Conditions | Yield |
---|---|
Stage #1: 4-chloro-phenol With sodium hydroxide In water for 2h; Autoclave; Reflux; Stage #2: carbon dioxide In N,N-dimethyl-formamide at 80 - 145℃; under 2250.23 - 3750.38 Torr; for 15h; Autoclave; Stage #3: With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene pH=6.5; | 97.65% |
Stage #1: 4-chloro-phenol With Mesitol; sodium hydride In mineral oil at 100℃; for 0.0833333h; Glovebox; Stage #2: carbon dioxide In mineral oil at 185℃; under 760.051 Torr; for 2h; | 85% |
With potassium carbonate at 140℃; under 29420.3 Torr; |
Conditions | Yield |
---|---|
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; under 3800.26 Torr; for 15h; | 95% |
With oxygen; potassium acetate; p-benzoquinone; palladium diacetate In ISOPROPYLAMIDE at 115℃; under 3800.26 Torr; for 15h; Product distribution / selectivity; | 95% |
Multi-step reaction with 2 steps 1: fuming nitric acid / Reduzieren des Nitrierungsprodukts mit Zinn und Salzsaeure 2: water; nitrous acid View Scheme |
Conditions | Yield |
---|---|
Stage #1: salicylic acid With sulfuric acid In acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-chloro-succinimide In acetonitrile at 20℃; for 2.5h; regioselective reaction; | 92% |
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 2h; | 85% |
With hydrogenchloride; sodium percarbonate; dihydrogen peroxide In dichloromethane; water at 40 - 45℃; Reagent/catalyst; Solvent; Green chemistry; | 82.5% |
Conditions | Yield |
---|---|
With pyridine; water; potassium carbonate; copper for 0.25h; sonication; | 92% |
With pyridine; copper; potassium carbonate In water for 2h; Heating; | 84% |
With sodium methylate at 150℃; Eintragen des Reaktionsgemisches in Wasser; | |
With copper(l) iodide; copper; potassium carbonate at 170℃; under 4413.05 Torr; |
Conditions | Yield |
---|---|
With carbon dioxide at 190℃; under 7600.51 Torr; for 6h; Time; Temperature; Pressure; Autoclave; regioselective reaction; | 86.1% |
2-bromo-5-chlorobenzoic acid
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With copper(I) oxide; 2-pyridinealdoxime; cesium hydroxide; tetrabutylammomium bromide In water at 100℃; for 48h; Inert atmosphere; | 81% |
6-chloro-2-methyl-4H-chromen-4-one
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium permanganate beim Erwaermen mit Jodwasserstoffsaeure; |
5-chloro-2-hydroxybenzonitrile
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sulfuric acid; water at 200℃; |
Conditions | Yield |
---|---|
With sulfuryl dichloride; benzene |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With tetrachloromethane; potassium hydroxide; ethanol at 140℃; im geschlossenen Rohr; | |
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 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere View Scheme | |
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; for 15h; Schlenk technique; regioselective reaction; | |
With tetrachloromethane; sodium hydroxide; copper |
Conditions | Yield |
---|---|
With water; cis-nitrous acid |
N,N-dichloro-p-toluenesulfonamide
salicylic acid
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With chloroform |
salicylic acid
A
5-chloro-2-hydroxybenzoic acid
B
3,5-dichlorosalicylic acid
Conditions | Yield |
---|---|
With ethanol; chlorine | |
With tert-butylhypochlorite In water | |
With ethanol beim Chlorieren; Trennung ueber die Bariumsalze; | |
With antimonypentachloride |
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 sulfuryl dichloride Behandeln mit Kalilauge; |
Conditions | Yield |
---|---|
With sodium hydroxide; alpha cyclodextrin In water at 25℃; Rate constant; Ionic strength: 1.0 (NaCl); effect of pH, concentration of α-cyclodextrin; | |
With water at 25℃; Kinetics; |
4-chlorosalicylate
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
In ethanol; water at 25℃; Equilibrium constant; |
6-chloro-2-methyl-4H-chromen-4-one
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide In methanol at 20℃; Oxidation; | |
