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552-16-9 Usage

Uses

NH2-protecting reagent.

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.]

Definition

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

Chemical Properties

off-white powder

Health Hazard

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

General Description

Yellowish white crystals with an intensely sweet taste.

Reactivity Profile

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

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data concerning 2-Nitrobenzoic acid are not available, however, 2-Nitrobenzoic acid is probably combustible.
InChI:InChI=1/C7H5NO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)/p-1

552-16-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A10393)  2-Nitrobenzoic acid, 95%    552-16-9 2500g 2422.0CNY Detail
Alfa Aesar (A10393)  2-Nitrobenzoic acid, 95%    552-16-9 500g 1012.0CNY Detail
Alfa Aesar (A10393)  2-Nitrobenzoic acid, 95%    552-16-9 100g 253.0CNY Detail
TCI America (N0155)  2-Nitrobenzoic Acid  >90.0%(GC) 552-16-9 500g 1,440.00CNY Detail
TCI America (N0155)  2-Nitrobenzoic Acid  >90.0%(GC) 552-16-9 25g 210.00CNY Detail

552-16-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-nitrobenzoic acid

1.2 Other means of identification

Product number -
Other names Benzoic acid, 2-nitro-

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:552-16-9 SDS

552-16-9Synthetic route

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

2-nitrobenzaldehyde oxime

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

2-nitro-benzaldehyde

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

1,3-dihydroxy-2-(2-nitrophenyl)propane

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With jones reagent In acetone for 6h; Ambient temperature; addition at 0 deg C;96%
4-methyl-N'-(2-nitrobenzylidene)-benzenesulfonohydrazide
58809-90-8

4-methyl-N'-(2-nitrobenzylidene)-benzenesulfonohydrazide

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 8h; Heating;96%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

2-Nitrobenzyl alcohol

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

o-nitrobenzonitrile

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

methyl 2-nitrobenzoate

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

2-ethyl-3-nitrophenol

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

bis-(2-nitro-benzylidene)-hydrazine

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 86h; Heating;93%
C9H6Cl3NO4

C9H6Cl3NO4

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With indium; ammonium chloride In tetrahydrofuran for 3.5h; Heating;93%
2-Nitrobenzyl alcohol
612-25-9

2-Nitrobenzyl alcohol

A

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

B

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

Conditions
ConditionsYield
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

4-bromo-2-nitrobenzoic acid

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

2-acetylnitrobenzene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

o-nitrobenzonitrile

A

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

B

2-nitrobenzamide
610-15-1

2-nitrobenzamide

Conditions
ConditionsYield
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

2-(2-nitrophenyl)-1,3-dioxolane

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With aluminium trichloride; silver bromate In acetonitrile for 1.5h; Heating;87%
2,4,6-trinitrophenyl ester of 2-nitrobenzenecarbothioic acid
42546-69-0

2,4,6-trinitrophenyl ester of 2-nitrobenzenecarbothioic acid

A

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

B

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

2,4,6-trinitronitrosobenzene

Conditions
ConditionsYield
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

1-nitro-2-(2-nitrovinyl)benzene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With Amberlyst A-26 (OH-); dihydrogen peroxide In 1,4-dioxane at 20℃; for 8h;82%
2-nitrostyrene
579-71-5

2-nitrostyrene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

2-nitro-N-(quinolin-8-yl)benzamide

A

8-amino quinoline
578-66-5

8-amino quinoline

B

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; water for 12h; Reflux;A 80%
B 78%
carbon monoxide
201230-82-2

carbon monoxide

2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

carbon monoxide

2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

water
7732-18-5

water

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

carbon dioxide

o-(trimethylsilyl)nitrobenzene
15290-22-9

o-(trimethylsilyl)nitrobenzene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
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

