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578-57-4

Basic Information
CAS No.: 578-57-4
Name: Benzene,1-bromo-2-methoxy-
Molecular Structure:
Molecular Structure of 578-57-4 (Benzene,1-bromo-2-methoxy-)
Formula: C7H7BrO
Molecular Weight: 187.03
Synonyms: Anisole,o-bromo- (6CI,7CI,8CI);1-Bromo-2-methoxybenzene;2-Bromo-1-methoxybenzene;2-Bromomethoxybenzene;2-Methoxyphenylbromide;NSC 6977;o-Anisyl bromide;o-Bromoanisole;o-Bromomethoxybenzene;o-Bromophenyl methyl ether;o-Methoxyphenyl bromide;2-Bromoanisole;
EINECS: 209-425-8
Density: 1.443 g/cm3
Melting Point: 2 °C(lit.)
Boiling Point: 215.999 °C at 760 mmHg
Flash Point: 96.667 °C
Solubility: soluble in ethanol and diethyl ether, insoluble in water
Appearance: colourless liquid
Hazard Symbols: DangerousN,IrritantXi
Risk Codes: 51/53
Safety: 61-24/25
Transport Information: UN 3082 9/PG 3
PSA: 9.23000
LogP: 2.45770
Synthetic route
100-66-3

methoxybenzene

A

104-92-7

1-bromo-4-methoxy-benzene

B

578-57-4

2-bromoanisole

C

21702-84-1

2,4-dibromoanisole

Conditions
ConditionsYield
With bromine; tetramethylammonium bromide In liquid sulphur dioxide at -23℃; Rate constant; Product distribution; Thermodynamic data; in H2O at 25 deg C, NaBr, HClO4; ΔH (excit), -ΔS (excit);A 98.99%
B 0.56%
C 0.43%
With (CH3)4Br In liquid sulphur dioxide at -23℃; Kinetics; Thermodynamic data; Product distribution; ΔH(excit.); ΔS(excit.);A 98.99%
B 0.56%
C 0.43%
With (CH3)4Br In liquid sulphur dioxide at -23℃;A 98.99%
B 0.56%
C 0.43%
90-04-0

2-methoxy-phenylamine

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With tert.-butylnitrite; tetrabutylammomium bromide; copper(I) bromide; 10-camphorsulfonic acid In acetonitrile at 20℃; for 24h; Reagent/catalyst; Time; Solvent;98%
Stage #1: 2-methoxy-phenylamine With tert.-butylnitrite In dichloromethane; water at 0℃; for 0.166667h;
Stage #2: With carbon tetrabromide; dimethylglyoxal In dichloromethane; water at 15 - 35℃; for 16h;
78%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 23h;74%
100-66-3

methoxybenzene

A

104-92-7

1-bromo-4-methoxy-benzene

B

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With Oxone; potassium bromide In methanol at 20℃; for 1h;A 97%
B 2%
With Oxone; potassium bromide In acetonitrile at 20℃; for 24h;A 84%
B 15%
With PyHBrCl2 In methanol at 20℃; for 0.0833333h;A 78%
B 18%
5720-06-9

2-Methoxyphenylboronic acid

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 80℃; for 12h;97%
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; for 8h; Sealed tube;82%
With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide In N,N-dimethyl-formamide at 130℃; for 20h;67%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sodium methylate In methanol; water; acetonitrile at 23℃;94 % Chromat.
95-56-7

2-hydroxybromobenzene

74-88-4

methyl iodide

578-57-4

2-bromoanisole

Conditions
ConditionsYield
Stage #1: 2-hydroxybromobenzene With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1.16667h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 19h; Inert atmosphere; Reflux;
97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere;96%
With potassium hydroxide In CD2Cl2; hexane; acetonitrile89%
95-56-7

2-hydroxybromobenzene

77-78-1

dimethyl sulfate

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With potassium carbonate at 60℃; for 0.3h; Williamson synthesis;94%
With sodium hydroxide
With potassium hydroxide
With sodium hydroxide for 3h; Heating;
With potassium carbonate In acetone Inert atmosphere;
579-75-9

