4771-47-5

Basic information

• Product Name: 3-Chloro-2-nitrobenzoic acid
• Synonyms: 3-CHLORO-2-NITROBENZOIC ACID;3-chloro-2-nitrobenzoicacidt;3-CHOLORO-2-NITROBNZOIC ACID;2-NITRO-3-CHLOROBENZOICACID;Benzoic acid, 3-chloro-2-nitro-;3-CHLORO-2-NITROBENZOIC ACID 99%;3-Chloro-2-nitrobenzoic acid,98%
• CAS NO: 4771-47-5
• Molecular Formula: C₇H₄ClNO₄
• Molecular Weight: 201.56
• EINECS: 225-313-1
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;C7;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 4771-47-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 237-239 °C(lit.)
• Boiling Point: 365.552 °C at 760 mmHg
• Flash Point: 174.88 °C
• Appearance: almost white to beige crystalline powder
• Density: 1.5660
• Vapor Pressure: 5.5E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Room temperature.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 1.82±0.10(Predicted)
• Water Solubility: 0.47g/L(25 oC)
• BRN: 2109828
• CAS DataBase Reference: 3-Chloro-2-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-2-nitrobenzoic acid(4771-47-5)
• EPA Substance Registry System: 3-Chloro-2-nitrobenzoic acid(4771-47-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25-36
• WGK Germany: 3
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 4771-47-5(Hazardous Substances Data)

Usage

Chemical Properties

almost white to beige crystalline powder

Uses

3-Chloro-2-nitrobenzoic acid has been used in the preparation of:2-amino-3-chlorobenzonitrile3-chloro-2-nitrobenzaldehyde

General Description

Hydrogen-bonded structures of isomeric compounds of 3-chloro-2-nitrobenzoic acid with quinoline have been investigated.

InChI:InChI=1/C7H4ClNO4/c8-5-3-1-2-4(7(10)11)6(5)9(12)13/h1-3H,(H,10,11)/p-1

Synthetic route

2-amino-3-chlorobenzoic acid (6388-47-2) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
With sodium perborate; titanium(IV) hydroxide; acetic acid at 85 - 90℃; for 1h; Temperature; Inert atmosphere;	84.9%

3-chloro-2-nitrotoluene (5367-26-0) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
With potassium permanganate; water; magnesium sulfate
With potassium permanganate; tetrabutylammomium bromide

3-chlorobenzoate (535-80-8) → 5-chloro-2-nitrobenzoic acid (2516-95-2) + 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
With nitric acid
With nitric acid das Gemisch wird in Wasser von 50grad gegossen;
beim Nitrieren;

2-Nitroso-3-chlor-toluol (23082-43-1) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
With potassium dichromate

3-Chloro-2-nitroso-benzoic acid → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
With nitric acid

nitric acid (7697-37-2) + 3-chlorobenzoate (535-80-8) → 5-chloro-2-nitrobenzoic acid (2516-95-2) + 3-chloro-2-nitro-benzoic acid (4771-47-5)

3-chloro-2-nitrotoluene (5367-26-0) + magnesium sulfate (7487-88-9) + KMnO4 → 3-chloro-2-nitro-benzoic acid (4771-47-5)

2,4-dinitrotoluene (121-14-2) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sodium acetate / bei der elektrolytischen Reduktion 2: hydrochloric acid 3: Verkochen des Diazoniumsulfats mit Alkohol.Diazotization 4: KMnO4; water; MgSO4 View Scheme

2,6-dinitrotoluene (606-20-2) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: bei der elektrolytischen Reduktion 2: concentrated hydrochloric acid 3: sulfuric acid / Diazotization.Verkochen der Loesung mit Alkohol 4: KMnO4; water; MgSO4 View Scheme

4-hydroxylamino-2-nitrotoluene (43192-03-6) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrochloric acid 2: Verkochen des Diazoniumsulfats mit Alkohol.Diazotization 3: KMnO4; water; MgSO4 View Scheme

2-hydroxylamino-6-nitrotoluene (5805-95-8) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated hydrochloric acid 2: sulfuric acid / Diazotization.Verkochen der Loesung mit Alkohol 3: KMnO4; water; MgSO4 View Scheme

2-chloro-4-methyl-3-nitro-aniline (39053-44-6) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Verkochen des Diazoniumsulfats mit Alkohol.Diazotization 2: KMnO4; water; MgSO4 View Scheme

4-chloro-2-methyl-3-nitro-aniline (219312-08-0) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / Diazotization.Verkochen der Loesung mit Alkohol 2: KMnO4; water; MgSO4 View Scheme

