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5794-88-7

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5794-88-7 Usage

Description

2-Amino-5-bromobenzoic acid is a brominated derivative of Antharilinic Acid (A679222), characterized by its unique chemical structure that features a bromo substituent at the 5th position and an amino group at the 2nd position on the benzene ring. 2-Amino-5-bromobenzoic acid exhibits plant growth-regulator activity and is known for its applications in various fields due to its distinct properties.

Uses

Used in Pharmaceutical Industry:
2-Amino-5-bromobenzoic acid is used as a key intermediate in the synthesis of hepatitis C virus NS5b RNA polymerase inhibitors. These inhibitors play a crucial role in the development of antiviral drugs targeting the hepatitis C virus, contributing to the treatment and management of the disease.
Used in Analytical Chemistry:
2-Amino-5-bromobenzoic acid serves as a reagent in the determination of trace amounts of certain metal ions, such as cobalt, copper, nickel, and zinc. Its ability to form complexes with these metals makes it a valuable tool in analytical chemistry for detecting and quantifying these elements in various samples.
Used in Agriculture:
As a plant growth regulator, 2-Amino-5-bromobenzoic acid is utilized in the agricultural industry to modulate and control the growth and development of plants. This application can lead to improved crop yields and enhanced resistance to various environmental stresses, ultimately contributing to more efficient and sustainable agricultural practices.

Synthesis

A solution of bromine (7.2 g, 2 mL, 40 mmol) in 47 mL glacial acetic acid was added dropwise to sodium 2-aminobenzoate (6.4 g, 40 mmol) in 32 mL of glacial acetic acid at 15 °С and the mixture was stirred for 1 h at the same temperature. The product was filtered off, washed with benzene and dried in the dark. The bromobenzoic acids containing mixture (0.5 g) was added to 10 mL of boiling water followed by the addition of 1.3 mL of concentrated hydrochloric acid and hot filtration under vacuum. The insoluble material contained 2-amino-3,5-dibromobenzoic acid, whereas 2- amino-5-bromobenzoic acid precipitated upon cooling of the filtrate.?IR (suspension in nujol, cm?1 ): 3497, 3383, ?1675, 1616, 1587, 1548, 1423, 1377, 1316, 1292, 1239, 1160, 1127, 812, 748, 691.

Preparation

2-Amino-5-bromobenzoic acid is synthesized from o-aminobenzoic acid by bromination.Synthesis of 2-amino-5-bromobenzoic acid (4c, CAS: 5794-88-7) and 2-amino3,5-dibromobenzoic acid (4d, CAS: 609-85-8): A solution of bromine (7.2 g, 2 mL, 40 mmol) in 47 mL glacial acetic acid was added dropwise to sodium 2-aminobenzoate (6.4 g, 40 mmol) in 32 mL of glacial acetic acid at 15 °С and the mixture was stirred for 1 h at the same temperature. The product was filtered off, washed with benzene and dried in the dark. The bromobenzoic acids containing mixture (0.5 g) was added to 10 mL of boiling water followed by the addition of 1.3 mL of concentrated hydrochloric acid and hot filtration under vacuum. The insoluble material contained 2-amino-3,5-dibromobenzoic acid, whereas 2- amino-5-bromobenzoic acid precipitated upon cooling of the filtrate.2-Amino-5-bromobenzoic acid (4c) IR (suspension in nujol, cm?1 ): 3497, 3383, 1675, 1616, 1587, 1548, 1423, 1377, 1316, 1292, 1239, 1160, 1127, 812, 748, 691.

Check Digit Verification of cas no

The CAS Registry Mumber 5794-88-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,9 and 4 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5794-88:
(6*5)+(5*7)+(4*9)+(3*4)+(2*8)+(1*8)=137
137 % 10 = 7
So 5794-88-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H6BrNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11)/p-1

5794-88-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A11915)  2-Amino-5-bromobenzoic acid, 98%   

