3-chloro-2-hydroxy-thiobenzoic acid S-methyl ester
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With lithium hydroxide In methanol at 20℃; for 6h; | 100% |
carbon dioxide
chloro-1 methoxymethylenoxy-2 benzene
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: chloro-1 methoxymethylenoxy-2 benzene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1.5h; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; | 91% |
Conditions | Yield |
---|---|
With pyridine; copper; potassium carbonate In water for 2h; Heating; | 85% |
With copper(l) iodide; copper; potassium carbonate at 180℃; under 7355.08 Torr; |
A
3-Chloro-2-hydroxybenzoic acid
B
N-(4-fluorophenyl)-N-(2-carboxyphenyl)glycin
Conditions | Yield |
---|---|
Stage #1: N-(4-fluorophenyl)glycine potassium salt With potassium 2,5-dichlorobenzoate; copper; potassium carbonate In water for 20.5h; Heating / reflux; Stage #2: With hydrogenchloride In water at 75 - 80℃; for 0.5h; | A n/a B 80.3% |
2-monochlorophenol
sodium ethyl carbonate
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With carbon dioxide at 190℃; under 7600.51 Torr; for 6h; Autoclave; regioselective reaction; | 68.2% |
Conditions | Yield |
---|---|
Stage #1: 2-monochlorophenol With Mesitol; sodium hydride In mineral oil at 100℃; for 0.0833333h; Glovebox; Stage #2: carbon dioxide In mineral oil at 185℃; under 3800.26 Torr; for 2h; | 55% |
With potassium carbonate at 170℃; under 29420.3 Torr; |
3-chloro-2-hydroxy-benzoic acid-(2,2,2-trichloro-1-hydroxy-ethylamide)
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
salicylic acid disodium salt
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium hypochlorite |
Conditions | Yield |
---|---|
With chlorine; acetic acid Behandeln des Reaktionsprodukts mit ueberhitztem Wasserdampf; | |
With hydrogenchloride; potassium permanganate Behandeln des Reaktionsprodukts mit ueberhitztem Wasserdampf; |
tetrachloromethane
tert-butylhypochlorite
salicylic acid
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With tetrachloromethane |
salicylic acid
A
5-chloro-2-hydroxybenzoic acid
B
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium carbonate bei der Chlorierung; | |
With sodium hydroxide; sodium hypochlorite at 20℃; for 2.5h; pH > 12; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With N-chlorotriethylammonium chloride In trifluoroacetic acid Ambient temperature; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With sodium hydroxide; potassium permanganate Heating; |
Conditions | Yield |
---|---|
With copper(II) sulfate 1.) diazotized; Yield given. Multistep reaction; |
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With HCl-chloroacetate; potassium chloride at 70℃; Rate constant; dependence on pH; |
7-chloro-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one
water
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
beim Schmelzen; |
chlorine
acetic acid
5-sulfosalicylic Acid
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Behandeln des Reaktionsprodukts mit Wasserdampf; |
Conditions | Yield |
---|---|
at 140 - 150℃; im Autoklaven; |
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride Sonnenlicht; |
sodium salicylate
chlorine
A
5-chloro-2-hydroxybenzoic acid
B
3-Chloro-2-hydroxybenzoic acid
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water pH=1; | 3.19 g |
3-chlorobenzoate
A
5-chloro-2-hydroxybenzoic acid
B
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: 3-chlorobenzoate With [bis(acetonitrile)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-diaminoethane)iron(II)] perchlorate; dihydrogen peroxide In acetonitrile at 20℃; for 0.333333h; Stage #2: With hydrogenchloride In acetonitrile | |
With [Fe(II)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethylenediamine)(CH3CN)2](ClO4)2; dihydrogen peroxide In water; acetonitrile at 20℃; Inert atmosphere; regioselective reaction; |
chloro-1 methoxymethylenoxy-2 benzene
