Product Name

  • Name

    4-Bromo-3-methylbenzoic acid

  • EINECS 231-713-7
  • CAS No. 7697-28-1
  • Article Data19
  • CAS DataBase
  • Density 1.599 g/cm3
  • Solubility
  • Melting Point 212-216 °C(lit.)
  • Formula C8H7BrO2
  • Boiling Point 311.4 °C at 760 mmHg
  • Molecular Weight 215.046
  • Flash Point 142.1 °C
  • Transport Information
  • Appearance White or reddish crystal powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 7697-28-1 (4-Bromo-3-methylbenzoic acid)
  • Hazard Symbols IrritantXi
  • Synonyms m-Toluicacid, 4-bromo- (6CI,8CI);Benzoicacid, 4-bromo-3-methyl-;4-Bromo-3-methylbenzoicacid;3-Methyl-4-bromobenzoic acid;
  • PSA 37.30000
  • LogP 2.45570

Synthetic route

4-amino 3-methylbenzoic acid
2486-70-6

4-amino 3-methylbenzoic acid

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
Stage #1: 4-amino 3-methylbenzoic acid With hydrogen bromide In water at 25℃; for 1h;
Stage #2: With sodium nitrate In water at -2 - -1℃; for 1.75h;
Stage #3: With hydrogen bromide; copper(I) bromide In water at -2 - 70℃; for 2h;
90%
Diazotization.Kochen der Diazoverbindung mit Bromwasserstoffsaeure;
With hydrogen bromide; sodium nitrite; copper(I) chloride In water
4,4'-dibromo-5,3'-dimethyl-2-nitrodiphenylmethane
84797-77-3

4,4'-dibromo-5,3'-dimethyl-2-nitrodiphenylmethane

A

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

B

6-bromo-5-methyl-3-(4'-bromo-3'-methylphenyl)-2,1-isoxazole
93099-47-9

6-bromo-5-methyl-3-(4'-bromo-3'-methylphenyl)-2,1-isoxazole

C

3,6-dibromo-2,7-dimethylacridone
84658-94-6

3,6-dibromo-2,7-dimethylacridone

Conditions
ConditionsYield
With sulfuric acid In ethanol for 5h; Irradiation;A 63%
B 20%
C 6%
With sulfuric acid In ethanol for 5h; Product distribution; Mechanism; Irradiation;A 51%
B 20%
C 6%
4-bromo-3-methyl-N-(2-methyl-4-cyanophenyl)benzamide
146308-26-1

4-bromo-3-methyl-N-(2-methyl-4-cyanophenyl)benzamide

A

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

B

4-amino-3-methylbenzonitrile
78881-21-7

4-amino-3-methylbenzonitrile

Conditions
ConditionsYield
With potassium hydroxide In ethanol a) 70 deg C, 4.5 h, b) 80 deg C, 3 h; Yields of byproduct given;A 63%
B n/a
With potassium hydroxide In ethanol a) 70 deg C, 4.5 h, b) 80 deg C, 3 h; Yield given;A 63%
B n/a
1-bromo-2,4-dimethylbenzene
583-70-0

1-bromo-2,4-dimethylbenzene

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
With nitric acid60%
With nitric acid for 24h; Heating / reflux;60%
With nitric acid at 150℃;
With nitric acid
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

1,4-dibromo-2-methylbenzene
615-59-8

1,4-dibromo-2-methylbenzene

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
With diethyl ether Aufgiessen des Reaktionsgemisches auf festes Kohlendioxid;
1,4-dibromo-2-methylbenzene
615-59-8

1,4-dibromo-2-methylbenzene

A

2-methylterephthalic acid
5156-01-4

2-methylterephthalic acid

B

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
With n-butyllithium; Petroleum ether anschliessendes Behandeln mit festem Kohlendioxid;
1-bromo-4-isopropyl-2-methyl-benzene
92243-75-9

1-bromo-4-isopropyl-2-methyl-benzene

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
With nitric acid
1-(4-bromo-3-methylphenyl)ethan-1-one
37074-40-1

