2516-95-2

Basic information

• Product Name: 5-Chloro-2-nitrobenzoic acid
• Synonyms: 6-Nitro-3-chlorobenzoic acid;5-Chloro-2-nitrobenzoic acid,99%;5-Chloro-2-nitrobenzoic acid, 99% 100GR;5-Chloro-2-nitrobenzoic acid, 99% 10GR;5-CHLORO-2-NITROBENZOIC ACID FOR SYNTHES;2-Carboxy-4-chloronitrobenzene;RARECHEM AL BO 1106;TIMTEC-BB SBB009922
• CAS NO: 2516-95-2
• Molecular Formula: C₇H₄ClNO₄
• Molecular Weight: 201.56
• EINECS: 219-738-1
• Product Categories: Pharmaceutical Intermediates;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Tolvaptan intermediate;FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzene series;Organic acids;C7;Carbonyl Compounds;Carboxylic Acids
• Mol File: 2516-95-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 137-139 °C(lit.)
• Boiling Point: 160.5°C (rough estimate)
• Flash Point: 100 °C
• Appearance: Light yellow to yellow-green/Crystalline Powder
• Density: 1,608g/cm
• Vapor Pressure: 7.1E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 9.67g/l
• PKA: 1.86±0.25(Predicted)
• Water Solubility: SLIGHTLY SOLUBLE
• BRN: 1963952
• CAS DataBase Reference: 5-Chloro-2-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-nitrobenzoic acid(2516-95-2)
• EPA Substance Registry System: 5-Chloro-2-nitrobenzoic acid(2516-95-2)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-50/53-41-37/38-22
• Safety Statements: 22-24/25-61-60-36/37/39-26-36
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 9
• PackingGroup: Ⅲ
• Hazardous Substances Data: 2516-95-2(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to yellowish-green crystalline powder

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

Synthetic route

5-chloro-2-nitrobenzyl alcohol (73033-58-6) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
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;	87%

5-chloro-2-nitrobenzyl alcohol (73033-58-6) → 5-chloro-2-nitrobenzaldehyde (6628-86-0) + 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
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 22% B 60%

5-chloro-2-nitrobenzaldehyde (6628-86-0) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
With potassium permanganate

5-chloro-2-nitrotoluene (5367-28-2) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
With potassium permanganate
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;

ethyl 2-(5-chloro-2-nitrophenyl)-2-cyanoacetate (62567-91-3) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
With potassium permanganate; potassium carbonate

diethyl 2-(5-chloro-2-nitrophenyl)propanedioate (62567-90-2) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
With potassium permanganate; potassium carbonate

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)

5-chloro-2-nitrotoluene (5367-28-2) + neutral potassium permanganate solution → 5-chloro-2-nitrobenzoic acid (2516-95-2)

2,4-dinitrotoluene (121-14-2) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sodium acetate / bei der elektrolytischen Reduktion 2: hydrochloric acid 3: Verkochen des Diazoniumsulfatsmit Alkohol.Diazotization 4: potassium permanganate View Scheme

4-hydroxylamino-2-nitrotoluene (43192-03-6) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrochloric acid 2: Verkochen des Diazoniumsulfatsmit Alkohol.Diazotization 3: potassium permanganate View Scheme

2-chloro-4-methyl-5-nitro-aniline → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Verkochen des Diazoniumsulfatsmit Alkohol.Diazotization 2: potassium permanganate View Scheme

2,4-dichloronitrobenzene (611-06-3) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaOEt, DMSO, (ii) /BRN= 1451655/ 2: KMnO4, aq. K2CO3 View Scheme
Multi-step reaction with 2 steps 1: (i) NaOEt, DMSO, (ii) /BRN= 1451655/ 2: KMnO4, aq. K2CO3 View Scheme

3-chlorobenzoate (535-80-8) → 5-chloro-2-nitrobenzoic acid (2516-95-2)

Conditions	Yield
With sulfuric acid; nitric acid at -5 - 0℃; for 1h;
With nitric acid; acetic anhydride at 20℃;

