99-60-5

Basic information

• Product Name: 2-Chloro-4-nitrobenzoic acid
• Synonyms: 2-CHLORO-4-NITROBENZOIC ACID;4-NITRO-2-CHLOROBENZOIC ACID;2-Chloro-4-Nitobenzoic Acid;2,4-CNBA;2-Chloride-4-Nitrobenzoic Acid;2-Chloro-4-nitrobenzoic acid,98%;Clc6h3(no2)cooh;O-chloro-p-nitrobenzoic acid
• CAS NO: 99-60-5
• Molecular Formula: C₇H₄ClNO₄
• Molecular Weight: 201.56
• EINECS: 202-771-0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;C7;Carbonyl Compounds;Carboxylic Acids;Pyridines
• Mol File: 99-60-5.mol

Chemical Properties

• Melting Point: 136-140 °C(lit.)
• Boiling Point: 160.5°C (rough estimate)
• Flash Point: 172.8 °C
• Appearance: Light yellow to light green/Crystalline Powder
• Density: 1.5719 (rough estimate)
• Vapor Pressure: 7.04E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: pK1: 1.96 (25°C)
• Water Solubility: 1 g/L (20 ºC)
• BRN: 1912836
• CAS DataBase Reference: 2-Chloro-4-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-nitrobenzoic acid(99-60-5)
• EPA Substance Registry System: 2-Chloro-4-nitrobenzoic acid(99-60-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DG5425000
• TSCA: Yes
• Hazardous Substances Data: 99-60-5(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to light green crystalline powder

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

Synthetic route

2-chloro-4-nitro-6-hydroxyisopropylbenzene → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
Stage #1: 2-chloro-4-nitro-6-hydroxyisopropylbenzene With 4-methyl-morpholine at 46℃; for 1.16667h; Stage #2: With titanium tetra-n-propoxide at 55℃; for 1.83333h;	96%

2-chloro-4-nitrobenzaldehyde (5568-33-2) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
With copper(II) oxide; dihydrogen peroxide In acetonitrile at 60℃; for 2.5h; Green chemistry;	85%
With potassium permanganate

2-chloro-4-nitrotoluene (121-86-8) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
With nitric acid at 120 - 180℃;
With manganese(IV) oxide; sulfuric acid
With manganese(IV) oxide; potassium hydroxide

4-nitro-2-chlorobenzonitrile (28163-00-0) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
With sulfuric acid Behandeln des Reaktionsgemisches mit wss. Natriumnitrit-Loesung;

2-chloro-4-nitrobenzoyl chloride (7073-36-1) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
With potassium permanganate

N-(2-chloro-4-nitrobenzoyl)imidazole → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
With 1H-imidazole; potassium chloride In water; acetonitrile at 25 - 50℃; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.);

1-(bromomethyl)-2-chloro-4-nitrobenzene (42533-63-1) + potassium permanganate → 2-chloro-4-nitrobenzoic acid (99-60-5)

2-chloro-4-nitrotoluene (121-86-8) + nitric acid (7697-37-2) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
at 170 - 180℃;

2-chloro-4-nitrotoluene (121-86-8) + sulfuric acid (7664-93-9) + K2cr2O7 → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
at 65℃;

2-chloro-4-nitrotoluene (121-86-8) + K3fe(CN)6 + aqueous KOH + MnO2 → 2-chloro-4-nitrobenzoic acid (99-60-5)

2-chloro-4-nitrotoluene (121-86-8) + permanganate solution → 2-chloro-4-nitrobenzoic acid (99-60-5)

diazotized 4-nitro-2-amino-benzoic acid → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
With hydrogenchloride; copper(l) chloride

hot 2-chloro-4-nitro-toluene → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
With sodium hydroxide; potassium permanganate
With potassium dichromate; sulfuric acid at 65℃;
With bromine at 170℃; Irradiation.Erhitzen der Reaktionsloesung mit Kaliumacetat und Aethanol und Erwaermen des Reaktionsprodukts mit wss. Kalilauge unter Zusatz von Kaliumpermanganat;

2,2'-dichloro-4,4'-dinitro-trans-stilbene (107016-63-7) + acetone (67-64-1) + KMnO4 → 2-chloro-4-nitrobenzoic acid (99-60-5)

phosphorus pentachloride (10026-13-8, 874483-75-7) + 2-carboxy-5-nitrobenzenesulfonic acid (22952-26-7) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
at 170℃; man destilliert das Reaktionsprodukt im Vakuum und kocht das Destillat mit Wasser;

1-methyl-4-nitrobenzene (99-99-0) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: SbCl5 / 100 °C 2: permanganate View Scheme

1-(bromomethyl)-2-chloro-4-nitrobenzene (42533-63-1) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Pb(NO3)2; water 2: KMnO4 View Scheme

