552-16-9

Basic information

• Product Name: 2-Nitrobenzoic acid
• Synonyms: Benzoicacid,2-nitro-;o-carboxynitrobenzene;o-Nitrobenaoicacid;o-nitro-benzoicaci;1-CARBOXY-2-NITROBENZENE;2-NITROBENZOIC ACID;2-NITRODRACYLIC ACID;LABOTEST-BB LT00853998
• CAS NO: 552-16-9
• Molecular Formula: C₇H₅NO₄
• Molecular Weight: 167.12
• EINECS: 209-004-9
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Biochemistry;Reagents for Oligosaccharide Synthesis;C7;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;carboxylic acid| nitro-compound;Pharmaceutical Intermediates;Pyridines
• Mol File: 552-16-9.mol
• Article Data: 194

Chemical Properties

• Melting Point: 146-148 °C(lit.)
• Boiling Point: 295.67°C (rough estimate)
• Flash Point: 157.5°C
• Appearance: Off-white/Fine Powder
• Density: 1,58 g/cm3
• Vapor Pressure: 3.26E-05mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Storage Temp.: Store at RT.
• Solubility: 7.8g/l
• PKA: 2.16(at 18℃)
• Water Solubility: 6.8 g/L
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,6588
• BRN: 1910632
• CAS DataBase Reference: 2-Nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrobenzoic acid(552-16-9)
• EPA Substance Registry System: 2-Nitrobenzoic acid(552-16-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-68-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: DH5050000
• TSCA: Yes
• Hazardous Substances Data: 552-16-9(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

Uses

Different sources of media describe the Uses of 552-16-9 differently. You can refer to the following data:
1. NH2-protecting reagent.
2. 2-Nitrobenzoic Acid is used as a reagent in the synthesis of several organic compounds including that of novel triazoles and a tetrazole of escitalopram which act as cholinesterase inhibitors. It is also used in the one pot synthesis of 1,4-disubstituted 1,2,3-triazoles.

Definition

ChEBI: A nitrobenzoic acid carrying the nitro substituent at position 2.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 5924, 1991 DOI: 10.1021/jo00020a040Tetrahedron Letters, 35, p. 219, 1994 DOI: 10.1016/S0040-4039(00)76515-4

General Description

Yellowish white crystals with an intensely sweet taste.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Nitrobenzoic acid is incompatible with strong oxidizing agents. Also incompatible with strong bases. May react with cyanides .

Health Hazard

ACUTE/CHRONIC HAZARDS: When 2-Nitrobenzoic acid is heated to decomposition it emits very toxic fumes.

Fire Hazard

Flash point data concerning 2-Nitrobenzoic acid are not available, however, 2-Nitrobenzoic acid is probably combustible.

Purification Methods

Crystallise the acid from *benzene (twice), n-butyl ether (twice), then water (twice). Dry and store it in a vacuum desiccator. [Le Noble & Wheland J Am Chem Soc 80 5397 1958.] It has also been crystallised from EtOH/H2O. The amide has m 176.5o (from H2O). [Beilstein 9 III 1466, 9 IV 1046.]

InChI:InChI=1/C7H5NO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)/p-1

Synthetic route

2-nitrobenzaldehyde oxime (3717-25-7, 4836-00-4, 6635-41-2) → ortho-nitrobenzoic acid (552-16-9)

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%

2-nitro-benzaldehyde (552-89-6) → ortho-nitrobenzoic acid (552-16-9)

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%

1,3-dihydroxy-2-(2-nitrophenyl)propane (15121-85-4) → ortho-nitrobenzoic acid (552-16-9)

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

4-methyl-N'-(2-nitrobenzylidene)-benzenesulfonohydrazide (58809-90-8) → ortho-nitrobenzoic acid (552-16-9)

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

1-methyl-2-nitrobenzene (88-72-2) → ortho-nitrobenzoic acid (552-16-9)

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%

2-Nitrobenzyl alcohol (612-25-9) → ortho-nitrobenzoic acid (552-16-9)

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%

o-nitrobenzonitrile (612-24-8) → ortho-nitrobenzoic acid (552-16-9)

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%

methyl 2-nitrobenzoate (606-27-9) → ortho-nitrobenzoic acid (552-16-9)

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 → ortho-nitrobenzoic acid (552-16-9)

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%

bis-(2-nitro-benzylidene)-hydrazine (1929-19-7) → ortho-nitrobenzoic acid (552-16-9)

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

C9H6Cl3NO4 → ortho-nitrobenzoic acid (552-16-9)

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

2-Nitrobenzyl alcohol (612-25-9) → ortho-nitrobenzoic acid (552-16-9) + 2-nitro-benzaldehyde (552-89-6)