5-chloro-2-nitrobenzoic acid (2516-95-2) → 5-chloro-2-nitrobenzoyl chloride (41994-44-9)

Conditions	Yield
With thionyl chloride	100%
With thionyl chloride Heating / reflux;	98%
With thionyl chloride In dichloromethane for 4h; Reflux;	66%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 5-chloroanthranilic acid (635-21-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 735.5 Torr; for 2h; Ambient temperature;	100%
With hydrogen; nickel In ethanol at 20℃;	96%
Reduction;	85%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 5-chloro-2-nitrobenzyl alcohol (73033-58-6)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;	100%
With borane-THF In tetrahydrofuran at 50℃; for 96h;	91%
With dimethylsulfide borane complex In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;	90%

5-chloro-2-nitrobenzoic acid (2516-95-2) → anthranilic acid (118-92-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 735.5 Torr; for 80h;	100%

5-chloro-2-nitrobenzoic acid (2516-95-2) + dimethyl sulfate (77-78-1) → methyl 5-chloro-2-nitrobenzoate (51282-49-6)

Conditions	Yield
With potassium carbonate In acetone for 0.5h; Esterification; Heating;	100%
With sodium carbonate In acetone for 3h; Heating;	78%
With potassium carbonate In acetone Reflux;
With potassium carbonate In [(2)H6]acetone for 0.5h; Reflux;	534 g

morpholine (110-91-8) + 5-chloro-2-nitrobenzoic acid (2516-95-2) → 2-nitro-5-(morpholin-4-yl)benzoic acid (153437-51-5)

Conditions	Yield
Stage #1: morpholine; 5-chloro-2-nitrobenzoic acid at 110℃; for 2h; Neat (no solvent); Stage #2: pH=Ca. 3; Acidic aq. solution;	100%
at 120℃; for 6h;

5-chloro-2-nitrobenzoic acid (2516-95-2) + dimethyl amine (124-40-3) → 5-dimethylamino-2-nitrobenzoic acid (62876-66-8)

Conditions	Yield
In water at 60℃; for 23h;	99%
In water at 0 - 60℃; for 23h;	99%
In water at 70℃; for 25h; Autoclave;	99%
In water at 100℃; for 6h;

5-chloro-2-nitrobenzoic acid (2516-95-2) → 5-hydroxy-2-nitrobenzoic acid (610-37-7)

Conditions	Yield
With sodium hydroxide for 72h; Inert atmosphere; Reflux;	99%
With sodium hydroxide In water for 72h; Inert atmosphere;	96.5%
With potassium hydroxide In water for 24h; Reflux;	90%

methanol (67-56-1) + 5-chloro-2-nitrobenzoic acid (2516-95-2) → methyl 5-chloro-2-nitrobenzoate (51282-49-6)

Conditions	Yield
With thionyl chloride at 80℃; for 4h; Cooling with ice; Reflux;	98.2%
With thionyl chloride at 0℃; for 15h; Heating / reflux;	92%
With sulfuric acid for 20h; Reflux; Inert atmosphere;	89%

ethanol (64-17-5) + 5-chloro-2-nitrobenzoic acid (2516-95-2) → ethyl-5-chloro-2-nitrobenzoate (51282-56-5)

Conditions	Yield
With thionyl chloride at 0℃; for 48h; Heating / reflux;	97%
With sulfuric acid for 24h; Reflux;	85%

pyrrolidine (123-75-1) + 5-chloro-2-nitrobenzoic acid (2516-95-2) → 2-nitro-5-(pyrrolidin-1-yl)benzoic acid

Conditions	Yield
Stage #1: pyrrolidine; 5-chloro-2-nitrobenzoic acid at 110℃; for 2h; Neat (no solvent); Stage #2: pH=Ca. 3; Acidic aq. solution;	95.66%

piperidine (110-89-4) + 5-chloro-2-nitrobenzoic acid (2516-95-2) → 2-nitro-5-(piperidin-N-yl)-benzoic acid (118159-39-0)

Conditions	Yield
Stage #1: piperidine; 5-chloro-2-nitrobenzoic acid at 110℃; for 2h; Neat (no solvent); Stage #2: pH=Ca. 3; Acidic aq. solution;	95.04%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 4-chloro-2-deuteronitrobenzene

