96-99-1

Basic information

• Product Name: 4-Chloro-3-nitrobenzoic acid
• Synonyms: 4-Chloro-3-nitrobenzoic acid, 99.5%, 99.5%;Chlorine - 4-3 - nitro benzoic acid;4-Nitro-3-chloro benzoic acid;RARECHEM AL BO 0284;LABOTEST-BB LT00013440;BENZOIC ACID, 4-CHLORO-3-NITRO-;CHLORO(4-)-3-NITROBENZOIC ACID;4-CHLORO-3-NITROBENZOIC ACIC
• CAS NO: 96-99-1
• Molecular Formula: C₇H₄ClNO₄
• Molecular Weight: 201.56396
• EINECS: 202-550-9
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;C7;Carbonyl Compounds;Carboxylic Acids;API Intermediate
• Mol File: 96-99-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 180-183 °C(lit.)
• Boiling Point: 371.6 °C at 760 mmHg
• Flash Point: 178.5 °C
• Appearance: Light yellow to cream/Powder
• Density: 1.64
• Vapor Pressure: 3.53E-06mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 3.35±0.10(Predicted)
• Water Solubility: 342.7mg/L(temperature not stated)
• BRN: 783626
• CAS DataBase Reference: 4-Chloro-3-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-nitrobenzoic acid(96-99-1)
• EPA Substance Registry System: 4-Chloro-3-nitrobenzoic acid(96-99-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25-36
• WGK Germany: 2
• RTECS: DG5425050
• TSCA: Yes
• Hazardous Substances Data: 96-99-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

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

Synthetic route

para-chlorobenzoic acid (74-11-3) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With sulfuric acid; nitric acid In dichloromethane; water	97.3%
With sulfuric acid; nitric acid at 30 - 35℃; for 6h;	97.56%
With nitric acid for 1h; Heating;	85%

4-chloro-3-nitro-benzaldehyde (16588-34-4) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With copper(II) oxide; dihydrogen peroxide In acetonitrile at 60℃; for 5h; Green chemistry;	82%
With permanganate(VII) ion

4-chloro-3-nitrobenzonitrile (939-80-0) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With sulfuric acid
With nitric acid

4-n-butanoyl-2-nitrochlorobenzene (66353-38-6) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With chromium(III) oxide; sulfuric acid

1-chloro-4-methyl-2-nitro-benzene (89-60-1) → 4-chloro-3-nitrobenzoate (96-99-1)

1-chloro-4-(chloromethyl)-2-nitrobenzene (57403-35-7) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With potassium permanganate

4-Chloro-3-nitro-benzoic acid 4-nitro-phenyl ester (193606-98-3) → p-nitrophenolate (14609-74-6) + 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With hydroxide In water; dimethyl sulfoxide at 25℃; Rate constant; for determination of Hammett plot;
With sodium hydroxide In water; dimethyl sulfoxide at 25℃; Kinetics;

sulfuric acid (7664-93-9) + nitric acid (7697-37-2) + para-chloroacetophenone (99-91-2) → 4-chloro-3-nitrobenzoate (96-99-1) + 1-<4-chloro-3-nitro-phenyl>-ethanone-(1)

Conditions	Yield
at -12 - -10℃;

1-<4-chloro-3-nitro-phenyl>-ethanone-(1) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With potassium permanganate; water; magnesium sulfate

sulfuric acid (7664-93-9) + 2-chloro-3-nitro-5-trifluoromethylbenzene (121-17-5) → 4-chloro-3-nitrobenzoate (96-99-1)

4-n-butanoyl-2-nitrochlorobenzene (66353-38-6) + diluted Cr2O3-H2SO4 → 4-chloro-3-nitrobenzoate (96-99-1)

1-chloro-4-(2-chloro-propyl)-2-nitro-benzene + KMnO4 → 4-chloro-3-nitrobenzoate (96-99-1)

phosphorus pentachloride (10026-13-8, 874483-75-7) + 3-nitro-4-sulfo-benzoic acid (439693-71-7) → 3,4-dichlorbenzoic acid (51-44-5) + 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
at 180 - 200℃; Kochen des Produktes mit Wasser;

