2-Nitrobenzoic Acid supplier

Name
2-Nitrobenzoic acid
EINECS 209-004-9
CAS No. 552-16-9
Article Data341
CAS DataBase
Density 1.468g/cm³
Solubility 6.8 g/L
Melting Point 141-148 ºC
Formula C7H5 N O4
Boiling Point 340.7°Cat760mmHg
Molecular Weight 167.121
Flash Point 157.5°C
Transport Information
Appearance off-white powder
Safety Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS.
Risk Codes R22;R36/37/38;R68
Molecular Structure
Hazard Symbols
Synonyms Benzoicacid, o-nitro- (8CI); 2-Nitrobenzoic acid; NSC 9576; o-Carboxynitrobenzene;o-Nitrobenzoic acid
PSA 83.12000
LogP 1.81620

Synthetic route

: 3717-25-7, 4836-00-4, 6635-41-2
2-nitrobenzaldehyde oxime

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 63h; Heating;	100%
With zinc dichromate(VI) In dichloromethane for 3.5h; Ambient temperature;	90%

: 552-89-6
2-nitro-benzaldehyde

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
Stage #1: 2-nitro-benzaldehyde With potassium permanganate; disodium hydrogenphosphate In methanol; water at 25℃; Continuous flow conditions; Sonication; Stage #2: With hydrogenchloride; sodium thiosulfate; sodium chloride In methanol; water; ethyl acetate Stage #3: With hydrogenchloride; sodium thiosulfate; sodium chloride In methanol; water; ethyl acetate	98%
With C54H24F15N5Pd; oxygen In dichloromethane; acetonitrile at 20℃; Catalytic behavior; Reagent/catalyst; Solvent; Irradiation;	98%
With potassium bromate In acetic acid for 0.25h; Heating;	95%

: 15121-85-4
1,3-dihydroxy-2-(2-nitrophenyl)propane

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With jones reagent In acetone for 6h; Ambient temperature; addition at 0 deg C;	96%

: 58809-90-8
4-methyl-N'-(2-nitrobenzylidene)-benzenesulfonohydrazide

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 8h; Heating;	96%

: 88-72-2
1-methyl-2-nitrobenzene

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; Rate constant; pH 9;	95%
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h;	95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium bromide at 40℃; for 12h; Temperature;	94.2%

: 612-25-9
2-Nitrobenzyl alcohol

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With tetra-N-butylammonium tribromide In acetonitrile at 20℃; for 15h; Irradiation;	95%
With dihydrogen peroxide; methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate at 90℃; for 9h;	91%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 20℃; for 6h;	90%

: 612-24-8
o-nitrobenzonitrile

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With water; hydrogen bromide; acetic acid for 24h; Reflux;	95%
With phosphate buffer at 30℃; for 96h; rhodococcus rhodocrous AJ270, pH 7.0;	86%
With potassium phosphate buffer at 30℃; for 90h; Rhodococcus sp. AJ270 cells;	85.7%

: 606-27-9
methyl 2-nitrobenzoate

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With iron(III) sulfate; water In toluene at 110℃; for 4h; Ionic liquid;	95%
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 90℃; for 0.25h;	70%
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 190℃; for 0.166667h; Substitution;	65%

: 2-ethyl-3-nitrophenol

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
Stage #1: 2-ethyl-3-nitrophenol With 2-propoxyethanol at 35℃; for 0.833333h; Stage #2: With triphenylphosphine for 1.5h; Temperature;	95%

: 1929-19-7
bis-(2-nitro-benzylidene)-hydrazine

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 86h; Heating;	93%

: C9H6Cl3NO4

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With indium; ammonium chloride In tetrahydrofuran for 3.5h; Heating;	93%

: 612-25-9
2-Nitrobenzyl alcohol

A: 552-16-9
ortho-nitrobenzoic acid

B: 552-89-6
2-nitro-benzaldehyde

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) chloride In decane; acetonitrile at 20℃; for 2h;	A 92% B 5%
With peracetic acid; C24H29INO5 In acetic acid at 30℃; for 48h;	A 92% B 5%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique;	A 46% B 46%

: 99277-71-1
4-bromo-2-nitrobenzoic acid

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With 0.82mol% Pd/C; hydrogen; sodium hydrogencarbonate In methanol at 20℃; for 0.416667h; regioselective reaction;	92%
With hydrogen; sodium hydrogencarbonate; palladium on activated carbon In methanol at 20℃; for 0.416667h; Inert atmosphere;	92%

