4-NITROANTHRANILIC ACID supplier

Name
4-Nitroanthranilic acid
EINECS 210-583-5
CAS No. 619-17-0
Article Data31
CAS DataBase
Density 1.568 g/cm³
Solubility <0.01 g/100 mL at 22 °C in water
Melting Point 257 °C (dec.)(lit.)
Formula C₇H₆N₂O₄
Boiling Point 431.4 °C at 760 mmHg
Molecular Weight 182.136
Flash Point 214.7 °C
Transport Information
Appearance Orange crystalline powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Anthranilicacid, 4-nitro- (6CI,7CI,8CI);2-Amino-4-nitrobenzoic acid;2-Carboxy-5-nitroaniline;4-Nitro-2-aminobenzoic acid;NSC 7789;
PSA 109.14000
LogP 1.97960

Synthetic route

: 87840-68-4
diethyl 2,4-dinitrobenzylidenemalonate

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With diethylamine; tert-butyl alcohol for 48h; Ambient temperature;	75%
With sodium hydrogencarbonate; diethylamine; tert-butyl alcohol Mechanism; 1.) room temp., 48 h, 2.) chloroform;	75%

: 610-30-0
2,4-dinitrobenzoic acid

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With ferrous(II) sulfate heptahydrate; ammonia In water at 50 - 60℃;	67%

: 99-60-5
2-chloro-4-nitrobenzoic acid

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
Stage #1: 2-chloro-4-nitrobenzoic acid With copper(l) iodide; sodium azide; ethanol; caesium carbonate; N,N`-dimethylethylenediamine at 20 - 95℃; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In water pH=2 - 3;	62%

: 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;

: 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

: 951-97-3
2-acetamido-4-nitrobenzoic acid

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With ethanol; sulfuric acid
With hydrogenchloride; ethanol
With hydrogenchloride
With hydrogenchloride In water for 1h; Reflux;

: 65911-47-9
4-nitro-2-carbamoylbenzoic acid

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With hydrogenchloride; potassium hydroxide; bromine 1.) heating, 1 h, 2.) 0 deg C; Yield given. Multistep reaction;
With sodium hypochlorite In water at 0 - 30℃; Temperature;

: 121-14-2
2,4-dinitrotoluene

: 71-43-2
benzene

A: 92-52-4
biphenyl

B: 109466-84-4
2-amino-4-nitrobenzaldehyde

C: 99-09-2
3-nitro-aniline

D: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
at 343℃; Product distribution; Mechanism; thermolysis in supercritical benzene; other temperature, pressure;	A 100.0 (unit not given) B 35.8 (unit not given) C 20.0 (unit not given) D 22.5 (unit not given)

...Expand

: N-(2-methyl-7-nitro-4-oxo-4H-quinazolin-3-yl)-diacetamide

permanganate: permanganate

: 619-17-0
4-Nitroanthranilic acid

: 38527-51-4
7-nitro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one

alkali: alkali

A: 65-85-0
benzoic acid

B: 619-17-0
4-Nitroanthranilic 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

<4-nitro-isatoic acid >-anhydride: <4-nitro-isatoic acid >-anhydride

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid

<4-nitro-phthalic acid >-imide: <4-nitro-phthalic acid >-imide

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

B: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With sodium hydroxide; calcium chloride Erwaermen der Mischung auf 100grad;

: 121-14-2
2,4-dinitrotoluene

A: 99-65-0
meta-dinitrobenzene

B: 15264-44-5
6-nitro-2,1-benzoisoxazole

C: 109466-84-4
2-amino-4-nitrobenzaldehyde

D: 619-17-0
4-Nitroanthranilic acid

E P - NO2 + H: P - NO2 + H

Conditions

Conditions	Yield
In benzene at 340℃; Product distribution; Kinetics; Rate constant; in sealed tube; other solvent (neat);

...Expand

: 13138-53-9
4-nitrophthalic amide

alkaline aqueous potassium hypobromite: alkaline aqueous potassium hypobromite

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

B: 619-17-0
4-Nitroanthranilic acid

...Expand

: 7664-93-9
sulfuric acid

: 342045-62-9
4-acetylamino-6-nitro-isophthalic acid

A: 610-36-6
4-amino-2-nitrobenzoic acid

B: 619-17-0
4-Nitroanthranilic acid

...Expand

: 342045-62-9
4-acetylamino-6-nitro-isophthalic acid

alkali: alkali

A: 610-36-6
4-amino-2-nitrobenzoic acid

B: 619-17-0
4-Nitroanthranilic acid

...Expand

: 611-03-0
4-amino-2-aminobenzoic acid

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
With Streptomyces thioluteus para-aminobenzoate N-oxygenase

