17264-74-3

Basic information

• Product Name: 2-CHLOROBENZOIC ACID, SODIUM SALT
• Synonyms: 2-CHLOROBENZOIC ACID, SODIUM SALT;SODIUM 2-CHLOROBENZOATE
• CAS NO: 17264-74-3
• Molecular Formula: C₇H₄ClO₂*Na
• Molecular Weight: 178.55
• EINECS: 241-297-9
• Mol File: 17264-74-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 275.7 °C at 760 mmHg
• Flash Point: 120.5 °C
• Appearance: /
• Vapor Pressure: 0.00242mmHg at 25°C
• CAS DataBase Reference: 2-CHLOROBENZOIC ACID, SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROBENZOIC ACID, SODIUM SALT(17264-74-3)
• EPA Substance Registry System: 2-CHLOROBENZOIC ACID, SODIUM SALT(17264-74-3)

Safety Data

• Hazardous Substances Data: 17264-74-3(Hazardous Substances Data)

Usage

General Description

2-Chlorobenzoic acid, sodium salt, is a chemical compound that is formed when 2-chlorobenzoic acid is reacted with sodium hydroxide. It is a white crystalline powder with the chemical formula C7H5ClO2Na. 2-CHLOROBENZOIC ACID, SODIUM SALT is commonly used as an intermediate in the manufacture of pharmaceuticals, dyes, and other organic compounds. It is also used as a chemical reagent in organic synthesis. Additionally, it has applications in the production of agricultural chemicals and as a corrosion inhibitor. Slightly soluble in water, 2-chlorobenzoic acid, sodium salt is typically handled and stored in a dry, cool, and well-ventilated area.

InChI:InChI=1/C7H5ClO2.Na/c8-6-4-2-1-3-5(6)7(9)10;/h1-4H,(H,9,10);/q;+1/p-1

Synthetic route

4-nitrophenol sodium salt (824-78-2) + ortho-chlorobenzoic acid (118-91-2) → 4-nitro-phenol (100-02-7) + sodium 2-chlorobenzoate (17264-74-3)

Conditions	Yield
With 1-butyl-2,3-dimethylimidazolium bis-(trifluoromethanesulfonyl)amide In methanol at 24.84℃; Equilibrium constant; Reagent/catalyst;

bis(cyclopentadienyl)titanium dichloride (1271-19-8) + sodium 2-chlorobenzoate (17264-74-3) → (C5H5)2Ti(ClC6H4COO)2

Conditions	Yield
In water; acetylacetone addn. of 2 mmol (C5H5)2TiCl2 to water containing acetylacetone; stirring for 2 h; dropwise addn. of an aq. soln. 5.2 mmol o-ClC6H4CO2Na; filtration;; dissolving in CH2Cl2 soln.; drying with anhydrous CaCl2 for 2 h; distillation of solvent in vac.; recrystallization from CH2Cl2-hexane; elem. anal.;;	93%
In benzene mixt. of complex and Na-salt of benzoic acid in dry benzene was stirredfor 3-8 h at 30°C; filtered, filtrate was evapd., recrystd. from boiling benzene; elem. anal.;	62%
In benzene a mixt. of (η-C5H5)2TiCl2 and Na salt of the substituted benzoic acid in anhydrous benzene stirred at 30°C for 4 h; orange soln. filtered, concd., crystn. (refrigerator), recrystd. (benzene);	48%
In not given

dichlorobis(η5-methylcyclopentadienyl)titanium(IV) (1282-40-2) + sodium 2-chlorobenzoate (17264-74-3) → (C5H4CH3)2Ti(O2CC6H4Cl)2

Conditions	Yield
In water; acetylacetone addn. of 2 mmol (C5H4CH3)2TiCl2 to water containing acetylacetone; stirring for 2 h; dropwise addn. of an aq. soln. 5.2 mmol o-ClC6H4CO2Na; filtration;; dissolving in CH2Cl2 soln.; drying with anhydrous CaCl2 for 2 h; distillation of solvent in vac.; recrystallization from CH2Cl2-hexane; elem. anal.;;	92%

C12H11BrO3 (1320275-72-6) + sodium 2-chlorobenzoate (17264-74-3) → 4-(2-(2-chlorophenylformyloxyl)ethoxy)-3-phenylfuran-2(5H)-one (1450824-36-8)

Conditions	Yield
In dimethyl sulfoxide at 20℃;	86.5%

sodium 2-chlorobenzoate (17264-74-3) + Chloroacetamide (79-07-2) → 2-(2-Chlorbenzoyloxy)acetamid

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 95℃;	85%

pyridine-3-carbonitrile (100-54-9) + cobalt(II) chloride hexahydrate + water (7732-18-5) + sodium 2-chlorobenzoate (17264-74-3) → [Co(3-cyanopyridine)2(2-chlorobenzoate)2(H2O)2]

Conditions	Yield
at 20℃; for 2h;	83%

pyridine-4-carbonitrile (100-48-1) + copper(ll) sulfate pentahydrate + sodium 2-chlorobenzoate (17264-74-3) → tetra-μ-2-chlorobenzoatoκ8O:O’-bis[(4-cyanopyridine-κN)copper(II)]