[4-(4-chloro-3-nitro-benzoylamino)-3-nitro-phenyl]-arsonic acid (861789-63-1) + diluted NaOH-solution → 3-nitro-4-hydroxybenzoic acid (616-82-0) + (4-amino-3-nitro-phenyl)-arsonic acid (5440-06-2) + 4-chloro-3-nitrobenzoate (96-99-1)

4-(4-chloro-3-nitrophenyl)-4-oxobutanoic acid (84314-04-5) → malonic acid (141-82-2) + 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With sodium hydroxide; sodium hydrogencarbonate; sodium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide In water at 36.85℃; Activation energy;

2,4-dinitrophenyl 4-chloro-3-nitrobenzoate → 2,4-dinitrophenolate (20350-26-9) + 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With hydroxide In water; dimethyl sulfoxide at 25℃; Kinetics; Alkaline hydrolysis;

4-Chloro-3-nitroaniline (635-22-3) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: durch Austausch von NH2 gegen CN nach Sandmeyer 2: concentrated sulfuric acid View Scheme

4-n-butanoylchlorobenzene (4981-63-9) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3+H2SO4 / <-5 2: Cr2O3-H2SO4 View Scheme

2-Chloronitrobenzene (88-73-3) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; hydrogen chloride / 85 °C 2: aqueous KMnO4 View Scheme
Multi-step reaction with 2 steps 1: H2SO4; paraformaldehyde; HCl / 85 °C 2: aqueous KMnO4 View Scheme

chlorobenzene (108-90-7) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminium chloride / 40 - 60 °C 2: HNO3+H2SO4 / <-5 3: Cr2O3-H2SO4 View Scheme

4-Cyanochlorobenzene (623-03-0) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid 2: aqueous nitric acid View Scheme

para-chlorotoluene (106-43-4) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium dichromate; aqueous sulfuric acid; acetic acid 2: nitric acid View Scheme
Multi-step reaction with 2 steps 1: nitric acid / 70 °C 2: nitric acid / 50 °C View Scheme

4-chloro-3-nitrobenzamide (16588-06-0) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus oxychloride / 170 °C 2: aqueous nitric acid View Scheme

4-chloro-3-nitro-benzoyl chloride (38818-50-7) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrachloromethane; aqueous ammonia 2: phosphorus oxychloride / 170 °C 3: aqueous nitric acid View Scheme
Multi-step reaction with 3 steps 1: triethylamine / diethyl ether 2: hydrogenchloride / water; acetonitrile 3: water; dimethyl sulfoxide / 25 °C View Scheme

concentrated H2 SO4 + para-chlorobenzoic acid (74-11-3) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With Concentrated HNO3

C6H3N2O5(1-)*C12H9ClN3O3(1+) → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
With water; dimethyl sulfoxide at 25℃; Kinetics;

2,4-dinitrophenyl 4-chloro-3-nitrobenzoate → 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water; acetonitrile 2: water; dimethyl sulfoxide / 25 °C View Scheme

4-nitro-phenol (100-02-7) + 4-chloro-3-nitro-benzoyl chloride (38818-50-7) → p-nitrophenolate (14609-74-6) + 4-chloro-3-nitrobenzoate (96-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / diethyl ether 2: sodium hydroxide / dimethyl sulfoxide; water / 25 °C View Scheme

methylamine (74-89-5) + 4-chloro-3-nitrobenzoate (96-99-1) → 4-(methylamino)-3-nitrobenzoic acid (41263-74-5)

Conditions	Yield
In water at 100℃; for 14h;	100%
In water at 80℃; for 5h;	100%
Stage #1: methylamine; 4-chloro-3-nitrobenzoate In water for 4h; Reflux; Stage #2: With sulfuric acid In water at 20℃; pH=2; Product distribution / selectivity;	95.5%

ethanol (64-17-5) + 4-chloro-3-nitrobenzoate (96-99-1) → ethyl 4-chloro-3-nitrobenzoate (16588-16-2)

