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616-79-5 Usage

Chemical Properties

BRIGHT YELLOW POWDER

Uses

2-Amino-5-nitrobenzoic acid, is used as an intermediate for dyes and pharmaceuticals.

Definition

ChEBI: An aminobenzoic acid in which the the amino group is ortho- to the carboxylic acid group, and which is substituted para- to the amino group by a nitro group.

Check Digit Verification of cas no

The CAS Registry Mumber 616-79-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 6 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 616-79:
(5*6)+(4*1)+(3*6)+(2*7)+(1*9)=75
75 % 10 = 5
So 616-79-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N2O4/c8-6-2-1-4(9(12)13)3-5(6)7(10)11/h1-3H,8H2,(H,10,11)/p-1

616-79-5 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (A10426)  2-Amino-5-nitrobenzoic acid, 98%   

  • 616-79-5

  • 10g

  • 622.0CNY

  • Detail
  • Alfa Aesar

  • (A10426)  2-Amino-5-nitrobenzoic acid, 98%   

  • 616-79-5

  • 50g

  • 2393.0CNY

  • Detail
  • Alfa Aesar

  • (A10426)  2-Amino-5-nitrobenzoic acid, 98%   

  • 616-79-5

  • 250g

  • 9894.0CNY

  • Detail
  • Aldrich

  • (382116)  2-Amino-5-nitrobenzoicacid  95%

  • 616-79-5

  • 382116-5G

  • 638.12CNY

  • Detail
  • Aldrich

  • (382116)  2-Amino-5-nitrobenzoicacid  95%

  • 616-79-5

  • 382116-25G

  • 2,265.12CNY

  • Detail
  • Aldrich

  • (340693)  2-Amino-5-nitrobenzoicacid  technical grade, 90%

  • 616-79-5

  • 340693-25G

  • 889.20CNY

  • Detail

616-79-5SDS

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 5-nitroanthranilic acid

1.2 Other means of identification

Product number -
Other names 1-amino-2-carboxy-4-nitrobenzene

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:616-79-5 SDS

616-79-5Synthetic route

5-nitroisatin
611-09-6

5-nitroisatin

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
Stage #1: 5-nitroisatin With potassium hydroxide; dihydrogen peroxide for 0.5h; cooling;
Stage #2: With sulfuric acid at 20℃; pH=1 - 2;
98%
Stage #1: 5-nitroisatin With sodium hydroxide at 10℃; for 3h;
Stage #2: With dihydrogen peroxide
89.8%
With dihydrogen peroxide; sodium hydroxide at 10℃; for 3h;76.7%
With dihydrogen peroxide; sodium hydroxide
2-(4,5-dihydrooxazol-2-yl)-4-nitroaniline

2-(4,5-dihydrooxazol-2-yl)-4-nitroaniline

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
Stage #1: 2-(4,5-dihydrooxazol-2-yl)-4-nitroaniline With hydrogenchloride In water at 100℃; for 2h; Sealed tube;
Stage #2: With sodium hydroxide In methanol; water at 100℃; for 1h;
81%
5-nitroanthranilonitrile
17420-30-3

5-nitroanthranilonitrile

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With sodium hydroxide; acetic acid for 6h; Heating;80%
2-bromo-5-nitrobenzoic acid
943-14-6

2-bromo-5-nitrobenzoic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
Stage #1: 2-bromo-5-nitrobenzoic acid With copper(l) iodide; sodium azide; ethanol; caesium carbonate at 20 - 95℃; Inert atmosphere; Sealed tube;
Stage #2: With hydrogenchloride In water pH=2 - 3;
79%
With ammonium hydroxide at 140 - 150℃;
3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With 4-amino-1,2,4-triazole; potassium tert-butylate In dimethyl sulfoxide for 4h; Ambient temperature;60%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h;18%
4-nitrophthalic anhydride
5466-84-2

