Conditions | Yield |
---|---|
With sodium perborate In acetic acid for 1.5h; steam bath; | 100% |
With sodium chlorite; dimethyl sulfoxide In water; acetonitrile at 10℃; for 1h; | 98% |
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 9h; Heating; | 97% |
Conditions | Yield |
---|---|
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 90℃; for 0.25h; | 100% |
With iodine; aluminium In acetonitrile at 80℃; for 18h; | 98% |
With potassium hydroxide In toluene at 150℃; for 0.166667h; microwave irradiation; | 97% |
2-Chlorobenzyl alcohol
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With NH-pyrazole; sodium hydride In tetrahydrofuran for 20h; Ambient temperature; | 100% |
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 24h; Reagent/catalyst; Solvent; | 99% |
With sodium hydroxide; sodium periodate; trans-Na6 In water for 1.5h; | 96% |
2-chlorobenzaldehyde N-[(2-chlorophenyl)methylidene]hydrazone
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 140h; Heating; | 98% |
With [bis(acetoxy)iodo]benzene In tetrahydrofuran at 20℃; for 4h; Green chemistry; | 76% |
N’-(2-chlorobenzylidene)-4-methylbenzenesulfonohydrazide
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 85h; Heating; | 98% |
1-(2-chlorophenyl)-4,4,4-trifluorobutane-1,3-dione
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation; | 98% |
Conditions | Yield |
---|---|
With potassium hydroxide In toluene at 150℃; for 0.166667h; microwave irradiation; | A 2% B 97% |
With phosphate buffer at 30℃; for 6.5h; rhodococcus rhodocrous AJ270, pH 7.0; | A 94% B 4% |
With potassium phosphate buffer at 30℃; for 6.5h; Rhodococcus sp. AJ270 cells; | A 94.1% B 4.4% |
With potassium hydroxide; cetyltrimethylammonim bromide In toluene at 100℃; for 0.166667h; microwave irradiation; | A 45% B 5% |
2-methylchlorobenzene
A
2-chloro-benzaldehyde
B
1-bromomethyl-2-chlorobenzene
C
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 0.666667h; Kinetics; Mechanism; Rate constant; other time; other temperature; various concentrations of Co(OAc)2 and NaBr; | A n/a B n/a C 96% |
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 0.666667h; | A n/a B n/a C 95% |
methyl 3-(2-chlorophenyl)-3-oxopropanedithioate
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water at 100℃; for 8.5h; Reflux; chemoselective reaction; | 96% |
Conditions | Yield |
---|---|
With benzene-1,2-dicarboxylic acid for 0.833333h; microwave-irradiation; | 94% |
With phosphate buffer at 30℃; for 168h; rhodococcus rhodocrous AJ270, pH 7.0; | 80% |
With potassium phosphate buffer at 30℃; for 168h; Rhodococcus sp. AJ270 cells; | 79.9% |
With sulfuric acid |
Conditions | Yield |
---|---|
Stage #1: 2-chlorostyrene With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; sodium hydroxide In water at 80℃; for 10h; Stage #2: With hydrogenchloride In water at 20℃; | 94% |
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 24h; | 79% |
Stage #1: 2-chlorostyrene With tert.-butylhydroperoxide; iodine; sodium hydroxide In water at 105℃; for 16h; Sealed tube; Stage #2: With hydrogenchloride In water | 58% |
Conditions | Yield |
---|---|
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; | 93% |
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 60h; UV-irradiation; | 91.5% |
With oxygen; Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Green chemistry; | 91% |
L-tyrosine ethyl ester
o-chlorobenzoyl chloride
A
N-(2-chlorobenzoyl)-(L)-tyrosine ethyl ester
B
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
Stage #1: L-tyrosine ethyl ester With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; Stage #2: o-chlorobenzoyl chloride In tetrahydrofuran; water at 0 - 20℃; for 0.5h; | A 92% B 5% |
benzyl 2-chlorobenzoate
toluene
A
1-methyl-3-(phenylmethyl)-benzene
B
1-methyl-4-(phenylmethyl)benzene
C
2-benzyltoluene
D
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction; | A n/a B n/a C n/a D 92% |
2-chloro-benzaldehyde
A
2-Chlorobenzyl alcohol
B
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
