Product Name

  • Name

    5-Chloro-2-hydroxybenzoic acid

  • EINECS 206-283-9
  • CAS No. 321-14-2
  • Article Data95
  • CAS DataBase
  • Density 1.536 g/cm3
  • Solubility water: 1 g/L (20 °C) in water
  • Melting Point 171-176 °C
  • Formula C7H5ClO3
  • Boiling Point 320.5 °C at 760 mmHg
  • Molecular Weight 172.568
  • Flash Point 147.6 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance white crystalline powder
  • Safety 26-36-37/39
  • Risk Codes 22-36/38-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 321-14-2 (5-Chloro-2-hydroxybenzoic acid)
  • Hazard Symbols HarmfulXn
  • Synonyms Salicylicacid, 5-chloro- (6CI,7CI,8CI);2-Hydroxy-5-chlorobenzoic acid;5-Chloro-2-hydroxybenzoic acid;NSC 30111;
  • PSA 57.53000
  • LogP 1.74380

Synthetic route

carbon dioxide
124-38-9

carbon dioxide

4-chloro-phenol
106-48-9

4-chloro-phenol

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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;
3-chlorobenzoate
535-80-8

3-chlorobenzoate

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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
salicylic acid
69-72-7

salicylic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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%
2,5-dichlorobenzoic acid
50-79-3

2,5-dichlorobenzoic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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;
sodium ethyl carbonate
17201-44-4

sodium ethyl carbonate

4-chloro-phenol
106-48-9

4-chloro-phenol

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With carbon dioxide at 190℃; under 7600.51 Torr; for 6h; Time; Temperature; Pressure; Autoclave; regioselective reaction;86.1%
2-bromo-5-chlorobenzoic acid
21739-93-5

2-bromo-5-chlorobenzoic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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
69693-00-1

6-chloro-2-methyl-4H-chromen-4-one

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

2-methyl-4-chloroanisole
3260-85-3

2-methyl-4-chloroanisole

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With potassium permanganate beim Erwaermen mit Jodwasserstoffsaeure;
5-chloro-2-hydroxybenzonitrile
13589-72-5

5-chloro-2-hydroxybenzonitrile

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sulfuric acid; water at 200℃;
5,5'-thio-bis(2-hydroxy-benzoic acid)
1820-99-1

5,5'-thio-bis(2-hydroxy-benzoic acid)

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sulfuryl dichloride; benzene
tetrachloromethane
56-23-5

tetrachloromethane

4-chloro-phenol
106-48-9

4-chloro-phenol

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide
4-chloro-phenol
106-48-9

4-chloro-phenol

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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
5-chloroanthranilic acid
635-21-2

5-chloroanthranilic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With water; cis-nitrous acid
N,N-dichloro-p-toluenesulfonamide
473-34-7

N,N-dichloro-p-toluenesulfonamide

salicylic acid
69-72-7

salicylic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With chloroform
salicylic acid
69-72-7

salicylic acid

A

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

B

3,5-dichlorosalicylic acid
320-72-9

3,5-dichlorosalicylic acid

Conditions
ConditionsYield
With ethanol; chlorine
With tert-butylhypochlorite In water
With ethanol beim Chlorieren; Trennung ueber die Bariumsalze;
With antimonypentachloride
salicylic acid
69-72-7

salicylic acid

A

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

B

3-Chloro-2-hydroxybenzoic acid
1829-32-9

3-Chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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;
2-hydroxy-benzoic acid ethyl ester
118-61-6

2-hydroxy-benzoic acid ethyl ester

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sulfuryl dichloride Behandeln mit Kalilauge;
2-acetoxy-5-chloro-benzoic acid
1734-62-9

2-acetoxy-5-chloro-benzoic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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
45866-17-9

4-chlorosalicylate

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
In ethanol; water at 25℃; Equilibrium constant;
6-chloro-2-methyl-4H-chromen-4-one
69693-00-1

6-chloro-2-methyl-4H-chromen-4-one

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
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
144880-76-2

3-(6-chloro-4-oxo-4H-chromen-2-yl)-2-oxo-propionic acid ethyl ester

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide Hydrolysis;
6-Chloro-2-(3-phthalidenemethylene)chromone
144880-82-0

