Conditions | Yield |
---|---|
With sodium hydroxide; carbon monoxide; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine In xylene at 90℃; for 4h; Hydrolysis; | 100% |
With sodium hydroxide |
Conditions | Yield |
---|---|
With Oxone In N,N-dimethyl-formamide at 20℃; for 3h; | 97% |
Stage #1: m-bromobenzoic aldehyde With sodium dihydrogenphosphate In tetrahydrofuran; water at 20℃; for 0.166667h; Stage #2: With sodium chlorite; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 3h; | 95% |
With sodium chlorite; disodium hydrogenphosphate; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 3h; Cooling with ice; | 95% |
Conditions | Yield |
---|---|
With iodine; aluminium In acetonitrile at 80℃; for 18h; | 97% |
With potassium hydroxide In methanol at 35℃; for 0.0833333h; | 80% |
Conditions | Yield |
---|---|
With oxygen; pyridinium chlorochromate In water at 120℃; under 45004.5 Torr; for 2h; | 95% |
With Oxone; potassium bromide In dichloromethane; water at 20℃; for 24h; visible light irradiation; | 93% |
With oxygen; Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Green chemistry; | 93% |
3-bromo-β-nitro-styrene
m-bromobenzoic acid
Conditions | Yield |
---|---|
With Amberlyst A-26 (OH-); dihydrogen peroxide In 1,4-dioxane at 20℃; for 9h; | 95% |
5-bromo-1H-indole
A
5-bromo-1H-indazole-3-carboxaldehyde
B
m-bromobenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water; sodium nitrite In N,N-dimethyl-formamide at 0 - 50℃; for 5h; Inert atmosphere; | A 94% B n/a |
Conditions | Yield |
---|---|
With sodium bromate; potassium sulfate; sulfuric acid In water at 85 - 90℃; for 1.5h; regioselective reaction; | 93.7% |
With sulfuric acid; bromine; mercury(II) oxide In tetrachloromethane for 2.5h; Heating; | 79% |
With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid at 25℃; for 44h; Bromination; | 78% |
(3-Bromophenyl)methanol
m-bromobenzoic acid
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; acetic acid at 80℃; under 760.051 Torr; for 3h; | 91% |
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube; | 89% |
With tert.-butylhydroperoxide at 100℃; for 5h; | 80% |
3-bromo-N,N-diisopropylbenzamide
A
m-bromobenzoic acid
B
3-bromobenzoic acid isopropylamide
Conditions | Yield |
---|---|
With hydrogenchloride; zinc(II) chloride at 160℃; for 72h; | A 90% B 8% |
benzyl 3-bromobenzoic acid
m-bromobenzoic acid
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.166667h; chemoselective reaction; | 90% |
1,2-di-(3-bromophenyl)-1,2-ethanediol
m-bromobenzoic acid
Conditions | Yield |
---|---|
With sodium hypochlorite In acetonitrile at 20℃; for 3h; | 89% |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran at -78℃; for 0.5h; | 88% |
1,3-dibromobenzene
diphenylmethylsilanecarboxylic acid
A
isophthalic acid
B
m-bromobenzoic acid
Conditions | Yield |
---|---|
With lithium trimethylsilanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 80℃; for 16h; Glovebox; Overall yield = 40 mg; | A 88% B 7% |
3-bromobenzylamine
m-bromobenzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide at 120℃; for 5h; Ionic liquid; | 85% |
Conditions | Yield |
---|---|
With sulfuric acid; bromine; mercury(II) oxide In tetrachloromethane for 2.5h; Heating; | A 80% B n/a |
Conditions | Yield |
---|---|
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In N,N-dimethyl acetamide at 70℃; for 24h; Schlenk technique; Sealed tube; | 79% |
Conditions | Yield |
---|---|
With sulfuric acid; bromine; mercury(II) oxide In tetrachloromethane for 2.5h; Heating; | A 78% B n/a |
2,5-dibromobenzoic acid
A
m-bromobenzoic acid
B
benzoic acid
C
2-bromobenzoic-acid
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran | A 78% B 13% C 2% |
Conditions | Yield |
---|---|
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 10h; | 78% |
With hydroxylamine hydrochloride; iodine In dimethyl sulfoxide at 100℃; for 6h; | 70% |
With 18-crown-6 ether; acetophenone In benzene at 25℃; for 24h; Mechanism; relative reactivity; further oxidative agents; |
carbon monoxide
3-bromo-1-iodylbenzene
A
1-Bromo-3-iodobenzene
B
isophthalic acid
C
m-bromobenzoic acid
Conditions | Yield |
---|---|
With sodium tetrachloropalladate; sodium carbonate In water at 40℃; for 5.5h; Yields of byproduct given; | A n/a B 14% C 76% |
carbon monoxide
3-bromo-1-iodylbenzene
