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321-14-2

Basic Information
CAS No.: 321-14-2
Name: 5-Chloro-2-hydroxybenzoic acid
Article Data: 95
Molecular Structure:
Molecular Structure of 321-14-2 (5-Chloro-2-hydroxybenzoic acid)
Formula: C7H5ClO3
Molecular Weight: 172.568
Synonyms: Salicylicacid, 5-chloro- (6CI,7CI,8CI);2-Hydroxy-5-chlorobenzoic acid;5-Chloro-2-hydroxybenzoic acid;NSC 30111;
EINECS: 206-283-9
Density: 1.536 g/cm3
Melting Point: 171-176 °C
Boiling Point: 320.5 °C at 760 mmHg
Flash Point: 147.6 °C
Solubility: water: 1 g/L (20 °C) in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/38-36/37/38-20/21/22
Safety: 26-36-37/39
Transport Information: UN 2811 6.1/PG 3
PSA: 57.53000
LogP: 1.74380
Synthetic route
124-38-9

carbon dioxide

106-48-9

4-chloro-phenol

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;
535-80-8

3-chlorobenzoate

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
69-72-7

salicylic 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%
50-79-3

2,5-dichlorobenzoic 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;
17201-44-4

sodium ethyl carbonate

106-48-9

4-chloro-phenol

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%
21739-93-5

2-bromo-5-chlorobenzoic 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%
69693-00-1

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

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

321-14-2

5-chloro-2-hydroxybenzoic acid

3260-85-3

2-methyl-4-chloroanisole

321-14-2

5-chloro-2-hydroxybenzoic acid

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

5-chloro-2-hydroxybenzonitrile

321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sulfuric acid; water at 200℃;
1820-99-1

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

321-14-2

5-chloro-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sulfuryl dichloride; benzene
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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.