Product Name

  • Name

    3-Bromoanisole

  • EINECS 219-264-5
  • CAS No. 2398-37-0
  • Article Data22
  • CAS DataBase
  • Density 1.442 g/cm3
  • Solubility Miscible in methanol, benzene, hexane, toluene and dichloromethane. Practically insoluble in water.
  • Melting Point 2 °C
  • Formula C7H7BrO
  • Boiling Point 210.5 °C at 760 mmHg
  • Molecular Weight 187.036
  • Flash Point 93.3 °C
  • Transport Information
  • Appearance colorless clear liquid
  • Safety 23-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 2398-37-0 (3-Bromoanisole)
  • Hazard Symbols IrritantXi
  • Synonyms Anisole,m-bromo- (6CI,7CI,8CI);1-Bromo-3-methoxybenzene;3-Methoxy-1-bromobenzene;3-Methoxyphenyl bromide;NSC82293;m-Anisyl bromide;m-Bromoanisole;m-Methoxybromobenzene;
  • PSA 9.23000
  • LogP 2.45770

Synthetic route

3-Bromophenol
591-20-8

3-Bromophenol

methyl iodide
74-88-4

methyl iodide

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran for 16h;99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;92%
3-Bromophenol
591-20-8

3-Bromophenol

dimethyl sulfate
77-78-1

dimethyl sulfate

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
Stage #1: 3-Bromophenol With potassium carbonate In acetone for 0.25h;
Stage #2: dimethyl sulfate In acetone for 10h; Reflux;
95%
With sodium hydroxide
With sodium hydroxide
3-Bromophenol
591-20-8

3-Bromophenol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In sulfolane at 220℃; for 0.166667h;95%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 220℃; for 0.166667h; Inert atmosphere;94%
methanol
67-56-1

methanol

3-Bromonitrobenzene
585-79-5

3-Bromonitrobenzene

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
Stage #1: methanol With tetrabutyl-ammonium chloride; potassium hydroxide In cyclohexane at 55℃; for 0.0833333h;
Stage #2: m-nitrobromobenzene In cyclohexane at 55 - 60℃; for 3h; Reagent/catalyst;
83%
3-Bromonitrobenzene
585-79-5

3-Bromonitrobenzene

sodium methylate
124-41-4

sodium methylate

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium hydroxide In n-heptane at 20 - 50℃; for 3h; Reagent/catalyst;82%
3-methoxybenzenediazonium o-benzenedisulfonimide

3-methoxybenzenediazonium o-benzenedisulfonimide

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;78%
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;72%
methanol
67-56-1

methanol

3-bromophenyl(mesityl)iodonium bromide

3-bromophenyl(mesityl)iodonium bromide

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
Stage #1: methanol With sodium hydride In tert-butyl methyl ether; mineral oil at 20℃; for 0.25h; Inert atmosphere; Sealed tube;
Stage #2: 3-bromophenyl(mesityl)iodonium bromide In tert-butyl methyl ether; mineral oil at 50℃; for 1h; Inert atmosphere; Sealed tube; chemoselective reaction;
77%
(2,4,6-trimethylphenyl)(3’-methoxyphenyl)iodonium triflate
1464149-60-7

(2,4,6-trimethylphenyl)(3’-methoxyphenyl)iodonium triflate

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h;64%
m-Anisidine
536-90-3

m-Anisidine

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
Stage #1: m-Anisidine With Bromotrichloromethane; sodium nitrite In dichloromethane; water at 23℃; for 0.0833333h;
Stage #2: With acetic acid In dichloromethane; water at 23℃; for 24h; Temperature;
28%
With sulfuric acid; sodium nitrite anschliessend Erwaermen mit Kupfer(I)-bromid;
With hydrogen bromide; sodium nitrite anschliessend Erwaermen mit Kupfer-Pulver;
methanol
67-56-1

methanol

m-bromobenzene diazonium nitrate

m-bromobenzene diazonium nitrate

A

bromobenzene
108-86-1

bromobenzene

B

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

methanol
67-56-1

methanol

3-bromo-benzenediazonium; sulfate

3-bromo-benzenediazonium; sulfate

A

bromobenzene
108-86-1

bromobenzene

B

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-Bromophenol
591-20-8

3-Bromophenol

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
With potassium hydroxide
dimethyl sulfate
77-78-1

dimethyl sulfate

alkaline m-bromo-phenol

alkaline m-bromo-phenol

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-methoxyphenyl(phenyl)iodonium tetrafluoroborate