: 577-59-3
2-acetylnitrobenzene

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With N-bromophthalimide; mercury(II) diacetate In chloroform at 20℃; for 2h;	90%
With sodium hypochlorite; lithium hypochlorite In ethanol at 77℃; for 2h;	71%
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 12h;	68%

: 612-24-8
o-nitrobenzonitrile

A: 552-16-9
ortho-nitrobenzoic acid

B: 610-15-1
2-nitrobenzamide

Conditions

Conditions	Yield
With phosphate buffer at 30℃; for 4h; rhodococcus rhodocrous AJ270, pH 7.0;	A 10% B 90%
With potassium phosphate buffer at 30℃; for 4h; Rhodococcus sp. AJ270 cells;	A 10% B 89.5%

: 48140-35-8
2-(2-nitrophenyl)-1,3-dioxolane

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With aluminium trichloride; silver bromate In acetonitrile for 1.5h; Heating;	87%

: 42546-69-0
2,4,6-trinitrophenyl ester of 2-nitrobenzenecarbothioic acid

A: 552-16-9
ortho-nitrobenzoic acid

B: 10123-09-8
2,4,6-trinitronitrosobenzene

Conditions

Conditions	Yield
With nitric acid 25 to 30 deg. C and then 1 h at room temp.;	A 85% B 60%
With nitric acid at 25 - 30℃; Product distribution;	A 85% B 60%

: 5670-66-6, 5670-67-7, 3156-39-6
1-nitro-2-(2-nitrovinyl)benzene

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With Amberlyst A-26 (OH-); dihydrogen peroxide In 1,4-dioxane at 20℃; for 8h;	82%

: 579-71-5
2-nitrostyrene

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With Oxone In water; acetonitrile for 17h; Reflux;	82%
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 24h;	43%

: 33757-51-6
2-nitro-N-(quinolin-8-yl)benzamide

A: 578-66-5
8-amino quinoline

B: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water for 12h; Reflux;	A 80% B 78%

: 201230-82-2
carbon monoxide

: 577-19-5
2-nitrophenyl bromide

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In water; N,N-dimethyl-formamide at 80℃; under 2068.65 Torr; Inert atmosphere;	78%
With water; triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate at 60℃; under 760.051 Torr;	77%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine In xylene at 90℃; for 4h; Carbonylation;	18%

: 201230-82-2
carbon monoxide

: 577-19-5
2-nitrophenyl bromide

: 7732-18-5
water

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 80℃; under 2327.23 Torr;	77%

...Expand

: 124-38-9
carbon dioxide

: 15290-22-9
o-(trimethylsilyl)nitrobenzene

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
potassium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃; under 38000 Torr; for 24h; further catalyst: CsF;	76%

: 88-72-2
1-methyl-2-nitrobenzene

A: 552-16-9
ortho-nitrobenzoic acid

B: 612-25-9
2-Nitrobenzyl alcohol

C: 552-89-6
2-nitro-benzaldehyde

Conditions

Conditions	Yield
With ozone; cobalt(II) acetate In acetic acid at 100℃; Kinetics; Product distribution; Further Variations:; Catalysts; Temperatures;	A 75.4% B n/a C n/a
With Coprinus sp. peroxidase; tartaric acid buffer; dihydrogen peroxide In water; acetone at 20℃; pH=5;
Stage #1: 1-methyl-2-nitrobenzene With oxygen; cobalt(II) acetate; 2-hydroxy-4,5,6,7-tetraphenylisoindoline-1,3-dione at 110℃; under 2250.23 Torr; Stage #2: With water; oxygen at 61℃; under 1500.15 Torr;

...Expand

: 2-(2-nitrophenyl)-1,3-oxathiolane

A: 552-16-9
ortho-nitrobenzoic acid

B: 552-89-6
2-nitro-benzaldehyde

Conditions

Conditions	Yield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃; for 2.5h;	A n/a B 73%

: 62673-13-6
o-Nitrobenzyloxytrimethylsilane

A: 552-16-9
ortho-nitrobenzoic acid

B: 552-89-6
2-nitro-benzaldehyde

Conditions

Conditions	Yield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃;	A 14% B 72%

: 85907-57-9
(Z)-3-Dimethylamino-2-(2-nitro-phenyl)-propenal

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With sodium periodate In tetrahydrofuran; water for 18h;	71%

