2-Amino-5-nitrobenzoic acid supplier

Name
2-Amino-5-nitrobenzoic acid
EINECS 210-493-6
CAS No. 616-79-5
Article Data54
CAS DataBase
Density 1.568 g/cm³
Solubility Insoluble in water
Melting Point 270 °C (dec.)(lit.)
Formula C₇H₆N₂O₄
Boiling Point 437.9 °C at 760 mmHg
Molecular Weight 182.136
Flash Point 218.6 °C
Transport Information
Appearance bright yellow powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Anthranilic acid, 5-nitro- (6CI,7CI,8CI);5-Nitroanthranilic acid;
PSA 109.14000
LogP 1.97960

Synthetic route

: 611-09-6
5-nitroisatin

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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%

: 17420-30-3
5-nitroanthranilonitrile

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

Conditions

Conditions	Yield
With sodium hydroxide; acetic acid for 6h; Heating;	80%

: 943-14-6
2-bromo-5-nitrobenzoic acid

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

Conditions

Conditions	Yield
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℃;

: 121-92-6
3-nitrobenzoic acid

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

Conditions

Conditions	Yield
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%

: 5466-84-2
4-nitrophthalic anhydride

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

B: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With ammonium hydroxide Behandeln des entstandenen Gemisches mit alkal. Natriumhypochlorit-Loesung;

: 7304-32-7
2-fluoro-5-nitrobenzoic acid

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

Conditions

Conditions	Yield
With ammonia at 130 - 140℃;

: 13138-53-9
4-nitrophthalic amide

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

B: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With alkaline aqueous potassium hypobromite

: 91538-60-2
N-(2-formyl-4-nitrophenyl)acetamide

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

Conditions

Conditions	Yield
With potassium hydroxide

: 91538-60-2
N-(2-formyl-4-nitrophenyl)acetamide

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

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

Conditions

Conditions	Yield
With potassium hydroxide at 0℃;

: 80074-90-4
2-ethoxy-5-nitro-benzoic acid ethyl ester

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

Conditions

Conditions	Yield
With ammonia at 130 - 160℃; Kochen des Produkts mit Barytwasser;

: 98437-11-7
5-nitro-2-(N'-nitro-ureido)-benzoic acid

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

Conditions

Conditions	Yield
With water

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

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

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

: 6146-52-7
5-nitroindole

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

Conditions

Conditions	Yield
With chromium(VI) oxide

: 3558-18-7
5-nitro-N-acetylanthranilic acid

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

Conditions

Conditions	Yield
With hydrogenchloride
With potassium hydroxide
With sulfuric acid; acetic acid
With hydrogenchloride Hydrolysis;

: 88785-76-6
5-nitro-2-(trifluoroacetylamino)benzoic acid

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

Conditions

Conditions	Yield
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;

: 88785-76-6
5-nitro-2-(trifluoroacetylamino)benzoic acid

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

B: 76-05-1
trifluoroacetic acid

Conditions

Conditions	Yield
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;

: 65911-48-0
5-Nitro-phthalamic acid

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

Conditions

Conditions	Yield
With sodium hypochlorite

: 121-92-6
3-nitrobenzoic acid

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

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

Conditions

Conditions	Yield
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide Ambient temperature; Yield given. Yields of byproduct given;

: 2516-96-3
2-chloro-5-nitrobenzoic acid

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

Conditions

Conditions	Yield
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;

: 121-92-6
3-nitrobenzoic acid

A: 606-18-8
3-nitroanthranilic acid

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

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

Conditions

Conditions	Yield
With O-Methylhydroxylamin; potassium tert-butylate; copper diacetate In 1,2-dimethoxyethane at 20℃; Substitution; Amination;

...Expand

: 7647-01-0
hydrogenchloride

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

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

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

concentrated KOH-solution: concentrated KOH-solution

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

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

permanganate: permanganate

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

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

permanganate: permanganate

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

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

: 7664-93-9
sulfuric acid

A: 96-97-9
5-nitrosalicylic acid

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

Conditions

Conditions	Yield
erst Produkt1,dann Produkt2;

...Expand

: 7647-01-0
hydrogenchloride

: 4693-02-1
6-nitroisatoic anhydride

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

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

...Expand

: 4693-02-1
6-nitroisatoic anhydride

: 7732-18-5
water

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

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

...Expand

: 89-40-7
4-nitrophthalimide

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

calcium chloride: calcium chloride

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

B: 619-17-0
4-Nitroanthranilic acid

...Expand

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

concentrated KOH-solution: concentrated KOH-solution

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

B: 108-95-2
phenol

C nitrogen: nitrogen

...Expand

: 67-56-1
methanol

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

: 3816-62-4
5-nitroanthranilic acid methyl ester

Conditions

Conditions	Yield
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

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

: 3816-62-4
5-nitroanthranilic acid methyl ester

Conditions

Conditions	Yield
In methanol	100%

: 57-13-6
urea

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

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

Conditions

Conditions	Yield
In water at 200℃; for 2h; Inert atmosphere;	100%
In water at 100 - 160℃;	99%
at 160℃;	99%

