Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium tribromide at 25℃; for 0.666667h; | 98% |
Stage #1: anthranilic acid With bromine In tetrachloromethane at 10 - 20℃; for 4h; Stage #2: With potassium carbonate In water | 98% |
With [bmim]Br3 In dichloromethane at 20℃; for 0.666667h; | 95% |
5-bromo-2-aminobenzoic acid methyl ester
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-aminobenzoic acid methyl ester With water; sodium hydroxide In tetrahydrofuran; ethanol at 20℃; for 12h; Stage #2: With hydrogenchloride In water pH=4; | 97% |
With water; sodium hydroxide In tetrahydrofuran; ethanol at 20℃; for 12h; | 97% |
With water; sodium hydroxide In tetrahydrofuran at 60℃; Inert atmosphere; Sealed tube; | 72% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium hydroxide In water at 80℃; for 1h; | 96% |
Ring cleavage; oxidation; | |
With dihydrogen peroxide; sodium hydroxide In water | |
Stage #1: 5-Bromo-1H-indole-2,3-dione With sodium hydroxide at 80℃; Stage #2: With dihydrogen peroxide at 80℃; for 1.25h; |
Conditions | Yield |
---|---|
Stage #1: 5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione With bromamine B; sodium hydroxide; palladium dichloride In water; acetonitrile at 60℃; for 3.66667h; pH=12; Stage #2: In water Acidic conditions; | 95% |
Conditions | Yield |
---|---|
With polymer-supported formate; magnesium In methanol at 20℃; for 2.5h; | 94% |
With ammoniummethyl polystyrene resin formate; palladium on activated charcoal In methanol at 20℃; for 5h; | 93% |
With aminomethyl polystyrene resin formic acid salt; zinc In methanol at 20℃; for 2.5h; | 93% |
With hydrogenchloride; tin |
5-bromo-1H-indole
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
Stage #1: 5-bromo-1H-indole With bromamine B; sodium hydroxide; palladium dichloride In water; acetonitrile at 60℃; for 3.66667h; pH=12; Stage #2: In water Acidic conditions; | 94% |
With ruthenium trichloride; osmium(VIII) oxide; bromamine B; sodium hydroxide In water; acetonitrile at 39.84℃; for 5.5h; | 94% |
5-bromo-N-acetylanthranilic acid
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide for 4h; Reflux; | 93% |
2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
anthranilic acid
A
5-Bromo-2-aminobenzoic acid
B
o-acetylamino-benzoic acid
Conditions | Yield |
---|---|
In benzene for 6h; Heating; | A 45% B 42% |
2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
A
5-Bromo-2-aminobenzoic acid
B
o-acetylamino-benzoic acid
Conditions | Yield |
---|---|
With anthranilic acid In benzene for 6h; Heating; | A 45% B 42% |
2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
1,2-diamino-benzene
A
N-(2-aminophenyl)acetamide
B
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
In benzene for 6h; Heating; | A 28% B 32% C 36% |
2-azido-5-bromobenzoic acid
C
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane; water at 25℃; for 3h; UV-irradiation; | A 18% B 34% C 10% |
anthranilic acid
A
2-amino-3-bromo benzoic acid
B
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
With N-Bromosuccinimide at 25℃; for 0.025h; Solid phase reaction; bromination; | A 25% B 25% |
With sodium perborate; ammonium heptamolybdate; potassium bromide In acetic acid at 20℃; for 2h; Bromination; | |
With dihydrogen peroxide; ammonium bromide; acetic acid at 20℃; for 3h; |
Conditions | Yield |
---|---|
With ethanol; sulfuric acid; zinc |
4'-bromo-2'-methylacetanilide
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
With potassium permanganate; water Verseifen des Produkts mit konz. Salzsaeure; | |
Multi-step reaction with 2 steps 1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux 2: sodium hydroxide; water / 4 h / Reflux View Scheme |
N,N'-(2,2,2-trichloro-ethylidene)-di-anthranilic acid
A
acetic acid
B
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
