2-Chlorobenzyl alcohol
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
With 1,1,1,2,2,2-hexamethyldisilane In chloroform for 1.5h; Reflux; | 96% |
With phosphorus pentoxide; potassium bromide In acetonitrile at 20℃; for 0.5h; | 89% |
With hydrogen bromide; benzene |
2-methylchlorobenzene
A
2-chloro-benzaldehyde
B
1-bromomethyl-2-chlorobenzene
C
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 0.666667h; Kinetics; Mechanism; Rate constant; other time; other temperature; various concentrations of Co(OAc)2 and NaBr; | A n/a B n/a C 96% |
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 0.666667h; | A n/a B n/a C 95% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reflux; | 94% |
With N-Bromosuccinimide In acetonitrile at 40℃; for 0.216667h; Flow reactor; Irradiation; | 88% |
With sodium bromate; 2,2'-azobis(isobutyronitrile); sulfuric acid; sodium bromide; dibenzoyl peroxide In water; 1,2-dichloro-ethane Reflux; | 80% |
Conditions | Yield |
---|---|
With Dichloromethylsilane; phosphorus tribromide; iron(III) chloride In acetonitrile for 4h; Heating; | 93% |
With chloro-trimethyl-silane; 1,1,3,3-Tetramethyldisiloxane; lithium bromide In acetonitrile at 80℃; for 0.25h; | 64% |
With chloro-trimethyl-silane; 1,1,3,3-Tetramethyldisiloxane; lithium bromide 1.) acetonitrile, room temperature, 10 min, 2.) 15 min, 80 deg C; Yield given. Multistep reaction; |
1-chloro-2-(chloromethyl)benzene
A
2-bromo-2’-chlorodiethyl ether
B
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
With sodium bromide; 1,2-dibromomethane In N,N-dimethyl-formamide at 100℃; for 6h; | A n/a B 93% |
Conditions | Yield |
---|---|
With 1,1'-[1,2-phenylenebis(nitrilomethylylidene)dinaphthalen-2-olato]uranyl(VI); bromine In dichloromethane at 20℃; for 0.583333h; | 82% |
2-chloro-1-(methoxymethoxy)methyl benzene
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0833333h; Microwave irradiation; Neat (no solvent); chemoselective reaction; | 81% |
2-chloro-1-[(ethoxymethoxy)methyl]benzene
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0833333h; Microwave irradiation; Neat (no solvent); chemoselective reaction; | 79% |
2-methylchlorobenzene
A
1-bromomethyl-2-chlorobenzene
B
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(ll) bromide In acetic anhydride | A 72% B 12% |
bromocyane
1-(2-chlorophenyl)-N,N-dimethylmethanamine
1-bromomethyl-2-chlorobenzene
bromocyane
(2-chloro-benzyl)-methyl-(4-nitro-benzyl)-amine
A
methyl-(4-nitro-benzyl)-carbamonitrile
B
1-bromomethyl-2-chlorobenzene
bromocyane
(2-bromo-benzyl)-(2-chloro-benzyl)-methyl-amine
B
1-bromomethyl-2-chlorobenzene
bromocyane
(2-chloro-benzyl)-methyl-(2-nitro-benzyl)-amine
B
1-bromomethyl-2-chlorobenzene
bromocyane
1-(2-chlorophenyl)-N,N-dimethylmethanamine
A
1-bromomethyl-2-chlorobenzene
B
NCNMe2
chlorobenzene
1,1-dibromomethane
A
1-bromomethyl-2-chlorobenzene
B
4-chlorobenzyl bromide
Conditions | Yield |
---|---|
Stage #1: chlorobenzene With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: 1,2-dibromomethane In N,N-dimethyl-formamide at 60℃; for 2h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C 2: phosphorus tribromide / dichloromethane / 0.5 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; iodine / tetrahydrofuran / 12 h / 0 °C / Heating 2: acetic acid; hydrogen bromide / water / 2 h / 100 °C View Scheme |
methyl 2-hydroxy-5-(tetrahydropyranyloxy)benzoate
1-bromomethyl-2-chlorobenzene
C20H21ClO5
Conditions | Yield |
---|---|
With caesium carbonate In acetone at 40℃; for 4h; | 100% |
ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenylcarbamate
1-bromomethyl-2-chlorobenzene
ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 50℃; for 1h; | 100% |
1,3-Dihydro-3,3-dimethyl-5-nitro-2H-indol-2-one