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: butyllithium / tetrahydrofuran; hexane / 6 h / -75 °C 1.2: tetrahydrofuran; hexane 2.1: 3.19 g / HCl / H2O / pH 1 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: BCl3; AlCl3 / 1,2-dichloro-ethane / 4 h / 20 °C 1.2: 51 percent / aq. HCl / 1,2-dichloro-ethane / 0.17 h / 20 °C 2.1: 100 percent / aq. LiOH / methanol / 6 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 96 percent / NaH / tetrahydrofuran; methyl acetate / 2 h / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / 0 °C 2.2: tetrahydrofuran; hexane / 1.5 h / -78 °C 2.3: 91 percent / 6M HCl / tetrahydrofuran; hexane / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: (i) aq. NaOH, (ii) /BRN= 1731042/ 2: KMnO4, aq. NaOH / Heating View Scheme | |
Multi-step reaction with 4 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: water; sodium hydrogencarbonate / N,N-dimethyl-formamide; diethyl ether / 0.5 h / 20 °C / Inert atmosphere 3.1: palladium diacetate; silver(I) acetate; N-tert-butoxycarbonyl-L-leucine; 2,2,2-trifluoroethanol / 1,2-dichloro-ethane / 0.08 h / 95 °C / Inert atmosphere 3.2: 18 h / 95 °C / Inert atmosphere 3.3: 18 h / 95 °C / Inert atmosphere; Glovebox 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / tin, hydrochloric acid 2: 2.) CuSO4 / 1.) diazotized View Scheme |
B
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium carbonate; copper In water at 50℃; for 15 - 20.5h; Heating / reflux; Industry scale; |
2-monochlorophenol
potassium hydrogencarbonate
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With 2,3-dihydroxybenzoate decarboxylase from Aspergillus oryzae In aq. phosphate buffer at 30℃; for 24h; Kolbe-Schmidt Synthesis; Enzymatic reaction; regioselective reaction; |
salicylic acid
A
5-chloro-2-hydroxybenzoic acid
B
3,5-dichlorosalicylic acid
C
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium hypochlorite In methanol; water |
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 23h; | 100% |
With potassium carbonate In N-methyl-acetamide |
formaldehyd
3-Chloro-2-hydroxybenzoic acid
3,3'-dicarboxy-5,5'-dichloro-4,4'-dihydroxydiphenylmethane
Conditions | Yield |
---|---|
With sulfuric acid In methanol; water 1.)0 deg C, 1h 2.) r. t., 24h; | 96% |
With sulfuric acid In methanol; water at -5 - 0℃; for 24.3333h; | 92% |
With sulfuric acid; water In methanol at -5 - 20℃; for 26h; | 92% |
3-Chloro-2-hydroxybenzoic acid
2-amino-benzenethiol
2-(2'-Hydroxy-3'-chlorophenyl)benzothiazole
Conditions | Yield |
---|---|
With phosphorus trichloride In toluene for 4h; Heating; | 94% |
With phosphorus trichloride In toluene at 100℃; | 45% |
Conditions | Yield |
---|---|
With thionyl chloride for 6h; Inert atmosphere; Reflux; | 82% |
2-iodo-propane
3-Chloro-2-hydroxybenzoic acid
3-chloro-2-isopropoxybenzoic acid isopropyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 66h; | 77% |
3-Chloro-2-hydroxybenzoic acid
acetic anhydride
2-(acetylocy)-3-chlorobenzoic acid
Conditions | Yield |
---|---|
Stage #1: 3-Chloro-2-hydroxybenzoic acid; acetic anhydride With triethylamine In tetrahydrofuran at 20℃; for 22.5h; Stage #2: With hydrogenchloride In water | 76% |
With sulfuric acid at 140℃; for 2h; | 43% |
With sulfuric acid | |
With sulfuric acid In water at 20℃; Heating; |
3-aminoquinoline
3-Chloro-2-hydroxybenzoic acid
3-chloro-2-hydroxy-N-(quinolin-3-yl)benzamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 40℃; for 8h; | 76% |
3-Chloro-2-hydroxybenzoic acid
1,2-diamino-benzene
2-(2'-Hydroxy-3'-chlorophenyl)benzimidazole
Conditions | Yield |
---|---|
With PPA at 150℃; | 75% |
Conditions | Yield |
---|---|
With methanesulfonic acid; phosphorus pentoxide at 90℃; | 71% |
2-(4-pyridylmethylene amino) ethanol
Cyclohexyl isocyanide
3-Chloro-2-hydroxybenzoic acid
C22H26ClN3O4
Conditions | Yield |
---|---|
With 3 A molecular sieve In methanol at 20℃; Ugi reaction; | 64% |
Cyclohexyl isocyanide
3-Chloro-2-hydroxybenzoic acid
