5344-49-0

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-6-nitro-benzoic acid is used as a starting material for the synthesis of various chemical compounds. Its unique structure, featuring a chlorine and nitro group, makes it a valuable intermediate in the preparation of a range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-6-nitro-benzoic acid is used as a reagent in the development of new drugs. Its chemical properties allow it to be a key component in the synthesis of potential therapeutic agents.
Used in Research and Development:
2-Chloro-6-nitro-benzoic acid is employed in research and development settings to explore its potential applications in various fields, including material science and organic chemistry. Its unique properties make it an interesting subject for scientific investigation.

InChI:InChI=1/C12H13ClN2OS/c1-12(2,3)10(16)15-11-14-9-7(13)5-4-6-8(9)17-11/h4-6H,1-3H3,(H,14,15,16)

Synthetic route

(2-chloro-6-nitrobenzene)methanol (50907-57-8) → 2-chloro-6-nitrobenzoic acid (5344-49-0)

Conditions	Yield
With water; nitric acid In 1,2-dichloro-benzene at 100 - 140℃; under 7500.75 Torr; for 8.66667h; Product distribution / selectivity;	78%
With water; nitric acid In 1,2-dichloro-benzene at 140℃; for 6h; Product distribution / selectivity;	60%
With potassium permanganate; sodium carbonate In water for 4h; Heating;	250 mg

6-chloro-2-nitrotoluene (83-42-1) → 2-chloro-6-nitrobenzoic acid (5344-49-0)

Conditions	Yield
With bromine at 170℃; Irradiation.Erhitzen der Reaktionsloesung mit Kaliumacetat und Aethanol und Erwaermen des Reaktionsprodukts mit wss. Kalilauge unter Zusatz von Kaliumpermanganat;
With potassium permanganate
With nitric acid
With potassium hydroxide; potassium permanganate In water

2-chloro-6-nitrobenzonitrile (6575-07-1) → 2-chloro-6-nitrobenzoic acid (5344-49-0)

Conditions	Yield
(i) H2SO4, (ii) aq. NaNO2; Multistep reaction;

6-chloro-2-nitrotoluene (83-42-1) + nitric acid (7697-37-2) → 2-chloro-6-nitrobenzoic acid (5344-49-0)

6-chloro-2-nitrotoluene (83-42-1) + KMnO4 → 2-chloro-6-nitrobenzoic acid (5344-49-0)

6-chloro-2-nitrotoluene (83-42-1) + sunlight → 2-chloro-6-nitrobenzoic acid (5344-49-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 700 mg / N-bromosuccinimide, azobisisobutyronitril / CCl4 / 24 h / Heating; Irradiation 2: ethanol / 4 h / Heating 3: 400 mg / 10percent KOH / 4 h / 90 °C 4: 250 mg / KMnO4, Na2CO3 / H2O / 4 h / Heating View Scheme

2-chloro-6-nitrobenzyl bromide (56433-01-3) → 2-chloro-6-nitrobenzoic acid (5344-49-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 4 h / Heating 2: 400 mg / 10percent KOH / 4 h / 90 °C 3: 250 mg / KMnO4, Na2CO3 / H2O / 4 h / Heating View Scheme

acetate of 2-chloro-6-nitrobenzyl alcohol (919076-97-4) → 2-chloro-6-nitrobenzoic acid (5344-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 400 mg / 10percent KOH / 4 h / 90 °C 2: 250 mg / KMnO4, Na2CO3 / H2O / 4 h / Heating View Scheme

1-methyl-2-nitrobenzene (88-72-2) → 2-chloro-6-nitrobenzoic acid (5344-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: SbCl5; chlorine / <40 2: nitric acid View Scheme

2-Fluoroaniline (348-54-9) + 2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-chloro-N-(2-fluorophenyl)-6-nitrobenzamide

Conditions	Yield
Stage #1: 2-chloro-6-nitrobenzoic acid With thionyl chloride In toluene at 110℃; Stage #2: 2-Fluoroaniline With sodium hydrogencarbonate In 1,4-dioxane; toluene at 20℃;	100%

meta-fluoroaniline (372-19-0) + 2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-chloro-N-(3-fluorophenyl)-6-nitrobenzamide

Conditions	Yield
Stage #1: 2-chloro-6-nitrobenzoic acid With thionyl chloride In toluene at 110℃; Stage #2: meta-fluoroaniline With sodium hydrogencarbonate In 1,4-dioxane; toluene at 20℃;	100%

2-chloro-6-nitrobenzoic acid (5344-49-0) + Cyclopropylamine (765-30-0) → 2-chloro-N-cyclopropyl-6-nitrobenzamide

Conditions	Yield
Stage #1: 2-chloro-6-nitrobenzoic acid With thionyl chloride In toluene at 110℃; Stage #2: Cyclopropylamine With sodium hydrogencarbonate In 1,4-dioxane; toluene at 5 - 20℃; for 24h; Concentration; Solvent; Temperature;	98%

2-chloro-6-nitrobenzoic acid (5344-49-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-chloro-6-nitro-benzoic acid methyl ester (80563-87-7)