1-methyl-2-nitrobenzene

A

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

B

2-Nitrobenzyl alcohol
612-25-9

2-Nitrobenzyl alcohol

C

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

Conditions
ConditionsYield
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

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

A

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

B

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

Conditions
ConditionsYield
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

o-Nitrobenzyloxytrimethylsilane

A

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

B

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

Conditions
ConditionsYield
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

(Z)-3-Dimethylamino-2-(2-nitro-phenyl)-propenal

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With sodium periodate In tetrahydrofuran; water for 18h;71%
benzoic acid
65-85-0

benzoic acid

A

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

B

3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

C

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
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

tert-butyl 2-nitrobenzoate

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 16h;70%
ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

2-nitrobenzyl chloride
610-14-0

2-nitrobenzyl chloride

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

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

(3,5-dibromo-2-(methoxymethoxy)phenyl)methanamine

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

N-(3,5-dibromo-2-(methoxymethoxy)benzyl)-2-nitrobenzamide

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

2-nitrobenzoic acid cesium salt

2-nitrobenzoic acid cesium salt

Conditions
ConditionsYield
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

1,2,3-Benzotriazole

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

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

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

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

anthranilic acid
118-92-3

anthranilic acid

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

nitrobenzene
98-95-3

nitrobenzene

Conditions
ConditionsYield
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

diethyl sulfate

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

ethyl 2-nitrobenzoate
610-34-4

ethyl 2-nitrobenzoate

Conditions
ConditionsYield
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

bromochlorobenzene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

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

4'-chloro-2-nitrobiphenyl

Conditions
ConditionsYield
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

9-bromophenanthrene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

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

1-(9-phenanthryl)-2-nitrobenzene

Conditions
ConditionsYield
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

(4-bromophenyl)(phenyl)methanone

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

4-(2-nitrophenyl)benzophenone

4-(2-nitrophenyl)benzophenone

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

diphenyl acetylene
501-65-5

diphenyl acetylene

C21H15NO4

C21H15NO4

Conditions
ConditionsYield
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

3-butene-1-amine

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

tert-butylisonitrile

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

benzaldehyde
100-52-7

benzaldehyde

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

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

Conditions
ConditionsYield
With indium(III) chloride In methanol at 20℃; for 18h; Ugi Condensation;99%
ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

<2H9>trimethylsulphoxonium iodide
23726-00-3

<2H9>trimethylsulphoxonium iodide

methyl-d3 2-nitrobenzoate
1613036-83-1

methyl-d3 2-nitrobenzoate

Conditions
ConditionsYield
With potassium carbonate at 20℃; for 3h; Sealed tube;99%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2,2-dimethoxyethylamine
22483-09-6

2,2-dimethoxyethylamine

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

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

Conditions
ConditionsYield
In methanol at 20℃; for 24h;99%
(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

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

methyl-(2'-nitro-[1,1'-biphenyl]-4-yl)sulfane

Conditions
ConditionsYield
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

3-Bromopyridine

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

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

3-(2-nitro-phenyl)-pyridine

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

n-butylstannoic acid
2273-43-0

n-butylstannoic acid

n-butyloxotin o-nitrobenzoate hexamer * 3C6H6

n-butyloxotin o-nitrobenzoate hexamer * 3C6H6

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

potassium o-nitrobenzoate
15163-59-4

potassium o-nitrobenzoate

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

4-methoxy-aniline
104-94-9

4-methoxy-aniline

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

2-nitro-N-(4-methoxyphenyl)benzamide

Conditions
ConditionsYield
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

dichloromethane

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

bis(2-nitrobenzoyloxy)methane

bis(2-nitrobenzoyloxy)methane

Conditions
ConditionsYield
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

tris(3-fluorophenyl)antimony

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

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

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

Conditions
ConditionsYield
With tert.-butylhydroperoxide In diethyl ether; water at 20℃; for 24h;98%
ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

Conditions
ConditionsYield
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

ortho-nitrobenzoic acid

2-Nitrobenzyl alcohol
612-25-9

2-Nitrobenzyl alcohol

Conditions
ConditionsYield
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

para-bromotoluene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

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

4-methyl-2'-nitrobiphenyl

Conditions
ConditionsYield
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

Ethyl 4-bromobenzoate

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

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

ethyl 2'-nitrobiphenyl-4-carboxylate

Conditions
ConditionsYield
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.

552-16-9Upstream product

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