Conditions | Yield |
---|---|
With dichloromethylsilane; iron(III) chloride In 1,2-dimethoxyethane for 4h; Heating; | 93% |
Conditions | Yield |
---|---|
With N-chloro-succinimide; N-hydroxyphthalimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 80℃; for 3h; Sealed tube; Inert atmosphere; | 91% |
With hydrogenchloride; potassium chloride; tetrabutyl-ammonium chloride In water at 20℃; Irradiation; Green chemistry; | 90% |
With 2,2'-azobis(isobutyronitrile); benzyl(trimethyl)ammonium tetrachloroiodate In tetrachloromethane for 5h; Heating; | 80% |
C7H6Cl2S
A
1,2-bis(2-chlorobenzyl)disulfane
B
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; pentane at 20 - 23℃; for 24h; | A 81% B 10% |
2-chloro-benzaldehyde
A
2,2'-(oxybis(methylene))bis(chlorobenzene)
B
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; thionyl chloride; 1,1,3,3-Tetramethyldisiloxane; zinc(II) iodide at 70℃; for 1h; | A 45% B 55% |
2-Chlorobenzyl alcohol
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
With pyridine; thionyl chloride | |
With phosphorus pentachloride at 100℃; | |
With phosphorus pentachloride | |
With thionyl chloride In pyridine Ambient temperature; |
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
With phosphorus pentachloride durch Schmelzen; |
benzyl chloride
A
1-Chloro-4-(chloromethyl)benzene
B
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
With iodine at 30 - 40℃; beim Chlorieren; |
Conditions | Yield |
---|---|
With chlorine; phosphorus trichloride at 110 - 130℃; |
1-chloro-1-(4-methylphenyl)-2,2,2-trifluoroethane
A
C9H8F3(1+)
B
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
at 69.85℃; Thermodynamic data; chloride-transfer; |
1-(1-Chloro-2,2,2-trifluoro-ethyl)-3,5-dimethyl-benzene
A
C10H10F3(1+)
B
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
at 69.85℃; Thermodynamic data; chloride-transfer; |
iodine
benzyl chloride
A
1-Chloro-4-(chloromethyl)benzene
B
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
at 30 - 40℃; beim Chlorieren; |
iodine
benzyl chloride
A
2,3,4-trichlorobenzyl chloride
B
1,2,3,4-Tetrachloro-5-chloromethyl-benzene
C
1-Chloro-4-(chloromethyl)benzene
D
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
Chlorierung; |
antimonypentachloride
benzyl chloride
A
1-Chloro-4-(chloromethyl)benzene
B
1-chloro-2-(chloromethyl)benzene
C
2,3-dichlorobenzyl chloride
Conditions | Yield |
---|---|
Chlorierung; |
chlorine
phosphorus trichloride
Toluene-2-sulfonyl chloride
A
2-methylchlorobenzene
B
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
at 110 - 130℃; |
sulfuryl dichloride
2-methylphenyl bromide
dibenzoyl peroxide
A
2-methylchlorobenzene
B
1-chloro-2-(chloromethyl)benzene
C
2-bromobenzylchloride
D
1-Bromo-2-bromomethyl-benzene
Conditions | Yield |
---|---|
at 110℃; |
phosphorus pentachloride
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
Destillieren im Vakuum; |
2-Chlorobenzyl alcohol
o-chlorobenzoyl chloride
A
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 12h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-hydroxyphthalimide; trichloroisocyanuric acid; cobalt(II) diacetate tetrahydrate / dichloromethane; methanol / 19 h / 25 °C 2: N-hydroxyphthalimide; trichloroisocyanuric acid; copper(II) acetate monohydrate; carbon tetrabromide / dichloromethane / 40 h / 25 °C View Scheme |
4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester
1-chloro-2-(chloromethyl)benzene
1-(2-Chloro-benzyl)-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; | 100% |
7-Chloro-4-(3,5-dimethylpyrazol-1-yl)imidazo<4,5-d>pyridazine-2-thiol
1-chloro-2-(chloromethyl)benzene
7-Chloro-4-(3,5-dimethylpyrazol-1-yl)-2-(2-chlorobenzylthio)imidazo<4,5-d>pyridazine
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 50℃; for 4h; | 100% |
phenyltellurotrimethylsilane
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
at 20℃; for 0.5h; | 100% |
In acetonitrile at 20℃; for 0.5h; | 100 % Spectr. |
8-benzyloxy-2,2-dimethyl-benzo[1,3]dioxin-4-one
1-chloro-2-(chloromethyl)benzene
C17H15ClO4
Conditions | Yield |
---|---|
With potassium carbonate; tetra-(n-butyl)ammonium iodide In DMF (N,N-dimethyl-formamide) at 20 - 50℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; tetra-(n-butyl)ammonium iodide In DMF (N,N-dimethyl-formamide) at 60℃; for 4h; | 100% |
