behandlung der Diazoniumchloridloesung mit Cuprochlorid;

4-methyl-2-nitroaniline (89-62-3) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
Austausch der Aminogruppe gegen Chlor, Reduktion der Nitrogruppe und Ersatz der neu entstandenen Aminogruppe durch Chlor;

phosphorus pentachloride (10026-13-8, 874483-75-7) + 2-methyl-8-nitro-thianthrene-5,5,10,10-tetraoxide → 3,4-Dichlorotoluene (95-75-0) + 4-nitro-benzene-disulfonic acid-(1.2)-dichloride (?)

Conditions	Yield
at 250 - 280℃; im Rohr;

sulfuryl dichloride (7791-25-5) + toluene (108-88-3) → para-chlorotoluene (106-43-4) + 3,4-Dichlorotoluene (95-75-0) + benzyl chloride (100-44-7)

Conditions	Yield
at 160℃; Product distribution;

para-chlorotoluene (106-43-4) + iron → 3,4-Dichlorotoluene (95-75-0) + 2,4-dichlorotoluene (95-73-8)

Conditions	Yield
at 20℃; sowie bei 40grad; Chlorierung;

3.4-dichloro-toluene-sulfonic acid-(2) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
With steam; sulfuric acid at 190 - 230℃;

4.5-dichloro-toluene-sulfonic acid-(3) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
With steam; sulfuric acid at 190 - 230℃;

toluene (108-88-3) → 3,4-Dichlorotoluene (95-75-0) + p-chloro-toluene; benzyl chloride

Conditions	Yield
With sulfuryl dichloride at 160℃;

dinitrodichlorotoluene + 1,2-dichloro-4-methyl-3,5-dinitro-benzene (53278-85-6) → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
In methanol

3,4-dichlorobenzaldehyde p-toluenesulfonylhydrazone → 3,4-Dichlorotoluene (95-75-0)

Conditions	Yield
With methanol; palladium 10% on activated carbon; hydrogen; potassium carbonate at 65℃; under 760.051 Torr; for 24h; Catalytic behavior;

para-chlorotoluene (106-43-4) + 2-methylchlorobenzene (95-49-8) → 3,4-Dichlorotoluene (95-75-0) + 2,4-dichlorotoluene (95-73-8)

Conditions	Yield
With aluminum (III) chloride; chlorine; iron at 40℃; for 16h; Molecular sieve; Overall yield = 90.5 %;

glycolamide (598-42-5) + 3,4-Dichlorotoluene (95-75-0) → 6-methyl-4H-benzo[1,4]oxazin-3-one (39522-26-4)

Conditions	Yield
With copper acetylacetonate; potassium hydroxide; N,N`-dimethylethylenediamine In dichloromethane; N,N-dimethyl-formamide at 60℃; for 5h; Reagent/catalyst;	98.4%

3,4-Dichlorotoluene (95-75-0) → 1,2-dichloro-4-methyl-5-nitrobenzene (7494-45-3)

Conditions	Yield
With nitric acid at 0 - 20℃; for 2h;	98%
With sulfuric acid; cis-nitrous acid	95%
With nitric acid In 1,2-dichloro-ethane at 40 - 45℃; for 2h; Temperature;	95%

3,4-Dichlorotoluene (95-75-0) + 2-(4-chlorobenzylidene)-1-cyclohexanone (31020-78-7) → 4-chloro-2'-hydroxydiphenylmethane (31480-68-9)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; hydrogen sulfide; nitrogen In ethyl acetate; toluene	97.8%

3,4-Dichlorotoluene (95-75-0) → 3,4-dichlorbenzoic acid (51-44-5)

Conditions	Yield
With sulfuric acid; ozone; acetic acid; manganese(II) acetate at 16℃; for 2.91667h;	96%
With sodium bromate; sulfuric acid; sodium bromide In water at 100℃; for 8h; Irradiation;	83%
Stage #1: 3,4-Dichlorotoluene With tert.-butylhydroperoxide; sodium hydroxide; tungsten(VI) oxide In water at 80℃; for 10h; Stage #2: With hydrogenchloride In water	80%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + 3,4-Dichlorotoluene (95-75-0) + triethylphosphine (554-70-1) → Ni(2+)*2P(C2H5)3*C6H3(CH3)Cl(1-)*Cl(1-)=Ni(Cl)(C6H3(CH3)Cl)(P(C2H5)3)2