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

: 4635-59-0
4-Chlorobutanoyl chloride

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	100%

: 1575-61-7
5-Chlorovaleroyl chloride

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

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

Conditions

Conditions	Yield
In dichloromethane at 20℃;	100%

: 39229-33-9
2-(2-chloroethoxy)acetyl chloride

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

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

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 4h; Inert atmosphere;	100%

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

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

Conditions

Conditions	Yield
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

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

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

: C21H11ClN4O3

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0583333h; Microwave irradiation; Green chemistry;	96%

: 79-04-9
chloroacetyl chloride

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

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	95%

: 1082429-86-4
2-chloro-3-(4-fluorophenyl)-1,8-naphthyridine

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

: C21H11FN4O3

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0583333h; Microwave irradiation; Green chemistry;	95%

: 1191445-84-7
C15H8ClF3N2

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

: C22H11F3N4O3

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0583333h; Microwave irradiation; Green chemistry;	94%

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

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

: C22H14N4O4

Conditions

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

: benzoxazin-3-one

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

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

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

Conditions

Conditions	Yield
With pyridine In diethyl ether; dichloromethane; N,N-dimethyl-formamide	93.6%

...Expand

: 75-04-7
ethylamine

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

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

Conditions

Conditions	Yield
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%

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

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

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

Conditions

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

: C15H11ClN2

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

: C22H14N4O3

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0416667h; Microwave irradiation; Green chemistry;	93%

: 62-53-3
aniline

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

trialkyl orthoformate: trialkyl orthoformate

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

Conditions

Conditions	Yield
With silicagel supported phosphomolybdic acid at 20℃; for 0.166667h; Inert atmosphere;	92%

...Expand

: 75-44-5
phosgene

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

: 4693-02-1
6-nitroisatoic anhydride

Conditions

Conditions	Yield
In tetrahydrofuran; toluene at 20℃; for 0.5h;	92%

: 534-15-6
1,1-dimethoxyethane

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

: 3816-62-4
5-nitroanthranilic acid methyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.25h; Inert atmosphere; Microwave irradiation;	92%

: 2133-40-6
L-proline methyl ester monohydrochloride

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

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

Conditions

Conditions	Yield
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%

: 3473-63-0
formamidine acetic acid

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

: 6943-17-5
6-nitroquinazolone

Conditions

Conditions	Yield
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;

: 1191445-85-8
2-chloro-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine

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

: C22H11F3N4O3

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.05h; Microwave irradiation; Green chemistry;	92%

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

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

: C21H11ClN4O3

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.05h; Microwave irradiation; Green chemistry;	92%

: 1082475-88-4
2-chloro-3-(2-fluorophenyl)-1,8-naphthyridine

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

: C21H11FN4O3

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0416667h; Microwave irradiation; Green chemistry;	92%

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

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

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

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0333333h; Microwave irradiation; Green chemistry;	92%

: 6089-09-4
4-pentynoic acid

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

: 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

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

: C15H11ClN2O

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

: C22H14N4O4

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In neat (no solvent) for 0.0416667h; Microwave irradiation; Green chemistry;	91%

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

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

: 6943-17-5
6-nitroquinazolone

Conditions

Conditions	Yield
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%

: 1082349-60-7
2-chloro-3-(3-fluorophenyl)-1,8-naphthyridine

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

: C21H11FN4O3

Conditions

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

2-Amino-5-nitrobenzoic acid Chemical Properties

Molecular Structure of Benzoic acid, 2-amino-5-nitro- (CAS NO.616-79-5):

IUPAC Name: 2-amino-5-nitrobenzoic acid
Empirical Formula: C₇H₆N₂O₄
Molecular Weight: 182.1335
H bond acceptors: 6
H bond donors: 3
Freely Rotating Bonds: 3
Polar Surface Area: 75.36Å²
Index of Refraction: 1.681
Molar Refractivity: 43.96 cm³
Molar Volume: 116 cm³
Surface Tension: 83.3 dyne/cm
Density: 1.568 g/cm³
Flash Point: 218.6 °C
Enthalpy of Vaporization: 73.21 kJ/mol
Boiling Point: 437.9 °C at 760 mmHg
Vapour Pressure: 1.92E-08 mmHg at 25°C
Melting point: 270 °C (dec.)(lit.)
Water Solubility: Insoluble
BRN: 646219
EINECS: 210-493-6
InChI
InChI=1/C7H6N2O4/c8-6-2-1-4(9(12)13)3-5(6)7(10)11/h1-3H,8H2,(H,10,11)
Smiles
c1(cc(ccc1N)[N+](=O)[O-])C(O)=O
Product Categories: Fine chemical & intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; pharmacetical

2-Amino-5-nitrobenzoic acid Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 2
Hazard Note: Irritant

2-Amino-5-nitrobenzoic acid Specification

Benzoic acid, 2-amino-5-nitro- , with CAS number of 616-79-5, can be called 2-Amino-5-nitrobenzoic acid ; 5-Nitroanthranilic acid ; Anthranilic acid, 5-nitro- (8CI) . It is a bright yellow powder.

Product Name

2-Amino-5-nitrobenzoic acid

Synthetic route

2-Amino-5-nitrobenzoic acid Chemical Properties

2-Amino-5-nitrobenzoic acid Safety Profile

2-Amino-5-nitrobenzoic acid Specification

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