2-Methoxybenzoic acid

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With potassium phosphate; tetrabuthylammonium tribromide In acetonitrile at 100℃; for 16h; Reagent/catalyst;90%
108-86-1

bromobenzene

potassium ferrocyanide

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 4h;90%
95-56-7

2-hydroxybromobenzene

616-38-6

carbonic acid dimethyl ester

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0583333h; microwave irradiation;84%
With leucine intercalated Mg-Al layered double hydorxide at 180℃; for 6h; Autoclave; Green chemistry; chemoselective reaction;87 %Chromat.

2-bromophenyltrimethylammonium trifluoromethanesulfonate

865-33-8

potassium methanolate

578-57-4

2-bromoanisole

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique;84%

triethyl(2-methoxyphenyl)germane

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h;75%
95-56-7

2-hydroxybromobenzene

121-45-9

phosphorous acid trimethyl ester

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With boron trifluoride In diethyl ether for 0.0416667h; microwave irradiation;74%
21702-84-1

2,4-dibromoanisole

A

104-92-7

1-bromo-4-methoxy-benzene

B

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With butyl magnesium bromide; zirconocene dichloride In tetrahydrofuran for 3h; Ambient temperature;A 72%
B 22%
5720-06-9

2-Methoxyphenylboronic acid

A

578-57-4

2-bromoanisole

B

100-66-3

methoxybenzene

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; for 8h; Sealed tube;A 64%
B 20%
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; for 8h; Sealed tube;A 12%
B 26%
579-75-9

2-Methoxybenzoic acid

A

578-57-4

2-bromoanisole

B

2476-35-9

5-bromo-2-methoxybenzoic acid

Conditions
ConditionsYield
With potassium phosphate; bromine In acetonitrile at 100℃; for 4h; Reagent/catalyst;A 26%
B 56%

2-methoxybenzenediazonium o-benzenedisulfonamide

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;55%
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;53%
1232133-61-7

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

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h;47%
579-75-9

2-Methoxybenzoic acid

A

578-57-4

2-bromoanisole

B

21702-84-1

2,4-dibromoanisole

C

2476-35-9

5-bromo-2-methoxybenzoic acid

Conditions
ConditionsYield
With potassium phosphate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In acetonitrile at 100℃; for 4h;A 40%
B 7%
C 32%
766-51-8

2-Chloroanisole

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With dibromodifluoromethane; ISOPROPYLAMIDE; copper at 150℃; for 8h; Further byproducts given;11%
phosgene

phosgene

60-29-7

diethyl ether

21702-84-1

2,4-dibromoanisole

phenylmagnesium bromide

A

104-92-7

1-bromo-4-methoxy-benzene

B

578-57-4

2-bromoanisole

C

100-66-3

methoxybenzene

95-56-7

2-hydroxybromobenzene

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With potassium hydroxide; methyl iodide
With diazomethane; diethyl ether
(methylation);
95-56-7

2-hydroxybromobenzene

80-48-8

methyl p-toluene sulfonate

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With potassium hydroxide
38603-09-7

2,6-dibromoanisole

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With water; isopropylmagnesium chloride 1) THF, 40 deg C, 3 h; 2) 0 deg C; Yield given. Multistep reaction;
704-43-8