Conditions	Yield
In hexane N2-atmosphere; filtering, crystn.; elem. anal.;	95%

3,4-Dichlorotoluene (95-75-0) → 4,5-dichloro-2-methylbenzene-1-sulfonyl chloride

Conditions	Yield
With chlorosulfonic acid; thionyl chloride at 0 - 20℃; for 20h;	95%

3,4-Dichlorotoluene (95-75-0) → dichlorodinitrotoluene

Conditions	Yield
In 2-methylundecane	94.4%
With sulfuric acid; nitric acid In dichloromethane
With nitric acid In 2-methylundecane; water
With nitric acid In 2-methylundecane

3,4-Dichlorotoluene (95-75-0) → 3,4-dichloro-1-trichloromethylbenzene (13014-24-9)

Conditions	Yield
With chlorine; dibenzoyl peroxide at 90℃; Temperature; Green chemistry;	93.9%
With chlorine at 115 - 117℃; for 24h;
With chlorine at 115 - 117℃; for 24h; Temperature;
With chlorine at 115 - 117℃; for 24h; Temperature;

3,4-Dichlorotoluene (95-75-0) + 4-methylphenylboronic acid (5720-05-8) → 4'-methyl-4,4''-dimethyl-(1,1',2',1'')-terphenyl (128644-83-7)

Conditions	Yield
With C28H44N2PPd; potassium carbonate In ethanol; water at 60℃; for 6h; Suzuki coupling;	93%

chloro-trimethyl-silane (75-77-4) + 3,4-Dichlorotoluene (95-75-0) → 1,2-bis(trimethylsilyl)-4-methylbenzene (101300-64-5)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone; magnesium; copper(l) chloride; lithium chloride at 55℃; for 17h;	92%
With N,N,N,N,N,N-hexamethylphosphoric triamide; iodine; magnesium at 130℃; for 96h; Substitution;	62%

3,4-Dichlorotoluene (95-75-0) + acetyl chloride (75-36-5) → 2-methyl-4,5-dichloroacetophenone (53803-91-1)

Conditions	Yield
With aluminium trichloride In carbon disulfide for 24h; Heating;	90%
With aluminium trichloride

3,4-Dichlorotoluene (95-75-0) + benzoyl chloride (98-88-4) → 4,5-Dichloro-2-methylbenzophenon (33184-51-9)

Conditions	Yield
With aluminium trichloride In carbon disulfide for 192h; Heating;	88%

3,4-Dichlorotoluene (95-75-0) → 3,4-dichlorobenzyl dibromide (6425-25-8)

Conditions	Yield
With sodium bromate; 2,2'-azobis(isobutyronitrile); sulfuric acid; sodium bromide In water; 1,2-dichloro-ethane Reflux;	82%
With bromine

3,4-Dichlorotoluene (95-75-0) → 3,4-dichlorobenzyl bromide (18880-04-1)

Conditions	Yield
With sodium bromate; 2,2'-azobis(isobutyronitrile); sulfuric acid; sodium bromide; dibenzoyl peroxide In water; 1,2-dichloro-ethane Reflux;	81%
With bromine	66%
With hydrogen bromide; dihydrogen peroxide In water at 0℃; Incandescent lamp light;	61.1%

3,4-Dichlorotoluene (95-75-0) → 1,2-Cl2-4-CF3-5-MeC6H2 (74483-51-5)

Conditions	Yield
With hydrogen fluoride In tetrachloromethane	74%

3,4-Dichlorotoluene (95-75-0) + benzamidine monohydrochloride (1670-14-0) → 5-(3,4-dichlorophenyl)-3-phenyl-1,2,4-oxadiazole

Conditions	Yield
With tert.-butylhydroperoxide; potassium phosphate; copper diacetate In 1,2-dichloro-ethane at 20℃; for 12h;	74%