Stage #1: 2-chloro-benzaldehyde With potassium hydroxide In water at 20℃; Cannizzaro reaction; Stage #2: With hydrogenchloride In water | A 85% B 91% |
With sodium hydroxide In water at 20℃; for 2.5h; Cannizzaro Reaction; | A n/a B 90% |
Stage #1: 2-chloro-benzaldehyde In neat (no solvent) for 0.0333333h; Green chemistry; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 40℃; for 0.00833333h; Reagent/catalyst; Cannizzaro Reaction; Microwave irradiation; Green chemistry; |
Conditions | Yield |
---|---|
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 63h; Heating; | 90% |
(DL)-o-chlorophenyl-1,2-ethanediol
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; potassium tert-butylate In water at 80℃; for 8h; | 90% |
Conditions | Yield |
---|---|
With water; palladium diacetate; triethylamine; triphenylphosphine In 1,4-dioxane at 110℃; under 11251.1 Torr; for 2h; Reagent/catalyst; Temperature; Pressure; Flow reactor; | 90% |
Stage #1: carbon monoxide; 2-iodochlorobenzene With potassium carbonate In water at 100℃; under 3750.38 Torr; for 12h; Autoclave; Stage #2: With hydrogenchloride In water | 85% |
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h; | 74% |
2-chloro-N,N-diisopropylbenzamide
A
3-chlorobenzoic acid isopropylamide
B
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; zinc(II) chloride at 160℃; for 72h; | A 9% B 89% |
carbon dioxide
2-(2-chlorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; 2-(2-chlorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane With potassium tert-butylate; silver(I) acetate; triphenylphosphine In tetrahydrofuran at 70℃; under 15201 Torr; for 16h; Inert atmosphere; Autoclave; Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere; | 89% |
furan
benzenedizolium-2-carboxylate
A
1,4-dihydronaphthalene-1,4-epoxide
B
2-Methoxybenzoic acid
C
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With 1,2-dichloro-ethane at 80℃; for 2h; Product distribution; Mechanism; acids were detected as methyl esters (methylated by CH2N2); | A 88% B n/a C n/a |
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccasefrom Trametes versicolor; oxygen In water at 30℃; for 240h; pH=4.5; Enzymatic reaction; | 88% |
2'-chloro-sec-phenethyl alcohol
A
2-chloro-benzaldehyde
B
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With sodium nitrate; water; oxygen In dimethyl sulfoxide at 130℃; for 36h; | A 9% B 87% |
furan
benzenedizolium-2-carboxylate
A
1,4-dihydronaphthalene-1,4-epoxide
B
chlorobenzene
C
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With triethylamine hydrochloride In chloroform at 60℃; for 48h; Product distribution; Mechanism; var. temp.: RT; acid was identified as methyl ester (methylated by CH2N2); | A 85% B 6% C 15% |
2-chloro-benzoic acid tert-butyl ester
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With water; iodine In acetonitrile for 4h; Heating; | 85% |
Conditions | Yield |
---|---|
Stage #1: anthranilic acid With hydrogenchloride; sodium nitrite In water at 6 - 8℃; for 0.416667h; Stage #2: With aluminum sulfate; potassium chloride; copper(II) sulfate In water for 1 - 1.5h; | 84% |
With hydrogenchloride; water; sodium nitrite man giesst dann in eine Loesung von CuCl; | |
With tert.-butylnitrite; copper dichloride In acetonitrile |
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With iodine In cyclohexane for 6h; Ambient temperature; | 84% |
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.0833333h; chemoselective reaction; | 83% |
Conditions | Yield |
---|---|
With iodine; dimethyl sulfoxide at 120℃; for 25h; Sealed tube; Green chemistry; | 83% |
Conditions | Yield |
---|---|
With sulfuric acid for 4h; Reflux; | 100% |
With sulfuric acid Heating; | 99% |
With 1,3,5-trichloro-2,4,6-triazine; sodium carbonate at 50℃; for 0.333333h; Sonication; | 94% |
Conditions | Yield |
---|---|
With thionyl chloride In toluene at 75℃; | 100% |
With thionyl chloride Reflux; | 100% |
With thionyl chloride at 100℃; | 100% |
Conditions | Yield |
---|---|
With hydrogen; triethylamine; palladium on activated charcoal In methanol at 20℃; for 3h; | 100% |
With borane-ammonia complex In water; isopropyl alcohol at 40℃; for 3h; Sealed tube; | 97% |