1-(4-bromo-3-methylphenyl)ethan-1-one

A

4-bromo-isophthalic acid
6939-93-1

4-bromo-isophthalic acid

B

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
With potassium permanganate
With alkaline potassium permanganate
m-Toluic acid
99-04-7

m-Toluic acid

A

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

B

2-bromo-5-methylbenzoic acid
6967-82-4

2-bromo-5-methylbenzoic acid

Conditions
ConditionsYield
With bromine
amino-5-bromo-2-toluene
6933-10-4

amino-5-bromo-2-toluene

copper(I) cyanide
544-92-3

copper(I) cyanide

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
(i) NaNO2, aq. HCl, (ii) /BRN= 3587244/, (iii) NaOH, EtOH; Multistep reaction;
bromine
7726-95-6

bromine

m-Toluic acid
99-04-7

m-Toluic acid

A

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

B

2-bromo-5-methylbenzoic acid
6967-82-4

2-bromo-5-methylbenzoic acid

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

1,4-dibromo-2-methylbenzene
615-59-8

1,4-dibromo-2-methylbenzene

petroleum ether

petroleum ether

A

4-bromo-2-methylbenzoic acid
68837-59-2

4-bromo-2-methylbenzoic acid

B

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
at 20℃; anschliessend Behandlung mit CO2;
1-bromo-2,4-dimethylbenzene
583-70-0

1-bromo-2,4-dimethylbenzene

chromic acid mixture

chromic acid mixture

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-ethyl-1-bromo-2-methyl-benzene
90560-90-0

4-ethyl-1-bromo-2-methyl-benzene

nitric acid
7697-37-2

nitric acid

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

1-bromo-4-isopropyl-2-methyl-benzene
92243-75-9

1-bromo-4-isopropyl-2-methyl-benzene

nitric acid
7697-37-2

nitric acid

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

asymm. bromo-m-xylene

asymm. bromo-m-xylene

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
With dichromate mixture
1-(4-bromo-3-methylphenyl)ethan-1-one
37074-40-1

1-(4-bromo-3-methylphenyl)ethan-1-one

KMnO4

KMnO4

aqueous KOH

aqueous KOH

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

methyl iodide
74-88-4

methyl iodide

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
Stage #1: 4-Bromobenzoic acid With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at -78℃; for 4h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃;
12 % Spectr.
3-Methylacetanilide
537-92-8

3-Methylacetanilide

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) (bromination), (ii) (hydrolysis)
2: (i) NaNO2, aq. HCl, (ii) /BRN= 3587244/, (iii) NaOH, EtOH
View Scheme
4-Bromo-3-methylbenzoic acid methyl ester
148547-19-7

4-Bromo-3-methylbenzoic acid methyl ester

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
Stage #1: 4-Bromo-3-methylbenzoic acid methyl ester With water; sodium hydroxide In tetrahydrofuran at 20℃; for 16h;
Stage #2: With hydrogenchloride In water
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-bromo-3-methylbenzylalcohol
149104-89-2

4-bromo-3-methylbenzylalcohol

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 0 - 20℃;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.25h;100%
With borane In tetrahydrofuran at -30 - 20℃;98%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

phenylboronic acid
98-80-6

phenylboronic acid

2-methyl[1,1'-biphenyl]-4-carboxylic acid
178313-67-2

2-methyl[1,1'-biphenyl]-4-carboxylic acid

Conditions
ConditionsYield
With disodium hydrogenphosphate; disodium bis(2-aminopyrimidine-4,6-diolate)palladium acetate In water at 50 - 120℃; for 0.166667h; Microwave irradiation;100%
With disodium hydrogenphosphate; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 In water at 120℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation;99%
With potassium fluoride; palladium diacetate; XPhos In tetrahydrofuran for 1h; Heating / reflux;
3-METHOXYBENZYLAMINE
5071-96-5

3-METHOXYBENZYLAMINE

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-bromo-N-(3-methoxybenzyl)-3-methylbenzamide
1623120-19-3

4-bromo-N-(3-methoxybenzyl)-3-methylbenzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 1h; Inert atmosphere;100%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

m-tolylboronic acid
17933-03-8

m-tolylboronic acid

3-methyl-4-(m-tolyl)benzoic acid

3-methyl-4-(m-tolyl)benzoic acid

Conditions
ConditionsYield
With disodium hydrogenphosphate; disodium bis(2-aminopyrimidine-4,6-diolate)palladium acetate In water at 50 - 120℃; for 0.166667h; Microwave irradiation;100%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

isopropylamine
75-31-0

isopropylamine

4-bromo-N-isopropyl-3-methylbenzamide

4-bromo-N-isopropyl-3-methylbenzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 0 - 20℃; for 1h;100%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2,2’-dimethyl-1,1’-biphenyl-4-carboxylic acid
69535-85-9

2,2’-dimethyl-1,1’-biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With disodium hydrogenphosphate; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 In water at 120℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation;99%
With disodium hydrogenphosphate; disodium bis(2-aminopyrimidine-4,6-diolate)palladium acetate In water at 50 - 120℃; for 0.166667h; Microwave irradiation;95%
3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)aniline
1428155-06-9