: 89-40-7
4-nitrophthalimide

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) aq. KOH, 2.) 6 N aq. HCl / 1.) RT, 4 h, 2.) 0 deg C, 90 min 2: 1.) Br2, 1 N aq. KOH, 2.) 2 N aq. HCl / 1.) heating, 1 h, 2.) 0 deg C View Scheme

: 528-75-6
2,4-dinitrobenzaldehyde

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / pyridine / titanium(IV) chloride / CCl4; tetrahydrofuran / 24 h 2: 75 percent / 1.) t-butyl alcohol, diethylamine, 2.) aq. sodium hydrogen carbonate / 1.) room temp., 48 h, 2.) chloroform View Scheme

: 2879-79-0
N-(2-methyl-5-nitrophenyl)acetamide

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium permanganate 2: alcohol; sulfuric acid View Scheme
Multi-step reaction with 2 steps 1: calcium permanganate 2: concentrated hydrochloric acid; alcohol View Scheme
Multi-step reaction with 2 steps 1: water; potassium permanganate; magnesium sulfate 2: aqueous hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: potassium permanganate / water / 1.5 h / 80 °C 2: hydrogenchloride / water / 1 h / Reflux View Scheme

: 99-55-8
2-methyl-5-nitroaniline

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 0.25 h 2: potassium permanganate / water / 1.5 h / 80 °C 3: hydrogenchloride / water / 1 h / Reflux View Scheme

: 85-44-9
phthalic anhydride

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid / 0.17 h 1.2: 1 h / 70 °C 2.1: acetic anhydride / 2 h / 90 - 120 °C 3.1: 5 - 70 °C 4.1: sodium hypochlorite / water / 0 - 30 °C View Scheme

: 610-27-5
4-nitrophthalic acid

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic anhydride / 2 h / 90 - 120 °C 2: 5 - 70 °C 3: sodium hypochlorite / water / 0 - 30 °C View Scheme

: 5466-84-2
4-nitrophthalic anhydride

: 619-17-0
4-Nitroanthranilic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 - 70 °C 2: sodium hypochlorite / water / 0 - 30 °C View Scheme

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

: 619-17-0
4-Nitroanthranilic acid

: 113290-38-3
(E)-methyl 2-([(dimethylamino)methylene]amino)-4-nitrobenzoate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Heating;	99%
In N,N-dimethyl-formamide at 105℃; for 0.25h; Microwave irradiation;	92%

: 123-62-6
propionic acid anhydride

: 619-17-0
4-Nitroanthranilic acid

: 2-Ethyl-7-nitro-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
for 1h; Heating;	98.2%

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

: 619-17-0
4-Nitroanthranilic acid

: 20872-93-9
7-nitroquinazolin-4(3H)-one

Conditions

Conditions	Yield
In neat (no solvent) at 150℃; Sealed tube;	95%
at 160℃; for 12h; Inert atmosphere;	93%
at 160℃;	93%

: 619-17-0
4-Nitroanthranilic acid

: 20872-93-9
7-nitroquinazolin-4-one

Conditions

Conditions	Yield
With formamide In water	95%

: 2580-79-2
diaminoglyoxime

: 619-17-0
4-Nitroanthranilic acid

: 1446556-87-1
N'-hydroxy-7-nitro-4-oxo-3,4-dihydroquinazoline-2-carboximidamide

Conditions

Conditions	Yield
With acetic acid for 0.5h; Reflux;	95%

: 534-15-6
1,1-dimethoxyethane

: 619-17-0
4-Nitroanthranilic acid

: 3558-19-8
methyl 2-amino-4-nitrobenzoate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.25h; Inert atmosphere; Microwave irradiation;	95%

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

: 619-17-0
4-Nitroanthranilic acid

: 20872-93-9
7-nitroquinazolin-4-one

Conditions

Conditions	Yield
In water at 165℃; for 4h;	95%

: 13037-22-4
methyl (N-(4-methylphenyl))dithiocarbamate

: 619-17-0
4-Nitroanthranilic acid

: 81066-88-8
7-Nitro-2-thioxo-3-p-tolyl-2,3-dihydro-1H-quinazolin-4-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 6h; Heating;	93%

: 3473-63-0
formamidine acetic acid

: 619-17-0
4-Nitroanthranilic acid

: 20872-93-9
7-nitroquinazolin-4(3H)-one

Conditions

Conditions	Yield
In 2-methoxy-ethanol at 130℃; for 18h;	93%
In 2-methoxy-ethanol at 130℃; for 18h;	84%
for 24h; Reflux;	73.3%
In ethanol Reflux;