Conditions	Yield
With sulfuric acid for 4h; Heating;	100%
With thionyl chloride for 2.25h; Heating / reflux;	96%
With hydrogenchloride Heating;	95%

ethyl iodide (75-03-6) + 4-chloro-3-nitrobenzoate (96-99-1) → ethyl 4-chloro-3-nitrobenzoate (16588-16-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;	100%
Stage #1: 4-chloro-3-nitrobenzoate With potassium carbonate In DMF (N,N-dimethyl-formamide) for 0.5h; Stage #2: ethyl iodide In DMF (N,N-dimethyl-formamide) at 50℃; for 4h;	86%
Stage #1: 4-chloro-3-nitrobenzoate With potassium carbonate In DMF (N,N-dimethyl-formamide) for 0.5h; Stage #2: ethyl iodide In DMF (N,N-dimethyl-formamide) at 50℃; for 4h;	86%

ethylamine (75-04-7) + 4-chloro-3-nitrobenzoate (96-99-1) → 4-(ethylamino)-3-nitrobenzoic acid (2788-74-1)

Conditions	Yield
In water at 80℃; for 5h;	100%
at 70℃; for 5h;	99%
In water at 80℃;	95%

methanol (67-56-1) + 4-chloro-3-nitrobenzoate (96-99-1) → methyl 3-nitro-4-chlorobenzoate (14719-83-6)

Conditions	Yield
With sulfuric acid for 16h; Reflux;	98%
With sulfuric acid at 80℃;	98%
With hydrogenchloride Heating;	97%

4-chloro-3-nitrobenzoate (96-99-1) → 3-nitro-4-hydroxybenzoic acid (616-82-0)

Conditions	Yield
With water; sodium hydroxide at 100℃;	98%
With sodium hydroxide In water at 95℃; for 10h;	91.83%
With sodium hydroxide In water	430 g (90 %)

6a-hydroxy-artemisinin + 4-chloro-3-nitrobenzoate (96-99-1) → C22H24ClNO9

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;	98%

tert-butylisonitrile (119072-55-8, 7188-38-7) + benzaldehyde (100-52-7) + p-aminoiodobenzene (540-37-4) + 4-chloro-3-nitrobenzoate (96-99-1) → N-(2-tert-butylamino)-2-oxo-1-phenylethyl-4-chloro-N-(4-iodophenyl)-3-nitrobenzamide

Conditions	Yield
In methanol at 20℃; for 24h;	98%

4-chloro-3-nitrobenzoate (96-99-1) → ethyl 4-chloro-3-nitrobenzoate (16588-16-2)

Conditions	Yield
With sulfuric acid In ethanol	97%
Stage #1: 4-chloro-3-nitrobenzoate With potassium carbonate In DMF (N,N-dimethyl-formamide) for 0.5h; Stage #2: With ethyl iodide at 50℃; for 4h; Heating / reflux;	86%
Multi-step reaction with 2 steps 1: 95 percent / cerium(IV) ammonium nitrate / 336 h / 20 °C 2: 98 percent / cerium(IV) ammonium nitrate / 144 h / 20 °C View Scheme
In ethanol

aniline (62-53-3) + 4-chloro-3-nitrobenzoate (96-99-1) → 4-chloro-3-nitro-N-phenylbenzamide (41614-16-8)

Conditions	Yield
With thionyl chloride In chlorobenzene at 70 - 100℃; for 2h; Reagent/catalyst; Solvent; Temperature; Large scale; Green chemistry;	97%

C15H17NO3 + 4-chloro-3-nitrobenzoate (96-99-1) → C22H19ClN2O6

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	97%

4-chloro-3-nitrobenzoate (96-99-1) → 4-chloro-3-nitrobenzyl alcohol (55912-20-4)

Conditions	Yield
With borane-THF; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 18h;	96%
With borane-THF In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	96%
With dimethylsulfide borane complex In tetrahydrofuran Ambient temperature;	95%