Multi-step reaction with 2 steps 1: 59 percent / AcONa / 2 h / 260 - 270 °C 2: 10 percent aq. NaOH / ethanol / 4 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 88 percent / Na / diethyl ether 2: 10 percent aq. KOH View Scheme |
3-(6-chloro-4-oxo-4H-chromen-2-yl)-2-oxo-propionic acid ethyl ester
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide Hydrolysis; |
6-Chloro-2-(3-phthalidenemethylene)chromone
A
5-chloro-2-hydroxybenzoic acid
B
benzene-1,2-dicarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 4h; Hydrolysis; Heating; |
6-chloro-2,3-dimethyl-chromen-4-one
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
beim Schmelzen; |
water
cis-nitrous acid
5-chloroanthranilic acid
5-chloro-2-hydroxybenzoic acid
chlorine
nitrobenzene
salicylic acid
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
bei Siedetemperatur; |
tetrachloromethane
ethanol
4-chloro-phenol
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
at 140℃; |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-Chloro-2-methylpropene In N,N-dimethyl-formamide at 65℃; for 21h; | 100% |
With potassium carbonate In N-methyl-acetamide |
5-chloro-2-hydroxybenzoic acid
2-Methylphenylboronic acid
4-hydroxy-2'-methylbiphenyl-3-carboxylic acid
Conditions | Yield |
---|---|
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 20℃; for 12h; Suzuki-Miyaura coupling; | 99% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 0.75h; Heating; | 97% |
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 4.5h; | 96% |
With borane-THF; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 18h; | 85% |
5-chloro-2-hydroxybenzoic acid
acetic anhydride
2-acetoxy-5-chloro-benzoic acid
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Heating / reflux; | 97% |
With sulfuric acid | 93% |
With sulfuric acid | 93% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: tributyltin chloride In methanol for 5h; | 97% |
zirconocene dichloride
5-chloro-2-hydroxybenzoic acid
[Cp2Zr(μ2-O',O''C-C6H3(OH)Cl)2]
Conditions | Yield |
---|---|
In hydrogenchloride; dichloromethane mixt. of zirconocene dichloride in 1 M aq. HCl and dichlorobenzoic acidin CH2Cl2 was stirred for 30 min at room temp.; organic layer was separated, dried over MgSO4, filtered, concd. in vac.,crystd. form CH2Cl2/Et2O/hexane, elem. anal.; | 96.3% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 20℃; | 96% |
With sulfuric acid; nitric acid at 0 - 20℃; for 5.66667h; | 95% |
With sulfuric acid; nitric acid for 6h; Ambient temperature; | 90.5% |
Conditions | Yield |
---|---|
With bromine In chloroform | 96% |
With N-Bromosuccinimide In carbon disulfide at 25℃; for 14h; | |
With bromine; acetic acid at 80℃; for 8h; | 204.6 g |
With bromine; acetic acid at 80℃; for 8h; | 204.6 g |
dichloromethane
5-chloro-2-hydroxybenzoic acid
6-chloro-4H-benzo[d][1,3]dioxin-4-one
Conditions | Yield |
---|---|
With potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 6h; Green chemistry; | 96% |
5-chloro-2-hydroxybenzoic acid
5,5-dibenzyl-2,3,4,5-tetrahydropyridine
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 20h; | 96% |
5-chloro-2-hydroxybenzoic acid
acetyl chloride
2-acetoxy-5-chloro-benzoic acid
Conditions | Yield |
---|---|
With pyridine; sulfuric acid In toluene | 95.6% |
With triethylamine In tetrahydrofuran at 20℃; | 46.7% |
Conditions | Yield |
---|---|
Stage #1: sebacoyl chloride; 5-chloro-2-hydroxybenzoic acid With pyridine In tetrahydrofuran for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2; | 95% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: dibutyltin chloride In methanol for 5h; | 95% |
5-chloro-2-hydroxybenzoic acid
2,4-difluorophenylboronic acid
2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid
Conditions | Yield |
---|---|
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); tetrabutylammomium bromide; potassium carbonate In ethanol; water for 8h; Concentration; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Reflux; | 95% |