3,4-Dichlorotoluene (95-75-0) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With bismuth(III) vanadate; ammonia at 440℃; under 760.051 Torr; Catalytic behavior; Temperature;	73.1%
With ammonia at 380℃; Reagent/catalyst; Flow reactor;	72.5%
With vanadyl pyrophosphate; ammonia; water; oxygen at 414.84℃;	55%
With ammonia; oxygen; DC-108 at 425℃; Yield given;

3,4-Dichlorotoluene (95-75-0) + Acetanilid (103-84-4) → N-(2-(3,4-dichlorobenzoyl)phenyl)acetamide (1415473-87-8)

Conditions	Yield
With tert.-butylhydroperoxide; palladium diacetate In dimethyl sulfoxide at 100℃; for 20h; regioselective reaction;	67%

3,4-Dichlorotoluene (95-75-0) + N-(2-(methylthio)phenyl)ferrocene-1-carboxamide → 2,5-bis(3,4-dichlorobenzyl)-N-(quinolin-8-yl)ferrocenecarboxamide

Conditions	Yield
With di-tert-butyl peroxide; palladium diacetate; iron(II) chloride at 110℃; for 10h; Inert atmosphere; regioselective reaction;	67%

3,4-Dichlorotoluene (95-75-0) + 2-amino-benzenethiol (137-07-5) → 2-(3,4-dichlorophenyl)-1,3-benzothiazole (6265-89-0)

Conditions	Yield
With methanesulfonic acid; di-tert-butyl peroxide; copper(II) oxide at 120℃; for 20h;	60%

3,4-Dichlorotoluene (95-75-0) → 3,4-dichlorobenzyl bromide (18880-04-1) + 3,4-dichlorophenylmethyl nitrate

Conditions	Yield
With cerium(III) ammonium nitrate; potassium bromide In acetic acid at 80 - 90℃; for 1.5h;	A 57% B 35%

3,4-Dichlorotoluene (95-75-0) + 2-methoxy-phenylamine (90-04-0) → (2-chloro-4-methylphenyl)(2-methoxyphenyl)amine (1613638-37-1) + (2-chloro-5-methylphenyl)(2-methoxyphenyl)amine (1613638-38-2)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1′-(diisopropylphosphino)-4-tert-butylferrocene; sodium t-butanolate In toluene at 115℃; for 20h; Schlenk technique; Inert atmosphere; Overall yield = 85 %; regioselective reaction;	A 57% B 28%

3,4-Dichlorotoluene (95-75-0) + m-Anisidine (536-90-3) → (2-chloro-4-methylphenyl)(3-methoxyphenyl)amine (1613638-39-3) + (2-chloro-5-methylphenyl)(3-methoxyphenyl)amine (1613638-40-6)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1′-(diisopropylphosphino)-4-tert-butylferrocene; sodium t-butanolate In toluene at 115℃; for 20h; Schlenk technique; Inert atmosphere; Overall yield = 79 %; regioselective reaction;	A 24% B 55%

3,4-Dichlorotoluene (95-75-0) + 4-nitro-benzoyl chloride (122-04-3) → 3,4-dichloro-2-(4-nitrobenzoyl)toluene (280744-28-7)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane for 5h; Heating;	53%

3,4-Dichlorotoluene (95-75-0) + (2,2’-bipyridine)Zn(CF3)2 → 1,2-dichloro-4-(2,2,2-trifluoroethyl)benzene

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); 1-methyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) In dichloromethane; acetonitrile at 20℃; for 24h; Sealed tube; Inert atmosphere;	52%

3,4-Dichlorotoluene (95-75-0) + aniline (62-53-3) → 2-chloro-4-methyl-N-phenylaniline (1449248-80-9) + (2-chloro-5-methyl)diphenylamine (1613638-34-8)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1′-(diisopropylphosphino)-4-tert-butylferrocene; sodium t-butanolate In toluene at 115℃; for 20h; Schlenk technique; Inert atmosphere; Overall yield = 68 %; regioselective reaction;	A 51% B 17%

3,4-Dichlorotoluene (95-75-0) → p-toluidine (106-49-0) + toluene (108-88-3) + 1-amino-3-methylbenzene (108-44-1)