: 65-85-0
benzoic acid

A: 552-16-9
ortho-nitrobenzoic acid

B: 121-92-6
3-nitrobenzoic acid

C: 62-23-7
4-nitro-benzoic acid

Conditions

Conditions	Yield
With Iron(III) nitrate nonahydrate; phosphorus pentoxide In neat (no solvent) at 20℃; for 6h; Milling; Green chemistry; Overall yield = 95 percent;	A 19% B 70% C 6%
With trinitratooxovanadium(V) In dichloromethane for 120h; Ambient temperature;	A 15% B 37% C 2%
With oxygen; Nitrogen dioxide; ozone In 1,2-dichloro-ethane at 0℃; for 1.5h; Product distribution; further oxidants and solvents;

...Expand

: 55666-41-6
tert-butyl 2-nitrobenzoate

: 552-16-9
ortho-nitrobenzoic acid

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 16h;	70%

: 552-16-9
ortho-nitrobenzoic acid

: 610-14-0
2-nitrobenzyl chloride

Conditions

Conditions	Yield
With thionyl chloride at 80 - 100℃; for 2h;	100%
With thionyl chloride In toluene for 3h; Heating;	100%
With thionyl chloride for 6h; Reflux;	100%

: 552-16-9
ortho-nitrobenzoic acid

: 577-19-5
2-nitrophenyl bromide

Conditions

Conditions	Yield
With bromine; dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; Reagent/catalyst; Concentration; UV-irradiation;	100%
With Bromotrichloromethane; trichloroisocyanuric acid; bromine In tetrachloromethane at 10 - 120℃; for 18h; Temperature; Reagent/catalyst; Concentration; Photolysis;	97%
With [bis(acetoxy)iodo]benzene; bromine In various solvent(s) for 22h; bromodecarboxylation; Heating; irradiation;	51%

: 552-16-9
ortho-nitrobenzoic acid

: 1276560-33-8
(3,5-dibromo-2-(methoxymethoxy)phenyl)methanamine

: 1276560-34-9
N-(3,5-dibromo-2-(methoxymethoxy)benzyl)-2-nitrobenzamide

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (3,5-dibromo-2-(methoxymethoxy)phenyl)methanamine In N,N-dimethyl-formamide at 20℃; for 19h;	100%

: 552-16-9
ortho-nitrobenzoic acid

: 2-nitrobenzoic acid cesium salt

Conditions

Conditions	Yield
With caesium carbonate In methanol at 20℃; for 2h; Inert atmosphere;	100%
With caesium carbonate In methanol at 20℃; for 1h;

: 95-14-7
1,2,3-Benzotriazole

: 552-16-9
ortho-nitrobenzoic acid

: (1H-benzo[d][1,2,3]triazol-1-yl)(2-nitrophenyl)methanone

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃; for 8.5h;	100%
Stage #1: ortho-nitrobenzoic acid With trichloroisocyanuric acid; triphenylphosphine In dichloromethane at 20℃; for 0.5h; Stage #2: 1,2,3-Benzotriazole In dichloromethane at 20℃;	64%
With thionyl chloride In dichloromethane at 20℃;

: 552-16-9
ortho-nitrobenzoic acid

: 118-92-3
anthranilic acid

Conditions

Conditions	Yield
With hydrazine In ethanol at 80℃; for 0.166667h; Catalytic behavior; chemoselective reaction;	99.9%
With palladium 10% on activated carbon; ammonium formate; silica gel In methanol for 1.5h; Milling;	98%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 4h;	98%

: 552-16-9
ortho-nitrobenzoic acid

: 98-95-3
nitrobenzene

Conditions

Conditions	Yield
With copper(I) oxide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Time; Inert atmosphere;	99%
With silver(I) acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 16h; Inert atmosphere;	92%
With silver carbonate In dimethyl sulfoxide at 120℃; for 16h;	91%

: 64-67-5
diethyl sulfate

: 552-16-9
ortho-nitrobenzoic acid

: 610-34-4
ethyl 2-nitrobenzoate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetone at 55 - 60℃; for 10h;	99%
With potassium hydroxide; tetrabutylammomium bromide 1.) 60 deg C, 0.1 Torr, 6 h, 2.) room temp., 6 h; Yield given. Multistep reaction;

: 106-39-8
bromochlorobenzene

: 552-16-9
ortho-nitrobenzoic acid

: 6271-80-3
4'-chloro-2-nitrobiphenyl

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With potassium carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: bromochlorobenzene With 1,10-Phenanthroline; copper(l) iodide In various solvent(s) at 160℃; for 24h; Further stages.;	99%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N,N-dimethyl-aniline; silver carbonate; palladium dichloride at 150℃; for 2h;	35%
Stage #1: ortho-nitrobenzoic acid; copper(II) carbonate In 1-methyl-pyrrolidin-2-one Stage #2: bromochlorobenzene; bis(acetylacetonato)palladium(II); triphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity;	9 %Chromat.

