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
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
With copper(II) oxide; dihydrogen peroxide In acetonitrile at 60℃; for 5h; Green chemistry; | 82% |
With permanganate(VII) ion |
Conditions | Yield |
---|---|
With sulfuric acid | |
With nitric acid |
4-n-butanoyl-2-nitrochlorobenzene
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
With chromium(III) oxide; sulfuric acid |
1-chloro-4-(chloromethyl)-2-nitrobenzene
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
With potassium permanganate |
4-Chloro-3-nitro-benzoic acid 4-nitro-phenyl ester
A
p-nitrophenolate
B
4-chloro-3-nitrobenzoate
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
nitric acid
para-chloroacetophenone
A
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
at -12 - -10℃; |
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
With potassium permanganate; water; magnesium sulfate |
4-n-butanoyl-2-nitrochlorobenzene
4-chloro-3-nitrobenzoate
phosphorus pentachloride
3-nitro-4-sulfo-benzoic acid
A
3,4-dichlorbenzoic acid
B
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
at 180 - 200℃; Kochen des Produktes mit Wasser; |
[4-(4-chloro-3-nitro-benzoylamino)-3-nitro-phenyl]-arsonic acid
A
3-nitro-4-hydroxybenzoic acid
B
(4-amino-3-nitro-phenyl)-arsonic acid
C
4-chloro-3-nitrobenzoate
4-(4-chloro-3-nitrophenyl)-4-oxobutanoic acid
A
malonic acid
B
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hydrogencarbonate; sodium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide In water at 36.85℃; Activation energy; |
A
2,4-dinitrophenolate
B
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
With hydroxide In water; dimethyl sulfoxide at 25℃; Kinetics; Alkaline hydrolysis; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: durch Austausch von NH2 gegen CN nach Sandmeyer 2: concentrated sulfuric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HNO3+H2SO4 / <-5 2: Cr2O3-H2SO4 View Scheme |
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 |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aluminium chloride / 40 - 60 °C 2: HNO3+H2SO4 / <-5 3: Cr2O3-H2SO4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: nitric acid 2: aqueous nitric acid View Scheme |
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
4-chloro-3-nitrobenzoate
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
4-chloro-3-nitrobenzoate
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 |
Conditions | Yield |
---|---|
With Concentrated HNO3 |
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
With water; dimethyl sulfoxide at 25℃; Kinetics; |
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water; acetonitrile 2: water; dimethyl sulfoxide / 25 °C View Scheme |
4-nitro-phenol
4-chloro-3-nitro-benzoyl chloride
A
p-nitrophenolate
B
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / diethyl ether 2: sodium hydroxide / dimethyl sulfoxide; water / 25 °C View Scheme |
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% |
Conditions | Yield |
---|---|
With sulfuric acid for 4h; Heating; | 100% |
With thionyl chloride for 2.25h; Heating / reflux; | 96% |
With hydrogenchloride Heating; | 95% |
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% |
Conditions | Yield |
---|---|
In water at 80℃; for 5h; | 100% |
at 70℃; for 5h; | 99% |
In water at 80℃; | 95% |
Conditions | Yield |
---|---|
With sulfuric acid for 16h; Reflux; | 98% |
With sulfuric acid at 80℃; | 98% |
With hydrogenchloride Heating; | 97% |
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 %) |
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; | 98% |
tert-butylisonitrile
benzaldehyde
p-aminoiodobenzene
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 98% |
4-chloro-3-nitrobenzoate
ethyl 4-chloro-3-nitrobenzoate
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 |
Conditions | Yield |
---|---|
With thionyl chloride In chlorobenzene at 70 - 100℃; for 2h; Reagent/catalyst; Solvent; Temperature; Large scale; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 97% |
4-chloro-3-nitrobenzoate