(2-methoxy-phenyl)-trimethyl-silane

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With N-chloro-succinimide; sodium bromide In methanol for 0.0833333h; Ambient temperature; Yield given;
With N-chloro-succinimide; sodium bromide In methanol for 0.0833333h; Ambient temperature;
67-56-1

methanol

sodium-<2-bromo-phenolate>

sodium-<2-bromo-phenolate>

578-57-4

2-bromoanisole

Conditions
ConditionsYield
With carbon monoxide at 180℃;
74-96-4

ethyl bromide

60-29-7

diethyl ether

21702-84-1

2,4-dibromoanisole

magnesium

magnesium

A

104-92-7

1-bromo-4-methoxy-benzene

B

578-57-4

2-bromoanisole

C

100-66-3

methoxybenzene

7647-01-0

hydrogenchloride

38603-09-7

2,6-dibromoanisole

578-57-4

2-bromoanisole

60333-75-7

O-allyl-2-bromophenol

74-88-4

methyl iodide

A

578-57-4

2-bromoanisole

B

100-66-3

methoxybenzene

Conditions
ConditionsYield
Stage #1: O-allyl-2-bromophenol With [2,2]bipyridinyl; tetrabutylammonium tetrafluoroborate; palladium dichloride In N,N-dimethyl-formamide at 20℃; Reduction; Electrochemical reaction;
Stage #2: methyl iodide With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 12h; Methylation;
5720-06-9

2-Methoxyphenylboronic acid

A

578-57-4

2-bromoanisole

B

21702-84-1

2,4-dibromoanisole

C

89694-45-1

5-bromo-2-methoxyphenylboronic acid

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In water; acetonitrile at 40℃; for 4h;A 45 % Chromat.
B 18 % Chromat.
C 34 % Chromat.
578-57-4

2-bromoanisole

21702-84-1

2,4-dibromoanisole

Conditions
ConditionsYield
With (CH3)4Br In liquid sulphur dioxide at -23℃; Rate constant;100%
With (CH3)4Br In liquid sulphur dioxide at -23℃;100%
With N-Bromosuccinimide; iodine In acetonitrile for 12h; Darkness;99%
With dihydrogen peroxide; ammonium bromide; acetic acid at 20℃; for 12h;54%
With bromine; tetramethylammonium bromide In liquid sulphur dioxide at -23℃; Product distribution; Rate constant;
578-57-4

2-bromoanisole

98-80-6

phenylboronic acid

86-26-0

2-methoxy-1,1'-biphenyl

Conditions
ConditionsYield
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water at 50℃; for 24h; Solvent; Temperature; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox;100%
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water at 50℃; Reagent/catalyst; Solvent; Temperature; Suzuki Coupling; Inert atmosphere; Glovebox;100%
With sodium carbonate In water at 100℃; Suzuki-Miyaura reaction;99.1%
578-57-4

2-bromoanisole

106-49-0

p-toluidine

107455-62-9

2-methoxy-N-(4-methylphenyl)aniline

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; Reflux;100%
With bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate; palladium dichloride In toluene at 80℃; for 3h;97%
With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene at 80℃; for 3h;94%
578-57-4

2-bromoanisole

100-52-7

benzaldehyde

22788-49-4

2-methoxyphenyl(phenyl)methanol

Conditions
ConditionsYield
Stage #1: 2-bromoanisole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 22℃; for 20h; Inert atmosphere;
100%
Stage #1: 2-bromoanisole With magnesium; lithium chloride In tetrahydrofuran at 50℃; for 0.125h; Flow reactor;
Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 0.333333h; Flow reactor;
95%
Stage #1: 2-bromoanisole With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Inert atmosphere;
90%
578-57-4

2-bromoanisole

88-18-6

2-tert-Butylphenol

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

Conditions
ConditionsYield
With caesium carbonate; diisopropyl(2-tert-butyl)phenoxyphosphine; RhCl(PPh3)3 In toluene for 18h; Heating;100%
578-57-4