With 1H-imidazole; copper ammonium sulphate hexahydrate; lithium tert-butoxide In N,N-dimethyl-formamide; isopropyl alcohol for 72h; Irradiation; | 87% |
Conditions | Yield |
---|---|
With pyridine; p-toluenesulfonyl chloride at 0 - 20℃; Esterification; | 100% |
Conditions | Yield |
---|---|
With hydrazine dihydrochloride; phosphoric acid; trichlorophosphate In water at 140℃; for 2h; Condensation; | 99.2% |
With hydrazine dihydrochloride; phosphoric acid; phosphorus pentoxide at 130℃; for 0.0833333h; microwave irradiation; | 96% |
With sodium tetrahydroborate; hydrazine dihydrochloride; phosphoric acid at 170 - 180℃; for 6h; Inert atmosphere; Neat (no solvent); | 87% |
With Montmorillonite K10 clay; hydrazine hydrate In ethanol for 0.05h; microwave irradiation; | 86% |
Multi-step reaction with 3 steps 1: sulfuric acid / 70 - 80 °C 2: hydrazine hydrate / ethanol / 60 - 70 °C 3: trichlorophosphate / 8 h View Scheme |
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h; | 99% |
With sulfuric acid at 100℃; for 12h; Sealed tube; | 95% |
With thionyl chloride for 2h; Heating; | 86% |
3-chloro-aniline
ortho-chlorobenzoic acid
N-(3-chlorophenyl)anthranilic acid
Conditions | Yield |
---|---|
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 24h; | 99% |
With pyridine; copper; potassium carbonate In water for 1h; Heating; | 60% |
With copper; potassium carbonate for 5h; Heating; | 44% |
Conditions | Yield |
---|---|
With N(Et)4(1+)*(2-pyrrolidone-anion) In N,N-dimethyl-formamide for 1h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
With copper(I) oxide; copper; potassium carbonate In various solvent(s) at 130℃; for 24h; | 99% |
With potassium hydroxide; copper(II) oxide; tetrabutylammomium bromide In water at 130℃; for 0.0833333h; Ullmann-type C-N coupling; microwave irradiation; | 55% |
With potassium phosphate; ethylene glycol; copper(l) iodide In butan-1-ol at 100℃; for 72h; | 48% |
With copper; potassium carbonate In pentan-1-ol at 140℃; for 4h; | 44% |
ortho-chlorobenzoic acid
3-amino-3',5'-dimethylbiphenyl
N-[3-(3,5-dimethylphenyl)phenyl]anthranilic acid
Conditions | Yield |
---|---|
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 24h; | 99% |
With copper(I) oxide; potassium carbonate; copper(II) oxide In 2-methoxy-ethanol for 2h; Heating; | 95% |
With copper(I) oxide; copper; potassium carbonate In ethyl methyl ether for 2h; Heating / reflux; | 95% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In water at 80℃; for 8h; | 99% |
cyclohexyl-N-tosyl aziridine
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 65℃; for 33h; stereoselective reaction; | 99% |
In N,N-dimethyl-formamide at 65℃; for 43h; | 97% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 50℃; Green chemistry; | 93% |
(1S,2S,4S,5R,6S)-di-tert-butyl 4-amino-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate
ortho-chlorobenzoic acid
Conditions | Yield |
---|---|
Stage #1: ortho-chlorobenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide Stage #2: (1S,2S,4S,5R,6S)-di-tert-butyl 4-amino-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate In N,N-dimethyl-formamide | 99% |
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine In toluene at 100℃; for 0.0166667h; Curtius Rearrangement; Microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; p-benzoquinone In dimethyl sulfoxide at 140℃; for 4h; Schlenk technique; Inert atmosphere; | 99% |
1-amino-3-methylbenzene
ortho-chlorobenzoic acid
2-(m-tolylamino)benzoic acid
Conditions | Yield |
---|---|
With copper; caesium carbonate; copper(II) oxide In water at 105℃; Reagent/catalyst; Temperature; Large scale; | 98.3% |
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 24h; | 80% |
With potassium carbonate; copper In N,N-dimethyl-formamide for 2h; Heating; | 63% |
Conditions | Yield |
---|---|
With copper; potassium carbonate for 5h; Heating; | 98% |
With copper; sodium carbonate; copper(II) oxide In water at 105℃; Large scale; | 97.9% |
With pyridine; copper; potassium carbonate In pentan-1-ol for 1h; Heating; | 84% |