2-chloro-6-methylaniline (87-63-8) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2S2O8, H2SO4 2: aq. K2Cr2O7 View Scheme

3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-hydroxy-2-nitrobenzoic acid (602-00-6)

Conditions	Yield
With potassium hydroxide; water for 12h; Heating / reflux;	100%
With water; potassium hydroxide Reflux;	100%
With potassium hydroxide In water at 110℃; for 12h;	99%

3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-chloro-2-nitrobenzamide (59772-47-3)

Conditions	Yield
Stage #1: 3-chloro-2-nitro-benzoic acid With thionyl chloride at 80℃; for 1h; Stage #2: With ammonia In dichloromethane; water at 0℃; for 0.416667h;	100%
Multi-step reaction with 2 steps 1: 51.1 g / thionyl chloride / toluene / 3 h / Heating 2: 96 percent / 28percent aq. NH3 / 0.33 h View Scheme
Multi-step reaction with 2 steps 1: PCl5 / benzene / 3 h / Heating 2: conc. NH4OH View Scheme
Stage #1: 3-chloro-2-nitro-benzoic acid With thionyl chloride In toluene at 80℃; for 4h; Stage #2: With ammonium hydroxide at 20℃; for 1h;
With thionyl chloride; aqueous NH3 In dichloromethane

3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-chloro-2,6-dinitrobenzoic acid (150272-17-6)

Conditions	Yield
With sulfuric acid; nitric acid at 20℃; for 2h; Heating / reflux;	99%

3-chloro-2-nitro-benzoic acid (4771-47-5) + methyl iodide (74-88-4) → 3-chloro-2-nitro-benzoic acid methyl ester (42087-81-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 1h;	99%
With potassium carbonate In acetone at 40℃; for 1h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 4.5h; Inert atmosphere;	97%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 1h;	94%

diazomethane (186581-53-3, 908094-01-9) + 3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-chloro-2-nitro-benzoic acid methyl ester (42087-81-0)

Conditions	Yield
In diethyl ether Inert atmosphere;	99%

morpholine (110-91-8) + 3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-morpholino-2-nitrobenzoic acid

Conditions	Yield
at 130℃; for 48h;	98%

3-chloro-2-nitro-benzoic acid (4771-47-5) → 1-chloro-4-iodo-2-nitrobenzene (41252-95-3)

Conditions	Yield
With copper(I) oxide; potassium phosphate; bismuth (III) nitrate pentahydrate; palladium(II) trifluoroacetate; oxygen; sodium iodide In dimethyl sulfoxide at 170℃; for 20h; Schlenk technique;	96%
With copper(I) oxide; potassium phosphate; bismuth (III) nitrate pentahydrate; palladium(II) trifluoroacetate; oxygen; sodium iodide In dimethyl sulfoxide at 170℃; for 10h; Catalytic behavior; Schlenk technique; Green chemistry; regioselective reaction;	93%

3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-chloro-2-nitrobenzoyl chloride (19088-99-4)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 2h; Reflux; Inert atmosphere;	94%
With phosphorus pentachloride In benzene for 3h; Heating;
With thionyl chloride In toluene for 3h; Heating;	51.1 g

3-chloro-2-nitro-benzoic acid (4771-47-5) + dimethyl sulfate (77-78-1) → 3-chloro-2-nitro-benzoic acid methyl ester (42087-81-0)

Conditions	Yield
With potassium carbonate In acetone for 0.5h; Esterification; Heating;	89%

3-chloro-2-nitro-benzoic acid (4771-47-5) → (3-chloro-2-nitrophenyl)methanol (77158-86-2)

Conditions	Yield
With diborane In tetrahydrofuran for 2h; Ambient temperature;	88%
Multi-step reaction with 2 steps 1: thionyl chloride; DMF / tetrahydrofuran / Heating 2: sodium borohydride / dimethylformamide; tetrahydrofuran / 20 °C View Scheme

3-chloro-2-nitro-benzoic acid (4771-47-5) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol; water for 1h; Ambient temperature;	85%
With hydrogenchloride; tin	72%
With ammonium hydroxide; sodium dithionite In water at 20℃; for 1h;	70%

selenium (7782-49-2) + iodobenzene (591-50-4) + 3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-chloro-2-nitrophenyl phenyl selenoether

Conditions	Yield
With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 100℃; for 24h;	80%

diphenyl diselenide (1666-13-3) + 3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-chloro-2-nitrophenyl phenyl selenoether

Conditions	Yield
With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 150℃; for 24h;	80%
With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 150℃; under 760.051 Torr; for 24h; Schlenk technique; Sealed tube;	67%