  • 5794-88-7

  • 5g

  • 546.0CNY

  • Detail
  • Alfa Aesar

  • (A11915)  2-Amino-5-bromobenzoic acid, 98%   

  • 5794-88-7

  • 25g

  • 1746.0CNY

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  • Alfa Aesar

  • (A11915)  2-Amino-5-bromobenzoic acid, 98%   

  • 5794-88-7

  • 100g

  • 6745.0CNY

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  • Aldrich

  • (260118)  2-Amino-5-bromobenzoicacid  97%

  • 5794-88-7

  • 260118-1G

  • 143.91CNY

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  • Aldrich

  • (260118)  2-Amino-5-bromobenzoicacid  97%

  • 5794-88-7

  • 260118-5G

  • 439.92CNY

  • Detail
  • Aldrich

  • (260118)  2-Amino-5-bromobenzoicacid  97%

  • 5794-88-7

  • 260118-25G

  • 1,407.51CNY

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5794-88-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Amino-5-bromobenzoic acid

1.2 Other means of identification

Product number -
Other names Benzoic acid, 2-amino-5-bromo-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5794-88-7 SDS

5794-88-7Synthetic route

anthranilic acid
118-92-3

anthranilic acid

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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
52727-57-8

5-bromo-2-aminobenzoic acid methyl ester

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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%
5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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;
5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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%
5-bromo-2-nitrobenzoic acid
6950-43-2

5-bromo-2-nitrobenzoic acid

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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
10075-50-0

5-bromo-1H-indole

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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
38985-79-4

5-bromo-N-acetylanthranilic acid

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
With water; sodium hydroxide for 4h; Reflux;93%
2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
19165-25-4

2-methyl-6-bromo-4H-3,1-benzoxazine-4-one

anthranilic acid
118-92-3

anthranilic acid

A

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

B

o-acetylamino-benzoic acid
89-52-1

o-acetylamino-benzoic acid

Conditions
ConditionsYield
In benzene for 6h; Heating;A 45%
B 42%
2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
19165-25-4

2-methyl-6-bromo-4H-3,1-benzoxazine-4-one

A

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

B

o-acetylamino-benzoic acid
89-52-1

o-acetylamino-benzoic acid

Conditions
ConditionsYield
With anthranilic acid In benzene for 6h; Heating;A 45%
B 42%
2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
19165-25-4

2-methyl-6-bromo-4H-3,1-benzoxazine-4-one

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

N-(2-aminophenyl)acetamide
34801-09-7

N-(2-aminophenyl)acetamide

B

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

C

2-Acetylamino-N-(2-amino-phenyl)-5-bromo-benzamide

2-Acetylamino-N-(2-amino-phenyl)-5-bromo-benzamide

Conditions
ConditionsYield
In benzene for 6h; Heating;A 28%
B 32%
C 36%
2-azido-5-bromobenzoic acid
112253-72-2

2-azido-5-bromobenzoic acid

A

5-bromo-2-oxo-3H-azepine-3-carboxylic acid

5-bromo-2-oxo-3H-azepine-3-carboxylic acid

B

5-bromo-2,1-benzisoxazole-3(1H)-one

5-bromo-2,1-benzisoxazole-3(1H)-one

C

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane; water at 25℃; for 3h; UV-irradiation;A 18%
B 34%
C 10%
anthranilic acid
118-92-3

anthranilic acid

A

2-amino-3-bromo benzoic acid
20776-51-6

2-amino-3-bromo benzoic acid

B

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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;
5-bromo-2-nitrobenzoic acid
6950-43-2

5-bromo-2-nitrobenzoic acid

A

5,5'-dibromo-2,2'-azo-di-benzoic acid

5,5'-dibromo-2,2'-azo-di-benzoic acid

B

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
With ethanol; sulfuric acid; zinc
4'-bromo-2'-methylacetanilide
24106-05-6

4'-bromo-2'-methylacetanilide

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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
859333-44-1

N,N'-(2,2,2-trichloro-ethylidene)-di-anthranilic acid

A

acetic acid
64-19-7

acetic acid

B

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
With bromine
N-chlorodiethylamine
5775-33-7

N-chlorodiethylamine

anthranilic acid
118-92-3

anthranilic acid

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
With acetic acid; potassium bromide
methanol
67-56-1

methanol

5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

A

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

B

5-bromo-2-aminobenzoic acid methyl ester
52727-57-8

5-bromo-2-aminobenzoic acid methyl ester

Conditions
ConditionsYield
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
122082-08-0