Conditions	Yield
Stage #1: 2-chloro-6-nitrobenzoic acid; N,N-dimethyl-formamide With oxalyl dichloride In dichloromethane at 20℃; for 2h; Stage #2: With methanol In dichloromethane	97%

2-chloro-6-nitrobenzoic acid (5344-49-0) + (1R,2S)-2-fluorocyclopropylamine p-toluenesulfonic acid salt (143062-84-4) → 2-chloro-N-((1R,2S)-2-fluorocyclopropyl)-6-nitrobenzamide

Conditions	Yield
Stage #1: 2-chloro-6-nitrobenzoic acid With thionyl chloride In toluene at 110℃; for 9h; Stage #2: (1R,2S)-2-fluorocyclopropylamine p-toluenesulfonic acid salt With sodium hydrogencarbonate In 1,4-dioxane; toluene at 5 - 20℃;	90.86%

2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-chloro-6-aminobenzoic acid (2148-56-3)

Conditions	Yield
With potassium bisulfite; cerium(III) chloride; potassium chloride; 2-methoxy-phenol In ethanol at 65℃; for 8h; Time;	90%
With platinum Hydrogenation;
With ammonium hydroxide; iron(II) sulfate
With iron(II) sulfate

2-chloro-6-nitrobenzoic acid (5344-49-0) + o-toluidine (95-53-4) → 2-chloro-6-nitro-N-(o-tolyl)benzamide

Conditions	Yield
Stage #1: 2-chloro-6-nitrobenzoic acid With thionyl chloride In N,N-dimethyl-formamide; toluene at 110℃; Stage #2: o-toluidine With sodium hydrogencarbonate In 1,4-dioxane; N,N-dimethyl-formamide; toluene at 5 - 20℃; for 7h;	87.4%

2-chloro-6-nitrobenzoic acid (5344-49-0) + 4-fluoroaniline (371-40-4) → 2-chloro-N-(4-fluorophenyl)-6-nitrobenzamide

Conditions	Yield
Stage #1: 2-chloro-6-nitrobenzoic acid With thionyl chloride In toluene at 120℃; Stage #2: 4-fluoroaniline With sodium hydrogencarbonate In 1,4-dioxane; toluene at 5 - 20℃;	87.1%
Stage #1: 2-chloro-6-nitrobenzoic acid With thionyl chloride; N,N-dimethyl-formamide In toluene for 1.5h; Reflux; Stage #2: 4-fluoroaniline With triethylamine In dichloromethane at 10 - 20℃;

2-chloro-6-nitrobenzoic acid (5344-49-0) + 2-(5-phenyl-2H-tetrazole-2-yl)acetohydrazide (67037-01-8) → 2-(2-chloro-6-nitrophenyl)-5-((5-phenyl-2H-tetrazol-2-yl)methyl)-1,3,4-oxadiazole

Conditions	Yield
In trichlorophosphate Reflux;	80%

2-chloro-6-nitrobenzoic acid (5344-49-0) + 1-(4-fluorophenylmethyl)piperazine (70931-28-1) → 1-[4-(4-fluorobenzyl)piperazin-1-yl]-(2-chloro-6-nitrophenyl)methanone

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 50℃; for 0.166667h; Microwave irradiation;	64%

2-chloro-6-nitrobenzoic acid (5344-49-0) + 4-chloro-phenol (106-48-9) → 2-(4-chlorophenoxy)-6-nitrobenzoic acid (76093-27-1)

Conditions	Yield
With copper(l) iodide; copper; sodium carbonate In pentan-1-ol for 3h; Heating;	60%

2-monochlorophenol (95-57-8) + 2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-(2-chlorophenoxy)-6-nitrobenzoic acid (76093-23-7)

Conditions	Yield
With copper(l) iodide; copper; sodium carbonate In pentan-1-ol for 3h; Heating;	51%

2-chloro-6-nitrobenzoic acid (5344-49-0) + phenol (108-95-2) → 2-nitro-6-phenoxybenzoic acid (76093-21-5)

Conditions	Yield
With copper(l) iodide; copper; sodium carbonate In pentan-1-ol for 3h; Heating;	49%
With potassium hydroxide; copper

2-chloro-6-nitrobenzoic acid (5344-49-0) + 3-(2,2,2-trifluoroethoxy)aniline → 2-chloro-6-nitro-N-(3-(2,2,2-trifluoroethoxy)phenyl)benzamide

Conditions	Yield
Stage #1: 2-chloro-6-nitrobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 23℃; for 1h; Inert atmosphere; Stage #2: 3-(2,2,2-trifluoroethoxy)aniline With triethylamine In dichloromethane at 0℃; for 0.25h; Inert atmosphere;	41%

1-amino-3-methylbutane (107-85-7) + 2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-(3-methylbutylamino)-6-nitrobenzoic acid