2-methyl-5-nitroaniline (99-55-8) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: ice; concentrated hydrochloric acid / mit NaNO2 diazotieren und in CuCl-Loesung giessen 2: permanganate View Scheme

2-chloro-4-nitrotoluene (121-86-8) → 2-chloro-4-nitrobenzaldehyde (5568-33-2) + 2-chloro-4-nitrobenzoic acid (99-60-5) + (2-chloro-4-nitrophenyl)methanol (52301-88-9)

Conditions	Yield
Stage #1: 2-chloro-4-nitrotoluene With 5,10,15,20-tetrakis(4-methylphenyl)porphyrinatocopper(II); C40H32MnN8; oxygen; cobalt(II) diacetate tetrahydrate; acetic acid at 130℃; under 5250.53 Torr; Stage #2: With water at 83℃; under 3750.38 Torr;

2-chloro-4-nitrobenzoic acid (99-60-5) → 2-chloro-4-nitrobenzoyl chloride (7073-36-1)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 25℃; for 0.5h;	100%
With thionyl chloride	93%
With thionyl chloride	93%

2-chloro-4-nitrobenzoic acid (99-60-5) → (2-chloro-4-nitrophenyl)methanol (52301-88-9)

Conditions	Yield
Stage #1: 2-chloro-4-nitrobenzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 35℃; for 1.5h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 1h;	100%
Stage #1: 2-chloro-4-nitrobenzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 16h;	98%
Stage #1: 2-chloro-4-nitrobenzoic acid With borane In tetrahydrofuran at 20℃; for 16h; Stage #2: With water; potassium carbonate In tetrahydrofuran Product distribution / selectivity;	97%
Stage #1: 2-chloro-4-nitrobenzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 15 - 20℃; for 16h; Stage #3: With hydrogenchloride; water In tetrahydrofuran pH=1;
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran / 20 °C View Scheme

2-chloro-4-nitrobenzoic acid (99-60-5) + 4-methoxy-aniline (104-94-9) → 2-[(4-methoxyphenyl)amino]-4-nitrobenzoic acid (91-42-9)

Conditions	Yield
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 24h;	99%
With copper(I) sulfate; potassium carbonate; copper(II) sulfate In water for 0.116667h; Ullmann condensation; microwave irradiation;	93%
With potassium carbonate; copper(II) sulfate for 0.0333333h; Ullmann condensation; microwave irradiation;	93%

2-chloro-4-nitrobenzoic acid (99-60-5) → 4-amino-2-chlorobenzoic acid (2457-76-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; under 760 Torr;	98%
With isopropyl alcohol; potassium hydroxide at 20℃; for 2.5h; Catalytic behavior;	88%
With iron; ammonium chloride In ethanol; water for 2h; Reflux;	24%

ethanol (64-17-5) + 2-chloro-4-nitrobenzoic acid (99-60-5) → ethyl 2-chloro-4-nitrobenzoate (73097-02-6)

Conditions	Yield
With sulfuric acid Reflux;	98%
With sulfuric acid at 120℃; for 24h;	94%
With sulfuric acid Reflux;	91%
With sulfuric acid

2-chloro-4-nitrobenzoic acid (99-60-5) + isobutene (115-11-7) → tert-butyl 2-chloro-4-nitro-benzoate

Conditions	Yield
With sulfuric acid In dichloromethane at 20℃; for 16h;	97%

2-chloro-4-nitrobenzoic acid (99-60-5) + Thiosalicylic acid (147-93-3) → 4-nitro-2,2'-thiodibenzoic acid (103626-83-1)

Conditions	Yield
Stage #1: Thiosalicylic acid With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: 2-chloro-4-nitrobenzoic acid With copper(I) oxide for 5h; Reflux; Inert atmosphere;	97%

2-chloro-4-nitrobenzoic acid (99-60-5) → 2-hydroxy-4-nitrobenzoic acid (619-19-2)

Conditions	Yield
With pyridine; water; potassium carbonate; copper for 0.25h; sonication;	96%
With pyridine; copper; potassium carbonate In water for 2h; Heating;	90%
With quicklime; water; copper at 160 - 170℃;
With copper(l) iodide; copper; potassium carbonate
With calcium hydroxide; copper diacetate In water at 160℃; for 7h;

4-chloro-3-(pyridin-2-yl)benzeneamine (879088-41-2) + 2-chloro-4-nitrobenzoic acid (99-60-5) → 2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-nitrobenzamide

Conditions	Yield
With 2-(7-azobenzotriazolyl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	95.1%

2-chloro-4-nitrobenzoic acid (99-60-5) → 2-chloro-4,5-dinitrobenzoic acid (33458-98-9)

Conditions	Yield
With sulfuric acid; nitric acid at 90℃; for 0.666667h;	95%
With sulfuric acid; nitric acid anschliessendes Erwaermen auf 100grad;