2-bromoanisole

5720-05-8

4-methylphenylboronic acid

92495-53-9

2-methoxy-4'-methylbiphenyl

Conditions
ConditionsYield
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.25h; Suzuki-Miyaura reaction;100%
With Pd/C; potassium carbonate In ethanol; water at 100℃; for 3h; Suzuki-Miyaura Coupling;95%
With cetyltrimethylammonim bromide; sodium hydroxide In water at 25℃; for 1h; Catalytic behavior; Suzuki Coupling; Microwave irradiation;94%
1663-39-4

tert-Butyl acrylate

578-57-4

2-bromoanisole

474097-69-3

tert-butyl (E)-3-(2-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With IMes-Pd(dmba)Cl; potassium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 18h; Heck-Mizoroki reaction; Inert atmosphere;100%
With dichlorobis(1,4-dimesityl-1H-1,2,3-triazol-5-ylidene)palladium(II); sodium acetate In N,N-dimethyl acetamide at 150℃; for 8h; Mizoroki-Heck reaction; Inert atmosphere; optical yield given as %de;51%
With C4H7Cl2Pd(1-)*C27H39N2(1+); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 40h; Heck Reaction; Sealed tube;51%
578-57-4

2-bromoanisole

138642-62-3

2-Cyanophenylboronic acid

2'-methoxy-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
With sodium tetrachloropalladate(II); 2-(1-(1-phenylethylamino)methyl)pyridine In water; N,N-dimethyl-formamide at 110℃; for 16h; Suzuki-Miyaura coupling;100%
578-57-4

2-bromoanisole

29841-69-8

(S,S)-1,2-diphenyl-1,2-diaminoethane

(1R,2R)-N1,N2-bis(2-methoxyphenyl)-1,2-diphenylethane-1,2-diamine

Conditions
ConditionsYield
Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 20℃; for 1.5h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: 2-bromoanisole In toluene at 120℃; for 9h; Inert atmosphere; Schlenk technique; Glovebox;
100%
578-57-4

2-bromoanisole

2043-61-0

cyclohexanecarbaldehyde

92300-73-7

cyclohexyl (2-methoxyphenyl)methanol

Conditions
ConditionsYield
Stage #1: 2-bromoanisole With iodine; magnesium In tetrahydrofuran for 6.16667h; Sealed tube; Inert atmosphere; Reflux;
Stage #2: cyclohexanecarbaldehyde In tetrahydrofuran at 20℃; Sealed tube; Inert atmosphere;
100%
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

578-57-4

2-bromoanisole

1-(2-methoxyphenyl)-3,7-dimethyloct-6-en-1-ol

Conditions
ConditionsYield
Stage #1: 2-bromoanisole With iodine; magnesium In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: 3,7-dimethyl-oct-6-enal In tetrahydrofuran at 20℃; for 1.25h; Inert atmosphere;
100%
578-57-4

2-bromoanisole

100-66-3

methoxybenzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); formaldehyd; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;99%
With butyl magnesium bromide; zirconocene dichloride for 12h; Ambient temperature;98%
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 4h; ultrasonic acceleration of reduction;98%
578-57-4

2-bromoanisole

31600-86-9

2-methoxyphenyllithium

Conditions
ConditionsYield
With n-butyllithium In hexane; pentane at 0 - 20℃; for 1h; Inert atmosphere;99%
With n-butyllithium In hexane; pentane at 0 - 20℃;97%
With n-butyllithium In hexane; pentane at 20℃; in evacuated, closed vessel;
578-57-4

2-bromoanisole

108-24-7

acetic anhydride

35310-75-9

3-bromo-4-methoxyacetophenone

Conditions
ConditionsYield
With lithium perchlorate at 100℃; for 5h;99%
With aluminum (III) chloride In dichloromethane at 20 - 40℃; Friedel-Crafts acylation; Inert atmosphere;96%
With aluminium trichloride In dichloromethane68%
578-57-4

2-bromoanisole

108-98-5

thiophenol

14065-22-6

1-methoxy-2-(phenylthio)benzene

Conditions
ConditionsYield
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; sodium t-butanolate In 1,2-dimethoxyethane at 110℃; for 2h; Inert atmosphere;99%
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Reflux;97%
With copper(l) iodide; N,N'-dihexyloxalamide; potassium tert-butylate In 1,4-dioxane at 110℃; for 24h; Sealed tube; Inert atmosphere;95%
578-57-4