: 573-17-1
9-bromophenanthrene

: 552-16-9
ortho-nitrobenzoic acid

: 911217-05-5
1-(9-phenanthryl)-2-nitrobenzene

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With potassium carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: 9-bromophenanthrene With 1,10-Phenanthroline; copper(l) iodide In various solvent(s) at 160℃; for 24h; Further stages.;	99%
With potassium fluoride; copper(II) carbonate; bis(acetylacetonato)palladium(II); isopropyldiphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity; Molecular sieve;	86 %Chromat.
copper(l) iodide; Phenanthroline; bis(acetylacetonato)palladium(II) In 1-methyl-pyrrolidin-2-one at 160℃; for 24h; Product distribution / selectivity; Molecular sieve;	99 %Chromat.

: 90-90-4
(4-bromophenyl)(phenyl)methanone

: 552-16-9
ortho-nitrobenzoic acid

: 4-(2-nitrophenyl)benzophenone

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With potassium carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: (4-bromophenyl)(phenyl)methanone With 1,10-Phenanthroline; copper(l) iodide In various solvent(s) at 160℃; for 24h; Further stages.;	99%
With potassium fluoride; copper(II) carbonate; bis(acetylacetonato)palladium(II); isopropyldiphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity; Molecular sieve;	94 %Chromat.

: 552-16-9
ortho-nitrobenzoic acid

: 501-65-5
diphenyl acetylene

: C21H15NO4

Conditions

Conditions	Yield
With [{Au(IPr)}2(μ-OH)][BF4] In neat (no solvent) at 80℃; for 10h; regioselective reaction;	99%

: 2524-49-4
3-butene-1-amine

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: 552-16-9
ortho-nitrobenzoic acid

: 100-52-7
benzaldehyde

: N-(but-3-en-1-yl)-N-(2-(tert-butylamino)-2-oxo-1-phenylethyl)-2-nitrobenzamide

Conditions

Conditions	Yield
With indium(III) chloride In methanol at 20℃; for 18h; Ugi Condensation;	99%

...Expand

: 552-16-9
ortho-nitrobenzoic acid

: 23726-00-3
<2H9>trimethylsulphoxonium iodide

: 1613036-83-1
methyl-d3 2-nitrobenzoate

Conditions

Conditions	Yield
With potassium carbonate at 20℃; for 3h; Sealed tube;	99%

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: 552-16-9
ortho-nitrobenzoic acid

: 104-88-1
4-chlorobenzaldehyde

: 22483-09-6
2,2-dimethoxyethylamine

: N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzamide

Conditions

Conditions	Yield
In methanol at 20℃; for 24h;	99%

...Expand

: 104-95-0
(4-bromophenyl)thioanisole

: 552-16-9
ortho-nitrobenzoic acid

: 911217-03-3
methyl-(2'-nitro-[1,1'-biphenyl]-4-yl)sulfane

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With potassium carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: (4-bromophenyl)thioanisole With 1,10-Phenanthroline; copper(l) iodide In various solvent(s) at 160℃; for 24h; Further stages.;	98%
With potassium fluoride; copper(II) carbonate; bis(acetylacetonato)palladium(II); isopropyldiphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity; Molecular sieve;	82 %Chromat.
copper(l) iodide; Phenanthroline; bis(acetylacetonato)palladium(II) In 1-methyl-pyrrolidin-2-one at 160℃; for 24h; Product distribution / selectivity; Molecular sieve;	98 %Chromat.

: 626-55-1
3-Bromopyridine

: 552-16-9
ortho-nitrobenzoic acid

: 4253-80-9
3-(2-nitro-phenyl)-pyridine

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With potassium carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: 3-Bromopyridine With 1,10-Phenanthroline; copper(l) iodide In various solvent(s) at 160℃; for 24h; Further stages.;	98%
copper(l) iodide; Phenanthroline; bis(acetylacetonato)palladium(II) In 1-methyl-pyrrolidin-2-one at 160℃; for 24h; Product distribution / selectivity; Molecular sieve;	98 %Chromat.