2-chloro-4-nitrobenzoic acid (99-60-5) + aniline (62-53-3) → 2-anilino-4-nitrobenzoic acid (49551-01-1)

Conditions	Yield
With copper(I) sulfate; potassium carbonate; copper(II) sulfate In water for 0.0833333h; Ullmann condensation; microwave irradiation;	95%
With potassium carbonate; copper(II) sulfate for 0.0333333h; Ullmann condensation; microwave irradiation;	95%
With copper diacetate; potassium carbonate at 185℃; for 2h; Ullmann Condensation; Inert atmosphere;	52%

2-chloro-4-nitrobenzoic acid (99-60-5) + glycine (56-40-6) → 2-[(carboxymethyl)amino]-4-nitrobenzoic acid (108302-73-4)

Conditions	Yield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.416667h; Ullmann condensation; ultrasonic irradiation;	95%
With copper; potassium carbonate In N,N-dimethyl-formamide for 2h; Heating;	75%

pyrrolidine (123-75-1) + 2-chloro-4-nitrobenzoic acid (99-60-5) → 3-chloro-4-(pyrrolidin-1-yl-carbonyl)-1-nitro-benzene (209959-68-2)

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;	95%
With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane

2-chloro-4-nitrobenzoic acid (99-60-5) + 4-chloro-3-[5-(trifluoromethyl)pyridin-2-yl]aniline → 2-chloro-N-{4-chloro-3-[5-(trifluoromethyl)pyridin-2-yl]phenyl}-4-nitrobenzamide

Conditions	Yield
With 2-(7-azobenzotriazolyl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	92.3%

2-chloro-4-nitrobenzoic acid (99-60-5) + malonic acid dimethyl ester (108-59-8) → 2-(2-methoxy-2-oxoethyl)-4-nitrobenzoic acid

Conditions	Yield
With sodium methylate; copper(I) bromide	92%
Stage #1: 2-chloro-4-nitrobenzoic acid; malonic acid dimethyl ester With sodium methylate; copper(I) bromide at 100℃; Inert atmosphere; Stage #2: With hydrogenchloride In hexane; water pH=1;

2-chloro-4-nitrobenzoic acid (99-60-5) + methyl iodide (74-88-4) → methyl 2-chloro-4-nitrobenzoate (13324-11-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 1.5h;	92%

2-chloro-4-nitrobenzoic acid (99-60-5) + toluene (108-88-3) → benzyl 2-chloro-4-nitrobenzoate (250790-07-9)

Conditions	Yield
With N,N-dimethyl acetamide; trifluorormethanesulfonic acid; oxygen; palladium diacetate at 115℃; under 760.051 Torr; for 24h; Schlenk technique;	91%

2-chloro-4-nitrobenzoic acid (99-60-5) + dimethyl sulfate (77-78-1) → methyl 2-chloro-4-nitrobenzoate (13324-11-3)

Conditions	Yield
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 60℃; for 1.5h;	91%

2-chloro-4-nitrobenzoic acid (99-60-5) + propynoic acid methyl ester (922-67-8) → methyl 3-(2-chloro-4-nitrobenzoyloxy)acrylate

Conditions	Yield
With 4-methyl-morpholine In acetonitrile at 40℃; for 12h; Esterification;	90%

4-amino-3-(4-methylthiobenzyl)-5-mercapto-1,2,4-triazole + 2-chloro-4-nitrobenzoic acid (99-60-5) → C17H12ClN5O2S2 (1144110-82-6)

Conditions	Yield
With trichlorophosphate for 8h; Heating;	90%

2-chloro-4-nitrobenzoic acid (99-60-5) + trans-2-ethynylcyclohexan-1-ol (55506-28-0) → C15H14ClNO4

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In toluene at 0℃; Inert atmosphere;	90%

2-chloro-4-nitrobenzoic acid (99-60-5) + dimethyl amine (124-40-3) → 2-chloro-N,N-dimethyl-4-nitrobenzamide (90649-54-0)

Conditions	Yield
With N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridine-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h;	90%

pyrrolidine (123-75-1) + 2-chloro-4-nitrobenzoic acid (99-60-5) → 4-nitro-2-(1-pyrrolidinyl)benzoic acid

Conditions	Yield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.25h; Ullmann condensation; ultrasonic irradiation;	88%

2-chloro-4-nitrobenzoic acid (99-60-5) + methyl-d3-amine hydrochloride (7436-22-8) → 2-chloro-4-nitro-N-trideuteromethyl benzamide

Conditions	Yield
Stage #1: 2-chloro-4-nitrobenzoic acid With thionyl chloride; N,N-dimethyl-formamide for 1h; Reflux; Stage #2: methyl-d3-amine hydrochloride With triethylamine In dichloromethane at 20℃; for 1h;	86.6%