Conditions	Yield
With potassium carbonate; copper(II) oxide Heating;	38%

pyruvic acid methyl ester (600-22-6) + 2-chloro-6-nitrobenzoic acid (5344-49-0) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 8-bromo-1-(2-chloro-6-fluorophenyl)-4-methyl[1,2,4]triazolo[4,3-a]quinoxaline (1417411-73-4) + 8-bromo-1-(2-chloro-6-fluorophenyl)-4-methyl[1,2,4]triazolo[4,3-a]quinoxaline (1417411-74-5)

Conditions	Yield
Stage #1: pyruvic acid methyl ester; 4-Bromo-benzene-1,2-diamine In toluene for 3h; Dean-Stark; Reflux; Stage #2: With trichlorophosphate at 120℃; for 2h; Stage #3: 2-chloro-6-nitrobenzoic acid	A 13.7% B 29%

4-hexylaniline (33228-45-4) + 2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-chloro-N-(4-hexylphenyl)-6-nitrobenzamide (1208255-45-1)

Conditions	Yield
With EDC-polymer In tetrahydrofuran at 20℃; for 4h;	23%

meta-nitrophenol (554-84-7) + 2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-nitro-6-(3-nitro-phenoxy)-benzoic acid (860699-16-7)

Conditions	Yield
With copper(l) iodide; copper; potassium carbonate

2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-hydroxy-6-nitrobenzoic acid (601-99-0)

Conditions	Yield
With copper(l) iodide; copper; potassium carbonate
Multi-step reaction with 3 steps 1: KOH; copper-powder 2: HNO3 3: aqueous NaOH View Scheme

2-chloro-6-nitrobenzoic acid (5344-49-0) → 2-chloro-6-nitro-benzoic acid chloride (50425-14-4)

Conditions	Yield
With thionyl chloride
With thionyl chloride
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃;
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 40℃; for 4h;
With thionyl chloride In toluene at 110℃;

2-chloro-6-nitrobenzoic acid (5344-49-0) + aniline (62-53-3) → 2-anilino-6-nitro-benzoic acid (37415-40-0)

Conditions	Yield
With copper; potassium carbonate

2-chloro-6-nitrobenzoic acid (5344-49-0) + anthranilic acid (118-92-3) → 2-(2-Carboxy-phenylamino)-6-nitro-benzoic acid (94654-71-4)

Conditions	Yield
With copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 0.5h;

2-chloro-6-nitrobenzoic acid (5344-49-0) + benzylamine (100-46-9) → 2-amino-N-benzyl-6-chloro-benzamide

Conditions	Yield
Multistep reaction;

Upstream product

• 6575-07-1 2-chloro-6-nitrobenzonitrile 
• 50907-57-8 (2-chloro-6-nitrobenzene)methanol 
• 83-42-1 6-chloro-2-nitrotoluene 
• 7697-37-2 nitric acid 
• 88-72-2 1-methyl-2-nitrobenzene 
• 919076-97-4 acetate of 2-chloro-6-nitrobenzyl alcohol 
• 56433-01-3 2-chloro-6-nitrobenzyl bromide 

Downstream Products

• 860699-16-7 2-nitro-6-(3-nitro-phenoxy)-benzoic acid 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 50425-14-4 2-chloro-6-nitro-benzoic acid chloride 
• 37415-40-0 2-anilino-6-nitro-benzoic acid 
• 76093-21-5 2-nitro-6-phenoxybenzoic acid 
• 94654-71-4 2-(2-Carboxy-phenylamino)-6-nitro-benzoic acid 
• 76093-27-1 2-(4-chlorophenoxy)-6-nitrobenzoic acid 
• 80563-87-7 2-chloro-6-nitro-benzoic acid methyl ester 
• 875836-71-8 2-acetylamino-6-(3-acetylamino-phenoxy)-benzoic acid 
• 1417411-71-2 C₁₆H₁₁BrClN₅O₃ 
• 1417411-72-3 C₁₆H₁₁BrClN₅O₃ 
• 121-73-3 3-Nitrochlorobenzene 
• 1417411-73-4 8-bromo-1-(2-chloro-6-fluorophenyl)-4-methyl[1,2,4]triazolo[4,3-a]quinoxaline 

Relevant academic research and scientific papers

Method for producing 2-halo-6-nitrobenzoic acids

The present invention relates to a process for the preparation of 2-halo-6-nitrobenzoic acids by oxidation of 2-halo-6-nitro-benzyl alcohols, esters, ethers, or mixtures thereof with nitric acid and to the use of this process as a step in the preparation of 2-halo-6-nitrobenzoic acids from 2-halo-6-nitrotoluenes.

Mass Spectrometric Fragmentation Reactions. XXXI-The Fragmentation Behaviour of o-Halobenzoic Acids Substituted in the 5-Position: A Novel Ortho Effect

A fragmentation sequence typical for o-halobenzoic acids carrying a heteroatom substituent in the 5-position is described.

4-Hydroxy-1,2-Benzisothiazol-3(2H)-one-1,1-dioxides and salts thereof

Compounds of the formula STR1 wherein R1 is hydrogen or hydroxyl, and non-toxic, pharmacologically acceptable salts thereof formed with inorganic or organic bases. The compounds as well as their salts are useful as sweetening agents.