4-nitrophthalic anhydride

A

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

B

4-Nitroanthranilic acid
619-17-0

4-Nitroanthranilic acid

Conditions
ConditionsYield
With ammonium hydroxide Behandeln des entstandenen Gemisches mit alkal. Natriumhypochlorit-Loesung;
2-fluoro-5-nitrobenzoic acid
7304-32-7

2-fluoro-5-nitrobenzoic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With ammonia at 130 - 140℃;
4-nitrophthalic amide
13138-53-9

4-nitrophthalic amide

A

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

B

4-Nitroanthranilic acid
619-17-0

4-Nitroanthranilic acid

Conditions
ConditionsYield
With alkaline aqueous potassium hypobromite
N-(2-formyl-4-nitrophenyl)acetamide
91538-60-2

N-(2-formyl-4-nitrophenyl)acetamide

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With potassium hydroxide
N-(2-formyl-4-nitrophenyl)acetamide
91538-60-2

N-(2-formyl-4-nitrophenyl)acetamide

A

(2-amino-5-nitrophenyl)methanol
77242-30-9

(2-amino-5-nitrophenyl)methanol

B

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With potassium hydroxide at 0℃;
2-ethoxy-5-nitro-benzoic acid ethyl ester
80074-90-4

2-ethoxy-5-nitro-benzoic acid ethyl ester

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With ammonia at 130 - 160℃; Kochen des Produkts mit Barytwasser;
5-nitro-2-(N'-nitro-ureido)-benzoic acid
98437-11-7

5-nitro-2-(N'-nitro-ureido)-benzoic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

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

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

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide
5-nitroindole
6146-52-7

5-nitroindole

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With chromium(VI) oxide
5-nitro-N-acetylanthranilic acid
3558-18-7

5-nitro-N-acetylanthranilic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With hydrogenchloride
With potassium hydroxide
With sulfuric acid; acetic acid
With hydrogenchloride Hydrolysis;
5-nitro-2-(trifluoroacetylamino)benzoic acid
88785-76-6

5-nitro-2-(trifluoroacetylamino)benzoic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With potassium chloride; water In acetonitrile at 70℃; Rate constant; also with D2O;
With Cu(N,N,N'-trimethyl-N'-tetradecylethylenediamine)Cl2 In acetonitrile Rate constant; also in pure water; also copper acetate and nitrate salts, cetyltrimethylammonium bromide or Triton X-100 as surfactants, pH 7.0, var. concentration of reagents;
5-nitro-2-(trifluoroacetylamino)benzoic acid
88785-76-6

5-nitro-2-(trifluoroacetylamino)benzoic acid

A

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

B

trifluoroacetic acid
76-05-1

trifluoroacetic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 50.8℃; Rate constant; Mechanism; Kinetics; var. pH, var. reagents and temperatures;
With water; C21H46N2*CuCl2 at 31℃; Mechanism; Rate constant; free Tris/Tris HCl buffer, also with cetyltrimethylammonium bromide, influence of pH, NaCl, Tris buffer concentration;
5-Nitro-phthalamic acid
65911-48-0

5-Nitro-phthalamic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With sodium hypochlorite
3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

A

4-amino-3-nitrobenzoic acid
1588-83-6

4-amino-3-nitrobenzoic acid

B

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide Ambient temperature; Yield given. Yields of byproduct given;
2-chloro-5-nitrobenzoic acid
2516-96-3

2-chloro-5-nitrobenzoic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With ammonia; potassium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 150℃; for 1h;
With ammonium hydroxide; copper(l) iodide at 200℃; for 6.5h; Autoclave; Green chemistry;
3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