1-bromomethyl-2-chlorobenzene
C17H15ClN2O3
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; | 100% |
1-hydroxy-3,6,7-tris(methoxymethoxy)-9H-xanthen-9-one
1-bromomethyl-2-chlorobenzene
C26H25ClO9
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h; | 100% |
Conditions | Yield |
---|---|
With sodium hydride at 0℃; for 5h; | 100% |
3,5-dibromo-4-hydroxybenzaldehyde
1-bromomethyl-2-chlorobenzene
(E)-2,6-dibromo-4-(2-chlorostyryl)phenol
Conditions | Yield |
---|---|
Stage #1: 1-bromomethyl-2-chlorobenzene With triethyl phosphite at 150℃; for 3h; Horner-Wittig reaction; Inert atmosphere; Stage #2: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Horner-Wittig reaction; Inert atmosphere; Stage #3: 3,5-dibromo-4-hydroxybenzaldehyde In N,N-dimethyl-formamide; mineral oil at 0℃; Horner-Wittig reaction; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 2-(N,N-dimethylamino)ethanol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Stage #2: 1-bromomethyl-2-chlorobenzene In N,N-dimethyl-formamide; mineral oil at 20℃; for 16h; Stage #3: With hydrogenchloride In 1,4-dioxane; methanol for 0.5h; | 99% |
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 2.5h; | 98% |
t-butyl 3-(2-fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)propanoate
1-bromomethyl-2-chlorobenzene
tert-butyl 2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)propanoate
Conditions | Yield |
---|---|
Stage #1: t-butyl 3-(2-fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)propanoate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.5h; Stage #2: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran at -78℃; for 0.5h; Stage #3: 1-bromomethyl-2-chlorobenzene In tetrahydrofuran at -78 - 0℃; for 1h; | 98% |
1-bromomethyl-2-chlorobenzene
malonic acid dimethyl ester
diethyl 2-(2-chlorobenzyl)malonate
Conditions | Yield |
---|---|
Stage #1: malonic acid dimethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: 1-bromomethyl-2-chlorobenzene In tetrahydrofuran; mineral oil at 60℃; | 98% |
1-bromomethyl-2-chlorobenzene
potassium selenocyanate
(2-chlorophenyl)methaneselenenyl cyanide
Conditions | Yield |
---|---|
In ethanol for 0.166667h; | 97% |
In ethanol for 5h; Ambient temperature; | 85% |
2-(2-chloro-5-hydroxyphenyl)-2-isopropyl-3-methylbutanenitrile
1-bromomethyl-2-chlorobenzene
2-(2-chloro-((2-chlorobenzyl)oxy)phenyl)-2-isopropyl-3-methylbutanenitrile
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50℃; | 97% |
1-bromomethyl-2-chlorobenzene
(piperidin-4-yl)carbamic acid tert-butyl ester
C17H25ClN2O2
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 97% |
With triethylamine In ethanol | |
With sodium hydride In tetrahydrofuran at -20℃; for 12h; |
methyl 2-(7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 97% |
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 40 - 50℃; | 96.53% |
1-bromomethyl-2-chlorobenzene
triethyl phosphite
2-chlorobenzyl diethylphosphonate
Conditions | Yield |
---|---|
at 150℃; Inert atmosphere; neat (no solvent); | 96% |
In xylene for 20h; Reflux; | 91% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃; for 2h; | 96% |
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; | 96% |
(Z)-β-bromostyrene
1-bromomethyl-2-chlorobenzene
1-(2-chlorobenzyl)-4-phenyl-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With copper(l) iodide; sodium azide; 1,8-diazabicyclo[5.4.0]undec-7-ene at 100℃; for 0.5h; | 96% |
Conditions | Yield |
---|---|
Stage #1: 1-bromomethyl-2-chlorobenzene With sodium azide In methanol at 20℃; Green chemistry; Stage #2: phenoxyacetylene In methanol at 20℃; Green chemistry; | 96% |
1-bromomethyl-2-chlorobenzene
phenylpropyolic acid