: 552-16-9
ortho-nitrobenzoic acid

: 2273-43-0
n-butylstannoic acid

: n-butyloxotin o-nitrobenzoate hexamer * 3C6H6

Conditions

Conditions	Yield
With C6H6 In dichloromethane; benzene byproducts: H2O; addn. of Sn-acid to a stirred soln. of CH2Cl2 and benzene, addn. of benzoic acid, reflux for 18 h, removal of H2O azeotropically, cream-white cloidy suspn., standing for 24 h; filtration of white powder, washing with benzene, standing gives larger crystals, drying; elem. anal.;	98%

: 552-16-9
ortho-nitrobenzoic acid

: 15163-59-4
potassium o-nitrobenzoate

Conditions

Conditions	Yield
With potassium tert-butylate In ethanol at 20℃; Inert atmosphere;	98%
With potassium tert-butylate In ethanol at 20℃; for 3h; Inert atmosphere;	98%
With potassium tert-butylate In ethanol at 20℃; for 3h;	98%

: 552-16-9
ortho-nitrobenzoic acid

: 104-94-9
4-methoxy-aniline

: 22979-83-5
2-nitro-N-(4-methoxyphenyl)benzamide

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h; Stage #2: 4-methoxy-aniline With triethylamine In dichloromethane at 20℃; for 18h;	98%
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; for 4h;	74%

: 75-09-2
dichloromethane

: 552-16-9
ortho-nitrobenzoic acid

: bis(2-nitrobenzoyloxy)methane

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 130℃; for 5h;	98%
With potassium carbonate In dimethyl sulfoxide at 60℃; for 3h;	94%

: tris(3-fluorophenyl)antimony

: 552-16-9
ortho-nitrobenzoic acid

: tris(3-fluorophenyl)antimony-bis(2-nitrobenzoate)

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In diethyl ether; water at 20℃; for 24h;	98%

: 552-16-9
ortho-nitrobenzoic acid

: 88-74-4
2-nitro-aniline

Conditions

Conditions	Yield
With 1-n-butyl-3-methylimidazolium azide; sulfuric acid; acetic acid at 54℃; for 4h; Schmidt Reaction;	97%
With sodium azide; chloroform; sulfuric acid
With thionyl chloride; hydroxylamine-O-sulfonic acid 1) 1h, reflux, 2) toluene, 2h, reflux; Yield given. Multistep reaction;

: 552-16-9
ortho-nitrobenzoic acid

: 552-89-6
2-nitro-benzaldehyde

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane at 20℃; for 18h;	97%
With (CH3)2NCH2NpSiH2Ph at 110 - 140℃;	50%
With carboxylic acid reductase Kinetics; Green chemistry; Enzymatic reaction;
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C 3: pyridinium chlorochromate / dichloromethane / 20 °C View Scheme

: 552-16-9
ortho-nitrobenzoic acid

: 612-25-9
2-Nitrobenzyl alcohol

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With 4-methyl-morpholine; 1,3,5-trichloro-2,4,6-triazine In 1,2-dimethoxyethane at 20℃; for 3h; Esterification; Stage #2: With sodium tetrahydroborate In water at 0℃; Reduction;	97%
Stage #1: ortho-nitrobenzoic acid With sodium aminodiboranate In tetrahydrofuran at 20℃; Stage #2: With water	92%
With pyridine; methanol; sodium tetrahydroborate; trifluoro-[1,3,5]triazine 1.) CH2Cl2, -20 to -010 deg C, 1 h, 2.) room temperature, 10-15 min; Yield given. Multistep reaction;
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 2h;	85 % Turnov.
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C View Scheme

: 106-38-7
para-bromotoluene

: 552-16-9
ortho-nitrobenzoic acid

: 70680-21-6
4-methyl-2'-nitrobiphenyl

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With copper(II) carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: para-bromotoluene With potassium fluoride; palladium acetylacetonate; iso-propyldiphenylphoshine In various solvent(s) at 120℃; for 24h; Further stages.;	97%
With potassium fluoride; copper(II) carbonate; bis(acetylacetonato)palladium(II); isopropyldiphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity; Molecular sieve;	97 %Chromat.