A

3-nitroanthranilic acid
606-18-8

3-nitroanthranilic acid

B

4-amino-3-nitrobenzoic acid
1588-83-6

4-amino-3-nitrobenzoic acid

C

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
With O-Methylhydroxylamin; potassium tert-butylate; copper diacetate In 1,2-dimethoxyethane at 20℃; Substitution; Amination;
hydrogenchloride
7647-01-0

hydrogenchloride

6-nitrobenzo[d][1,2,3]triazin-4(3H)-one
91532-29-5

6-nitrobenzo[d][1,2,3]triazin-4(3H)-one

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-nitrobenzo[d][1,2,3]triazin-4(3H)-one
91532-29-5

6-nitrobenzo[d][1,2,3]triazin-4(3H)-one

concentrated KOH-solution

concentrated KOH-solution

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-nitroquinolin-2-ol
64495-55-2

6-nitroquinolin-2-ol

permanganate

permanganate

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-nitro-[4]quinolylamine
116632-55-4

6-nitro-[4]quinolylamine

permanganate

permanganate

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-nitrobenzo[d][1,2,3]triazin-4(3H)-one
91532-29-5

6-nitrobenzo[d][1,2,3]triazin-4(3H)-one

sulfuric acid
7664-93-9

sulfuric acid

A

5-nitrosalicylic acid
96-97-9

5-nitrosalicylic acid

B

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

Conditions
ConditionsYield
erst Produkt1,dann Produkt2;
hydrogenchloride
7647-01-0

hydrogenchloride

6-nitroisatoic anhydride
4693-02-1

6-nitroisatoic anhydride

A

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

methylammonium carbonate

B

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-nitroisatoic anhydride
4693-02-1

6-nitroisatoic anhydride

water
7732-18-5

water

A

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

methylammonium carbonate

B

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

4-nitrophthalimide
89-40-7

4-nitrophthalimide

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

calcium chloride

calcium chloride

A

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

B

4-Nitroanthranilic acid
619-17-0

4-Nitroanthranilic acid

6-nitro-3-phenylbenzo[d][1,2,3]triazin-4(3H)-one
60041-99-8

6-nitro-3-phenylbenzo[d][1,2,3]triazin-4(3H)-one

concentrated KOH-solution

concentrated KOH-solution

A

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

B

phenol
108-95-2

phenol

C

nitrogen

nitrogen

methanol
67-56-1

methanol

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

5-nitroanthranilic acid methyl ester
3816-62-4

5-nitroanthranilic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 72h; Inert atmosphere;100%
With sulfuric acid at 80℃; for 3h;96.6%
With chloro-trimethyl-silane for 12h; Reflux;93.2%
ethereal diazomethane

ethereal diazomethane

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

5-nitroanthranilic acid methyl ester
3816-62-4

5-nitroanthranilic acid methyl ester

Conditions
ConditionsYield
In methanol100%
urea
57-13-6

urea

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-Nitro-1H-quinazoline-2,4-dione
32618-85-2

6-Nitro-1H-quinazoline-2,4-dione

Conditions
ConditionsYield
In water at 200℃; for 2h; Inert atmosphere;100%
In water at 100 - 160℃;99%
at 160℃;99%
2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

4-Chlorobutanoyl chloride
4635-59-0

4-Chlorobutanoyl chloride

2-(4-chlorobutanamido)-5-nitrobenzoic acid

2-(4-chlorobutanamido)-5-nitrobenzoic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;100%
5-Chlorovaleroyl chloride
1575-61-7

5-Chlorovaleroyl chloride

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

2-(5-chloropentanamido)-5-nitrobenzoic acid

2-(5-chloropentanamido)-5-nitrobenzoic acid

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
2-(2-chloroethoxy)acetyl chloride
39229-33-9

2-(2-chloroethoxy)acetyl chloride

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

2-(2-(2-chloroethoxy)acetamido)-5-nitrobenzoic acid

2-(2-(2-chloroethoxy)acetamido)-5-nitrobenzoic acid

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 4h; Inert atmosphere;100%
2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

