Conditions | Yield |
---|---|
With 2-pentanol; ReOCl3(SMe2)(OPPh3) for 17h; Green chemistry; chemoselective reaction; | 98% |
Multi-step reaction with 3 steps 1: diethylamino-sulfur trifluoride / dichloromethane / 1 h / -78 - 20 °C 2: tris(pentafluorophenyl)borate / 1,2-dichloro-ethane / 0.08 h / 20 °C / Glovebox; Schlenk technique 3: sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 2h; Heating; | 91% |
Conditions | Yield |
---|---|
With 2-pentanol; ReOCl3(SMe2)(OPPh3) for 17h; Green chemistry; chemoselective reaction; | 91% |
Conditions | Yield |
---|---|
With potassium bisulfite; potassium chloride; cobalt(II) chloride In water at 70 - 75℃; for 2.33333h; Concentration; Temperature; | 85% |
With nitrosylsulfuric acid; acetic acid Behandlung der erhaltenen Diazoniumsalz-Loesung mit CuCl in konz. wss. HCl; | |
With hydrogenchloride; copper dichloride; sodium nitrite |
2,4-dichlorobenzyl mercaptan
A
2,4-dichlorotoluene
B
bis-(2,4-dichloro-benzyl)-sulfide
C
2,4-dichlorobenzaldeyhde
Conditions | Yield |
---|---|
With tetrafluoroboric acid; triiron dodecarbonyl In benzene 1.) RT, 4 h; 2.) 60 deg C; | A 74% B 2% C 3% D 10% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; iron(III) chloride; chlorine; calcium chloride; zinc(II) chloride In water at 39℃; for 18h; Temperature; Molecular sieve; Autoclave; Inert atmosphere; | 68.9% |
With chlorine at 40 - 41℃; for 0.5h; Temperature; | 68% |
With perchloric acid; trichloroisocyanuric acid In water; acetic acid at 30℃; Rate constant; Thermodynamic data; Ea, ΔH(excit.), ΔS(excit.); |
2,4 dichlorobenzoic acid
A
(2,4-dichlorophenyl)methanol
B
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With tricarbonyl(η(4)-cycloocta-1,5-diene)iron; phenylsilane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; UV-irradiation; chemoselective reaction; | A 67% B n/a |
2,4-dichlorobenzyl mercaptan
2,4-dichlorotoluene
Conditions | Yield |
---|---|
dicobalt octacarbonyl In water; benzene at 185 - 190℃; under 46543.3 Torr; | 63% |
toluene
A
para-chlorotoluene
B
2-methylchlorobenzene
C
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hypochlorite In water at 20℃; Product distribution; Further Variations:; Temperatures; molar quantity of reagents; Chlorination; oxidative chlorination; | A 29% B 63% C 3.5% |
With oxone; potassium chloride In acetonitrile at 20℃; for 24h; Product distribution; Further Variations:; Reagents ratio; | |
With sulfuric acid; [BMIM]Cl; chlorine at 70℃; for 8h; |
Conditions | Yield |
---|---|
at 180℃; under 0.5 Torr; for 3h; | A 20% B 45% |
2,4-dichlorobenzyl mercaptan
A
2,4-dichlorotoluene
B
bis-(2,4-dichloro-benzyl)-sulfide
C
2,4-dichlorobenzaldeyhde
Conditions | Yield |
---|---|
With tetrafluoroboric acid; triiron dodecarbonyl In benzene 1.) RT, 4 h; 2.) 60 deg C; | A 41% B 32% C 3% |
4-methylphenyltellurium trichloride
A
para-chlorotoluene
B
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With oxygen In benzene at 20 - 30℃; for 4h; Irradiation; | A 36% B 2% |
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In chlorobenzene 1) 15 min, r.t. 2) 4 h, reflux; | 25% |
2,4-dichloro-benzenemethanamine
A
2,4-dichlorotoluene
B
2,4-dichlorobenzyl fluoride
Conditions | Yield |
---|---|
at 200℃; under 2 Torr; for 3h; | A 5% B 20% |