With bromine |
Conditions | Yield |
---|---|
With acetic acid; potassium bromide |
methanol
5-Bromo-1H-indole-2,3-dione
A
5-Bromo-2-aminobenzoic acid
B
5-bromo-2-aminobenzoic acid methyl ester
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium methylate 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction; |
2-benzyl-4-oxo-1,2,3-benzotriazin-2-ium-1-olate
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid |
hydrogenchloride
5-bromoisatoic anhydride
A
methylammonium carbonate
B
5-Bromo-2-aminobenzoic acid
bromine
anthranilic acid
acetic acid
5-Bromo-2-aminobenzoic acid
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With bromine |
bromine
anthranilic acid
acetic acid
A
5-Bromo-2-aminobenzoic acid
B
2-amino-3,5-dibromobenzoic acid
hydrogenchloride
5-bromo-2-nitrobenzoic acid
A
anthranilic acid
B
5-Bromo-2-aminobenzoic acid
N,N'-(2,2,2-trichloro-ethylidene)-di-anthranilic acid
bromine
acetic acid
5-Bromo-2-aminobenzoic acid
o-nitrobenzaldehyde benzylhydrazone
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 82 percent / iodosobenzene diacetate / CH2Cl2 / 4 h 2: 25percent HBr / acetic acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrochloric acid; alcohol; water; KBr; KBrO3 2: water; potassium permanganate / Verseifen des Produkts mit konz. Salzsaeure View Scheme |
dimethyl sulfide borane
5-Bromo-2-aminobenzoic acid
(2-amino-5-bromophenyl)methanol
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran | 100% |
5-Bromo-2-aminobenzoic acid
(2-amino-5-bromophenyl)methanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 100% |
Stage #1: 5-Bromo-2-aminobenzoic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: With water; sodium hydroxide In tetrahydrofuran | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; | 100% |
4-morpholino-4-yl-phenylamine
orthoformic acid triethyl ester
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
at 110℃; | 100% |
isobutyryl chloride
5-Bromo-2-aminobenzoic acid
6-bromo-2-isopropyl-4H-3,1-benzoxazin-4-one
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Product distribution / selectivity; | 99% |
Stage #1: isobutyryl chloride; 5-Bromo-2-aminobenzoic acid With triethylamine In dichloromethane at 0 - 20℃; for 15h; Stage #2: With acetic anhydride at 55℃; for 3h; Product distribution / selectivity; | 99% |
Stage #1: isobutyryl chloride; 5-Bromo-2-aminobenzoic acid With triethylamine In dichloromethane at 20℃; Stage #2: With acetic anhydride In dichloromethane at 50℃; Further stages.; | |
Stage #1: isobutyryl chloride; 5-Bromo-2-aminobenzoic acid With pyridine for 2h; Stage #2: With acetic anhydride for 1h; Heating; |
Conditions | Yield |
---|---|
Stage #1: 5-Bromo-2-aminobenzoic acid With thionyl chloride In toluene at 130℃; for 2h; Stage #2: aniline In tetrahydrofuran at 0 - 90℃; for 4h; | 99% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; |
ethylamine
5-Bromo-2-aminobenzoic acid
2-amino-5-bromo-N-ethylbenzamide
Conditions | Yield |
---|---|
Stage #1: 5-Bromo-2-aminobenzoic acid 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℃; for 0.166667h; Inert atmosphere; Stage #2: ethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; | 99% |
Stage #1: 5-Bromo-2-aminobenzoic acid With triethylamine; HATU In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: ethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; | 85% |
Stage #1: 5-Bromo-2-aminobenzoic acid With triethylamine; HATU In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: ethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; | 85% |
Conditions | Yield |
---|---|
for 1h; Heating; | 98% |
bis(trichloromethyl) carbonate
5-Bromo-2-aminobenzoic acid
5-bromoisatoic anhydride
Conditions | Yield |
---|---|
With pyridine In dichloromethane; acetonitrile at 50 - 55℃; for 2h; | 98% |