(2-amino-5-nitrophenyl)methanol
77242-30-9

(2-amino-5-nitrophenyl)methanol

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 0 - 30℃; for 23h; Inert atmosphere;98%
Stage #1: 2-amino-5-nitro-benzoic acid With borane-THF In tetrahydrofuran for 1h; Reflux;
Stage #2: With hydrogenchloride In ethyl acetate
98%
With borane-THF In tetrahydrofuran at 0 - 23℃;73%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
Multi-step reaction with 2 steps
1: sulfuric acid / 60 h / 15 - 90 °C
2: lithium borohydride / tetrahydrofuran / 21 h / 0 - 10 °C
View Scheme
2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

2-chloro-3-(4-chlorophenyl)-1,8-naphthyridine
439277-55-1

2-chloro-3-(4-chlorophenyl)-1,8-naphthyridine

C21H11ClN4O3

C21H11ClN4O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0583333h; Microwave irradiation; Green chemistry;96%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

2-(2-chloroacetamido)-5-nitrobenzoic acid
135590-27-1

2-(2-chloroacetamido)-5-nitrobenzoic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;95%
2-chloro-3-(4-fluorophenyl)-1,8-naphthyridine
1082429-86-4

2-chloro-3-(4-fluorophenyl)-1,8-naphthyridine

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

C21H11FN4O3

C21H11FN4O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0583333h; Microwave irradiation; Green chemistry;95%
C15H8ClF3N2
1191445-84-7

C15H8ClF3N2

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

C22H11F3N4O3

C22H11F3N4O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0583333h; Microwave irradiation; Green chemistry;94%
2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

2-chloro-3-(4-methoxyphenyl)-1,8-naphthyridine
474266-27-8

2-chloro-3-(4-methoxyphenyl)-1,8-naphthyridine

C22H14N4O4

C22H14N4O4

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0416667h; Microwave irradiation; Green chemistry;94%
benzoxazin-3-one

benzoxazin-3-one

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

p-tert-butyl benzoyl chloride
1710-98-1

p-tert-butyl benzoyl chloride

6-nitro-2-(4-t-butylphenyl)-4H-3,1-benzoxazin-4-one
117145-60-5

6-nitro-2-(4-t-butylphenyl)-4H-3,1-benzoxazin-4-one

Conditions
ConditionsYield
With pyridine In diethyl ether; dichloromethane; N,N-dimethyl-formamide93.6%
ethylamine
75-04-7

ethylamine

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

2-amino-N-ethyl-5-nitrobenzamide
32212-31-0

2-amino-N-ethyl-5-nitrobenzamide

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 tetrahydrofuran; N,N-dimethyl-formamide at 0 - 35℃; for 24h;93.32%
With diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran; N,N-dimethyl-formamide at 20 - 25℃; for 24h;93.32%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

(E)-methyl 2-((dimethylamino)methyleneamino)-5-nitrobenzoate
1427534-33-5

(E)-methyl 2-((dimethylamino)methyleneamino)-5-nitrobenzoate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 105℃; for 0.25h; Microwave irradiation;93%
C15H11ClN2

C15H11ClN2

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

C22H14N4O3

C22H14N4O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0416667h; Microwave irradiation; Green chemistry;93%
aniline
62-53-3

aniline

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

trialkyl orthoformate

trialkyl orthoformate

6-nitro-3-phenyl-4(3H)-quinazolinone
964-25-0

6-nitro-3-phenyl-4(3H)-quinazolinone

Conditions
ConditionsYield
With silicagel supported phosphomolybdic acid at 20℃; for 0.166667h; Inert atmosphere;92%
phosgene
75-44-5

phosgene

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-nitroisatoic anhydride
4693-02-1

6-nitroisatoic anhydride

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 20℃; for 0.5h;92%
1,1-dimethoxyethane
534-15-6

1,1-dimethoxyethane

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

5-nitroanthranilic acid methyl ester
3816-62-4

5-nitroanthranilic acid methyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 0.25h; Inert atmosphere; Microwave irradiation;92%
L-proline methyl ester monohydrochloride
2133-40-6