4-Benzyloxyphenol (103-16-2) + 4-chloro-3-nitrobenzoate (96-99-1) → 4-(4-benzyloxy-phenoxy)-3-nitro-benzoic acid (943771-70-8)

Conditions	Yield
Stage #1: 4-Benzyloxyphenol With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.166667h; Stage #2: 4-chloro-3-nitrobenzoate In dimethyl sulfoxide at 120℃; for 1h; Stage #3: With hydrogenchloride; water In dimethyl sulfoxide at 0℃; pH=3;	96%

propargyl alcohol (107-19-7) + 4-chloro-3-nitrobenzoate (96-99-1) → prop-2-yn-1-yl 4-chloro-3-nitrobenzoate

Conditions	Yield
With thionyl chloride at -20 - 20℃; for 18h; Inert atmosphere;	96%

4-Nitrophenylene-1,2-diamine (99-56-9) + 4-chloro-3-nitrobenzoate (96-99-1) → 2-(4-chloro-3-nitrophenyl)-5-nitro-1H-benzimidazole (1291074-93-5)

Conditions	Yield
With trichlorophosphate for 30h; Reflux;	95%

piperidine (110-89-4) + 4-chloro-3-nitrobenzoate (96-99-1) → 1-(4-chloro-3-nitro-benzoyl)-piperidine (91721-46-9)

Conditions	Yield
Stage #1: 4-chloro-3-nitrobenzoate With 1,1'-carbonyldiimidazole In ethyl acetate at 20℃; for 1h; Stage #2: piperidine In ethyl acetate at 20℃; for 1h;	95%

piperidine (110-89-4) + 4-chloro-3-nitrobenzoate (96-99-1) → 3-nitro-4-(piperidin-1-yl)benzoic acid (26586-26-5)

Conditions	Yield
With D-myo-inositol; copper; caesium carbonate In water at 100℃;	94%
With L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate; potassium carbonate In dimethyl sulfoxide at 110℃; for 20h; Inert atmosphere;	88%

aniline (62-53-3) + 4-chloro-3-nitrobenzoate (96-99-1) → 2-nitrodiphenylamine-4-carboxylic acid (16927-49-4)

Conditions	Yield
With potassium carbonate In water at 150℃; for 2h;	94%
In propan-1-ol for 12h; Heating;	80%
In propan-1-ol for 12h; Reflux;	80%
With 4-methyl-morpholine; copper In i-Amyl alcohol for 18h; Heating;

4-chloro-3-nitrobenzoate (96-99-1) + tert-butyl alcohol (75-65-0) → 4-Chloro-3-nitrobenzoic acid tert-butyl ester (157160-99-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;	94%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere;

2-amino-phenol (95-55-6) + 4-chloro-3-nitrobenzoate (96-99-1) → 2-(4-chloro-3-nitrophenyl)benzo[d]oxazole (32058-60-9)

Conditions	Yield
With samarium(III) trifluoromethanesulfonate In ethanol; water at 80℃; for 3h;	94%

2,2'-thiobis-ethanol (111-48-8) + 4-chloro-3-nitrobenzoate (96-99-1) → 3-amino-4-chloro-benzoic acid (2840-28-0)

Conditions	Yield
In methanol; water	92%

2,2-dimethoxyethylamine (22483-09-6) + 4-chloro-3-nitrobenzoate (96-99-1) → 4-[(2,2-dimethoxyethyl)amino]-3-nitrobenzoic acid

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 100℃; for 14h;	92%

N-butylamine (109-73-9) + 4-chloro-3-nitrobenzoate (96-99-1) → N-butyl-(4-chloro-3-nitrophenyl)carboxamide (59320-12-6)

Conditions	Yield
Stage #1: 4-chloro-3-nitrobenzoate With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane for 0.0833333h; ice bath; Stage #2: N-butylamine In dichloromethane at 20℃; for 0.25h;	91%

4-chloro-3-nitrobenzoate (96-99-1) → 4-chloro-3-nitro-benzoyl chloride (38818-50-7)