In tetrahydrofuran at 70℃; for 2h; | 97% |
In tetrahydrofuran for 4h; Reflux; | 96% |
2-Methoxybenzoyl chloride
5-Bromo-2-aminobenzoic acid
6-bromo-2-(2-methoxyphenyl)-4H-3,1-benzoxazin-4-one
Conditions | Yield |
---|---|
Stage #1: 2-Methoxybenzoyl chloride; 5-Bromo-2-aminobenzoic acid With triethylamine In 1,1-dichloroethane at 20℃; for 16h; Stage #2: With sulfuric acid; acetic anhydride In 1,1-dichloroethane at 55℃; for 5h; Product distribution / selectivity; | 98% |
Stage #1: 2-Methoxybenzoyl chloride; 5-Bromo-2-aminobenzoic acid With triethylamine In dichloromethane at 10 - 20℃; for 3h; Stage #2: With oxalyl dichloride In dichloromethane for 2h; Stage #3: With acetic anhydride In dichloromethane at 50℃; for 1h; Product distribution / selectivity; | 69% |
Stage #1: 2-Methoxybenzoyl chloride; 5-Bromo-2-aminobenzoic acid With triethylamine In dichloromethane at 20℃; Stage #2: With acetic anhydride In dichloromethane at 50℃; Further stages.; |
Conditions | Yield |
---|---|
With bromine In tetrachloromethane at 20℃; Cooling with ice; | 98% |
diazomethane
5-Bromo-2-aminobenzoic acid
5-bromo-2-aminobenzoic acid methyl ester
Conditions | Yield |
---|---|
In 2-methyltetrahydrofuran; diethyl ether at 20℃; for 0.358333h; Flow reactor; | 98% |
benzoyl chloride
5-Bromo-2-aminobenzoic acid
6-bromo-2-phenyl-4H-benzo[2,3-d]-1,3-oxazin-4-one
Conditions | Yield |
---|---|
at 140℃; for 3h; | 97% |
at 140℃; for 3h; | 97% |
97% |
2,4-difluorobenzoyl chloride
5-Bromo-2-aminobenzoic acid
6-bromo-2-(2,4-difluorophenyl)-4H-benzo[d] [1,3]oxazin-4-one
Conditions | Yield |
---|---|
With triethylamine In chloroform at 20℃; for 2h; | 97% |
Stage #1: 2,4-difluorobenzoyl chloride; 5-Bromo-2-aminobenzoic acid With triethylamine In chloroform at 20℃; for 2h; Stage #2: With acetic anhydride at 50℃; for 2h; | 97% |
Stage #1: 2,4-difluorobenzoyl chloride; 5-Bromo-2-aminobenzoic acid With triethylamine In dichloromethane at 20℃; for 12h; Stage #2: With acetic anhydride at 50℃; for 2h; | 85% |
Conditions | Yield |
---|---|
With Co(hfac)2·xH2O; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Sealed tube; | 97% |
acetic anhydride
5-Bromo-2-aminobenzoic acid
2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
Conditions | Yield |
---|---|
at 150℃; for 3h; | 96% |
for 2h; Heating; | 88.2% |
at 100℃; for 2h; | 85% |
chloroformic acid ethyl ester
5-Bromo-2-aminobenzoic acid
6-bromo-2-ethoxy-(4H)-3,1-benzoxazine-4-one
Conditions | Yield |
---|---|
With pyridine at 0℃; for 1h; | 96% |
formamidine acetic acid
5-Bromo-2-aminobenzoic acid
6-bromo-4-hydroxyquinazoline
Conditions | Yield |
---|---|
at 150 - 160℃; for 0.833333h; | 96% |
at 150 - 160℃; for 0.833333h; | 96% |
at 150 - 160℃; for 0.833333h; | 94% |
orthoformic acid triethyl ester
5-Bromo-2-aminobenzoic acid
6-bromo-4H-3,1-benzoxazin-4-one
Conditions | Yield |
---|---|
at 140℃; for 4h; | 96% |
at 140℃; for 4h; | 71% |
ethyl chlorocarbonylacetate
5-Bromo-2-aminobenzoic acid
2-carboxy-4-bromomalonanilic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine In acetone Ambient temperature; | 95% |
With triethylamine In dichloromethane |
chloroacetyl chloride
5-Bromo-2-aminobenzoic acid
N-chloroacetyl-5-bromoanthranilic acid
Conditions | Yield |
---|---|
In 1,4-dioxane; N,N-dimethyl-formamide for 1.5h; | 95% |
With pyridine In benzene for 5h; Heating; | 72% |
In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; Cooling with ice; |
5-Bromo-2-aminobenzoic acid
Conditions | Yield |
---|---|
Stage #1: chloro-formamidine hydrochloride; 5-Bromo-2-aminobenzoic acid In sulfolane; dimethylsulfone at 165℃; for 0.5h; Stage #2: With ammonia; water In sulfolane; dimethylsulfone pH=7 - 8; Product distribution / selectivity; | 95% |
