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
• Article Data: 4

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

Downstream Products

• 402847-57-8 4-nitro-2,4'-imino-di-benzoic acid 
• 71835-14-8 2-((2-carboxyphenyl)amino)-4-nitrobenzoic acid 
• 730978-48-0 4-nitro-2-(3-nitro-anilino)-benzoic acid 
• 26690-13-1 N-(4-bromophenyl)-4-nitroanthranilic acid 
• 97713-51-4 2-(3,5-Dimethyl-phenylamino)-4-nitro-benzoic acid 
• 105643-45-6 2-(biphenyl-2-ylamino)-4-nitrobenzoic acid 
• 2457-76-3 4-amino-2-chlorobenzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 936487-98-8 2-(3-acetylamino-phenylsulfanyl)-4-nitro-benzoic acid 
• 88086-70-8 4-nitro-2-p-tolyloxy-benzoic acid 
• 13324-11-3 methyl 2-chloro-4-nitrobenzoate 

Relevant articles and documents

A acrinol pharmaceutical intermediate 2 - chloro -4 - nitro benzoic acid (by machine translation)

A acrinol pharmaceutical intermediate 2 - chloro - 4 - nitro-benzoic acid, mainly comprising the following steps: in the reaction container by adding 3 μM of 2 - chloro - 4 - nitro - 6 - hydroxy - cumene, 4 - 6 μM of N - methyl morpholine solution, raising the temperature of the solution to 40 — 46 °C, the stirring speed is 170 — 190 rpm, maintaining 50 — 70 min after, adding 6 μM four n propyl titanate, raising the temperature of the solution to 50 — 55 °C, reflux 90 — 110 min, reduce the temperature of the solution to 10 — 15 °C, separating solid, filtering, solid allylamine solution washing, using the oxalic acid solution to adjust the pH to 3 - 4, reduced in temperature to 5 — 8 °C, separating out crystal, filtering, salicylic acid methyl ester solution for washing, dehydrating agent dehydration, to get the finished product 2 - chloro - 4 - nitro-benzoic acid. (by machine translation)

Bio-derived CuO nanocatalyst for oxidation of aldehyde: A greener approach

Eco-friendly synthesis of hierarchical CuO nanoparticles using the peel of Musa balbisiana and its application as a nanocatalyst in oxidation of aldehyde to the corresponding carboxylic acid is reported here. CuO nanoparticles were characterized by using XRD, XPS, SEM, TEM and PL techniques. In XRD analysis, significant peaks appeared at 18.2, 24.6, 33.3, 34.9, 35.5, 38.6 and 42.3. The SEM images indicate the formation of a micro flower hierarchical CuO architecture. The hierarchical CuO architecture is found to be made up of 2D nanosheets as building blocks, which were self assembled to form micro flower like assemblies. The synthesized CuO nanoparticles are efficiently utilised in the oxidation of aldehyde to the corresponding carboxylic acid in the presence of 30% H2O2 with high yields. The utilization of the CuO nanocatalyst in the oxidation reaction in environmental friendly conditions is the novelty in this study. This journal is the Partner Organisations 2014.