(E)-2-(benzylideneamino)ethanol
C23H27ClN2O4
Conditions | Yield |
---|---|
With 3 A molecular sieve In methanol at 20℃; Ugi reaction; | 63% |
Conditions | Yield |
---|---|
With pyridine; phosphorus trichloride In toluene Inert atmosphere; Reflux; | 59% |
With phosphorus trichloride In toluene Inert atmosphere; Reflux; | 24% |
With phosphorus trichloride In 5,5-dimethyl-1,3-cyclohexadiene for 5h; Reflux; |
3-Chloro-2-hydroxybenzoic acid
propyl bromide
3-chloro-2-propoxybenzoic acid propyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 30℃; for 66h; | 51% |
3-Chloro-2-hydroxybenzoic acid
ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate
2-(3-chloro-2-hydroxy-benzoylamino)-indan-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; | 49% |
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: methyl 3-[(4-acetylpiperazin-1-yl)methyl]benzoate With trichlorophosphate In dichloromethane at 0 - 25℃; for 1h; Stage #2: 3-Chloro-2-hydroxybenzoic acid In dichloromethane at 0 - 60℃; for 15h; Stage #3: With sodium acetate In dichloromethane at 60℃; for 4h; | 48.4% |
C20H15N2PS2
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
In dichloromethane | 48% |
Conditions | Yield |
---|---|
Stage #1: 3-Chloro-2-hydroxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere; Stage #2: tert-Octylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; | 43.08% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; | 36.58% |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 5h; Ambient temperature; | 41% |
3-Chloro-2-hydroxybenzoic acid
diazomethyl-trimethyl-silane
methyl 3-chloro-5-nitrosalicylate
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In methanol; hexane; benzene | 39% |
Conditions | Yield |
---|---|
With phosphorus trichloride In 5,5-dimethyl-1,3-cyclohexadiene for 5h; Reflux; | 39% |
Conditions | Yield |
---|---|
With phosphorus trichloride In toluene Inert atmosphere; Reflux; | 27% |
1-[4-(3-aminophenyl)piperazin-1-yl]-2-(5-methyl-3-trifluoromethylpyrazol-1-yl)ethanone
3-Chloro-2-hydroxybenzoic acid
3-chloro-2-hydroxy-N-(3-{4-[2-(5-methyl-3-trifluoromethylpyrazol-1-yl)acetyl]piperazin-1-yl}phenyl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-Chloro-2-hydroxybenzoic acid With 1,1'-carbonyldiimidazole In acetonitrile at 60℃; for 2h; Stage #2: 1-[4-(3-aminophenyl)piperazin-1-yl]-2-(5-methyl-3-trifluoromethylpyrazol-1-yl)ethanone With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; | 26% |
Stage #1: 3-Chloro-2-hydroxybenzoic acid With 1,1'-carbonyldiimidazole In acetonitrile at 60℃; for 2h; Stage #2: 1-[4-(3-aminophenyl)piperazin-1-yl]-2-(5-methyl-3-trifluoromethylpyrazol-1-yl)ethanone With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; |
2-amino-6-bromobenzothiazole
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: 3-Chloro-2-hydroxybenzoic acid With phosphorus trichloride In chlorobenzene for 0.5h; Reflux; Stage #2: 2-amino-6-bromobenzothiazole In chlorobenzene for 4h; Reflux; | 26% |
Conditions | Yield |
---|---|
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; | 21% |
IUPAC Name: 3-chloro-2-hydroxybenzoic acid
Synonyms of 3-Chlorosalicylic acid (CAS NO,1829-32-9): 3EINECS 217-379-5 ; NSC 18854 ; Benzoic acid, 3-chloro-2-hydroxy- (9CI) ; Salicylic acid, 3-chloro- (8CI)
CAS NO: 1829-32-9
Molecular Formula: C7H5ClO3
Molecular Weight: 172.5658
Molecular Structure:
Melting Point: 184-186 °C
ProductCategories: Aromatics ; C7 ; Carbonyl Compounds ; Carboxylic Acids
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 35.53 Å2
Index of Refraction: 1.629
Molar Refractivity: 39.95 cm3
Molar Volume: 112.3 cm3
Surface Tension: 66 dyne/cm
Density of 3-Chlorosalicylic acid (CAS NO,1829-32-9): 1.536 g/cm3
Flash Point: 130.2 °C
Enthalpy of Vaporization: 56.1 kJ/mol
Boiling Point: 291.7 °C at 760 mmHg
Vapour Pressure: 0.000876 mmHg at 25°C
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 3
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