A
3-iodochlorobenzene
B
isophthalic acid
C
m-bromobenzoic acid
Conditions | Yield |
---|---|
With sodium tetrachloropalladate; sodium carbonate In water at 40℃; for 5.5h; Yields of byproduct given; | A n/a B 14% C 76% |
methanol
m-bromobenzoic aldehyde
A
methyl 3-bromobenzoate
B
m-bromobenzoic acid
Conditions | Yield |
---|---|
With 3,3'-dimethyl-1,1'-(hexane-1,6-diyl)diimidazolium glutarate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 55℃; for 16h; Molecular sieve; | A 72% B 10% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 6h; | 72% |
Conditions | Yield |
---|---|
With ethanol In water at 85℃; for 60h; Time; von Richter Aromatic Carboxylation; Ionic liquid; | 67% |
3-bromobenzoyl cyanide
m-bromobenzoic acid
Conditions | Yield |
---|---|
With sulfuric acid; water at 103℃; for 0.5h; | 67% |
m-bromobenzoic acid
Conditions | Yield |
---|---|
With ferrocene; tert-Butyl peroxybenzoate In 1,2-dichloro-ethane at 80℃; for 12h; Sealed tube; | 66% |
1-Bromo-3-iodobenzene
carbon dioxide
A
isophthalic acid
B
m-bromobenzoic acid
Conditions | Yield |
---|---|
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique; Stage #2: 1-Bromo-3-iodobenzene With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 16h; Schlenk technique; Sealed tube; | A 62% B 20% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(ll) bromide In acetic anhydride | A 19% B 59% |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique; Stage #2: 1-Bromo-3-iodobenzene With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 2h; Schlenk technique; Sealed tube; | 52% |
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; diethylzinc In N,N-dimethyl acetamide at 70℃; under 760.051 Torr; | 51% |
Stage #1: 1-Bromo-3-iodobenzene With copper In tetrahydrofuran at 25℃; for 0.5h; Stage #2: carbon dioxide In tetrahydrofuran for 24h; | 49% |
m-bromobenzoic aldehyde
A
m-bromobenzoic acid
B
bis-(3-bromo-benzoyl)-peroxide
C
3-Bromperoxobenzoesaeure
Conditions | Yield |
---|---|
With oxygen; ozone; lithium chloride In tetrachloromethane at 50℃; | A n/a B 50.4% C n/a |
Conditions | Yield |
---|---|
With thionyl chloride at 90℃; for 3h; | 100% |
Stage #1: m-bromobenzoic acid With thionyl chloride at 70℃; for 5h; Stage #2: methanol With sodium hydrogencarbonate at 20℃; for 4h; Cooling with ice; | 98% |
With sulfuric acid for 0.3h; Reflux; Microwave irradiation; | 94% |
Conditions | Yield |
---|---|
Stage #1: m-bromobenzoic acid With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.0833333h; Stage #2: With oxalyl dichloride In dichloromethane at 20℃; for 12h; | 100% |
With thionyl chloride Reflux; | 97% |
With thionyl chloride |
Conditions | Yield |
---|---|
With sodium carbonate; palladium dichloride In water at 100℃; for 4h; other reagent, temperature, reaction time; | 100% |
With palladium on activated charcoal; sodium carbonate for 3h; Heating; | 90% |
With palladium on activated charcoal; sodium carbonate at 20℃; for 24h; Product distribution; influence of catalyst, reaction time, temperature; | 61% |
With palladium diacetate; sodium hydroxide In water at 25℃; for 2h; Product distribution; other reagent, reaction time, temperature; | 100 % Chromat. |
With sodium carbonate; palladium on activated charcoal In water for 1h; Suzuki reaction; Heating; | 97 % Chromat. |
m-bromobenzoic acid
4-methoxyphenylboronic acid
4'-methoxy-(1,1'-biphenyl)-3-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate; dichlorobis(4-pyridinaldoxime)palladium(II) In water for 1h; Suzuki reaction; Heating; | 100% |
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 1.5h; Suzuki-Miyaura Coupling; Green chemistry; | 98% |
With C26H24Cl4N8O4Pd2; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 20 - 100℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Solvent; Suzuki-Miyaura Coupling; Green chemistry; | 98% |
m-bromobenzoic acid
Conditions | Yield |
---|---|
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With triethylamine; 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 0 - 20℃; for 16h; | 100% |
Conditions | Yield |
---|---|
With nickel dibromide | 100% |
Conditions | Yield |
---|---|
With sulfated zirconia at 130℃; for 1h; Microwave irradiation; | 99.2% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydrogencarbonate In water at 90℃; for 24h; tri-n-butyltin hydride mediated dehalogenation of various organohalides in aqueous medium; | 99% |
