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321-14-2

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321-14-2 Usage

Chemical Properties

OFF-WHITE TO CREAM POWDER

Uses

Moth-proofing, insecticide, intermediate for pharmaceuticals, dyes, pesticides.

Definition

ChEBI: A monohydroxybenzoic acid that is 2-hydroxybenzoic acid in which the hydrogen at position 5 is replaced by chlorine.

Hazard

Toxic by ingestion.

Check Digit Verification of cas no

The CAS Registry Mumber 321-14-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,2 and 1 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 321-14:
(5*3)+(4*2)+(3*1)+(2*1)+(1*4)=32
32 % 10 = 2
So 321-14-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H5ClO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,(H,10,11)/p-1

321-14-2 Well-known Company Product Price

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  • Alfa Aesar

  • (B23984)  5-Chlorosalicylic acid, 99%   

  • 321-14-2

  • 100g

  • 194.0CNY

  • Detail
  • Alfa Aesar

  • (B23984)  5-Chlorosalicylic acid, 99%   

  • 321-14-2

  • 500g

  • 617.0CNY

  • Detail
  • Alfa Aesar

  • (B23984)  5-Chlorosalicylic acid, 99%   

  • 321-14-2

  • 2500g

  • 2831.0CNY

  • Detail

321-14-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-chlorosalicylic acid

1.2 Other means of identification

Product number -
Other names 5-Chlorosalicyclic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:321-14-2 SDS

321-14-2Synthetic 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%

321-14-2Relevant articles and documents

Palladium-catalyzed ortho-C-H hydroxylation of benzoic acids

Luo, Feihua,He, Shuhua,Gou, Quan,Chen, Jinyang,Zhang, mingzhong

, (2021/10/06)

A simple Pd(OAc)2 catalyzed ortho-hydroxylation of benzoic acids using TBHP as the sole oxidant has been explored. This protocol features relatively broad substrate scope and operational simplicity. The compatibility of ortho-substituted substrates is an effective complement to the previous ortho-hydroxylation reaction.

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

Granados, Albert,Jia, Zhiyu,del Olmo, Marc,Vallribera, Adelina

, p. 2812 - 2818 (2019/04/08)

Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.

Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl

Rajanna,Rao, A. Sambashiva,Chakravarthi,Reddy, K. Rajendar

, p. 167 - 170 (2017/12/26)

Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.

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