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%

4-bromo-2-nitrobenzoic acid (99277-71-1) → ortho-nitrobenzoic acid (552-16-9)

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%

2-acetylnitrobenzene (577-59-3) → ortho-nitrobenzoic acid (552-16-9)

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%

o-nitrobenzonitrile (612-24-8) → ortho-nitrobenzoic acid (552-16-9) + 2-nitrobenzamide (610-15-1)

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%

2-(2-nitrophenyl)-1,3-dioxolane (48140-35-8) → ortho-nitrobenzoic acid (552-16-9)

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

2,4,6-trinitrophenyl ester of 2-nitrobenzenecarbothioic acid (42546-69-0) → ortho-nitrobenzoic acid (552-16-9) + 2,4,6-trinitronitrosobenzene (10123-09-8)

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%

1-nitro-2-(2-nitrovinyl)benzene (5670-66-6, 5670-67-7, 3156-39-6) → ortho-nitrobenzoic acid (552-16-9)

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

2-nitrostyrene (579-71-5) → ortho-nitrobenzoic acid (552-16-9)

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%

2-nitro-N-(quinolin-8-yl)benzamide (33757-51-6) → 8-amino quinoline (578-66-5) + ortho-nitrobenzoic acid (552-16-9)

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

carbon monoxide (201230-82-2) + 2-nitrophenyl bromide (577-19-5) → ortho-nitrobenzoic acid (552-16-9)

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%

carbon monoxide (201230-82-2) + 2-nitrophenyl bromide (577-19-5) + water (7732-18-5) → ortho-nitrobenzoic acid (552-16-9)

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%

carbon dioxide (124-38-9) + o-(trimethylsilyl)nitrobenzene (15290-22-9) → ortho-nitrobenzoic acid (552-16-9)

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

1-methyl-2-nitrobenzene (88-72-2) → ortho-nitrobenzoic acid (552-16-9) + 2-Nitrobenzyl alcohol (612-25-9) + 2-nitro-benzaldehyde (552-89-6)

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;

2-(2-nitrophenyl)-1,3-oxathiolane → ortho-nitrobenzoic acid (552-16-9) + 2-nitro-benzaldehyde (552-89-6)

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

o-Nitrobenzyloxytrimethylsilane (62673-13-6) → ortho-nitrobenzoic acid (552-16-9) + 2-nitro-benzaldehyde (552-89-6)

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

(Z)-3-Dimethylamino-2-(2-nitro-phenyl)-propenal (85907-57-9) → ortho-nitrobenzoic acid (552-16-9)

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

benzoic acid (65-85-0) → ortho-nitrobenzoic acid (552-16-9) + 3-nitrobenzoic acid (121-92-6) + 4-nitro-benzoic acid (62-23-7)

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;

tert-butyl 2-nitrobenzoate (55666-41-6) → ortho-nitrobenzoic acid (552-16-9)

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

ortho-nitrobenzoic acid (552-16-9) → 2-nitrobenzyl chloride (610-14-0)

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%

ortho-nitrobenzoic acid (552-16-9) → 2-nitrophenyl bromide (577-19-5)

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%

ortho-nitrobenzoic acid (552-16-9) + (3,5-dibromo-2-(methoxymethoxy)phenyl)methanamine (1276560-33-8) → N-(3,5-dibromo-2-(methoxymethoxy)benzyl)-2-nitrobenzamide (1276560-34-9)

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%

ortho-nitrobenzoic acid (552-16-9) → 2-nitrobenzoic acid cesium salt

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

1,2,3-Benzotriazole (95-14-7) + ortho-nitrobenzoic acid (552-16-9) → (1H-benzo[d][1,2,3]triazol-1-yl)(2-nitrophenyl)methanone

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℃;

ortho-nitrobenzoic acid (552-16-9) → anthranilic acid (118-92-3)

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%

ortho-nitrobenzoic acid (552-16-9) → nitrobenzene (98-95-3)

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%

diethyl sulfate (64-67-5) + ortho-nitrobenzoic acid (552-16-9) → ethyl 2-nitrobenzoate (610-34-4)

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;

bromochlorobenzene (106-39-8) + ortho-nitrobenzoic acid (552-16-9) → 4'-chloro-2-nitrobiphenyl (6271-80-3)

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.

9-bromophenanthrene (573-17-1) + ortho-nitrobenzoic acid (552-16-9) → 1-(9-phenanthryl)-2-nitrobenzene (911217-05-5)

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.