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

: 619-17-0
4-Nitroanthranilic acid

: 3558-19-8
methyl 2-amino-4-nitrobenzoate

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide dimethyl acetal; 4-Nitroanthranilic acid In N,N-dimethyl-formamide at 105℃; for 0.25h; Microwave irradiation; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 100℃; for 0.166667h; pH=2; Microwave irradiation;	93%
Stage #1: N,N-dimethyl-formamide dimethyl acetal; 4-Nitroanthranilic acid In ethyl acetate at 100℃; for 0.25h; Sealed tube; Microwave irradiation; Green chemistry; Stage #2: With hydrogenchloride In water; ethyl acetate at 60 - 100℃; for 0.5h; Sealed tube; Microwave irradiation; Green chemistry;	88%

: 108-24-7
acetic anhydride

: 619-17-0
4-Nitroanthranilic acid

: 951-97-3
2-acetamido-4-nitrobenzoic acid

Conditions

Conditions	Yield
In pyridine Ambient temperature;	92.1%
Behandeln des Reaktionsproduktes mit Wasser;

: 57-13-6
urea

: 619-17-0
4-Nitroanthranilic acid

: 174565-63-0
7-nitro-1,2,3,4-tetrahydro-quinazoline-2,4-dione

Conditions

Conditions	Yield
at 160℃; for 6h;	91%
at 160℃; for 6h;	90%

: 67-56-1
methanol

: 619-17-0
4-Nitroanthranilic acid

: 3558-19-8
methyl 2-amino-4-nitrobenzoate

Conditions

Conditions	Yield
With sulfuric acid at 75℃; for 72h;	91%
Stage #1: methanol; 4-Nitroanthranilic acid With sulfuric acid for 48h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water	90%
With thionyl chloride Heating / reflux;	88%

: 32315-10-9
bis(trichloromethyl) carbonate

: 619-17-0
4-Nitroanthranilic acid

: 63480-10-4
4-nitroisatoic anhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 70℃; for 12h;	91%
In water at 0℃; for 5h; Inert atmosphere; Large scale;	88%
In 1,4-dioxane for 6h; Heating;	45%

: 619-17-0
4-Nitroanthranilic acid

: 78468-34-5
(2-Amino-4-nitrophenyl)methan-1-ol

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 30℃; for 1h; Inert atmosphere;	91%
Stage #1: 4-Nitroanthranilic acid With diborane In tetrahydrofuran at 65℃; Stage #2: With hydrogenchloride In tetrahydrofuran at 65℃;	82%
With borane-THF In tetrahydrofuran at 20℃; for 12h;	70%

: 107-10-8
propylamine

: 619-17-0
4-Nitroanthranilic acid

: 1414782-00-5
N-propyl-2-amino-4-nitrobenzamide

Conditions

Conditions	Yield
Stage #1: 4-Nitroanthranilic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; for 1h; Stage #2: propylamine In tetrahydrofuran; dichloromethane at 25℃; for 12h;	91%

: 6061-04-7
1,1-dichloro-2-nitro ethylene

: 619-17-0
4-Nitroanthranilic acid

: 4-nitro-2-(2-nitroacetamido)benzoic acid

Conditions

Conditions	Yield
In water at 50℃; for 45h; Green chemistry;	91%

: 1663-61-2
triethoxymethylbenzene

: 619-17-0
4-Nitroanthranilic acid

: 38527-51-4
7-nitro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
at 100℃; for 2h; Microwave irradiation; Inert atmosphere;	91%

: 619-17-0
4-Nitroanthranilic acid

: 78072-75-0
2-azido-4-nitrobenzoic acid

Conditions

Conditions	Yield
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 20℃; for 2h;	90%
With sodium azide; sodium carbonate; sodium nitrite 1.) H2O, 2.) H2O, r.t., 2 h; Yield given. Multistep reaction;

: 530-62-1
1,1'-carbonyldiimidazole

: 619-17-0
4-Nitroanthranilic acid

: 63480-10-4
4-nitroisatoic anhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 10℃; for 2h; Inert atmosphere;	90%
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

: 67-52-7
BARBITURIC ACID

: 122-51-0
orthoformic acid triethyl ester

: 619-17-0
4-Nitroanthranilic acid

: 4-nitro-2-{[(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}benzoic acid

Conditions

Conditions	Yield
In iso-butanol Reflux;	90%

...Expand

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 122-51-0
orthoformic acid triethyl ester

: 619-17-0
4-Nitroanthranilic acid

: 2-{[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}-4-nitrobenzoic acid

Conditions

Conditions	Yield
In iso-butanol Reflux;	90%

...Expand

: 1663-61-2
triethoxymethylbenzene

: 619-17-0
4-Nitroanthranilic acid

: (±)-2-ethoxy-7-nitro-2-phenyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
With acetic acid at 100℃; for 24h; Inert atmosphere;	90%