2-chloro-4-nitrobenzoic acid (99-60-5) + p-toluidine (106-49-0) → 4-nitro-2-p-toluidino-benzoic acid (26690-12-0)

Conditions	Yield
With potassium carbonate; copper(II) sulfate for 0.0221667h; Ullmann condensation; microwave irradiation;	86%
With copper; potassium carbonate In N,N-dimethyl-formamide Goldberg Reaction; Heating;

2-amino-benzthiazole (136-95-8) + 2-chloro-4-nitrobenzoic acid (99-60-5) → 3-nitro-12H-[1,3]benzothiazolo-[2,3-b]quinazolin-12-one

Conditions	Yield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.416667h; sonication;	86%
With copper Ullmann condensation; Sonication;

propylamine (107-10-8) + 2-chloro-4-nitrobenzoic acid (99-60-5) → 4-nitro-2-(propylamino)benzoic acid

Conditions	Yield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.416667h; Ullmann condensation; ultrasonic irradiation;	86%

2-chloro-4-nitrobenzoic acid (99-60-5) + 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (19541-96-9) → 2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]-4-nitrobenzoic acid (364727-81-1)

Conditions	Yield
	86%

2-chloro-4-nitrobenzoic acid (99-60-5) + phenethylamine (64-04-0) → 4-nitro-N-phenethylanthranilic acid (1002965-83-4)

Conditions	Yield
With copper(I) oxide; copper; potassium carbonate In various solvent(s) at 130℃; for 24h;	86%

Upstream product

• 121-86-8 2-chloro-4-nitrotoluene 
• 5568-33-2 2-chloro-4-nitrobenzaldehyde 
• 28163-00-0 4-nitro-2-chlorobenzonitrile 
• 7073-36-1 2-chloro-4-nitrobenzoyl chloride 
• 42533-63-1 1-(bromomethyl)-2-chloro-4-nitrobenzene 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 107016-63-7 2,2'-dichloro-4,4'-dinitro-trans-stilbene 
• 67-64-1 acetone 
• 10026-13-8 phosphorus pentachloride 
• 22952-26-7 2-carboxy-5-nitrobenzenesulfonic acid 
• 99-99-0 1-methyl-4-nitrobenzene 
• 99-55-8 2-methyl-5-nitroaniline 

Downstream Products

• 13324-11-3 methyl 2-chloro-4-nitrobenzoate 
• 106377-55-3 2-(6-methoxy-[3]pyridylamino)-4-nitro-benzoic acid 
• 88086-70-8 4-nitro-2-p-tolyloxy-benzoic acid 
• 61347-07-7 3,3'-dichloro-4,4'-azobenzenedicarboxylic acid 
• 33458-98-9 2-chloro-4,5-dinitrobenzoic acid 
• 619-19-2 2-hydroxy-4-nitrobenzoic acid 
• 100960-18-7 4-amino-2-chlorobenzohydrazide 
• 2457-76-3 4-amino-2-chlorobenzoic acid 
• 7073-36-1 2-chloro-4-nitrobenzoyl chloride 
• 26690-12-0 4-nitro-2-p-toluidino-benzoic acid 
• 728899-93-2 2-(3-amino-anilino)-4-nitro-benzoic acid 
• 90656-48-7 N-(4-chlorophenyl)-4-nitroanthranilic acid 
• 402847-57-8 4-nitro-2,4'-imino-di-benzoic acid 
• 71835-14-8 2-((2-carboxyphenyl)amino)-4-nitrobenzoic acid 

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KINETICS AND MECHANISM OF THE IMIDAZOLE-CATALYSED HYDROLYSIS OF SUBSTITUTED N-BENZOYLIMIDAZOLES

Imidazole (Imz)-catalysed hydrolysis of benzoate esters proceeds via the intermediate formation of N-benzoylimidazoles.This paper considers the second step of this reaction, viz., Imz-catalysed hydrolysis of N-(4-X-benzoyl)imidazoles, X = CH3, H, Cl, CN and NO2, and N-(disubstituted benzoyl)imidazoles, 2-chloro-4-nitro, 2,4-dinitro and 3,5-dinitro, in water-acetonitrile mixtures (10percent or 14percent, v/v, in organic solvent).On the basis of catalytic rate constants and the kinetic solvent isotope effect, it is shown that catalysis by Imz is of the general-base type.Unexpectedly, the hydrolysis of N-(2,4-dinitrobenzoyl)imidazole was found to be slower than that of N-(4-nitrobenzoyl)imidazole.It is shown that this reactivity order is due to a combination of a steric effect and stabilization of the reactant state due to a donor-acceptor interaction between the Imz moiety and the 2,4-dinitrophenyl ring.