Stage #1: chloro-formamidine hydrochloride; 5-Bromo-2-aminobenzoic acid In sulfolane; dimethylsulfone at 165℃; for 0.5h; Stage #2: With ammonia; water In sulfolane; dimethylsulfone pH=7 - 8; Product distribution / selectivity; | 95% |
5-Bromo-2-aminobenzoic acid
bis(2-hydroxycarbonyl-4-bromophenyl) disulfide
Conditions | Yield |
---|---|
Stage #1: 5-Bromo-2-aminobenzoic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: With potassium acetate; potassium ethyl xanthogenate; potassium carbonate In water at 80℃; for 2h; Cooling; Stage #3: With dihydrogen peroxide In water at 20℃; | 95% |
Multi-step reaction with 2 steps 1.1: NaNO2; NaOH; aq. HCl / 1 h / 0 - 5 °C 1.2: EtOC(S)SK / H2O / 2 h / 20 - 80 °C 2.1: aq. H2O2 / 20 °C View Scheme |
formamide
5-Bromo-2-aminobenzoic acid
6-bromo-4-hydroxyquinazoline
Conditions | Yield |
---|---|
at 165℃; for 6h; | 95% |
at 165℃; for 6h; | 95% |
for 5h; Reflux; | 80% |
N-Methylformamide
5-Bromo-2-aminobenzoic acid
6-bromo-3-N-methylquinazoline-4(3H)-one
Conditions | Yield |
---|---|
Stage #1: N-Methylformamide; 5-Bromo-2-aminobenzoic acid at 180℃; for 12h; Stage #2: With water | 95% |
In N,N-dimethyl-formamide at 180℃; for 12h; | 95% |
at 180℃; for 12h; | 95% |
for 6.5h; Sealed tube; Reflux; | 63% |
5-Bromo-2-aminobenzoic acid
2-amino-5-bromobenzoic acid hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 24h; | 95% |
With hydrogenchloride In water at 20℃; for 24h; | 95% |
With hydrogenchloride In water for 8h; |
Ethoxycarbonyl isothiocyanate
5-Bromo-2-aminobenzoic acid
5-bromo-2-({[(ethoxycarbonyl)amino]carbonothioyl}-amino)-benzoic acid
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 5h; | 95% |
In acetonitrile at 80℃; for 5h; | 95% |
The CAS register number of 2-Amino-5-bromobenzoic acid is 5794-88-7. It also can be called as 5-Bromoanthranilic acid and the IUPAC name about this chemical is 2-amino-5-bromobenzoic acid. The molecular formula about this chemical is C7H6BrNO2 and the molecular weight is 216.03. It belongs to the following product categories which include Fine Chemical & Intermediates; Amino Acids and Derivatives; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Carboxylic Acids; Phenyls & Phenyl-Het; Benzoic acid; Organic acids; Acids & Esters; Anilines, Amides & Amines; Bromine Compounds; Carboxylic Acids; Phenyls & Phenyl-Het; Benzoic acid series and so on. This chemical can be used as organic intermediates.
Physical properties about 2-Amino-5-bromobenzoic acid are: (1)ACD/LogP: 2.37; (2)ACD/LogD (pH 5.5): 1.02; (3)ACD/LogD (pH 7.4): -0.52; (4)ACD/BCF (pH 5.5): 1.66; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 20.64; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 29.54Å2; (12)Index of Refraction: 1.672; (13)Molar Refractivity: 45.1 cm3; (14)Molar Volume: 120.4 cm3; (15)Polarizability: 17.88x10-24cm3; (16)Surface Tension: 67.9 dyne/cm; (17)Enthalpy of Vaporization: 61.86 kJ/mol; (18)Boiling Point: 342.4 °C at 760 mmHg; (19)Vapour Pressure: 2.91E-05 mmHg at 25°C.
This chemical can be produced by the bromide of Anthranilic acid.
Preparation: this chemical can be prepared by 2-amino-benzoic acid. This reaction will need reagent bromine.
Uses of 2-Amino-5-bromobenzoic acid: it can be used to produce 6-bromo-3H-quinazolin-4-one with formamide at temperature of 180 ℃.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc1cc(C(=O)O)c(N)cc1
(2)InChI: InChI=1/C7H6BrNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11)
(3)InChIKey: CUKXRHLWPSBCTI-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C7H6BrNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11)
(5)Std. InChIKey: CUKXRHLWPSBCTI-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD | oral | > 500mg/kg (500mg/kg) | National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 12, 1953. |
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