2-bromoanisole

100-61-8

N-methylaniline

(2-methoxyphenyl)methylphenylamine

Conditions
ConditionsYield
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;99%
With dicyclohexyl(2-methoxy-6-methylbiphenyl-2,-yl)phosphine; potassium tert-butylate; palladium diacetate In 1,4-dioxane at 160℃; for 0.25h; Microwave irradiation; Inert atmosphere;80%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate at 80℃; for 29h; Arylation;77%
578-57-4

2-bromoanisole

52805-92-2

(E)-2-methoxystilbene

Conditions
ConditionsYield
With (1-adamantyl)di(tert-butyl) phosphine; triethylamine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 20℃; for 20h; Heck reaction;99%
With C27H21F3N6OPd; tetrabutylammomium bromide; sodium acetate at 140℃; for 12h; Heck reaction; Inert atmosphere;89%
With potassium phosphate In N,N-dimethyl-formamide at 130℃; for 15h; Heck Reaction;84%
578-57-4

2-bromoanisole

5720-06-9

2-Methoxyphenylboronic acid

4877-93-4

2,2'-Dimethoxybiphenyl

Conditions
ConditionsYield
With potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 0.166667h; Suzuki cross-coupling reaction;99%
With Ph2P(CH2CH2O)22CH3; triethylamine; palladium dichloride In water at 100℃; for 1h; Suzuki coupling; Inert atmosphere;98%
With potassium carbonate; Co0.38Fe0.57LaO3Pd0.05 In isopropyl alcohol at 80℃; for 1h; Suzuki reaction;89%
578-57-4

2-bromoanisole

172732-52-4

o-cyanophenylboronic acid-1,3-propylene glycol ester

2'-methoxy-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In toluene for 1h; Heating;99%
110-91-8

morpholine

578-57-4

2-bromoanisole

27347-13-3

N-(2-methoxyphenyl)morpholine

Conditions
ConditionsYield
With (1,3-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)PdCl2(triethylamine); potassium tert-butylate In 1,2-dimethoxyethane at 20℃; for 6h; Buchwald-Hartwig Coupling; Sealed tube;99%
With potassium tert-butylate In 1,2-dimethoxyethane at 20℃; for 6h; Buchwald-Hartwig Coupling;99%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;99%
67-56-1

methanol

578-57-4

2-bromoanisole

201230-82-2

carbon monoxide

606-45-1

2-methoxybenzoic acid methyl ester

Conditions
ConditionsYield
With dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II); triethylamine at 100℃; under 2585.74 Torr; for 16h;99%
3612-20-2

1-phenylmethyl-4-piperidone

578-57-4

2-bromoanisole

130305-58-7

1-benzyl-4-(2-methoxyphenyl)piperidin-4-ol

Conditions
ConditionsYield
Stage #1: 2-bromoanisole With iodine; magnesium In tetrahydrofuran Grignard reaction; Inert atmosphere; Reflux;
Stage #2: 1-phenylmethyl-4-piperidone In tetrahydrofuran at 20℃; for 3h; Grignard reaction; Inert atmosphere; Cooling with ice;
99%
Stage #1: 2-bromoanisole With n-butyllithium In tetrahydrofuran; hexane at -70 - 1℃;
Stage #2: 1-phenylmethyl-4-piperidone In tetrahydrofuran at 20℃;
23.1%
578-57-4

2-bromoanisole

156275-96-6

triisopropylsilanethiol

triisopropyl-(2-methoxyphenylsulfanyl)-silane

Conditions
ConditionsYield
With (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; lithium hexamethyldisilazane In toluene at 110℃; Inert atmosphere;99%
With caesium carbonate; triphenylphosphine; palladium diacetate In toluene at 100℃; for 16h;33%
578-57-4

2-bromoanisole

62-53-3

aniline

1207-92-7

2-methoxy-N-phenylaniline

Conditions
ConditionsYield
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;99%
With potassium tert-butylate; (ϖ-allyl)(diphosphinecyclobutene)palladium at 20℃; for 12h;97%
With potassium phosphate; copper(l) iodide In diethylene glycol at 70℃; for 14h; Sealed tube;93%
578-57-4