2-benzyl-4-oxo-1,2,3-benzotriazin-2-ium-1-olate

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
With hydrogen bromide In acetic acid
hydrogenchloride
7647-01-0

hydrogenchloride

5-bromoisatoic anhydride
4692-98-2

5-bromoisatoic anhydride

A

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

B

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

bromine
7726-95-6

bromine

anthranilic acid
118-92-3

anthranilic acid

acetic acid
64-19-7

acetic acid

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

bromoisatoic acid anhydride

bromoisatoic acid anhydride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride
<β.β.β-trichloro-ethyliden>-anthranilic acid

<β.β.β-trichloro-ethyliden>-anthranilic acid

A

acetic acid
64-19-7

acetic acid

B

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
With bromine
bromine
7726-95-6

bromine

anthranilic acid
118-92-3

anthranilic acid

acetic acid
64-19-7

acetic acid

A

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

B

2-amino-3,5-dibromobenzoic acid
609-85-8

2-amino-3,5-dibromobenzoic acid

hydrogenchloride
7647-01-0

hydrogenchloride

5-bromo-2-nitrobenzoic acid
6950-43-2

5-bromo-2-nitrobenzoic acid

tin

tin

A

anthranilic acid
118-92-3

anthranilic acid

B

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

N,N'-(2,2,2-trichloro-ethylidene)-di-anthranilic acid
859333-44-1

N,N'-(2,2,2-trichloro-ethylidene)-di-anthranilic acid

bromine
7726-95-6

bromine

acetic acid
64-19-7

acetic acid

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

5,5'-dibromo-2,2'-(2,2,2-trichloro-ethylidenediamino)-di-benzoic acid

5,5'-dibromo-2,2'-(2,2,2-trichloro-ethylidenediamino)-di-benzoic acid

water
7732-18-5

water

A

chloral
75-87-6

chloral

B

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

o-nitrobenzaldehyde benzylhydrazone
122100-61-2

o-nitrobenzaldehyde benzylhydrazone

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / iodosobenzene diacetate / CH2Cl2 / 4 h
2: 25percent HBr / acetic acid
View Scheme
N-(2-methylphenyl)acetamide
120-66-1

N-(2-methylphenyl)acetamide

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
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
13292-87-0

dimethyl sulfide borane

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

(2-amino-5-bromophenyl)methanol
20712-12-3

(2-amino-5-bromophenyl)methanol

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran100%
5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

(2-amino-5-bromophenyl)methanol
20712-12-3

(2-amino-5-bromophenyl)methanol

Conditions
ConditionsYield
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
2524-67-6

4-morpholino-4-yl-phenylamine

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-3-(4-morpholinophenyl)quinazolin-4(3H)-one

6-bromo-3-(4-morpholinophenyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
at 110℃;100%
isobutyryl chloride
79-30-1

isobutyryl chloride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-2-isopropyl-4H-3,1-benzoxazin-4-one
761458-01-9

6-bromo-2-isopropyl-4H-3,1-benzoxazin-4-one

Conditions
ConditionsYield
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;
aniline
62-53-3

aniline

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

2-amino-5-bromo-N-phenylbenzamide
82827-16-5

2-amino-5-bromo-N-phenylbenzamide

Conditions
ConditionsYield
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
75-04-7

ethylamine

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

2-amino-5-bromo-N-ethylbenzamide
1263377-68-9

2-amino-5-bromo-N-ethylbenzamide

Conditions
ConditionsYield
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%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-Bromo-2-propyl-benzo[d][1,3]oxazin-4-one

6-Bromo-2-propyl-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
for 1h; Heating;98%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

5-bromoisatoic anhydride
4692-98-2

5-bromoisatoic anhydride

Conditions
ConditionsYield
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
21615-34-9

2-Methoxybenzoyl chloride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-2-(2-methoxyphenyl)-4H-3,1-benzoxazin-4-one
693820-77-8

6-bromo-2-(2-methoxyphenyl)-4H-3,1-benzoxazin-4-one

Conditions
ConditionsYield
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.;
5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