L-proline methyl ester monohydrochloride

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

(S)-(+)-1,2,3,11a-tetrahydro-7-nitro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione
50424-48-1

(S)-(+)-1,2,3,11a-tetrahydro-7-nitro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Conditions
ConditionsYield
Stage #1: 2-amino-5-nitro-benzoic acid With hydrogenchloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; triethylamine In tetrahydrofuran; water; N,N-dimethyl-formamide for 0.25h;
Stage #2: L-proline methyl ester monohydrochloride In tetrahydrofuran; water; N,N-dimethyl-formamide for 16h;
92%
formamidine acetic acid
3473-63-0

formamidine acetic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-nitroquinazolone
6943-17-5

6-nitroquinazolone

Conditions
ConditionsYield
In 2-methoxy-ethanol at 124℃; for 1h; Wavelength; Microwave irradiation;92%
In ethanol at 60℃;82%
With 2-methoxy-ethanol Reflux;78.5%
In 2-methoxy-ethanol Reflux;
In 2-methoxy-ethanol Reflux;
2-chloro-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine
1191445-85-8

2-chloro-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

C22H11F3N4O3

C22H11F3N4O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.05h; Microwave irradiation; Green chemistry;92%
2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

2-chloro-3-2-(2-chlorophenyl)-1,8-naphthyridine
845533-62-2

2-chloro-3-2-(2-chlorophenyl)-1,8-naphthyridine

C21H11ClN4O3

C21H11ClN4O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.05h; Microwave irradiation; Green chemistry;92%
2-chloro-3-(2-fluorophenyl)-1,8-naphthyridine
1082475-88-4

2-chloro-3-(2-fluorophenyl)-1,8-naphthyridine

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

C21H11FN4O3

C21H11FN4O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0416667h; Microwave irradiation; Green chemistry;92%
2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

2-chloro-3-phenyl-1,8-naphthyridine
33760-73-5

2-chloro-3-phenyl-1,8-naphthyridine

6-phenyl-10-nitro-12H-[1,8]naphthyridino[2,1-b]quinazolin-12-one

6-phenyl-10-nitro-12H-[1,8]naphthyridino[2,1-b]quinazolin-12-one

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0333333h; Microwave irradiation; Green chemistry;92%
4-pentynoic acid
6089-09-4

4-pentynoic acid

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

3a-methyl-7-nitro-3,3a-dihydro-1H-benzo[d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione
1227624-57-8

3a-methyl-7-nitro-3,3a-dihydro-1H-benzo[d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione

Conditions
ConditionsYield
With Echavarren's catalyst In 1,1-dichloroethane at 120℃; for 12h; Sealed vial;91%
C15H11ClN2O

C15H11ClN2O

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

C22H14N4O4

C22H14N4O4

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0416667h; Microwave irradiation; Green chemistry;91%
2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

6-nitroquinazolone
6943-17-5

6-nitroquinazolone

Conditions
ConditionsYield
at 170℃; for 4h;90%
at 150℃; for 0.333333h; Niementowski reaction; microwave-assisted; microwave irradiation;87%
at 150℃; for 0.666667h; Niementowski condensation; microwave irradiation;87%
2-chloro-3-(3-fluorophenyl)-1,8-naphthyridine
1082349-60-7

2-chloro-3-(3-fluorophenyl)-1,8-naphthyridine

2-amino-5-nitro-benzoic acid
616-79-5

2-amino-5-nitro-benzoic acid

C21H11FN4O3

C21H11FN4O3

Conditions
ConditionsYield
With N,N-dimethyl-formamide In neat (no solvent) for 0.05h; Microwave irradiation; Green chemistry;90%

616-79-5Relevant articles and documents

The cleavage of heterocyclic compounds in organic synthesis II [1] use of 5-nitroisatine for synthesis of various nitrogenous heterocycles