Conditions | Yield |
---|---|
With copper(I) sulfate; potassium carbonate; copper(II) sulfate In water for 0.0833333h; Ullmann condensation; microwave irradiation; | 98% |
With potassium carbonate; copper(II) sulfate for 0.025h; Ullmann condensation; microwave irradiation; | 98% |
With sodium acetate; copper (I) acetate In water for 4h; Heating; | 91% |
Conditions | Yield |
---|---|
With sulfuric acid; acetonitrile at 80 - 85℃; for 16 - 18h; | 98% |
With thionyl chloride for 2h; Heating; | 81% |
With sulfuric acid |
4-amino-benzoic acid
ortho-chlorobenzoic acid
N-(4-carboxyphenyl)anthranilic acid
Conditions | Yield |
---|---|
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 24h; | 98% |
With copper; potassium carbonate In i-Amyl alcohol at 160℃; Ullmann Condensation; | 91% |
With copper; potassium carbonate In N,N-dimethyl-formamide at 140 - 145℃; for 3.5h; | 79% |
3-methylantranilic acid
ortho-chlorobenzoic acid
2-<(2-carboxyphenyl)amino>-3-methylbenzoic acid
Conditions | Yield |
---|---|
With copper; potassium carbonate; copper(I) bromide In various solvent(s) at 160℃; for 0.5h; | 98% |
Conditions | Yield |
---|---|
With hydrogen; water-d2; triethylamine; palladium on activated charcoal at 20℃; | 98% |
With 10% Pd/C; hydrogen; water-d2; triethylamine In methanol at 20℃; for 24h; chemoselective reaction; | 97% |
With deuteriated sodium hydroxide; aluminum nickel In water-d2 at 40℃; for 1h; Yield given; |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile for 1.5h; Heating; | 98% |
ortho-chlorobenzoic acid
2-chloro-6-iodobenzoic acid
Conditions | Yield |
---|---|
With N-iodo-succinimide; [Ir(III)(η5-pentamethylcyclopentadienyl)(H2O)3](SO4) at 60℃; for 16h; | 98% |
With [bis(acetoxy)iodo]benzene; iodine; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24h; Sealed tube; | 91% |
With [bis(acetoxy)iodo]benzene; iodine; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24h; | 87% |
Stage #1: ortho-chlorobenzoic acid With (E)-N,N,N′,N′-tetramethylethene-1,2-diamine; sec.-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With iodine In tetrahydrofuran at -78 - 0℃; | 53% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 98% |
IUPAC Name: 2-Chlorobenzoic acid
Empirical Formula: C7H5ClO2
Molecular Weight: 156.5664
Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)Cl
InChI: InChI=1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
InChIKey: IKCLCGXPQILATA-UHFFFAOYSA-N
EINECS: 204-285-4
Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organics; Highly Purified Reagents; Other Categories; Zone Refined Products; C7; Carbonyl Compounds; Carboxylic Acids; Alpha sort; C; CAlphabetic; CH; Pesticides&Metabolites
Water Solubility: soluble in hot water
Stability: Stable, combustible. Incompatible with strong bases, strong oxidizing agents.
Index of Refraction: 1.583
Molar Refractivity: 38.07 cm3
Molar Volume: 113.9 cm3
Surface Tension: 51.5 dyne/cm
Density: 1.374 g/cm3
Flash Point: 120.5 °C
Enthalpy of Vaporization: 54.31 kJ/mol
Boiling Point: 275.7 °C at 760 mmHg
Vapour Pressure: 0.00242 mmHg at 25 °C
Appearance: white crystals or powder
Melting Point: 138-140 °C(lit.)
Classification Code of 2-Chlorobenzoic acid (CAS NO.118-91-2): Skin / Eye Irritant
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD | oral | > 500mg/kg (500mg/kg) | National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 18, 1953. | |
rat | LD50 | intraperitoneal | 2300mg/kg (2300mg/kg) | Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973. |
Reported in EPA TSCA Inventory.
Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. An eye and skin irritant. When heated to decomposition it emits toxic fumes of Cl−.
Hazard Codes: Xi
Risk Statements: 36-36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
R36:Irritating to eyes.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: DG4976000
Hazard Note: Irritant
2-Chlorobenzoic acid (CAS NO.118-91-2), its Synonyms are Benzoic acid, 2-chloro- ; Benzoic acid, o-chloro- ; Kyselina o-chlorbenzoova ; o-Chlorobenzoic acid .
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