Conditions	Yield
With water-d2; silver carbonate In dimethyl sulfoxide at 120℃; for 16h;	95%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 5-dimethylamino-2-nitrobenzoic acid (62876-66-8)

Conditions	Yield
With dimethyl amine In water at 80℃; for 4h;	94%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With copper(l) iodide; oxygen; copper(l) chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 30h; Schlenk technique; Sealed tube;	93%
With oxygen; silver carbonate; potassium hydroxide; copper dichloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 130 - 140℃;	80%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique;	66%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper diacetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 20h; Schlenk technique;	64%

5-chloro-2-nitrobenzoic acid (2516-95-2) + methyl iodide (74-88-4) → methyl 5-chloro-2-nitrobenzoate (51282-49-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 1h;	92%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 40℃; for 1h;	92%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 1-iodo-5-chloro-2-nitrobenzene (160938-18-1)

Conditions	Yield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 30h; Schlenk technique; Sealed tube;	92%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper diacetate; silver sulfate; sodium iodide In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 20h; Schlenk technique;	76%

iodobenzene (591-50-4) + 5-chloro-2-nitrobenzoic acid (2516-95-2) → 5-chloro-2-nitro-1,1'-biphenyl (29547-09-9)

Conditions	Yield
With triphenylphosphine; silver carbonate; palladium dichloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 130℃; for 30h; Inert atmosphere;	92%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 5-chloro-2-nitrobenzyl alcohol (73033-58-6) + 5-(piperidin-1-yl)-2-nitrobenzaldehyde (113259-79-3)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran	A 91% B n/a

5-chloro-2-nitrobenzoic acid (2516-95-2) + dimethyl sulfate (77-78-1) → 5-methylthio-2-nitrobenzoic acid (68701-32-6)

Conditions	Yield
Stage #1: 5-chloro-2-nitrobenzoic acid With sodium sulfide nonahydrate; sodium hydroxide In water at 60℃; for 2.5h; Stage #2: dimethyl sulfate at 100℃; for 1h;	90%
With sodium sulfide; sodium hydroxide 1) water, 50-55 deg C, 2,5 h 2) reflux 1 h; Yield given. Multistep reaction;
Stage #1: 5-chloro-2-nitrobenzoic acid With sodium sulfide; sodium hydroxide at 60℃; Stage #2: dimethyl sulfate Heating;
Stage #1: 5-chloro-2-nitrobenzoic acid With sodium sulfide; sodium hydroxide In water at 60℃; for 2.5h; Stage #2: dimethyl sulfate With sodium hydroxide In water for 1h; Heating / reflux; Stage #3: With hydrogenchloride In water

5-chloro-2-pyridylamine (1072-98-6) + 5-chloro-2-nitrobenzoic acid (2516-95-2) → N-(5-chloropyridin-2-yl)-5-chloro-2-nitrobenzamide (280771-82-6)

Conditions	Yield
With pyridine; trichlorophosphate In acetonitrile at 0 - 30℃; for 1h; Inert atmosphere;	90%
With pyridine; trichlorophosphate at 20℃; for 0.0833333h;

5-chloro-2-nitrobenzoic acid (2516-95-2) → 4-chlorobenzonitrile (100-00-5)

Conditions	Yield
With copper(l) iodide; triethylamine In dimethyl sulfoxide at 120℃; under 760.051 Torr; for 20h; Inert atmosphere; Schlenk technique;	88%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium iodide In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique;	76%
With copper(I) oxide at 120℃; for 24h; Ionic liquid;

5-chloro-2-nitrobenzoic acid (2516-95-2) + 1,1'-carbonyldiimidazole (530-62-1) → C10H6ClN3O3

Conditions	Yield
In tetrahydrofuran for 1h; Reflux;	86%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 5,5'-dichloro-2,2'-dinitro-1,1'-biphenyl (19036-42-1)