2-amino-3,5-dibromobenzoic acid
609-85-8

2-amino-3,5-dibromobenzoic acid

Conditions
ConditionsYield
With bromine In tetrachloromethane at 20℃; Cooling with ice;98%
5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

5-bromo-2-aminobenzoic acid methyl ester
52727-57-8

5-bromo-2-aminobenzoic acid methyl ester

Conditions
ConditionsYield
In 2-methyltetrahydrofuran; diethyl ether at 20℃; for 0.358333h; Flow reactor;98%
benzoyl chloride
98-88-4

benzoyl chloride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-2-phenyl-4H-benzo[2,3-d]-1,3-oxazin-4-one
66387-70-0

6-bromo-2-phenyl-4H-benzo[2,3-d]-1,3-oxazin-4-one

Conditions
ConditionsYield
at 140℃; for 3h;97%
at 140℃; for 3h;97%
97%
2,4-difluorobenzoyl chloride
72482-64-5

2,4-difluorobenzoyl chloride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-2-(2,4-difluorophenyl)-4H-benzo[d] [1,3]oxazin-4-one
875270-49-8

6-bromo-2-(2,4-difluorophenyl)-4H-benzo[d] [1,3]oxazin-4-one

Conditions
ConditionsYield
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%
(4-chlorophenyl)phenylmethanol
119-56-2

(4-chlorophenyl)phenylmethanol

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

5-bromo-2-{[(4-chlorophenyl)(phenyl)methyl]amino}benzoic acid

5-bromo-2-{[(4-chlorophenyl)(phenyl)methyl]amino}benzoic acid

Conditions
ConditionsYield
With Co(hfac)2·xH2O; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Sealed tube;97%
acetic anhydride
108-24-7

acetic anhydride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

2-methyl-6-bromo-4H-3,1-benzoxazine-4-one
19165-25-4

2-methyl-6-bromo-4H-3,1-benzoxazine-4-one

Conditions
ConditionsYield
at 150℃; for 3h;96%
for 2h; Heating;88.2%
at 100℃; for 2h;85%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-2-ethoxy-(4H)-3,1-benzoxazine-4-one
116991-07-2

6-bromo-2-ethoxy-(4H)-3,1-benzoxazine-4-one

Conditions
ConditionsYield
With pyridine at 0℃; for 1h;96%
formamidine acetic acid
3473-63-0

formamidine acetic acid

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-4-hydroxyquinazoline
32084-59-6

6-bromo-4-hydroxyquinazoline

Conditions
ConditionsYield
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
122-51-0

orthoformic acid triethyl ester

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-4H-3,1-benzoxazin-4-one
449185-77-7

6-bromo-4H-3,1-benzoxazin-4-one

Conditions
ConditionsYield
at 140℃; for 4h;96%
at 140℃; for 4h;71%
ethyl chlorocarbonylacetate
36239-09-5

ethyl chlorocarbonylacetate

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

2-carboxy-4-bromomalonanilic acid ethyl ester
113117-47-8

2-carboxy-4-bromomalonanilic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In acetone Ambient temperature;95%
With triethylamine In dichloromethane
chloroacetyl chloride
79-04-9

chloroacetyl chloride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

N-chloroacetyl-5-bromoanthranilic acid
155104-20-4

N-chloroacetyl-5-bromoanthranilic acid

Conditions
ConditionsYield
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;
chloro-formamidine hydrochloride

chloro-formamidine hydrochloride

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

2-amino-4-hydroxy-6-bromoquinazoline

2-amino-4-hydroxy-6-bromoquinazoline

Conditions
ConditionsYield
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
5794-88-7

5-Bromo-2-aminobenzoic acid

bis(2-hydroxycarbonyl-4-bromophenyl) disulfide
100540-90-7

bis(2-hydroxycarbonyl-4-bromophenyl) disulfide

Conditions
ConditionsYield
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
5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-4-hydroxyquinazoline
32084-59-6

6-bromo-4-hydroxyquinazoline

Conditions
ConditionsYield
at 165℃; for 6h;95%
at 165℃; for 6h;95%
for 5h; Reflux;80%
N-Methylformamide
123-39-7