3-methoxyphenyl(phenyl)iodonium tetrafluoroborate

A

bromobenzene
108-86-1

bromobenzene

B

iodobenzene
591-50-4

iodobenzene

C

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

D

3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

Conditions
ConditionsYield
With BrNBu4 In chloroform at 55℃;
3-bromoaniline
591-19-5

3-bromoaniline

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous H2SO4 / Diazotization.Kochen der Diazoniumsalz-Loesung
2: aqueous NaOH
View Scheme
Multi-step reaction with 2 steps
1: aqueous H2SO4 / Diazotization.Kochen der Diazoniumsalz-Loesung
2: aqueous KOH
View Scheme
2-bromoanisole
578-57-4

2-bromoanisole

A

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

B

3-Bromophenol
591-20-8

3-Bromophenol

(3-methoxyphenyl)(triphenyl-λ5-phosphanyl)gold
870485-34-0

(3-methoxyphenyl)(triphenyl-λ5-phosphanyl)gold

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
With N-Bromosuccinimide In chloroform-d1 at 20℃; chemoselective reaction;> 95 %Spectr.
3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid
2: copper(I) bromide / acetonitrile / 2 h / 80 °C
View Scheme
(3-bromophenyl)boronic acid
89598-96-9

(3-bromophenyl)boronic acid

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere
1.2: 0.5 h / 20 °C
2.1: sodium hydride / tert-butyl methyl ether; mineral oil / 0.25 h / 20 °C / Inert atmosphere; Sealed tube
2.2: 1 h / 50 °C / Inert atmosphere; Sealed tube
View Scheme
3-bromo-4-iodoanisole
466639-53-2

3-bromo-4-iodoanisole

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
ConditionsYield
With nickel(II) iodide; 1,4-bis(dicyclohexylphosphino)butane; sodium carbonate; cesium iodide In tetrahydrofuran at 35℃; for 72h; Irradiation;
benzophenone
119-61-9

benzophenone

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

(3-methoxyphenyl)(diphenyl)methanol
78238-98-9

(3-methoxyphenyl)(diphenyl)methanol

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: benzophenone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
100%
With magnesium 1.) ether, 2.) a) RT, 6 h, b) reflux, 1 h; Yield given. Multistep reaction;
With n-butyllithium
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With tetraphenyldisilane; cesium fluoride In acetonitrile at 100℃; for 0.0833333h;100%
With tetrakis(triphenylphosphine) palladium(0); formaldehyd; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;85%
With N,N,N,N,-tetramethylethylenediamine; C39H46IrN4 In acetonitrile at 45℃; for 48h; Sealed tube; Glovebox; Inert atmosphere;80%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

bis(3-methoxyphenyl)methanol
55360-45-7

bis(3-methoxyphenyl)methanol

Conditions
ConditionsYield
With n-butyllithium In hexane; ethyl acetate100%
With magnesium In diethyl ether for 1h; Ambient temperature;62%
With magnesium 1.) ether, ultrasound; Yield given. Multistep reaction;
Stage #1: 3-methoxyphenyl bromide With magnesium In tetrahydrofuran at 0℃; Reflux; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran
Stage #1: 3-methoxyphenyl bromide With magnesium In diethyl ether at 20℃; for 2h; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In diethyl ether at 20℃; for 2h; Inert atmosphere;
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Dichlorophenylphosphine
644-97-3

Dichlorophenylphosphine

bis(3-methoxyphenyl)(phenyl)phosphine oxide
216164-54-4

bis(3-methoxyphenyl)(phenyl)phosphine oxide

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl bromide With magnesium Metallation;
Stage #2: Dichlorophenylphosphine Arylation;
Stage #3: With water; dihydrogen peroxide In tetrahydrofuran Oxidation; Further stages.;
100%
With magnesium Yield given;
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

phenylboronic acid
98-80-6

phenylboronic acid

3-methoxybiphenyl
2113-56-6

3-methoxybiphenyl

Conditions
ConditionsYield
With potassium phosphate; 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride; bis(η3-allyl-μ-chloropalladium(II)) In 1,4-dioxane at 80℃; for 12h; Suzuki cross-coupling;100%
With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene100%
With potassium phosphate; naphthidine di(radical cation)s-stabilized Pd nanoparticles In 1,4-dioxane at 80℃; for 5h; Suzuki-Miyaura cross-coupling reaction;99%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

(E)-n-butyl 3-(3-methoxyphenyl)acrylate
346586-17-2

(E)-n-butyl 3-(3-methoxyphenyl)acrylate

Conditions
ConditionsYield
With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride In N,N-dimethyl acetamide at 140℃; for 12h; Heck reaction;100%
With di-tert-butylneopentylphosphonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 24℃; for 24h; Heck Reaction; Glovebox;98%
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Heck Reaction; Inert atmosphere; Schlenk technique;96%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