Conditions	Yield
With triphenylphosphine; silver carbonate; palladium dichloride In dimethyl sulfoxide at 130℃; for 6h; Inert atmosphere;	85%
With copper(l) iodide In dimethyl sulfoxide at 140℃; for 20h; Inert atmosphere; Molecular sieve;	72%

morpholine (110-91-8) + 5-chloro-2-nitrobenzoic acid (2516-95-2) → N-<5-chloro-2-nitrobenzoyl>morpholide (142439-67-6)

Conditions	Yield
In thionyl chloride; acetone	84%
In acetone at 0℃; for 0.25h;

Cyclohexyl isocyanide (931-53-3) + phenylglyoxal hydrate (1074-12-0) + 5-chloro-2-nitrobenzoic acid (2516-95-2) + 3-bromopropylamine hydrochloride (5003-71-4) → 2-benzoyl-1-(5-chloro-2-nitrobenzoyl)-N-cyclohexylpyrrolidine-2-carboxamide

Conditions	Yield
Stage #1: Cyclohexyl isocyanide; phenylglyoxal hydrate; 5-chloro-2-nitrobenzoic acid; 3-bromopropylamine hydrochloride With sodium hydroxide In methanol at 20℃; for 24h; Stage #2: With caesium carbonate In methanol at 20℃; for 1h;	84%

5-chloro-2-nitrobenzoic acid (2516-95-2) → potassium 5-chloro-2-nitrobenzoate

Conditions	Yield
With potassium tert-butylate In ethanol at 20℃;	83%

5-chloro-2-nitrobenzoic acid (2516-95-2) + 2,6-difluorobenzoic acid (385-00-2) → 2,2',6,6'-tetrafluoro-1,1'-biphenyl (781-16-8) + 5-chloro-2',6'-difluoro-2-nitro-1,1'-biphenyl (1352638-58-4) + 5,5'-dichloro-2,2'-dinitro-1,1'-biphenyl (19036-42-1)

Conditions	Yield
With triphenylphosphine; silver carbonate; palladium dichloride In dimethyl sulfoxide at 130℃; for 6h; Inert atmosphere;	A 11 %Chromat. B 79% C 21%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 3-Amino-5-chloro-2-nitrobenzoic acid (193481-78-6)

Conditions	Yield
With O-Methylhydroxylamin; potassium tert-butylate; copper diacetate In 1,2-dimethoxyethane at 20℃; Substitution; Amination;	78%
With potassium tert-butylate; N-methoxylamine hydrochloride; copper diacetate In N,N-dimethyl-formamide at 0℃; for 3h;	60.5%
With potassium tert-butylate; N-methoxylamine hydrochloride; copper diacetate In N,N-dimethyl-formamide for 3h;	32%

Upstream product

• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 535-80-8 3-chlorobenzoate 
• 5367-28-2 5-chloro-2-nitrotoluene 
• 73033-58-6 5-chloro-2-nitrobenzyl alcohol 
• 611-06-3 2,4-dichloronitrobenzene 
• 43192-03-6 4-hydroxylamino-2-nitrotoluene 
• 121-14-2 2,4-dinitrotoluene 
• 7697-37-2 nitric acid 
• 62567-90-2 diethyl 2-(5-chloro-2-nitrophenyl)propanedioate 
• 62567-91-3 ethyl 2-(5-chloro-2-nitrophenyl)-2-cyanoacetate 

Downstream Products

• 69-78-3 5,5'-dithiobis-(2-nitrobenzoic acid) 
• 21739-93-5 2-bromo-5-chlorobenzoic acid 
• 41994-44-9 5-chloro-2-nitrobenzoyl chloride 
• 635-21-2 5-chloroanthranilic acid 
• 193481-78-6 3-Amino-5-chloro-2-nitrobenzoic acid 
• 51282-49-6 methyl 5-chloro-2-nitrobenzoate 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 454705-24-9 5-chloro-N-(1H-indazol-5-yl)-2-nitro-benzamide 
• 267891-87-2 2-amino-5-chloro-N-(1H-indazol-5-yl)-benzamide 
• 679426-53-0 C₃₀H₃₂Cl₂N₄O₆ 

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