3-chloro-2-nitro-benzoic acid (4771-47-5) + diazomethyl-trimethyl-silane (18107-18-1) → 3-chloro-2-nitro-benzoic acid methyl ester (42087-81-0)

Conditions	Yield
In methanol; hexanes; acetonitrile at 0℃; for 0.5h;	74%
In methanol; hexanes; acetonitrile at 0℃; for 0.5h;	74%

3-chloro-2-nitro-benzoic acid (4771-47-5) + phenylacetylene (536-74-3) → 1,4-diphenyl-1,3-butadiyne (886-66-8) + 1-chloro-2-nitro-3-(phenylethynyl)benzene

Conditions	Yield
With 1,10-Phenanthroline; oxygen; sodium hydrogencarbonate; copper(II) sulfate In N,N-dimethyl-formamide; toluene at 150℃; for 24h; Molecular sieve; Schlenk technique;	A 65% B 63%

3-chloro-2-nitro-benzoic acid (4771-47-5) → 1-hydroxy-1H-benzo[d][1,2,3]triazole-7-carboxylic acid

Conditions	Yield
With hydrazine hydrate In ethanol for 18h; Heating;	62%

3-chloro-2-nitro-benzoic acid (4771-47-5) + sodium 4-methylbenzenesulfinate (824-79-3) → 1-chloro-2-nitro-3-tosylbenzene (873970-95-7)

Conditions	Yield
With 1,10-Phenanthroline; silver carbonate at 160℃; for 18h; Schlenk technique; Sealed tube;	62%

3-chloro-2-nitro-benzoic acid (4771-47-5) → 2-amino-3-hydrothiobenzoic acid

Conditions	Yield
With sodiumsulfide nonahydrate In water Reflux;	59%

3-chloro-2-nitro-benzoic acid (4771-47-5) + 2-6-dimethoxybenzoic acid (1466-76-8) → 3-chloro-2',6'-dimethoxy-2-nitro-1,1'-biphenyl (1352638-56-2) + C12H6Cl2N2O4 (1352638-64-2)

Conditions	Yield
With triphenylphosphine; silver carbonate; palladium dichloride In dimethyl sulfoxide at 130℃; for 6h; Inert atmosphere;	A 57% B 22%

3,5-dimethylphenyl iodide (22445-41-6) + 3-chloro-2-nitro-benzoic acid (4771-47-5) → 4-chloro-3-nitro-3',5'-dimethyl-1,1'-biphenyl (1344681-48-6)

Conditions	Yield
Stage #1: 3,5-dimethylphenyl iodide; 3-chloro-2-nitro-benzoic acid With palladium diacetate; acetic acid; silver carbonate at 130℃; for 16h; Stage #2: With silver carbonate In dimethyl sulfoxide at 130℃; for 3h; regioselective reaction;	56%

3-chloro-2-nitro-benzoic acid (4771-47-5) + thiophenol (108-98-5) → (3-chloro-2-nitrophenyl)(phenyl)sulfane

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; oxygen; potassium carbonate In dimethyl sulfoxide at 140℃; for 24h; Molecular sieve;	56%

3-chloro-2-nitro-benzoic acid (4771-47-5) → 4-bromo-1-chloro-2-nitrobenzene (16588-24-2)

Conditions	Yield
With copper(I) oxide; potassium phosphate; tetrakis(triphenylphosphine) palladium(0); bismuth (III) nitrate pentahydrate; oxygen; sodium bromide In dimethyl sulfoxide at 170℃; for 10h; Schlenk technique; Green chemistry; regioselective reaction;	56%

oxalyl dichloride (79-37-8) + N-(5-amino-2-methylphenyl)-4-diethylaminomethylbenzamide (250681-65-3) + N-[2-methyl-5-(3-morpholino-2-nitrobenzamido)phenyl]-4-diethylaminomethylbenzamide (250682-02-1) + 3-chloro-2-nitrobenzoyl chloride (19088-99-4) + 3-chloro-2-nitro-benzoic acid (4771-47-5) → N-[5-(3-chloro-2-nitrobenzamido)-2-methylphenyl]-4-diethylaminomethylbenzamide (1431463-84-1)

Conditions	Yield
	55%

3-chloro-2-nitro-benzoic acid (4771-47-5) → 3-chloro-2-nitro-aniline (59483-54-4)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	53.4%
(i) NaN3, SO3/H2SO4, (ii) H2O; Multistep reaction;
Multi-step reaction with 4 steps 1: SOCl2 / 3 h / Heating 2: NaN3 / acetone; H2O / 0.5 h / Ambient temperature 3: benzene / Heating 4: 5 N aq. NaOH / benzene / 1 h / Ambient temperature View Scheme