Conditions	Yield
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide Heating;	90%
With thionyl chloride for 6h; Heating;	84.7%
With phosphorus pentachloride at 140 - 150℃;

chloromethyl-(4-chloro-2-methyl-phenyl)-ether (83144-02-9) + 4-chloro-3-nitrobenzoate (96-99-1) → 4-Chloro-3-nitro-benzoic acid 4-chloro-2-methyl-phenoxymethyl ester (83144-00-7)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 0.25h; Heating;	90%

toluene-4-sulfonamide (70-55-3) + 4-chloro-3-nitrobenzoate (96-99-1) → N-(4-chloro-3-nitrophenyl)-4-methylbenzenesulfonamide (16330-01-1)

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In toluene at 110℃; for 0.5h; Sealed tube;	90%

4-chloro-3-nitrobenzoate (96-99-1) → 4-Chloro-3-nitrobenzoic acid tert-butyl ester (157160-99-1)

Conditions	Yield
With thionyl chloride In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide	89%
	59%
Multi-step reaction with 2 steps 1: SOCl2, DMF / 1,2-dichloro-ethane / 14 h / Heating 2: tetrahydrofuran / 0.5 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: SOCl2 / dimethylformamide View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane 2: pyridine View Scheme

4-chloro-3-nitrobenzoate (96-99-1) → 1-cyclopropyl-1H-indole + 4-Chloro-3-nitrobenzoic acid tert-butyl ester (157160-99-1)

Conditions	Yield
With thionyl chloride In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide	A 89% B n/a

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + 4-chloro-3-nitrobenzoate (96-99-1) → 4-[N-(3′-aminopropyl)-2-pyrrolidone]-3-nitrobenzenesulfonic acid (312921-96-3)

Conditions	Yield
In dimethyl sulfoxide at 85℃; for 8h;	89%

Upstream product

• 89-60-1 1-chloro-4-methyl-2-nitro-benzene 
• 57403-35-7 1-chloro-4-(chloromethyl)-2-nitrobenzene 
• 16588-34-4 4-chloro-3-nitro-benzaldehyde 
• 74-11-3 para-chlorobenzoic acid 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 99-91-2 para-chloroacetophenone 
• 66353-38-6 4-n-butanoyl-2-nitrochlorobenzene 
• 10026-13-8 phosphorus pentachloride 
• 439693-71-7 3-nitro-4-sulfo-benzoic acid 
• 861789-63-1 [4-(4-chloro-3-nitro-benzoylamino)-3-nitro-phenyl]-arsonic acid 
• 84314-04-5 4-(4-chloro-3-nitrophenyl)-4-oxobutanoic acid 
• 100-02-7 4-nitro-phenol 
• 38818-50-7 4-chloro-3-nitro-benzoyl chloride 

Downstream Products

• 26586-26-5 3-nitro-4-(piperidin-1-yl)benzoic acid 
• 148304-21-6 3-nitro-4-(4-toluidino)benzoic acid 
• 387882-52-2 3-nitro-4-p-phenetidino-benzoic acid 
• 452088-45-8 4-(2,4-dimethyl-anilino)-3-nitro-benzoic acid 
• 147879-75-2 4-benzenesulfonyl-3-nitro-benzoic acid 
• 860698-95-9 3-nitro-4-o-toluidino-benzoic acid 
• 59003-98-4 4-(2,4-dichloro-phenoxy)-3-nitro-benzoic acid 
• 43023-31-0 2-thioxo-2,3-dihydro-benzothiazole-5-carboxylic acid 
• 2840-28-0 3-amino-4-chloro-benzoic acid 
• 1588-83-6 4-amino-3-nitrobenzoic acid 
• 118-97-8 4-chloro-3,5-dinitrobenzoic acid 
• 38818-50-7 4-chloro-3-nitro-benzoyl chloride 
• 82964-59-8 4-(benzylthio)-3-nitrobenzoic acid 
• 31431-16-0 4-chloro-4'-fluoro-3-nitrobenzophenone 

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