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydrogencarbonate In water at 90℃; for 24h; | 95% |
With tri-n-butyl-tin hydride; sodium hydrogencarbonate In water for 24h; Ambient temperature; Irradiation; | 93% |
m-bromobenzoic acid
4-fluoroboronic acid
4’-fluoro-[1,1’-biphenyl]-3-carboxylic acid
Conditions | Yield |
---|---|
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 1.5h; Suzuki-Miyaura Coupling; Green chemistry; | 99% |
With potassium carbonate In water at 20℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry; | 96% |
With palladium diacetate; sodium hydroxide In water for 0.166667h; Ambient temperature; | 95% |
With sodium hydroxide; palladium dichloride In water at 25℃; for 0.166667h; | 95% |
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In 1,4-dioxane; water at 95℃; Suzuki-Miyaura Coupling; Inert atmosphere; | 78% |
Conditions | Yield |
---|---|
With sodium carbonate; Pd-complex on fluorous reversed silica gel In water at 80℃; for 16h; Suzuki reaction; | 99% |
With potassium hydroxide; potassium carbonate; palladium-carbon In water | 98% |
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 1.5h; Suzuki-Miyaura Coupling; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate In water at 20℃; for 0.5h; | 99% |
m-bromobenzoic acid
4-methylphenylboronic acid
4'-methylbiphenyl-3-carboxylic acid
Conditions | Yield |
---|---|
With 4C3H6N6*Pd(2+)*2C2H3O2(1-); sodium carbonate In water at 80℃; for 2h; Suzuki-Miyaura Coupling; Green chemistry; | 99% |
Stage #1: m-bromobenzoic acid With palladium diacetate In water at 20℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Stage #2: 4-methylphenylboronic acid With potassium hydroxide In water for 5h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux; | 98% |
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 1.5h; Suzuki-Miyaura Coupling; Green chemistry; | 96% |
Conditions | Yield |
---|---|
Stage #1: m-bromobenzoic acid 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 0℃; for 0.5h; Stage #2: aniline In N,N-dimethyl-formamide at 25℃; for 16h; | 99% |
With oxygen; lithium hydroxide In water at 20℃; for 14h; Sonication; | 90% |
Conditions | Yield |
---|---|
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve; | 99% |
The IUPAC name of this chemical is 3-bromobenzoic acid. With the CAS registry number 585-76-2, it is also named as Benzoic acid, 3-bromo-. The product's categories are Blocks; Carboxes; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic Acid Derivative; Acids & Esters; Bromine Compounds; C7; Carbonyl Compounds; Carboxylic Acids. It is white to light yellow crystal powder which is soluble in alcohol and ether.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.71; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.03; (4)ACD/LogD (pH 7.4): -0.3; (5)ACD/BCF (pH 5.5): 1.41; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 14.78; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.608; (13)Molar Refractivity: 40.87 cm3; (14)Molar Volume: 118.1 cm3; (15)Polarizability: 16.2×10-24 cm3; (16)Surface Tension: 53.7 dyne/cm; (17)Enthalpy of Vaporization: 57.95 kJ/mol; (18)Vapour Pressure: 0.0003 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 199.947292; (21)MonoIsotopic Mass: 199.947292; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 10; (24)Complexity: 136.
Preparation of 3-Bromobenzoic acid: It can be obtained by m-bromotoluene through the oxidation of potassium permanganate. Mixing the m-bromotoluene, potassium hydroxide and water and heating to boiling. Adding potassium permanganate slowly, then refluxing 4h. After filtrate and acidification, filtering to get the crude. Using ammonia to disolve the crude in ethanol, and then using hydrochloric acid to acidize. Finally, after filtration and washing, we can get the product.
Uses of 3-Bromobenzoic acid: It can react with methanol to get 3-bromo-benzoic acid methyl ester. This reaction needs reagent HCl.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)c1cc(Br)ccc1
2. InChI:InChI=1/C7H5BrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10)
3. InChIKey:VOIZNVUXCQLQHS-UHFFFAOYAC
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