3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)aniline

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-bromo-3-methyl-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)phenyl)benzamide
1428155-45-6

4-bromo-3-methyl-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)phenyl)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;99%
methanol
67-56-1

methanol

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-Bromo-3-methylbenzoic acid methyl ester
148547-19-7

4-Bromo-3-methylbenzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid In methanol for 14h; Reflux;97%
With sulfuric acid Reflux;95%
Stage #1: methanol With acetyl chloride for 0.416667h;
Stage #2: 4-bromo-3-methylbenzoic acid for 18h; Heating / reflux;
93%
ethanol
64-17-5

ethanol

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

ethyl 3-methyl-4-bromobenzoate
160313-69-9

ethyl 3-methyl-4-bromobenzoate

Conditions
ConditionsYield
With thionyl chloride at 83℃; for 6h;96%
With sulfuric acid In toluene for 1h; Heating;80%
With hydrogenchloride
N-trimethylsilylmethylamine
18166-02-4

N-trimethylsilylmethylamine

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-bromo-3-methyl-N-trimethylsilanylmethyl-benzamide
1370257-42-3

4-bromo-3-methyl-N-trimethylsilanylmethyl-benzamide

Conditions
ConditionsYield
Stage #1: 4-bromo-3-methylbenzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: N-trimethylsilylmethylamine In dichloromethane at 20℃; Product distribution / selectivity;
94%
cyclobutylamine
2516-34-9

cyclobutylamine

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-bromo-N-cyclobutyl-3-methylbenzamide

4-bromo-N-cyclobutyl-3-methylbenzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;94%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

methylamine
74-89-5

methylamine

4-bromo-N,3-dimethylbenzamide

4-bromo-N,3-dimethylbenzamide

Conditions
ConditionsYield
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
Stage #2: methylamine In ethanol at 20℃; for 0.5h;
94%
2-(2-Hydroxyethyl)pyridine
103-74-2

2-(2-Hydroxyethyl)pyridine

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

2-(2-pyridyl)ethyl 4-bromo-3-methylbenzoate
920270-48-0

2-(2-pyridyl)ethyl 4-bromo-3-methylbenzoate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;92%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

3-(8-nitroquinolin-4-yl)benzenamine

3-(8-nitroquinolin-4-yl)benzenamine

4-bromo-3-methyl-N-(3-(8-nitroquinolin-4-yl)phenyl)benzamide

4-bromo-3-methyl-N-(3-(8-nitroquinolin-4-yl)phenyl)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;92%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-carboxyphenylboronic acid
14047-29-1

4-carboxyphenylboronic acid

2-methyl-[1,1′-biphenyl]-4,4′-dicarboxylic acid
1186048-28-1

2-methyl-[1,1′-biphenyl]-4,4′-dicarboxylic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; triphenylphosphine In water; N,N-dimethyl-formamide at 90℃; for 24h;91%
With {1,1'-bis(diphenylphosphino)ferrocene} palladium dibromide; sodium carbonate In water; N,N-dimethyl-formamide at 90℃; for 3h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Reflux;
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-phenyl-2,3-dihydro-1H-indole
179473-53-1

4-phenyl-2,3-dihydro-1H-indole

(4-bromo-3-methylphenyl)(4-phenylindolin-1-yl)methanone

(4-bromo-3-methylphenyl)(4-phenylindolin-1-yl)methanone

Conditions
ConditionsYield
Stage #1: 4-bromo-3-methylbenzoic acid; 4-phenyl-2,3-dihydro-1H-indole With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;
90.2%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 3h;87%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid
269409-74-7

3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 120℃; for 0.25h; Microwave irradiation;90%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In N,N-dimethyl-formamide at 120℃; for 0.25h; Microwave irradiation;90%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 125℃; for 0.333333h; Microwave irradiation;74%
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 20 - 80℃;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

tert-butyl 4-bromo-3-methylbenzoate
347174-28-1

tert-butyl 4-bromo-3-methylbenzoate

Conditions
ConditionsYield
With dmap In tetrahydrofuran Reflux;87%
With dmap In tetrahydrofuran Reflux;87%
With dmap In tetrahydrofuran; tert-butyl alcohol at 70℃; for 12h; Inert atmosphere;70%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

1-bromo-2-methyl-4-(trifluoromethyl)benzene
929000-62-4

1-bromo-2-methyl-4-(trifluoromethyl)benzene

Conditions
ConditionsYield
With sulfur tetrafluoride; hydrogen fluoride at 85℃; for 24h; Autoclave; Inert atmosphere;87%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

potassium tert-butylate
865-47-4

potassium tert-butylate

tert-butyl 4-bromo-3-methylbenzoate
347174-28-1

tert-butyl 4-bromo-3-methylbenzoate

Conditions
ConditionsYield
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2.33333h;
Stage #2: potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h;
86%
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 2h; Inert atmosphere;
Stage #2: potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 2h;
69%
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h; Inert atmosphere;
Stage #2: potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;
42%
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
Stage #2: potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h;
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-bromo-3-(bromomethyl)benzoic acid
887757-31-5