4-chloro-3-nitrobenzyl alcohol
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
4-chloro-3-nitrobenzoate
4-(4-benzyloxy-phenoxy)-3-nitro-benzoic acid
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% |
Conditions | Yield |
---|---|
With thionyl chloride at -20 - 20℃; for 18h; Inert atmosphere; | 96% |
4-Nitrophenylene-1,2-diamine
4-chloro-3-nitrobenzoate
2-(4-chloro-3-nitrophenyl)-5-nitro-1H-benzimidazole
Conditions | Yield |
---|---|
With trichlorophosphate for 30h; Reflux; | 95% |
piperidine
4-chloro-3-nitrobenzoate
1-(4-chloro-3-nitro-benzoyl)-piperidine
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
4-chloro-3-nitrobenzoate
3-nitro-4-(piperidin-1-yl)benzoic acid
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% |
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
tert-butyl alcohol
4-Chloro-3-nitrobenzoic acid tert-butyl ester
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
4-chloro-3-nitrobenzoate
2-(4-chloro-3-nitrophenyl)benzo[d]oxazole
Conditions | Yield |
---|---|
With samarium(III) trifluoromethanesulfonate In ethanol; water at 80℃; for 3h; | 94% |
2,2'-thiobis-ethanol
4-chloro-3-nitrobenzoate
3-amino-4-chloro-benzoic acid
Conditions | Yield |
---|---|
In methanol; water | 92% |
2,2-dimethoxyethylamine
4-chloro-3-nitrobenzoate
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide at 100℃; for 14h; | 92% |
N-butylamine
4-chloro-3-nitrobenzoate
N-butyl-(4-chloro-3-nitrophenyl)carboxamide
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
4-chloro-3-nitro-benzoyl chloride
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
4-chloro-3-nitrobenzoate
4-Chloro-3-nitro-benzoic acid 4-chloro-2-methyl-phenoxymethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 0.25h; Heating; | 90% |
toluene-4-sulfonamide
4-chloro-3-nitrobenzoate
N-(4-chloro-3-nitrophenyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver nitrate In toluene at 110℃; for 0.5h; Sealed tube; | 90% |
4-chloro-3-nitrobenzoate
4-Chloro-3-nitrobenzoic acid tert-butyl ester
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
B
4-Chloro-3-nitrobenzoic acid tert-butyl ester
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
4-chloro-3-nitrobenzoate
4-[N-(3′-aminopropyl)-2-pyrrolidone]-3-nitrobenzenesulfonic acid
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 85℃; for 8h; | 89% |
IUPAC Name: 4-Chloro-3-nitrobenzoic acid
Molecular Formula: C7H4ClNO4
Molecular Weight: 201.57 g/mol
SMILES: O=[N+]([O-])c1cc(ccc1Cl)C(=O)O Copy
InChI: InChI=1/C7H4ClNO4/c8-5-2-1-4(7(10)11)3-6(5)9(12)13/h1-3H,(H,10,11)
EINECS: 202-550-9
Classification Code: Mutation data
Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic acid; Organic acids; C7; Carbonyl Compounds; Carboxylic Acids
Melting Point: 180-183 °C(lit.)
Index of Refraction: 1.627
Molar Refractivity: 44.62 cm3
Molar Volume: 125.7 cm3
Surface Tension: 67.7 dyne/cm
Density: 1.602 g/cm3
Flash Point: 178.5 °C
Enthalpy of Vaporization: 65.26 kJ/mol
Boiling Point: 371.6 °C at 760 mmHg
Vapour Pressure of 4-Chloro-3-nitrobenzoic acid (CAS NO.96-99-1): 3.53E-06 mmHg at 25 °C
4-Chloro-3-nitrobenzoic acid (CAS NO.96-99-1) can be used as pharmaceutical intermediates in Organic synthesis , used in the manufacture of dyes and pharmaceutical , also can be used in producing methylimidazole.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 75mg/kg (75mg/kg) | Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. | |
rat | LD50 | oral | 3150mg/kg (3150mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 577, 1986. |
Reported in EPA TSCA Inventory.
Poison by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and Cl−.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-24/25-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
WGK Germany: 2
RTECS of 4-Chloro-3-nitrobenzoic acid (CAS NO.96-99-1): DG5425050
4-Chloro-3-nitrobenzoic acid (CAS NO.96-99-1), its Synonyms are 3-Nitro-4-chlorobenzoic acid ; Kyselina 4-chloro-3-nitrobenzoova ; Benzoic acid, 4-chloro-3-nitro- . It is white to light yellow crystal powder.
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