: 106-31-0
butanoic acid anhydride

: 619-17-0
4-Nitroanthranilic acid

: 7-Nitro-2-propyl-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
for 1h; Heating;	89.3%

: 116-31-4
all-trans-Retinal

: 619-17-0
4-Nitroanthranilic acid

: 144459-79-0
2-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-4-nitro-benzoic acid

Conditions

Conditions	Yield
In methanol; dichloromethane for 2h; Ambient temperature;	89%

: 3473-63-0
formamidine acetic acid

: 619-17-0
4-Nitroanthranilic acid

: 20872-93-9
4-hydroxy-7-nitroquinazoline

Conditions

Conditions	Yield
In ethanol for 5h; Reflux;	89%

: 1273-82-1
aminoferrocene

: 619-17-0
4-Nitroanthranilic acid

: N-(ferrocenylmethyl)-2-amino-4-nitrobenzamide

Conditions

Conditions	Yield
Stage #1: 4-Nitroanthranilic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; for 1h; Stage #2: aminoferrocene In tetrahydrofuran; dichloromethane at 25℃; for 12h;	89%

: 556-61-6
methyl thioisocyanate

: 619-17-0
4-Nitroanthranilic acid

: 926218-64-6
3-methyl-7-nitro-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
With triethylamine	89%
With triethylamine In ethanol for 6h; Reflux;	89%
With acetic acid at 160℃; for 24h;	11.4 g

: 619-17-0
4-Nitroanthranilic acid

: 89459-38-1
2-iodo-4-nitrobenzoic acid

Conditions

Conditions	Yield
Stage #1: 4-Nitroanthranilic acid With toluene-4-sulfonic acid In water for 0.05h; Stage #2: With sodium nitrite In water for 0.25h; Stage #3: With potassium iodide In water	88%
Stage #1: 4-Nitroanthranilic acid With sulfuric acid at 0℃; for 1h; Stage #2: With sodium nitrite In water at 0℃; for 1h; Stage #3: With potassium iodide In water at 0 - 60℃; for 4h;	68%
With sulfuric acid; potassium iodide; sodium nitrite In water at 0 - 60℃; for 6h;	68%

: 619-17-0
4-Nitroanthranilic acid

: 115-80-0
Triethyl orthopropionate

: (±)-2-ethoxy-2-ethyl-7-nitro-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
at 100℃; for 1.5h; Time; Microwave irradiation; Inert atmosphere;	88%

4-NITROANTHRANILIC ACID Chemical Properties

Detail of 4-NITROANTHRANILIC ACID (619-17-0).
Molecular Structure:

Name:4-NITROANTHRANILIC ACID
CAS Number:619-17-0
Molecular Formula:C₇H₆N₂O₄
Molecular Weight:182.15
EINECS:210-583-5
Density:1.568 g/cm³
Melting Point:268-270 ^oC (dec.)
Boiling Point:431.4 ^oC at 760 mmHg
Flash Point:214.7 ^oC
Solubility:<0.01 g/100 mL at 22^oC in water
Appearance:right yellow powder
Properties:Orange prisms from EtOH (aq).
CAS DataBase Reference:619-17-0(CAS DataBase Reference)
EPA Substance Registry System:619-17-0(EPA Substance)
Synonyms of 4-NITROANTHRANILIC ACID (619-17-0):
P-NITROANTHRANILIC ACID;2-amino-4-nitro-benzoicaci;4-nitro-anthranilicaci;4-Nitro-2-aminobenzoic acid;4-NITROANTHRANILIC ACID;2-AMINO-4-NITROBENZOIC ACID;4-NITROANTHRANILIC ACID, TECH., 90%;4-NitroAnthranillicAcid

4-NITROANTHRANILIC ACID Toxicity Data With Reference

mmo-sat 10 µg/plate

ENMUDM Environmental Mutagenesis. 8 (Suppl 7)(1986),1.

4-NITROANTHRANILIC ACID Consensus Reports

NCI Carcinogenesis Bioassay (feed); No Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-109 ,1978. . Reported in EPA TSCA Inventory.

4-NITROANTHRANILIC ACID Safety Profile

Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS.
Safety Information of 4-NITROANTHRANILIC ACID (619-17-0).
Hazard Codes:Xi
Risk Statements:36/37/38
Safety Statements:26-37/39
WGK Germany:3
RTECS:CB3675000
Hazardous Substances Data:619-17-0(Hazardous Substances Data)

Product Name

4-Nitroanthranilic acid

Synthetic route

4-NITROANTHRANILIC ACID Chemical Properties

4-NITROANTHRANILIC ACID Toxicity Data With Reference

4-NITROANTHRANILIC ACID Consensus Reports

4-NITROANTHRANILIC ACID Safety Profile

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