2-bromoanisole

363-72-4

Pentafluorobenzene

15945-35-4

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

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In Isopropyl acetate at 80℃; for 12h;99%
With potassium phosphate; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; Glovebox;96%
With potassium phosphate; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II); Trimethylacetic acid In N,N-dimethyl acetamide at 80℃; for 2 - 4h;96%
578-57-4

2-bromoanisole

68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With sodium methylate; nickel diacetate In 1,4-dioxane at 110℃;99%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trichlorophosphate at 165℃; for 24h; Inert atmosphere;67%

Conditions
ConditionsYield
With caesium carbonate; copper(I) oxide In N,N-dimethyl-formamide at 110℃; for 18h;99%
With copper diacetate; sodium hydroxide; 3-(diphenylphosphino)propionic acid In 1,4-dioxane at 120℃; for 36h; Sealed tube;51%
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    578-57-4

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  • Casno:

    578-57-4

    National Research Platform ISO 9001 578-57-4

    Min.Order: 0

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    578-57-4

    2-Bromoanisole

    Min.Order: 1 Gram

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  • 1-bromo-2-methoxy-benzenCAS NO.:578-57-4

  • Casno:

    578-57-4

    1-bromo-2-methoxy-benzenCAS NO.:578-57-4

    Min.Order: 1 Gram

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Reported in EPA TSCA Inventory.

Specification

The 2-Bromoanisole, with the CAS registry number 578-57-4, is also known as 2-Bromo-1-methoxybenzene. It belongs to the product categories of Aromatic Halides(substituted); Anisole; Miscellaneous; Anisoles, Alkyloxy Compounds & Phenylacetates; Bromine Compounds. Its EINECS number is 209-425-8. This chemical's molecular formula is C7H7BrO and molecular weight is 187.03. What's more, its systematic name is 1-Bromo-2-methoxybenzene. It is used in organic synthesis. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, light and moisture.

Physical properties of 2-Bromoanisole are: (1)ACD/LogP: 2.705; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.71 ; (4)ACD/LogD (pH 7.4): 2.71; (5)ACD/BCF (pH 5.5): 67.00; (6)ACD/BCF (pH 7.4): 67.00; (7)ACD/KOC (pH 5.5): 705.86; (8)ACD/KOC (pH 7.4): 705.86; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.539; (14)Molar Refractivity: 40.622 cm3; (15)Molar Volume: 129.621 cm3; (16)Polarizability: 16.104×10-24cm3; (17)Surface Tension: 34.6 dyne/cm; (18)Density: 1.443 g/cm3; (19)Flash Point: 96.667 °C; (20)Enthalpy of Vaporization: 43.392 kJ/mol; (21)Boiling Point: 215.999 °C at 760 mmHg; (22)Vapour Pressure: 0.2 mmHg at 25°C.

Preparation of 2-Bromoanisole: this chemical can be prepared by methoxybenzene at the temperature of 20 °C. This reaction will need reagents Oxone, potassium bromide and solvent methanol with the reaction time of 1 hour. The yield is about 97%.

2-Bromoanisole can be prepared by methoxybenzene at the temperature of 20 °C

Uses of 2-Bromoanisole: it can be used to produce (2-methoxy-phenyl)-acetone at the temperature of 100 °C. It will need regent tributyltin methoxide and solvent toluene with the reaction time of 5 hours. This reaction will also need catalyst dichlorobis(tri-o-tolylphosphine)palladium. The yield is about 90%.

2-Bromoanisole can be used to produce (2-methoxy-phenyl)-acetone at the temperature of 100 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. You should avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet. When using it, you must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: COc1ccccc1Br
(2)Std. InChI: InChI=1S/C7H7BrO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3
(3)Std. InChIKey: HTDQSWDEWGSAMN-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1544mg/kg (1544mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.
mouse LD50 oral 2466mg/kg (2466mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.