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With pyridine; dicyclohexyl-carbodiimide at 80℃; for 2h; Microwave irradiation; | 95% |
Conditions | Yield |
---|---|
With sulfuric acid In methanol | 94.8% |
With thionyl chloride In methanol; ethyl acetate | 74% |
With thionyl chloride In methanol; ethyl acetate | 74% |
Conditions | Yield |
---|---|
In methanol | 94.8% |
methanol
5-chloro-2-hydroxybenzoic acid
methyl 5-chloro-2-hydroxybenzoate
Conditions | Yield |
---|---|
With thionyl chloride for 168h; Inert atmosphere; Reflux; | 94% |
With sulfuric acid for 120h; Inert atmosphere; Reflux; | 91% |
With sulfuric acid for 120h; Reflux; | 91% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: triphenyltin chloride In methanol for 5h; | 94% |
2-fluoroethyl bromide
5-chloro-2-hydroxybenzoic acid
2-fluoroethyl 5-chloro-2-(2-fluoroethoxy)benzoate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 48h; | 93.4% |
With sodium hydride |
bis(3-bromopropyl) ether
5-chloro-2-hydroxybenzoic acid
5-chloro-2-(2-methoxyethoxy)benzoic acid 2-methoxyethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In ethyl acetate; acetonitrile | 93% |
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With sodium hydroxide In water Stage #2: copper dichloride In water for 24h; | 93% |
5-chloro-2-hydroxybenzoic acid
4-cyanophenylboronic acid
Conditions | Yield |
---|---|
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 80℃; for 12h; Suzuki-Miyaura coupling; | 92% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: dibutyltin chloride In methanol for 5h; | 92% |
bis(cyclopentadienyl)titanium dichloride
5-chloro-2-hydroxybenzoic acid
Ti(η5-C5H5)2(C6H3Cl(O)(CO2))
Conditions | Yield |
---|---|
With NaOH; catalyst: C2H5OH In ethanol; chloroform; water-d2 Kinetics; NaOH and C2H5OH added to mixt. of (C5H5)2TiCl2 and acid dissolved in CHCl3, stirred for 30 min at room temp.; dried (anhydrous MgSO4), filtered, filtrate concd. in vac., ppt. recrystd. from CH2Cl2/hexane; elem. anal.; | 91.1% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: trimethyltin(IV)chloride In methanol for 5h; | 91% |
The IUPAC name of 5-Chlorosalicylic acid is 5-chloro-2-hydroxybenzoic acid. With the CAS registry number 321-14-2, it is also named as 2-Hydroxy-5-chlorobenzoic acid. The product's categories are Fine Chemical & Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Amino Acid Derivatives. It is white crystalline powder which is soluble in hot water, insoluble in cold water, easily soluble in alcohol, ether, benzene, chloroform and acetic acid.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.34; (4)ACD/LogD (pH 7.4): 0.27; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.44; (8)ACD/KOC (pH 7.4): 1.22; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.629; (13)Molar Refractivity: 39.95 cm3; (14)Molar Volume: 112.3 cm3; (15)Polarizability: 15.84×10-24 cm3; (16)Surface Tension: 66 dyne/cm; (17)Enthalpy of Vaporization: 59.35 kJ/mol; (18)Vapour Pressure: 0.000132 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 4; (21)Exact Mass: 171.992722; (22)MonoIsotopic Mass: 171.992722; (23)Topological Polar Surface Area: 57.5; (24)Heavy Atom Count: 11; (25)Complexity: 160.
Preparation of 5-Chlorosalicylic acid: It can be obtained by salicylic acid and chlorine.
Uses of 5-Chlorosalicylic acid: It can be used as intermediate of pesticide, medicine and dyes. It also can react with methanol to get 5-chloro-2-hydroxy-benzoic acid methyl ester. This reaction needs reagent hydrogen chloride.
When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:Clc1cc(C(=O)O)c(O)cc1
2. InChI:InChI=1/C7H5ClO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,(H,10,11)
3. InChIKey:NKBASRXWGAGQDP-UHFFFAOYAL
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LDLo | intraperitoneal | 250mg/kg (250mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 7, Pg. 792, 1955. | |
rat | LD50 | oral | 250mg/kg (250mg/kg) | Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 9, Pg. 164, 1973. |
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