6-Chloro-2-(3-phthalidenemethylene)chromone

A

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 4h; Hydrolysis; Heating;
6-chloro-2,3-dimethyl-chromen-4-one
99852-42-3

6-chloro-2,3-dimethyl-chromen-4-one

diluted alkali

diluted alkali

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

6-Chloro-chromen-2-one
2051-59-4

6-Chloro-chromen-2-one

potassium hydroxide

potassium hydroxide

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
beim Schmelzen;
6-chloro-2,3-diphenyl-4H-chromen-4-one

6-chloro-2,3-diphenyl-4H-chromen-4-one

KOH-solution

KOH-solution

A

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

B

benzoic acid
65-85-0

benzoic acid

C

4-chloro-2-phenacetyl-phenol

4-chloro-2-phenacetyl-phenol

water
7732-18-5

water

cis-nitrous acid
7782-77-6

cis-nitrous acid

5-chloroanthranilic acid
635-21-2

5-chloroanthranilic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

chlorine
7782-50-5

chlorine

nitrobenzene
98-95-3

nitrobenzene

salicylic acid
69-72-7

salicylic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

5-chlorosalicyclaldehyde
635-93-8

5-chlorosalicyclaldehyde

chromic acid

chromic acid

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

tetrachloromethane
56-23-5

tetrachloromethane

4-chloro-phenol
106-48-9

4-chloro-phenol

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

copper

copper

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
bei Siedetemperatur;
tetrachloromethane
56-23-5

tetrachloromethane

ethanol
64-17-5

ethanol

4-chloro-phenol
106-48-9

4-chloro-phenol

KOH

KOH

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
at 140℃;
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2-methylallyl 5-chloro-2-(2-methylallyloxy)benzoate

2-methylallyl 5-chloro-2-(2-methylallyloxy)benzoate

Conditions
ConditionsYield
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
321-14-2

5-chloro-2-hydroxybenzoic acid

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

4-hydroxy-2'-methylbiphenyl-3-carboxylic acid
25205-15-6

4-hydroxy-2'-methylbiphenyl-3-carboxylic acid

Conditions
ConditionsYield
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%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

4-chloro-2-hydroxymethylphenol
5330-38-1

4-chloro-2-hydroxymethylphenol

Conditions
ConditionsYield
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
321-14-2

5-chloro-2-hydroxybenzoic acid

acetic anhydride
108-24-7

acetic anhydride

2-acetoxy-5-chloro-benzoic acid
1734-62-9

2-acetoxy-5-chloro-benzoic acid

Conditions
ConditionsYield
With sulfuric acid for 3h; Heating / reflux;97%
With sulfuric acid93%
With sulfuric acid93%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

tributyltin chloride
1461-22-9

tributyltin chloride

C19H31ClO3Sn

C19H31ClO3Sn

Conditions
ConditionsYield
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
1291-32-3

zirconocene dichloride

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

[Cp2Zr(μ2-O',O''C-C6H3(OH)Cl)2]
1192558-54-5

[Cp2Zr(μ2-O',O''C-C6H3(OH)Cl)2]

Conditions
ConditionsYield
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%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

5-chloro-2-hydroxy-3-nitrobenzoic acid
7195-78-0

5-chloro-2-hydroxy-3-nitrobenzoic acid

Conditions
ConditionsYield
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%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

3-bromo-5-chloro-2-hydroxy benzoic acid
4068-58-0

3-bromo-5-chloro-2-hydroxy benzoic acid

Conditions
ConditionsYield
With bromine In chloroform96%
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
75-09-2

dichloromethane

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

6-chloro-4H-benzo[d][1,3]dioxin-4-one
342411-03-4

6-chloro-4H-benzo[d][1,3]dioxin-4-one

Conditions
ConditionsYield
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
321-14-2

5-chloro-2-hydroxybenzoic acid

5,5-dibenzyl-2,3,4,5-tetrahydropyridine
1416767-53-7

5,5-dibenzyl-2,3,4,5-tetrahydropyridine

6,6-dibenzyl-2-chloro-6,7,8,9-tetrahydro-5aH,11H-pyrido[2,1-b][1,3]benzoxazin-11-one

6,6-dibenzyl-2-chloro-6,7,8,9-tetrahydro-5aH,11H-pyrido[2,1-b][1,3]benzoxazin-11-one

Conditions
ConditionsYield
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
321-14-2