(4-bromophenyl)(phenyl)methanone (90-90-4) + ortho-nitrobenzoic acid (552-16-9) → 4-(2-nitrophenyl)benzophenone

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.

ortho-nitrobenzoic acid (552-16-9) + diphenyl acetylene (501-65-5) → C21H15NO4

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

3-butene-1-amine (2524-49-4) + tert-butylisonitrile (119072-55-8, 7188-38-7) + ortho-nitrobenzoic acid (552-16-9) + benzaldehyde (100-52-7) → N-(but-3-en-1-yl)-N-(2-(tert-butylamino)-2-oxo-1-phenylethyl)-2-nitrobenzamide

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

ortho-nitrobenzoic acid (552-16-9) + <2H9>trimethylsulphoxonium iodide (23726-00-3) → methyl-d3 2-nitrobenzoate (1613036-83-1)

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

tert-butylisonitrile (119072-55-8, 7188-38-7) + ortho-nitrobenzoic acid (552-16-9) + 4-chlorobenzaldehyde (104-88-1) + 2,2-dimethoxyethylamine (22483-09-6) → N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzamide

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

(4-bromophenyl)thioanisole (104-95-0) + ortho-nitrobenzoic acid (552-16-9) → methyl-(2'-nitro-[1,1'-biphenyl]-4-yl)sulfane (911217-03-3)

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.

3-Bromopyridine (626-55-1) + ortho-nitrobenzoic acid (552-16-9) → 3-(2-nitro-phenyl)-pyridine (4253-80-9)

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.

ortho-nitrobenzoic acid (552-16-9) + n-butylstannoic acid (2273-43-0) → n-butyloxotin o-nitrobenzoate hexamer * 3C6H6

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%

ortho-nitrobenzoic acid (552-16-9) → potassium o-nitrobenzoate (15163-59-4)

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%

ortho-nitrobenzoic acid (552-16-9) + 4-methoxy-aniline (104-94-9) → 2-nitro-N-(4-methoxyphenyl)benzamide (22979-83-5)

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%

dichloromethane (75-09-2) + ortho-nitrobenzoic acid (552-16-9) → bis(2-nitrobenzoyloxy)methane

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 + ortho-nitrobenzoic acid (552-16-9) → tris(3-fluorophenyl)antimony-bis(2-nitrobenzoate)

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

ortho-nitrobenzoic acid (552-16-9) → 2-nitro-aniline (88-74-4)

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;

ortho-nitrobenzoic acid (552-16-9) → 2-nitro-benzaldehyde (552-89-6)

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

ortho-nitrobenzoic acid (552-16-9) → 2-Nitrobenzyl alcohol (612-25-9)

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

para-bromotoluene (106-38-7) + ortho-nitrobenzoic acid (552-16-9) → 4-methyl-2'-nitrobiphenyl (70680-21-6)

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.

Ethyl 4-bromobenzoate (5798-75-4) + ortho-nitrobenzoic acid (552-16-9) → ethyl 2'-nitrobiphenyl-4-carboxylate (108621-65-4)

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.

Upstream product

• 89-52-1 o-acetylamino-benzoic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 42546-69-0 2,4,6-trinitrophenyl ester of 2-nitrobenzenecarbothioic acid 
• 15121-85-4 1,3-dihydroxy-2-(2-nitrophenyl)propane 
• 91135-71-6 5-benzoyl-pyrimidine-2,4,6-trione 
• 7697-37-2 nitric acid 
• 67170-66-5 N'-(2,4-dibromo-phenyl)-2-nitro-benzohydrazonoyl bromide 
• 552-89-6 2-nitro-benzaldehyde 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 103-79-7 1-phenyl-acetone 
• 65-85-0 benzoic acid 
• 94-36-0 dibenzoyl peroxide 
• 7137-54-4 1-nitro-2-propyl-benzene 

Downstream Products

• 610-15-1 2-nitrobenzamide 
• 573-79-5 2,2'-azoxy-di-benzoic acid 
• 73376-03-1 (4-methoxyphenyl)(2-nitrophenyl)methanone 
• 1098-32-4 2-Nitro-N,N-dicyclohexyl-benzamid 
• 87895-60-1 3,5-dimethyl-2-(2-nitrobenzoyl)thiophene 
• 75007-80-6 2-(2-Nitro-phenyl)-1H-imidazo[4,5-c]pyridine 
• 97051-57-5 Cetyl 2-nitrobenzoate 
• 832-79-1 5-(2-nitrophenyl)-1,3,4-thiadiazol-2-amine 
• 5344-90-1 2-Aminobenzyl alcohol 
• 13280-60-9 5-amino-2-nitrobenzoic acid 
• 116465-92-0 3-Amino-2-nitrobenzoic acid 
• 98-95-3 nitrobenzene 
• 118-92-3 anthranilic acid 
• 591-50-4 iodobenzene 

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