p-hydroxyphenethyl alcohol
1-chloro-2-(chloromethyl)benzene
2-(4-(2-chlorobenzyloxy)phenyl)ethanol
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 24h; Reflux; | 100% |
1-chloro-2-(chloromethyl)benzene
(2-chlorobenzyl)magnesium chloride
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(chloromethyl)benzene With magnesium; ethylene dibromide In dibutyl ether at 20 - 30℃; for 0.166667h; Inert atmosphere; Stage #2: 1-chloro-2-(chloromethyl)benzene In dibutyl ether; cyclohexane at -5 - 5℃; for 4h; Solvent; Temperature; | 99.5% |
1-chloro-2-(chloromethyl)benzene
p-chlorophenacyl chloride
1-chloro-2-(4-chlorophenyl)-3-(2-chlorophenyl)propan-2-ol
Conditions | Yield |
---|---|
With magnesium In toluene | 99% |
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
With sodium chloride; tetra-(n-butyl)ammonium iodide In tetrahydrofuran; ethanol; dichloromethane; water; mineral oil | 99% |
3,5-dimethyl-1H-pyrazole
1-chloro-2-(chloromethyl)benzene
1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazole
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide | 99% |
Stage #1: 3,5-dimethyl-1H-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 1.5h; Stage #2: 1-chloro-2-(chloromethyl)benzene In dimethyl sulfoxide for 1.75h; | 99% |
Stage #1: 3,5-dimethyl-1H-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 1.5h; Inert atmosphere; Stage #2: 1-chloro-2-(chloromethyl)benzene In dimethyl sulfoxide at 20℃; for 1.25h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone Reflux; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(chloromethyl)benzene With sodium azide In methanol at 20℃; Green chemistry; Stage #2: phenoxyacetylene In methanol at 20℃; Green chemistry; | 99% |
morpholine
1-chloro-2-(chloromethyl)benzene
2-(morpholinomethyl)chlorobenzene
Conditions | Yield |
---|---|
With sodium hydroxide In toluene for 16h; Heating / reflux; | 98.9% |
With sodium hydroxide In water; toluene Solvent; Reflux; |
1-chloro-2-(chloromethyl)benzene
dimethyl amine
1-(2-chlorophenyl)-N,N-dimethylmethanamine
Conditions | Yield |
---|---|
With sodium hydroxide In water at -10 - 40℃; for 13.17h; Solvent; Large scale; | 98.4% |
In water at 140℃; for 0.5h; Time; Temperature; Autoclave; | 95.4% |
at 100℃; |
1,2,3-Benzotriazole
1-chloro-2-(chloromethyl)benzene
1-(2-chlorobenzyl)-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
In toluene for 24h; Heating; | 98% |
1-chloro-2-(chloromethyl)benzene
ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
1-(2-Chloro-benzyl)-6,7,8-trifluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 12h; | 98% |
4-nitro-phenol
1-chloro-2-(chloromethyl)benzene
2-chlorobenzyl-4-nitrophenyl ether
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 78℃; for 5h; | 98% |
With potassium carbonate; sodium iodide In acetone at 50℃; |
N-allylbenzotriazole
1-chloro-2-(chloromethyl)benzene
1-{1-[(2-chlorophenyl)methyl]prop-2-enyl}-1H-1,2,3-benzotriazole
Conditions | Yield |
---|---|
Stage #1: N-allylbenzotriazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: 1-chloro-2-(chloromethyl)benzene In tetrahydrofuran Further stages.; | 98% |
4-morpholinecarboxaldehyde
1-chloro-2-(chloromethyl)benzene
2-(morpholinomethyl)chlorobenzene
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique; | 98% |
With potassium hydroxide In water at 50℃; for 3h; Green chemistry; | 96% |
diphenylmaleimide
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
Stage #1: diphenylmaleimide With potassium tert-butylate In ethanol at 90℃; for 0.333333h; Microwave irradiation; Stage #2: 1-chloro-2-(chloromethyl)benzene In acetonitrile at 90℃; for 0.25h; Solvent; Temperature; Reagent/catalyst; Microwave irradiation; | 98% |
N-tosyl-4-iodoaniline
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(chloromethyl)benzene With chloro-trimethyl-silane; ethylene dibromide; lithium chloride; zinc In tetrahydrofuran at 25℃; for 24h; Inert atmosphere; Stage #2: N-tosyl-4-iodoaniline With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 25℃; Negishi Coupling; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