1-(2-chlorobenzyl)-4-phenyl-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With copper(l) iodide; sodium azide; potassium carbonate at 60℃; for 0.5h; | 96% |
1,2,3,4-tetrahydroisoquinoline
1-bromomethyl-2-chlorobenzene
2-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium hydride; N,N-dimethyl-formamide In mineral oil at 50℃; | 96% |
1-bromomethyl-2-chlorobenzene
Conditions | Yield |
---|---|
Stage #1: 8-tert-butyl-3,3,5-trimethyl-3H,11H-pyrano[3,2-a]carbazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 1-bromomethyl-2-chlorobenzene In tetrahydrofuran at 0 - 20℃; for 3h; | 96% |
(2-chlorophenyl)methaneselenenyl cyanide
1-bromomethyl-2-chlorobenzene
bis-(2-chloro-benzyl)-selenide
Conditions | Yield |
---|---|
With sodium tetrahydroborate In benzene for 1h; Ambient temperature; | 95% |
1-bromomethyl-2-chlorobenzene
α-deuterio-o-chlorotoluene
Conditions | Yield |
---|---|
With lithium aluminium deuteride In tetrahydrofuran | 95% |
With sodium borodeuteride In dimethylsulfoxide-d6 at 0 - 20℃; for 4h; Inert atmosphere; | 72% |
1-bromomethyl-2-chlorobenzene
2-chlorobenzylazide
Conditions | Yield |
---|---|
With sodium azide In N,N-dimethyl-formamide at 20 - 80℃; for 4h; | 95% |
With sodium azide In dimethyl sulfoxide at 20℃; for 24h; | 92% |
With sodium azide In water; acetone at 20 - 60℃; |
2-aminopyrimidine
1-bromomethyl-2-chlorobenzene
N-(2-chlorobenzyl)-(2-pyrimidyl)amine
Conditions | Yield |
---|---|
Stage #1: 2-aminopyrimidine With sodium hydride In tetrahydrofuran for 0.25h; Cooling with ice; Stage #2: 1-bromomethyl-2-chlorobenzene In tetrahydrofuran at 20℃; for 24h; Cooling with ice; | 95% |
benzyl 2-(benzyloxy)-4-(N-(4-cyclohexylbenzyl)-2-(perfluorophenylsulfonamido)acetamido)benzoate
1-bromomethyl-2-chlorobenzene
benzyl 2-(benzyloxy)-4-(2-(N-(2-chlorobenzyl)-2,3,4,5,6-pentafluorophenylsulfonamido)-N-(4-cyclohexylbenzyl)acetamido)benzoate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 95% |
The IUPAC name of o-Chlorobenzyl bromide is 1-(bromomethyl)-2-chlorobenzene. With the CAS registry number 611-17-6, it is also named as Toluene, alpha-bromo-o-chloro-. The product's categorie is benzyl. It is clear yellow liquid which is soluble in benzene and chloroform. In addition, this chemical can decompose in hot water. Furthermore, it should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.51; (4)ACD/LogD (pH 7.4): 3.51; (5)ACD/BCF (pH 5.5): 275.87; (6)ACD/BCF (pH 7.4): 275.87; (7)ACD/KOC (pH 5.5): 1943.87; (8)ACD/KOC (pH 7.4): 1943.87; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.583; (13)Molar Refractivity: 43.79 cm3; (14)Molar Volume: 130.8 cm3; (15)Polarizability: 17.36×10-24 cm3; (16)Surface Tension: 41.4 dyne/cm; (17)Enthalpy of Vaporization: 45.28 kJ/mol; (18)Vapour Pressure: 0.0777 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 203.934141; (21)MonoIsotopic Mass: 203.934141; (22)Heavy Atom Count: 9; (23)Complexity: 85.
Preparation of o-Chlorobenzyl bromide: o-Chlorotoluene reacts with bromine in the light, and then carry on vacuum distillation of brominated products. We collect 100-120 °C (1.33kPa) fractions. The yield is 98%.
Uses of o-Chlorobenzyl bromide: It can be used in organic synthesis. For example: It reacts with pyridine to get 1-(2-chloro-benzyl)-pyridinium; bromide. This reaction needs reagent tetrahydrothiophene 1,1-dioxide at ambient temperature. The reaction time is 3 days. The yield is 60%.
When you are using this chemical, please be cautious about it as the following:
It can cause burns. And it is also irritating to eyes and respiratory system. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
1. SMILES:BrCc1ccccc1Cl
2. InChI:InChI=1/C7H6BrCl/c8-5-6-3-1-2-4-7(6)9/h1-4H,5H2
3. InChIKey:PURSZYWBIQIANP-UHFFFAOYAV
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