Conditions | Yield |
---|---|
With sulfuric acid; sodium chloride; sodium periodate In water; acetonitrile at 80℃; for 6h; | 15% |
With iron(III) chloride beim Chlorieren; | |
With molybdenum(V) chloride beim Chlorieren; |
Conditions | Yield |
---|---|
bei der Chlorierung; | |
With aluminium; mercury durch Chlorieren; | |
With iodine; chlorine |
2-methylchlorobenzene
A
2,5-dichlorotoluene
B
2,6-dichlorotoluene
C
2,4-dichlorotoluene
D
2,3-dichlorotoluene
Conditions | Yield |
---|---|
bei der Chlorierung; | |
With sulfuric acid; 1-butyl-3-methylimidazolium chloroaluminate; chlorine at 30℃; for 12h; Reagent/catalyst; Temperature; | |
With sulfuric acid; chlorine at 35℃; for 12h; Temperature; Molecular sieve; |
Conditions | Yield |
---|---|
With iron(III) chloride beim Chlorieren; | |
With molybdenum(V) chloride beim Chlorieren; |
Conditions | Yield |
---|---|
Diazotization.Behandlung der Diazoniumchloridloesung mit Cuprochlorid; |
Conditions | Yield |
---|---|
Austausch der NH2-Gruppe gegen Chlor, Reduktion und Ersatz der neu gebildeten NH2-Gruppe durch Chlor; |
2,4-dichlorobenzyl mercaptan
A
2,4-dichlorotoluene
B
bis-(2,4-dichloro-benzyl)-sulfide
C
2,4-dichloro-1-{[(2,4-dichlorobenzyl)disulfanyl]methyl}benzene
Conditions | Yield |
---|---|
With sodium hydroxide; triiron dodecarbonyl; tetra(n-butyl)ammonium hydrogensulfate In water; benzene at 60℃; for 16h; | A 95 % Chromat. B 3 % Chromat. C 2 % Chromat. |
With sodium hydroxide; triiron dodecarbonyl; tetra(n-butyl)ammonium hydrogensulfate In water; benzene at 60℃; for 16h; | A 95 % Chromat. B 3 % Chromat. C 2 % Chromat. |
hydrogenchloride
water
acetic acid
toluene
A
para-chlorotoluene
B
2-methylchlorobenzene
C
2,4-dichlorotoluene
Conditions | Yield |
---|---|
im Dunkeln an Platin-Anoden mit einer Stromdichte von 0.005 Amp./cm2.Electrolysis; |
Conditions | Yield |
---|---|
at 20℃; sowie bei 40grad; Chlorierung; |
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With steam; sulfuric acid at 230 - 240℃; | |
With phosphoric acid; steam at 230 - 240℃; |
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With steam; sulfuric acid at 230 - 240℃; | |
With phosphoric acid; steam at 230 - 240℃; |
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With steam; sulfuric acid at 230 - 240℃; | |
With phosphoric acid; steam at 230 - 240℃; |
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With steam; sulfuric acid at 230 - 240℃; | |
With phosphoric acid; steam at 230 - 240℃; |
2,4-dichlorophenylethyl alcohol
A
2,4-dichlorotoluene
B
2,4-dichlorostyrene
Conditions | Yield |
---|---|
Stage #1: 2,4-dichlorophenylethyl alcohol With sodium hydride In pyridine at 40℃; for 0.25h; Metallation; Stage #2: copper(l) chloride In pyridine for 4h; Cyclization; Ullman reaction; Heating; |
Conditions | Yield |
---|---|
With sodium bromate; hydrogen bromide In water at 65℃; for 0.333333h; Flow reactor; Irradiation; Green chemistry; | 99% |
With hydrogen bromide; sodium bromide In chloroform; water at 5 - 15℃; Electrolysis; | 85% |
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Reflux; | 84% |
With bromine |
Conditions | Yield |
---|---|
With aluminium trichloride In carbon disulfide for 240h; Heating; | 92% |
Conditions | Yield |
---|---|