5-chloro-2-hydroxybenzoic acid

acetyl chloride
75-36-5

acetyl chloride

2-acetoxy-5-chloro-benzoic acid
1734-62-9

2-acetoxy-5-chloro-benzoic acid

Conditions
ConditionsYield
With pyridine; sulfuric acid In toluene95.6%
With triethylamine In tetrahydrofuran at 20℃;46.7%
sebacoyl chloride
111-19-3

sebacoyl chloride

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

1,10-bis-4-chlorosalicyl-sebacate

1,10-bis-4-chlorosalicyl-sebacate

Conditions
ConditionsYield
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%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

dibutyltin chloride
683-18-1

dibutyltin chloride

2C7H4ClO3(1-)*Sn(4+)*2C4H9(1-)

2C7H4ClO3(1-)*Sn(4+)*2C4H9(1-)

Conditions
ConditionsYield
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
321-14-2

5-chloro-2-hydroxybenzoic acid

2,4-difluorophenylboronic acid
144025-03-6

2,4-difluorophenylboronic acid

2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid
22494-42-4

2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid

Conditions
ConditionsYield
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
321-14-2

5-chloro-2-hydroxybenzoic acid

2-[(N,N-dimethylamino)methyl]ferrocenylmethylamine

2-[(N,N-dimethylamino)methyl]ferrocenylmethylamine

C21H23ClFeN2O2

C21H23ClFeN2O2

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide at 80℃; for 2h; Microwave irradiation;95%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

methyl 5-chloro-2-hydroxybenzoate
4068-78-4

methyl 5-chloro-2-hydroxybenzoate

Conditions
ConditionsYield
With sulfuric acid In methanol94.8%
With thionyl chloride In methanol; ethyl acetate74%
With thionyl chloride In methanol; ethyl acetate74%
conc. H2 SO4

conc. H2 SO4

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

methyl 5-chloro-2-hydroxybenzoate
4068-78-4

methyl 5-chloro-2-hydroxybenzoate

Conditions
ConditionsYield
In methanol94.8%
methanol
67-56-1

methanol

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

methyl 5-chloro-2-hydroxybenzoate
4068-78-4

methyl 5-chloro-2-hydroxybenzoate

Conditions
ConditionsYield
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%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

triphenyltin chloride
639-58-7

triphenyltin chloride

C25H19ClO3Sn

C25H19ClO3Sn

Conditions
ConditionsYield
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
762-49-2

2-fluoroethyl bromide

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

2-fluoroethyl 5-chloro-2-(2-fluoroethoxy)benzoate
334652-76-5

2-fluoroethyl 5-chloro-2-(2-fluoroethoxy)benzoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 48h;93.4%
With sodium hydride
bis(3-bromopropyl) ether
58929-72-9

bis(3-bromopropyl) ether

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

5-chloro-2-(2-methoxyethoxy)benzoic acid 2-methoxyethyl ester
521065-04-3

5-chloro-2-(2-methoxyethoxy)benzoic acid 2-methoxyethyl ester

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate; acetonitrile93%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

copper dichloride

copper dichloride

5-chloro-2-hydroxy benzoic acid copper (II) salt

5-chloro-2-hydroxy benzoic acid copper (II) salt

Conditions
ConditionsYield
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
321-14-2

5-chloro-2-hydroxybenzoic acid

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

4'-cyano-4-hydroxybiphenyl-3-carboxylic acid

4'-cyano-4-hydroxybiphenyl-3-carboxylic acid

Conditions
ConditionsYield
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%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

dibutyltin chloride
683-18-1

dibutyltin chloride

C15H22Cl2O3Sn

C15H22Cl2O3Sn

Conditions
ConditionsYield
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
1271-19-8

bis(cyclopentadienyl)titanium dichloride

5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

Ti(η5-C5H5)2(C6H3Cl(O)(CO2))
233600-03-8

Ti(η5-C5H5)2(C6H3Cl(O)(CO2))

Conditions
ConditionsYield
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%
5-chloro-2-hydroxybenzoic acid
321-14-2

5-chloro-2-hydroxybenzoic acid

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

C10H13ClO3Sn

C10H13ClO3Sn

Conditions
ConditionsYield
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%

5-Chlorosalicylic acid Consensus Reports

Reported in EPA TSCA Inventory.

5-Chlorosalicylic acid Specification

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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