: 5798-75-4
Ethyl 4-bromobenzoate

: 552-16-9
ortho-nitrobenzoic acid

: 108621-65-4
ethyl 2'-nitrobiphenyl-4-carboxylate

Conditions

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With copper(II) carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: Ethyl 4-bromobenzoate With potassium fluoride; palladium acetylacetonate; iso-propyldiphenylphoshine In various solvent(s) at 120℃; for 24h; Further stages.;	97%
With potassium fluoride; copper(II) carbonate; bis(acetylacetonato)palladium(II); isopropyldiphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity; Molecular sieve;	97 %Chromat.

2-Nitrobenzoic Acid Chemical Properties

Molecule structure of 2-Nitrobenzoic Acid (CAS NO.552-16-9) :

IUPAC Name: 2-nitrobenzoic acid
Molecular Weight: 167.1189 g/mol
Molecular Formula: C₇H₅NO₄
Density: 1.468 g/cm³
Melting Point: 147.5 deg C
Boiling Point: 340.7 °C at 760 mmHg
Flash Point: 157.5 °C
Appreance: off-white powder
Storage temp.: store at RT.
Merck: 14,6589
Molar Volume: 113.8 cm³
Polarizability: 15.74*10^-24 cm³
Surface Tension: 66.4 dyne/cm
Enthalpy of Vaporization: 61.67 kJ/mol
pKa Dissociation Constant: 2.47
log P (octanol-water): 1.46
Water Solubility: 7850 mg/L
Vapor Pressure: 7.14E-05 mm Hg
Henry's Law Constant: 4.28E-10 atm-m³/mole
Atmospheric OH Rate Constant: 5.86E-13 cm³/molecule-sec
XLogP3: 1.5
H-Bond Donor: 1
H-Bond Acceptor: 4
Rotatable Bond Count: 1
Exact Mass: 167.021858
MonoIsotopic Mass: 167.021858
Topological Polar Surface Area: 80.4
Heavy Atom Count: 12
Complexity: 198
Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)[N+](=O)[O-]
InChI: InChI=1S/C7H5NO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)
InChIKey: SLAMLWHELXOEJZ-UHFFFAOYSA-N
EINECS: 209-004-9
Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Biochemistry; Reagents for Oligosaccharide Synthesis; C7; Carbonyl Compounds; Carboxylic Acids

2-Nitrobenzoic Acid Uses

2-Nitrobenzoic Acid (CAS NO.552-16-9) is used in pharmaceutical synthesis and organic synthesis.

2-Nitrobenzoic Acid Production

O-nitro toluene , water, potassium hydroxide mixture heated to boiling, and then adding potassium permanganate in batches. Oxidation reaction is complete, filtering, sub-tilting to the oil, the filtrate acidification, filtration, washing, water re-crystallization of crude product derived product.

2-Nitrobenzoic Acid Safety Profile

Hazard Codes: Irritant Xi, Harmful Xn
Risk Statements: 36/37/38-68-22
R36/37/38: Irritating to eyes, respiratory system and skin
R68: Possible risk of irreversible effects
R22: Harmful if swallowed
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
WGK Germany: 3
RTECS: DH5050000
HS Code: 29163900

2-Nitrobenzoic Acid Specification

2-Nitrobenzoic Acid (CAS NO.552-16-9) is also called AI3-08821 ; CCRIS 2334 ; o-Carboxynitrobenzene ; o-Nitrobenzoic acid ; Benzoic acid, 2-nitro- ; Benzoic acid, o-nitro- ; o-Nitrobenzoic acid . 2-Nitrobenzoic Acid (CAS NO.552-16-9) is soluble in ethanol, ethyl ether, acetone, methanol, soluble in water and chloroform, very slightly soluble in benzene and carbon disulfide. 2-Nitrobenzoic acid is incompatible with strong oxidizing agents. Also incompatible with strong bases. May react with cyanides. When 2-Nitrobenzoic acid is heated to decomposition it emits very toxic fumes. Flash point data concerning 2-Nitrobenzoic acid are not available, however, 2-Nitrobenzoic acid is probably combustible.

Product Name

2-Nitrobenzoic acid

Synthetic route

2-Nitrobenzoic Acid Chemical Properties

2-Nitrobenzoic Acid Uses

2-Nitrobenzoic Acid Production

2-Nitrobenzoic Acid Safety Profile

2-Nitrobenzoic Acid Specification

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