1,3-diphenylisobenzofuran
5471-63-6

1,3-diphenylisobenzofuran

1-methoxy-9,10-diphenyl-9,10-dihydro-9,10-epoxyanthracene

1-methoxy-9,10-diphenyl-9,10-dihydro-9,10-epoxyanthracene

Conditions
ConditionsYield
With Me2Zn(TMP)Li In tetrahydrofuran at 20℃; for 12h;100%
With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at -78 - 20℃; for 8h; Inert atmosphere;84%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

2-tert-Butylphenol
88-18-6

2-tert-Butylphenol

3-tert-butyl-3'-methoxybiphenyl-2-ol

3-tert-butyl-3'-methoxybiphenyl-2-ol

Conditions
ConditionsYield
With caesium carbonate; diisopropyl(2-tert-butyl)phenoxyphosphine; RhCl(PPh3)3 In toluene for 18h; Heating;100%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

m-Anisidine
536-90-3

m-Anisidine

3-methoxy-N-(3-methoxyphenyl)benzenamine
92248-06-1

3-methoxy-N-(3-methoxyphenyl)benzenamine

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 48h; Buchwald-Hartwig amination;100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium t-butanolate In toluene at 100℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere;72%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 120℃;40%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 72h; Reflux; Inert atmosphere;
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

1-(3-Bromophenyl)ethanone
2142-63-4

1-(3-Bromophenyl)ethanone

1-(3-bromo-phenyl)-1-(3-methoxy-phenyl)-ethanol
1180015-29-5

1-(3-bromo-phenyl)-1-(3-methoxy-phenyl)-ethanol

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl bromide With bromine; magnesium In diethyl ether at 20℃;
Stage #2: 1-(3-Bromophenyl)ethanone In diethyl ether for 3h; Reflux;
100%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

4-methyl-3-(triisopropylsilyloxy)aniline
582322-76-7

4-methyl-3-(triisopropylsilyloxy)aniline

N-(3-methoxyphenyl)-4-methyl-3-(triisopropylsilyloxy)aniline
1643447-98-6

N-(3-methoxyphenyl)-4-methyl-3-(triisopropylsilyloxy)aniline

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 31h; Buchwald-Hartwig Coupling; Inert atmosphere;100%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Methyl 4-amino-2-methoxybenzoate
27492-84-8

Methyl 4-amino-2-methoxybenzoate

methyl 2-Methoxy-4-[(3-methoxyphenyl)amino]benzoate
1644060-68-3

methyl 2-Methoxy-4-[(3-methoxyphenyl)amino]benzoate

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 21h; Inert atmosphere;100%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

3-methoxy-N-(3-methylphenyl)aniline
1449248-83-2

3-methoxy-N-(3-methylphenyl)aniline

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 15h; Buchwald-Hartwig Coupling; Inert atmosphere;100%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

4-amino-2-(benzyloxy)benzonitrile
284044-40-2

4-amino-2-(benzyloxy)benzonitrile

4-(3-methoxyphenylamino)-2-benzyloxybenzonitrile

4-(3-methoxyphenylamino)-2-benzyloxybenzonitrile

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 31h; Buchwald-Hartwig Coupling;100%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-(3-methoxyphenyl)imidazo[1,2-a]pyridine
1338248-69-3

3-(3-methoxyphenyl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere;100%
With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere;53%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

(2-cyclopropylethynyl)trimethylsilane
81166-84-9

(2-cyclopropylethynyl)trimethylsilane

1-(2-cyclopropylethynyl)-3-methoxybenzene
445424-01-1

1-(2-cyclopropylethynyl)-3-methoxybenzene

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl bromide With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; cesium fluoride In water at 20℃; for 0.25h; Sealed tube; Inert atmosphere;
Stage #2: (2-cyclopropylethynyl)trimethylsilane In water at 80℃; for 16h; Sealed tube; Inert atmosphere;
100%
1H-imidazole
288-32-4

1H-imidazole

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

1-(3-methoxyphenyl)-1H-imidazole
10040-94-5

1-(3-methoxyphenyl)-1H-imidazole

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; L-lysine at 130℃; for 5h; Microwave irradiation;99%
With copper(l) iodide; N-((4-nitro-1-oxy-pyridin-2-yl)methyl)oxalamic acid; tetrabutylammomium bromide; potassium hydroxide In water at 100℃; for 36h; Schlenk technique; Inert atmosphere; Sealed tube;99%
With potassium tert-butylate; copper(I) oxide In N,N-dimethyl-formamide at 130℃; for 24h;91%
N-Methylformamide
123-39-7