Stage #1: acetone oxime With potassium hydroxide; lithium hydroxide In N,N-dimethyl acetamide; water at 53℃; Stage #2: 1-chloro-2-(chloromethyl)benzene In N,N-dimethyl acetamide; water at 65℃; for 2.16667h; | 97.11% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 78℃; for 5h; | 97% |
With sodium hydroxide |
4-(3,5-dimethylpyrazol-1-yl)imidazo<4,5-d>pyridazine-2-thiol
1-chloro-2-(chloromethyl)benzene
4-(3,5-Dimethylpyrazol-1-yl)-2-(2-chlorobenzylthio)imidazo<4,5-d>pyridazine
Conditions | Yield |
---|---|
With potassium hydroxide at 45℃; for 5h; | 97% |
Conditions | Yield |
---|---|
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 50℃; for 1h; | 97% |
1-chloro-2-(chloromethyl)benzene
Sodium 2-chlorobenzylsulphonate
Conditions | Yield |
---|---|
With sodium sulfite In water at 100℃; for 5h; | 97% |
With copper; sodium sulfite In ethanol; water for 1h; Reflux; | 92.1% |
With sodium sulphite-heptahydrate; tetrabutylammomium bromide In water at 80℃; for 6h; |
4-iodobenzoic acid ethyl ester
1-chloro-2-(chloromethyl)benzene
ethyl 4-(2-chlorobenzyl)benzoate
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(chloromethyl)benzene With chloro-trimethyl-silane; ethylene dibromide; lithium chloride; zinc In tetrahydrofuran at 0 - 25℃; for 2h; Inert atmosphere; Stage #2: 4-iodobenzoic acid ethyl ester With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60℃; for 5h; Negishi cross-coupling reaction; Inert atmosphere; | 97% |
1,2,3,4-tetrahydroisoquinoline
1-chloro-2-(chloromethyl)benzene
2-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 97% |
6-chloroisoquinoline
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 97% |
1-chloro-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 1α,2β,3β-trihydroxy-11-oxo-18β-olean-12-en-30-oic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 1-chloro-2-(chloromethyl)benzene In N,N-dimethyl-formamide at 20℃; for 4h; | 97% |
The Molecular Structure of 2-Chlorobenzyl chloride (CAS NO.611-19-8):
Empirical Formula: C7H6Cl2
Molecular Weight: 161.0285
IUPAC Name: 1-chloro-2-(chloromethyl)benzene
Appearance: Colorless to light yellow liquid
Nominal Mass: 160 Da
Average Mass: 161.0285 Da
Monoisotopic Mass: 159.984656 Da
Index of Refraction: 1.546
Molar Refractivity: 40.91 cm3
Molar Volume: 129 cm3
Surface Tension: 37 dyne/cm
Density: 1.247 g/cm3
Melting Point: -13 °C
Flash Point: 82.2 °C
Enthalpy of Vaporization: 43.17 kJ/mol
Boiling Point: 213.7 °C at 760 mmHg
Vapour Pressure: 0.236 mmHg at 25°C
Water Solubility: insoluble
InChI
InChI=1/C7H6Cl2/c8-5-6-3-1-2-4-7(6)9/h1-4H,5H2
Smiles
Synonyms: c1(c(cccc1)Cl)CCl ; 4-05-00-00816 (Beilstein Handbook Reference) ; AI3-14885 ; BRN 0471700 ; EINECS 210-258-8
2-Chlorobenzyl chloride (CAS NO.611-19-8) can be used for producing O-cypermethrin and benzyl, o-chlorobenzene methanol and synthetic of dyes.It is also used in pharmacy.
1. | ihl-rat LC50:>1140 mg/m3/1H | EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401M St., S.W., Washington, DC 20460) History Unknown 8EHQ-0990-1020 . | ||
2. | unr-rat LD50:430 mg/kg | EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401M St., S.W., Washington, DC 20460) History Unknown 8EHQ-0990-1020 . |
Moderately toxic by inhalation and an unspecified route. When heated to decomposition it emits toxic vapors of Cl−.
Reported in EPA TSCA Inventory.
Hazard Codes: CN
Risk Statements: 34-43-50/53-20/21/22
R34: Causes burns
R43: May cause sensitization by skin contact
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 26-36/37/39-45-29
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S29: Do not empty into drains
RIDADR: UN 2235 6.1/PG 3
WGK Germany: 3
RTECS: CZ0195000
F: 19-21
F 19: Lachrymator
F 21: Sensitive to humidity
HazardClass: 6.1
PackingGroup: III
2-Chlorobenzyl chloride (CAS NO.611-19-8) is also called as 1-Chloro-2-(chloromethyl)benzene ; Ortho-alpha-dichlorotoluene ; alpha,2-Dichlorotoluene ; alpha,o-Dichlorotoluene ; o-Chlorobenzyl chloride ; Benzene, 1-chloro-2-(chloromethyl)- ; Toluene, alpha,o-dichloro- (8CI) ; alpha,2-Dichlorotoluene ; Toluene, o,alpha-dichloro- .
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