3-chloro-2-nitro-benzoic acid (4771-47-5) + ethyl 1,2,3,4-tetrahydro-β-carboline-3-carboxylate (84518-77-4) → 2-Cyclohexyl-1-[(E)-cyclohexylimino]-1,2,3a,4,9,10-hexahydro-2,9,10a-triaza-cyclopenta[b]fluoren-3-one (130472-83-2) + 2-(3-Chloro-2-nitro-benzoyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester (130472-82-1)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane for 3h; Ambient temperature;	A 20% B 51%

3-chloro-2-nitro-benzoic acid (4771-47-5) + methyl(([1,2,4]triazolo-[4,3-a]pyridin-3-yl)methyl)amine hydrochloride → 3-chloro-N-methyl-2-nitro-N-(([1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)benzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;	40%

3-chloro-2-nitro-benzoic acid (4771-47-5) + 1-(4-fluorophenylmethyl)piperazine (70931-28-1) → 1-[4-(4-fluorobenzyl)piperazin-1-yl]-(3-chloro-2-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;	34%

3-chloro-2-nitro-benzoic acid (4771-47-5) + phenylmagnesium bromide (100-58-3) → (3-chloro-2-nitrophenyl)(phenyl)methanone (78940-48-4)

Conditions	Yield
Stage #1: 3-chloro-2-nitro-benzoic acid With thionyl chloride at 80℃; for 2h; Stage #2: phenylmagnesium bromide In tetrahydrofuran at -15 - 20℃;	31%

3-chloro-2-nitro-benzoic acid (4771-47-5) + methylamine (74-89-5) → 3-(methylamino)-2-nitrobenzoic acid (124341-37-3)

Conditions	Yield
In water at 100℃; for 96h;	26%

Upstream product

• 5367-26-0 3-chloro-2-nitrotoluene 
• 535-80-8 3-chlorobenzoate 
• 23082-43-1 2-Nitroso-3-chlor-toluol 
• 7697-37-2 nitric acid 
• 7487-88-9 magnesium sulfate 
• 121-14-2 2,4-dinitrotoluene 
• 606-20-2 2,6-dinitrotoluene 
• 43192-03-6 4-hydroxylamino-2-nitrotoluene 
• 5805-95-8 2-hydroxylamino-6-nitrotoluene 
• 39053-44-6 2-chloro-4-methyl-3-nitro-aniline 
• 219312-08-0 4-chloro-2-methyl-3-nitro-aniline 
• 87-63-8 2-chloro-6-methylaniline 
• 6388-47-2 2-amino-3-chlorobenzoic acid 

Downstream Products

• 124341-37-3 3-(methylamino)-2-nitrobenzoic acid 
• 42087-81-0 3-chloro-2-nitro-benzoic acid methyl ester 
• 150272-17-6 3-chloro-2,6-dinitrobenzoic acid 
• 714229-96-6 2-(3-chloro-2-nitro-phenyl)-thiochromen-4-one 
• 714229-86-4 2-(3-chloro-2-nitro-phenyl)-3-methanesulfinyl-thiochroman-4-one 
• 714229-78-4 1-[2-(p-methoxybenzylthio)phenyl]-2-(methylsulfinyl)-3-(3-chloro-2-nitrophenyl)-2-propen-1-one 
• 77326-39-7 2-amino-3-(dimethylamino)benzonitrile 
• 77326-49-9 2-(dimethylamino)-6-benzonitrile 
• 77326-48-8 2-nitro-3-(dimethylamino)benzamide 
• 77326-26-2 N-(2-Cyano-6-dimethylamino-phenyl)-oxalamic acid ethyl ester 
• 1829-32-9 3-Chloro-2-hydroxybenzoic acid 
• 851847-38-6 3-chloro-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-nitrobenzamide 
• 301672-64-0 3-chloro-2-nitro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide 
• 263270-30-0 N-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]-3-chloro-2-nitrobenzamide 

Relevant articles and documents

A process for the preparation of nitrobenzene derivative

The invention provides a preparation method of nitrobenzene derivatives, which comprises the following steps: mixing aromatic amino-compound with sodium perborate, a titanic acid catalyst and glacial acetic acid, and reacting to obtain nitrobenzene derivatives, wherein the titanic acid catalyst is prepared by reacting isopropyl titanate and oxydol, and the aromatic amino-compound is a compound with an electrophilic substitution group in the ortho-position of the amino group. By using the sodium perborate as the oxidizer and the titanic acid catalyst as the cocatalyst, the reaction yield is up to 80-85%, and the product purity is up to 99% above.

Studies on pyrrolnitrin, a new antibiotic. 3. Structure of pyrrolnitrin.

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