N-Methylformamide

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

N-methyl-N-(3-methoxyphenyl)carboxamide
14924-70-0

N-methyl-N-(3-methoxyphenyl)carboxamide

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h;99%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Arylation;98%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(3-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
401797-04-4

2-(3-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole Inert atmosphere; Schlenk technique; Sealed tube;99%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole at 100℃; for 16h; Schlenk technique; Inert atmosphere;96%
With Pinacolborane; 4,4'-di-tert-butylbipyridine In cyclohexane at 80℃;77%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

3-methoxy-4'-methylbiphenyl
24423-07-2

3-methoxy-4'-methylbiphenyl

Conditions
ConditionsYield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 25℃; for 1h; Catalytic behavior; Suzuki Coupling; Microwave irradiation;99%
With caesium carbonate; [PdCl(NNCNHC-nBu)]BF4 In water; N,N-dimethyl-formamide at 80℃; for 2h; Suzuki-Miyaura reaction;95%
With potassium phosphate; N-[(4-diphenylphosphinophenyl)methyl] D-gluconamide; PdCl2(GLCAphos)2 In water at 80℃; for 16h;93%
morpholine
110-91-8

morpholine

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

4-(3-methoxyphenyl)morpholine
32040-09-8

4-(3-methoxyphenyl)morpholine

Conditions
ConditionsYield
With [Pd(N,N'-bis(2,6-bis(di-p-tolylmethyl)-4-methylphenyl)-imidazol-2-ylidene)(acetylacetonate)Cl]; lithium hexamethyldisilazane In 1,4-dioxane at 110℃; for 3h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;99%
With sodium t-butanolate; palladium diacetate In toluene at 80℃; for 0.5h; Buchwald-Hartwig amination;98%
With C27H34N5P; sodium hydroxide; bis(dibenzylideneacetone)-palladium(0) In tert-Amyl alcohol at 100℃; Inert atmosphere;97.77%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(3-methoxybiphenyl)naphthalene
27331-43-7

1-(3-methoxybiphenyl)naphthalene

Conditions
ConditionsYield
With potassium fluoride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 18h; Suzuki coupling;99%
With KF; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In 1,2-dioxacyclohexane99%
With potassium phosphate In ethanol; water at 20℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry;98%
With ethyl 2-hydroxypropionate; palladium diacetate; potassium carbonate In water at 80℃; for 2h; Suzuki-Miyaura Coupling; Green chemistry;50%
With Br(1-)*C25H29BrN5O6(1+); potassium carbonate In water at 100℃; for 2h; Suzuki-Miyaura coupling;> 99 %Spectr.
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

3'-methoxy-2-methyl-1,1'-biphenyl
135227-03-1

3'-methoxy-2-methyl-1,1'-biphenyl

Conditions
ConditionsYield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 30℃; for 2h; Catalytic behavior; Temperature; Time; Suzuki Coupling; Microwave irradiation;99%
With C20H12N2O8PdS2(2-)*2Na(1+); sodium hydroxide In water at 100℃; for 3h;95%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water for 24h; Heating;90%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-methoxyphenyl azide
3866-16-8

3-methoxyphenyl azide

Conditions
ConditionsYield
With sodium azide In ethylene glycol at 100℃; for 3h; Green chemistry;99%
With copper(l) iodide; sodium azide; sodium L-ascorbate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In ethanol for 0.666667h; Heating;95%
With copper(l) iodide; sodium azide; L-proline; sodium hydroxide In ethanol at 95℃; for 24h;92%
pyrrolidine
123-75-1

pyrrolidine

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

1-(3-methoxyphenyl)pyrrolidine
32040-07-6

1-(3-methoxyphenyl)pyrrolidine

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 90℃; for 31h;99%
With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid In dimethyl sulfoxide at 80℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;71%
With 8-Hydroxyquinoline-N-oxide; caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 50℃; for 60h; Ullmann coupling; Inert atmosphere; Sealed tube; chemoselective reaction;
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

phenylacetylene
536-74-3

phenylacetylene

1-methoxy-3-(phenylethynyl)benzene
37696-01-8

1-methoxy-3-(phenylethynyl)benzene

Conditions
ConditionsYield
With copper(l) iodide; ethanolamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water at 60℃; for 26h; Sonogashira coupling;99%
With UC Pd; potassium carbonate; XPhos In ethanol; water at 50℃; for 5h; Sonogashira coupling; Inert atmosphere;95%
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine In 1,4-dioxane at 105℃; for 20h; Sonogashira coupling; Inert atmosphere;94%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Pentafluorobenzene
363-72-4