4-bromo-3-(bromomethyl)benzoic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 72h; Concentration; Reflux;86%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 76℃; for 72h;86%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 48h; Reflux;86%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)indoline

4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)indoline

C24H20BrNO3

C24H20BrNO3

Conditions
ConditionsYield
Stage #1: 4-bromo-3-methylbenzoic acid; 4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)indoline With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;
85.5%
oxalyl dichloride
79-37-8

oxalyl dichloride

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

tert-butyl 4-bromo-3-methylbenzoate
347174-28-1

tert-butyl 4-bromo-3-methylbenzoate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water85%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

potassium phenyltrifluoborate

potassium phenyltrifluoborate

C14H11BrO2

C14H11BrO2

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; oxygen; palladium diacetate; p-benzoquinone In tert-butyl alcohol at 100℃; under 22801.5 Torr; for 24h; regioselective reaction;85%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

methyl iodide
74-88-4

methyl iodide

4-Bromo-3-methylbenzoic acid methyl ester
148547-19-7

4-Bromo-3-methylbenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2.5h;83.1%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

dimethyl amine
124-40-3

dimethyl amine

4-bromo-N,N,3-trimethylbenzamide

4-bromo-N,N,3-trimethylbenzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 16h;83%
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In ethanol; water at 20℃; for 24h;65%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

{2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine

{2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine

N‐({2‐benzyl‐2‐azabicyclo[2.1.1]hexan‐1‐yl}methyl)‐4‐bromo‐3‐methylbenzamide

N‐({2‐benzyl‐2‐azabicyclo[2.1.1]hexan‐1‐yl}methyl)‐4‐bromo‐3‐methylbenzamide

Conditions
ConditionsYield
Stage #1: 4-bromo-3-methylbenzoic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h;
Stage #2: {2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine In dichloromethane at 20℃; for 1h;
82%
2-fluoro-N1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)benzene-1,4-diamine
1428155-04-7

2-fluoro-N1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)benzene-1,4-diamine

4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

4-bromo-N-(3-fluoro-4-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)phenyl)-3-methylbenzamide
1428155-17-2

4-bromo-N-(3-fluoro-4-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)phenyl)-3-methylbenzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;80%
4-bromo-3-methylbenzoic acid
7697-28-1

4-bromo-3-methylbenzoic acid

methyl 6-aminocaproate hydrochloride
1926-80-3

methyl 6-aminocaproate hydrochloride

methyl 6-(4-bromo-3-methylbenzamido)hexanoate
1255952-05-6

methyl 6-(4-bromo-3-methylbenzamido)hexanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethylamine In dichloromethane for 20h; Inert atmosphere;78%

4-Bromo-3-methylbenzoic acid Chemical Properties

Molecular Structure:

Molecular Formula: C8H7BrO2
Molecular Weight: 215.044
IUPAC Name: 4-Bromo-3-methylbenzoic acid
Synonyms of 3-Methyl-4-bromobenzoic acid (CAS NO.7697-28-1): EINECS 231-713-7 ; 4-Bromo-3-methylbenzoic acid
CAS NO: 7697-28-1
Product Categories: blocks ; Bromides ; Carboxes ; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts ; Benzoic acid ; Organic acids ; Acids & Esters ; Bromine Compounds ; C8 ; Carbonyl Compounds ; Carboxylic Acids
Melting Point: 212-216 °C 
Index of Refraction: 1.595
Molar Refractivity: 45.69 cm3
Molar Volume: 134.4 cm3
Surface Tension: 50 dyne/cm
Density: 1.599 g/cm3
Flash Point: 142.1 °C
Enthalpy of Vaporization: 58.31 kJ/mol
Boiling Point: 311.4 °C at 760 mmHg
Vapour Pressure: 0.000243 mmHg at 25°C

4-Bromo-3-methylbenzoic acid Uses

 3-Methyl-4-bromobenzoic acid (CAS NO.7697-28-1) is used as a pharmaceutical intermediate.

4-Bromo-3-methylbenzoic acid Safety Profile

Safety Information of 3-Methyl-4-bromobenzoic acid (CAS NO.7697-28-1):
Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin  
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing    
WGK Germany:3
Hazard Note:Irritant

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