With nitric acid In 1,2-dichloro-ethane at 30 - 35℃; for 2h; Temperature; Reagent/catalyst; | 91% |
With sulfuric acid; nitric acid at -10℃; | 80% |
With sodium nitrate; sulfuric acid at 40℃; for 3h; | 43% |
Conditions | Yield |
---|---|
With aluminium trichloride In carbon disulfide for 18h; Heating; | 90% |
Conditions | Yield |
---|---|
With aluminium trichloride In carbon disulfide for 72h; Heating; | 89% |
With carbon disulfide; aluminium trichloride |
Conditions | Yield |
---|---|
With N-chloro-succinimide; N-hydroxyphthalimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 80℃; for 16h; Time; Sealed tube; Inert atmosphere; | 89% |
With 2,2'-azobis(isobutyronitrile); chlorine at 110℃; for 3h; | 79.2% |
With thionyl chloride; dibenzoyl peroxide |
Conditions | Yield |
---|---|
With aluminium trichloride In carbon disulfide for 96h; Heating; | 89% |
Conditions | Yield |
---|---|
Stage #1: 2,4-dichlorotoluene With tert.-butylhydroperoxide; sodium hydroxide; tungsten(VI) oxide In water at 80℃; for 10h; Stage #2: With hydrogenchloride In water | 83% |
With sodium bromate; sulfuric acid; sodium bromide In water at 100℃; for 7h; Irradiation; | 82% |
With manganese(IV) oxide; sulfuric acid at 80℃; |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; ferrocene; iron(II) acetylacetonate In water; acetonitrile at 80℃; for 9h; | 80% |
With sodium molybdate; dihydrogen peroxide; cobalt(II) acetate; acetic acid; sodium bromide at 105℃; for 0.166667h; Temperature; Flow reactor; | 30.1% |
With bromine at 180 - 200℃; Erhitzen des Reaktionsgemisches mit konz. Schwefelsaeure auf 100-140grad; |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; sodium dodecyl-sulfate; iron(II) bromide In water at 100℃; for 24h; | 79% |
carbon dioxide
2,4-dichlorotoluene
A
ortho-methylbenzoic acid
B
3-chloro-4-methylbenzoic acid
C
5-chloro-2-methylbenzoic acid
D
p-Toluic acid
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Further byproducts given. Yields of byproduct given; | A n/a B n/a C n/a D 78% |
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Yield given. Further byproducts given. Yields of byproduct given; |
2,4-dichlorotoluene
4-methoxy-benzaldehyde
2,4-dichlorobenzyl 4-methoxybenzoate
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(II) acetate dihydrate In decane at 100℃; for 5h; | 78% |
Conditions | Yield |
---|---|
With ammonia at 390℃; Reagent/catalyst; | 77.3% |
With bismuth(III) vanadate; ammonia at 440℃; under 760.051 Torr; Catalytic behavior; Temperature; | 72.2% |
With ammonia; oxygen; DC-108 at 400℃; Yield given; |
2,4-dichlorotoluene
sodium thiomethoxide
A
3-Chloro-4-methylphenyl methyl sulphide
B
4-chloro-2-(methylsulphenyl)toluene
Conditions | Yield |
---|---|
In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 0.75h; | A 6% B 76% |
2,4-dichlorotoluene
2,4-dichloro-5-methyl-benzenesulfonyl chloride
Conditions | Yield |
---|---|
With chlorosulfonic acid at 60℃; for 3h; | 75% |
With chlorosulphuric acid | |
With chlorosulfonic acid | |
With chlorosulphuric acid |
2,4-dichlorotoluene
2,4-dichlorobenzaldoxime
Conditions | Yield |
---|---|
With tert.-butylnitrite; N-hydroxyphthalimide; copper diacetate In acetonitrile at 80℃; for 24h; Inert atmosphere; | 75% |
2,4-dichlorotoluene
sodium methansulfinate