Conditions	Yield
With ammonia; sodium at 25℃; for 0.00833333h; Product distribution; Further Variations:; Reagents; Dehalogenation; substitution;	A 32% B 47% C 18%

3,4-Dichlorotoluene (95-75-0) + 4-methoxy-aniline (104-94-9) → (2-chloro-5-methylphenyl)(4-methoxyphenyl)amine (1227060-11-8) + (2-chloro-4-methylphenyl)(4-methoxyphenyl)amine (857601-15-1)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1′-(diisopropylphosphino)-4-tert-butylferrocene; sodium t-butanolate In toluene at 115℃; for 20h; Schlenk technique; Inert atmosphere; Overall yield = 71 %; regioselective reaction;	A 46% B 25%

Upstream product

• 496-72-0 4-methyl-1,2-diaminobenzene 
• 108-88-3 toluene 
• 615-65-6 2-chloro-4-methyl-benzenamine 
• 89-62-3 4-methyl-2-nitroaniline 
• 106-43-4 para-chlorotoluene 
• 95-49-8 2-methylchlorobenzene 
• 53278-85-6 1,2-dichloro-4-methyl-3,5-dinitro-benzene 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 7791-25-5 sulfuryl dichloride 
• 10026-13-8 phosphorus pentachloride 
• 6640-27-3 2-chloro-p-cresol 
• 108-41-8 1-chloro-3-methylbenzene 

Downstream Products

• 615-74-7 2-chloro-5-methylphenol 
• 93088-70-1 3,4,3',4'-tetrachloro-bibenzyl 
• 51-44-5 3,4-dichlorbenzoic acid 
• 6639-30-1 2,4,5-trichlorotoluene 
• 53278-85-6 1,2-dichloro-4-methyl-3,5-dinitro-benzene 
• 56961-84-3 1,2-dichloro-4-dichloromethyl-benzene 
• 7494-45-3 1,2-dichloro-4-methyl-5-nitrobenzene 
• 108996-89-0 1-(3,4-dichloro-benzyl)-pyridinium; bromide 
• 102-47-6 3,4-Dichlorophenylmethyl chloride 
• 42803-19-0 3-chloro-1-(4,5-dichloro-2-methyl-phenyl)-propan-1-one 
• 74483-51-5 1,2-Cl₂-4-CF₃-5-MeC₆H₂ 
• 80245-33-6 1,2-Dichloro-5-methyl-3-trifluoromethyl-benzene 
• 108-88-3 toluene 
• 50-82-8 2,4,5-trichlorobenzoic acid 

Relevant articles and documents

Method for producing 2,4-dichlorotoluene by using parachlorotoluene

The invention discloses a method for producing 2,4-dichlorotoluene by using parachlorotoluene. The method comprises the steps of (a) adding a chlorination catalyst; (b) chlorinating the parachlorotoluene; and (c) separating components. According to the method, a mixture of iron powder, aluminum trichloride and a L-type molecular sieve is taken as the catalyst for a chlorination reaction, so that the selectivity for 2,4-dichlorotoluene is effectively promoted. The production of poly-chlorotoluene such as benzotrichloride and tetrachlorotoluene is effectively inhibited due to a low reaction temperature, and the yield of 2,4-dichlorotoluene is improved. Moreover, the method is simple and convenient; the operation is easy; the effects are good; and the product yield is high.

N-Tosylhydrazine-mediated deoxygenative hydrogenation of aldehydes and ketones catalyzed by Pd/C

A mild and efficient method for the deoxygenative hydrogenation of aldehydes and ketones has been developed. The reaction is mediated by N-tosylhydrazine with H2 (1 atm) as the reductant and 10% Pd/C as the catalyst.

Process for preparing 4, 5-dichloro-2-methylbenzoic acid

The present invention relates to a process for preparing 4,5-dichloro-2-methylbenzoic acid and also its salts in high yields and in high purities by reacting 3,4-dichlorotoluene with acetyl chloride or chloroacetyl chloride in the presence of a Friedel-Crafts catalyst and subsequently oxidizing the acetylated intermediate to give the carboxylic acid.