Pentafluorobenzene

2,3,4,5,6-pentafluoro-3'-methoxy-1,1'-biphenyl
198975-36-9

2,3,4,5,6-pentafluoro-3'-methoxy-1,1'-biphenyl

Conditions
ConditionsYield
With potassium phosphate; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); Trimethylacetic acid In N,N-dimethyl acetamide at 80℃; Glovebox;99%
With potassium phosphate; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II); Trimethylacetic acid In N,N-dimethyl acetamide at 80℃; for 2 - 4h;98%
With [Pd(trifluoroacetato)2(1,3-diisopropylbenzimidazolin-2-ylidene)(C2N3CH2Ph3)]; potassium carbonate In N,N-dimethyl acetamide at 120℃; for 24h;95%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

benzene
71-43-2

benzene

3-methoxybiphenyl
2113-56-6

3-methoxybiphenyl

Conditions
ConditionsYield
With C34H52Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 120℃; for 16h; Reagent/catalyst;99%
With pentamethylcyclopentadienyltricarbonylrhenium for 2.5h; Schlenk technique; Inert atmosphere; UV-irradiation;92%
With potassium tert-butylate at 100℃; for 24h; Inert atmosphere;89%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 5h; Inert atmosphere;99%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;93%
With ammonium hydroxide; copper(l) iodide; diethylenetriaminopentaacetic acid; potassium hydroxide In water at 100℃; for 12h; Sealed tube;90%

3-Bromoanisole Specification

1. Introduction of 3-Bromoanisole
3-Bromoanisole is also named as 1-Bromo-3-methoxybenzene; 3-Methoxy-1-bromobenzene; 3-Methoxybromobenzene; NSC 82293; m-Bromoanisole; m-Bromomethoxybenzene; m-Bromophenyl methyl ether; m-Methoxybromobenzene. 3-Bromoanisole is colorless clear liquid.

2. Properties of 3-Bromoanisole
Melting Point: 2 °C
Boiling Point: 210.5 °C at 760 mmHg 
Flash Point: 93.3 °C
Index of Refraction: 1.539
Molar Refractivity: 40.62 cm3
Molar Volume: 129.6 cm3
Surface Tension: 34.6 dyne/cm 
Enthalpy of Vaporization: 42.86 kJ/mol
Vapour Pressure: 0.278 mmHg at 25 °C
XLogP3: 3
H-Bond Acceptor: 1
Rotatable Bond Count: 1
Exact Mass: 185.968027
MonoIsotopic Mass: 185.968027
Topological Polar Surface Area: 9.2
Heavy Atom Count: 9

3. Structure Descriptors of 3-Bromoanisole
Canonical SMILES: COC1=CC(=CC=C1)Br
InChI: InChI=1S/C7H7BrO/c1-9-7-4-2-3-6(8)5-7/h2-5H,1H3
InChIKey: PLDWAJLZAAHOGG-UHFFFAOYSA-N

4. Safety Information of 3-Bromoanisole

Hazard Codes: IrritantXi
Safety Statements: 23-24/25 
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
F: 8
Hazard Note: Irritant
TSCA: T
HS Code: 29093038 

5. Use of
3-Bromoanisole
3-Bromoanisole is used in organic synthesis.

6. Preparation of 3-bromoanisole
Comprising methoxydenitrating 3-bromonitrobenzene in the presence of a phase-transfer catalyst (PTC), and the preparation of 3-bromonirtobenzene by the bromination of nitrobenzene with bromine in oleum. The methoxydenitration reagent in an alkali metal methoxide, which is selected from sodium methoxide and potassium methoxide. The amount of methoxide used is 1-1.5 mol per mol of 3-bromonitrobenzene. The alkali methoxide can be a pre-prepared solid or it can be prepared in situ, by the reaction of the corresponding alkali hydroxide and methanol. In the case when pre-prepared solid methoxide is used, the effective amount of alkali hydroxide is between 1.2-1.7 mol per mol of 3-bromonitrobenzebe. The reaction temperatures are between about 40 to 80° C., with preference to reaction temperatures of 50 to 55° C. In the case in which methoxide is prepared in situ, the effective amount of alkali hydroxide is between 2.2-2.4 mol per mol of 3-bromonitrobenzene. The reaction temperatures are between about 50 to 80° C. with preference to reaction temperatures of 55 to 65° C.

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