Hlavac, Jan,Soural, Miroslav,Hradil, Pavel,Frysova, Iveta,Slouka, Jan

, p. 633 - 636 (2004)

The reactions of 5-nitroisatine were studied with nucleophiles like heterocyclic amines and alkaline hydroxide. With the use of alkaline hydroxide it was converted into 2-amino-5-nitrophenylglyoxylic acid 2, with piperidine, morpholine and carbethoxypiperazine to its amides 4a-4c or by oxidation to 5-nitroanthranilic acid 7. This acid was used for synthesis of 3-hydroxy-6-nitro-2-phenyl-1H-quinolin-4-one 10. Semicarbazone of 5-nitroisatine 11 was converted to 5-(2-amino-5-nitrophenyl)-2,3,4,5-tetrahydro-1,2,4- triazine-3,5-dione 12. Cyclocondensation of this compound to afford 8-nitro-2,3-dihydro-5H-[1,2,4]triazino-[5,6-b]indol-3-one 13 was unsuccessful.

Isoxazole formamido-4 (3H)-quinazolinone derivative as well as synthesis method and application thereof

-

, (2021/06/06)

The invention relates to a 6-(isoxazolyl-3-formamido)-4 (3H)-quinazolinone derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituent groups. The invention discloses structures and synthesis methods of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activity of protein tyrosine phosphatase, and the compounds can be further developed into drugs for treating Alzheimer's disease.

A green and recyclable ligand-free copper (I) catalysis system for amination of halonitrobenzenes in aqueous ammonia solution

Li, Yan,Shi, Ruhui,Lin, Weiwei,Cheng, Haiyang,Zhang, Chao,Arai, Masahiko,Zhao, Fengyu

, (2019/06/18)

The amination of halonitrobenzenes is an important reaction to produce the corresponding nitroanilines. Direct amination of p-chloronitrobenzene (p-CNB) to p-nitroaniline (p-NAN) with aqueous NH3 solution was investigated over various transition metal salts in the absence of ligand, inorganic base and organic solvent. It was found that CuI is the most effective catalyst with respect to p-CNB conversion, p-NAN selectivity (≈ 100%) and the post-reaction separation and recycling. A high p-NAN yield of 97% could be obtained at 200 °C in 6.5 h with molar ratios of NH3/p-CNB and CuI/p-CNB of 21 and 0.1, respectively. A possible reaction mechanism was proposed, in which NH3 was not only a substrate but also a ligand to coordinate with CuI and formed a water-soluble Cu complex, and then it started the catalytic cycle. The influence of reaction variables such as NH3 concentration, CuI concentration, temperature and time on the p-CNB conversion and the p-NAN selectivity was examined. At room temperature the desired product of p-NAN is insoluble in water but the Cu complex catalyst is water-soluble and so the aqueous phase including the catalyst and NH3 can be easily separated and reused for the subsequent reaction runs. The green and sustainable system is effective for the conversion of diverse halonitrobenzenes to nitroanilines.

Nickel-Catalyzed Regioselective C–H Bond Mono- and Bis-Nitration of Aryloxazolines with tert-Butyl Nitrite as Nitro Source

Wan, Li,Qiao, Kai,Yuan, Xin,Zheng, Ming-Wei,Fan, Bing-Bing,Di, Zhe Chen,Zhang, Dong,Fang, Zheng,Guo, Kai

, p. 2596 - 2604 (2017/08/16)

An efficient and regioselective nickel-catalyzed remote C–H nitration of 2-aryloxazoline amides using the non-corrosive tert-butyl nitrite (TBN) as nitro source has been developed. The protocol makes use of inexpensive nickel salts as catalysts and delivers the corresponding products in excellent yields. Notably, bis-nitration products were obtained by simply increasing the amount of tert-butyl nitrite. This reaction proceeds in air and features excellent functional group compatibility, broad substrate scope and is suitable for gram-scale synthesis. (Figure presented.).

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