4-methylsulfonyl-1-methyl-2-chlorobenzene
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; (2S,4R)-4-hydroxy-N-(2-methylnaphthalen-1-yl)pyrrolidine-2-carboxamide In dimethyl sulfoxide at 120℃; Sealed tube; Inert atmosphere; | 74% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(II) acetate dihydrate In decane at 100℃; for 6h; | 71% |
2,4-dichlorotoluene
sodium isopropanethiolate
2,4-bis(i-propylthio)toluene
Conditions | Yield |
---|---|
In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 20h; | 69.5% |
triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With C34H28ClF12IrN2Si In methyl cyclohexane at 100℃; for 16h; Inert atmosphere; Glovebox; | 68% |
2,4-dichlorotoluene
1-bromo-3,5-dichloro-2-toluene
Conditions | Yield |
---|---|
With bromine; iron(III) chloride In tetrachloromethane for 0.25h; | 67% |
With iron(III) chloride; bromine In tetrachloromethane at 20℃; for 0.5h; Inert atmosphere; | 67% |
With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 12h; | 50% |
With FeCl3; bromine In tetrachloromethane |
2,4-dichlorotoluene
acetophenone O-acetyloxime
4-(2',4'-dichlorophenyl)-2,6-diphenylpyridine
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; copper(II) bis(trifluoromethanesulfonate) In toluene at 100℃; for 8h; | 64% |
The Molecular Structure of 2,4-Dichlorotoluene (CAS NO.95-73-8):
Empirical Formula: C7H6Cl2
Molecular Weight: 161.0285
Index of Refraction: 1.543
Molar Refractivity: 40.86 cm3
Molar Volume: 129.6 cm3
Surface Tension: 35.6 dyne/cm
Density: 1.242 g/cm3
Flash Point: 79.4 °C
Enthalpy of Vaporization: 41.71 kJ/mol
Boiling Point: 198.6 °C at 760 mmHg
Vapour Pressure: 0.502 mmHg at 25°C
IUPAC Name: 2,4-dichloro-1-methylbenzene
Appearance: clear colorless liquid
Product Categories: Organics;Aryl;C7;Halogenated Hydrocarbons
Synonyms: 2,4-Dichlorotoluene ; 2,4-Dichloro-1-methylbenzene ; 4-05-00-00815 (Beilstein Handbook Reference) ; BRN 1931691 ; Benzene, 2,4-dichloro-1-methyl- ; EINECS 202-445-8 ; HSDB 2567 ; Toluene, 2,4-dichloro- ; Benzene, 2,4-dichloro-1-methyl- ; Toluene, 2,4-dichloro-
2,4-Dichlorotoluene (CAS NO.95-73-8) is used as raw materials for organic synthesis. In medicine industry, 2,4-Dichlorotoluene (CAS NO.95-73-8) is used as high boiling point solvents and for the synthesis of chlorinated-nitrated pesticides and medicinal products. For pesticide intermediates, It is used for manufacture 2,4-dichloro-benzyl chloride , 2,4-Dichlorobenzoyl chloride for synthesis and 2,4-dichloro-benzoic acid .
Through 2.3-chloro-4-toluidine and sodium nitrate's diazo reaction, then through the sandmyer-reaction with copper chloride, we can obtain 2,4-Dichlorotoluene (CAS NO.95-73-8).
1. | orl-rat LD50:4600 mg/kg | GISAAA Gigiena i Sanitariya. 53 (2)(1988),80. | ||
2. | orl-mus LD50:2900 mg/kg | GISAAA Gigiena i Sanitariya. 53 (2)(1988),80. | ||
3. | orl-gpg LD50:5 g/kg | GISAAA Gigiena i Sanitariya. 53 (2)(1988),80. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 23-24/25
S23: Do not breathe vapour
S24/25: Avoid contact with skin and eyes
RIDADR: UN 2810
WGK Germany: 2
RTECS: XT0730000
Hazard Note: Harmful
HazardClass: 9
PackingGroup: III
HS Code: 29036990
ASSAY: 99.0% min
ISOMER IMPURITY: 1.0% max
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