N-Methylformamide

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

6-bromo-3-N-methylquinazoline-4(3H)-one
57573-59-8

6-bromo-3-N-methylquinazoline-4(3H)-one

Conditions
ConditionsYield
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
5794-88-7

5-Bromo-2-aminobenzoic acid

2-amino-5-bromobenzoic acid hydrochloride
74189-16-5

2-amino-5-bromobenzoic acid hydrochloride

Conditions
ConditionsYield
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
16182-04-0

Ethoxycarbonyl isothiocyanate

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

5-bromo-2-({[(ethoxycarbonyl)amino]carbonothioyl}-amino)-benzoic acid
1189797-80-5

5-bromo-2-({[(ethoxycarbonyl)amino]carbonothioyl}-amino)-benzoic acid

Conditions
ConditionsYield
In acetonitrile at 80℃; for 5h;95%
In acetonitrile at 80℃; for 5h;95%

5794-88-7Relevant articles and documents

Discovery of Novel Tacrine-Pyrimidone Hybrids as Potent Dual AChE/GSK-3 Inhibitors for the Treatment of Alzheimer's Disease

Yao, Hong,Uras, Giuseppe,Zhang, Pengfei,Xu, Shengtao,Yin, Ying,Liu, Jie,Qin, Shuai,Li, Xinuo,Allen, Stephanie,Bai, Renren,Gong, Qi,Zhang, Haiyan,Zhu, Zheying,Xu, Jinyi

, p. 7483 - 7506 (2021/06/28)

Based on a multitarget strategy, a series of novel tacrine-pyrimidone hybrids were identified for the potential treatment of Alzheimer's disease (AD). Biological evaluation results demonstrated that these hybrids exhibited significant inhibitory activities toward acetylcholinesterase (AChE) and glycogen synthase kinase 3 (GSK-3). The optimal compound 27g possessed excellent dual AChE/GSK-3 inhibition both in terms of potency and equilibrium (AChE: IC50 = 51.1 nM; GSK-3β: IC50 = 89.3 nM) and displayed significant amelioration on cognitive deficits in scopolamine-induced amnesia mice and efficient reduction against phosphorylation of tau protein on Ser-199 and Ser-396 sites in glyceraldehyde (GA)-stimulated differentiated SH-SY5Y cells. Furthermore, compound 27g exhibited eligible pharmacokinetic properties, good kinase selectivity, and moderate neuroprotection against GA-induced reduction in cell viability and neurite damage in SH-SY5Y-derived neurons. The multifunctional profiles of compound 27g suggest that it deserves further investigation as a promising lead for the prospective treatment of AD.

Quinazolinone Compound and Application Thereof

-

Paragraph 0101-0102; 0104, (2020/11/27)

The present invention relates to a series of quinazolinone compounds and applications thereof as PI3Kα inhibitors. In particular, the present invention relates to a compound shown in formula (I) and a tautomer or pharmaceutically acceptable salt thereof.

Quinazoline based 1,3,5-triazine derivatives as cancer inhibitors by impeding the phosphorylated RET tyrosine kinase pathway: Design, synthesis, docking, and QSAR study

Pathak, Prateek,Naumovich, Vladislav,Grishina, Maria,Shukla, Parjanya Kumar,Verma, Amita,Potemkin, Vladimir

, (2019/08/16)

The present research focused on designing a quinazoline skeleton, framed via 1,3,5-triazine derivatives (QBT) through field mapping and alignment studies. The QBT derivatives were synthesized via time- and cost-effective protocol. The 3D-QSAR study, computational physicochemical properties, and ADME calculation of the derivatives were performed to establish the affinity towards the biological system. Molecular docking in the adenosine triphosphate binding site of the RET tyrosine kinase domain (PDB ID: 7IVU) was studied to elucidate vital structural residues necessary for bioactivity. The derivatives were evaluated for anticancer potency against TPC-1 cells (thyroid cancer), MCF-7 cells (breast cancer), and one normal cell line (human foreskin fibroblasts) via 3-(4,5-dimethylthiazol-2-y1)-2,5-diphenyltetrazolium bromide assay followed by an in ovo CAM assay. The entire series of derivatives (8a–o) showed mild to significant anticancer potency against the selected cancer cell lines.

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