Conditions	Yield
In water for 168h;	82.01%

ethyl bromide (74-96-4) + sodium 2-chlorobenzoate (17264-74-3) → ethyl 2-chlorobenzoate (7335-25-3)

Conditions	Yield
tetrabutyl phosphonium bromide at 150℃; under 20 Torr; g.l.p.t.c.;	78%

pyridine-3-carbonitrile (100-54-9) + water (7732-18-5) + sodium 2-chlorobenzoate (17264-74-3) + zinc(II) chloride (7646-85-7) → [Zn(3-cyanopyridine)2(2-chlorobenzoate)2(H2O)2]

Conditions	Yield
at 20℃; for 2h;	78%

pyridine-3-carbonitrile (100-54-9) + manganese(II) chloride tetrahydrate + water (7732-18-5) + sodium 2-chlorobenzoate (17264-74-3) → [Mn(3-cyanopyridine)2(2-chlorobenzoate)2(H2O)2]

Conditions	Yield
at 20℃; for 2h;	74%

zirconocene dichloride (1291-32-3) + sodium 2-chlorobenzoate (17264-74-3) → bis(η5-cyclopentadienyl)zirconium(IV)(o-ClC6H4COO)chloride

Conditions	Yield
In benzene byproducts: NaCl; under N2; anhydrous sodium salt of acid, complex and benzene stirred for 10h at 30°C, pptn. of NaCl; filtered, concd. (reduced pressure), addn. of petroleum ether, recrystd. (benzene/petroleum ether), dried (vac.); elem. anal.;	73.2%

oxovanadium(IV) sulfate + sodium 2-chlorobenzoate (17264-74-3) → oxovanadium(IV)(2-chlorobenzoate)2

Conditions	Yield
In methanol; water dropwise addn. of ClC6H4COONa/H2O soln. to soln. VO(SO4) in MeOH/H2O (1:1) (stirring, hot plate), immediate pptn., stirred (1h); filtered, washed (MeOH/H2O=1:1), dried (vac., room temp., anh. silica gel), elem. anal.;	68%

saccharin sodium salt (128-44-9) + sodium 2-chlorobenzoate (17264-74-3) → 2-(1,1,3-trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-benzoic acid (223518-39-6)

Conditions	Yield
With sodium hydroxide for 3h; Heating;	66%

sodium 2-chlorobenzoate (17264-74-3) + 1-(1H-imidazole-1-yl)-3-phenoxypropan-2-ol (64310-72-1) → 2-chlorobenzoic acid 2-(imidazol-1-yl)-1-phenoxymethylethyl ester

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; triethylamine In N,N-dimethyl-formamide for 7h; Heating;	65%

sodium 2-chlorobenzoate (17264-74-3) + chloro-diphenylphosphine (1079-66-9) → ortho-diphenylphosphinobenzoic acid (17261-28-8)

Conditions	Yield
Stage #1: chloro-diphenylphosphine With sodium In tetrahydrofuran at 65 - 66℃; for 2h; Industry scale; Stage #2: sodium 2-chlorobenzoate In tetrahydrofuran at 25℃; for 10h; Industry scale; Stage #3: In tetrahydrofuran Product distribution / selectivity; Acidic conditions; Industry scale;	64.9%
Multi-step reaction with 2 steps 1.1: sodium / tetrahydrofuran / 25 - 66 °C 1.2: 10 h 2.1: sodium hydroxide; water View Scheme

sodium 2-chlorobenzoate (17264-74-3) + chloromethyl methyl ether (107-30-2) → 2-Chlorbenzoesaeure-methoxymethylester

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide for 4h; Ambient temperature;	63%

methanol (67-56-1) + 2,2'-dipyridyl ketone (19437-26-4) + gadolinium(III) nitrate hexahydrate + manganese (II) nitrate tetrahydrate + sodium 2-chlorobenzoate (17264-74-3) → C70H58Cl2Gd2Mn4N14O28*2CH4O

Conditions	Yield
Stage #1: methanol; 2,2'-dipyridyl ketone; manganese (II) nitrate tetrahydrate; sodium 2-chlorobenzoate With pyridine for 0.25h; Stage #2: gadolinium(III) nitrate hexahydrate for 2h;	45%

N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1) + sodium 2-chlorobenzoate (17264-74-3) → C23H17ClN2O

Conditions	Yield
With nickel(II) acetate tetrahydrate; sodium carbonate; silver carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 110℃; for 24h; Inert atmosphere;	42%

2-(2-methylphenyl)pyridine (10273-89-9) + sodium 2-chlorobenzoate (17264-74-3) → 3-methyl-2-(pyridin-2-yl)phenyl 2-chlorobenzoate (1292847-91-6)

Conditions	Yield
With dipotassium peroxodisulfate; copper(II) bis(trifluoromethanesulfonate) In toluene at 130℃; for 24h;	36%

6-amino-2-methylbenzothiazole (2941-62-0) + sodium 2-chlorobenzoate (17264-74-3) → 2-(2-methyl-benzothiazol-6-ylamino)-benzoic acid (19950-27-7)

Conditions	Yield
With copper; potassium carbonate In i-Amyl alcohol for 4h; Heating;

3-methoxyphenyl bromide (2398-37-0) + sodium 2-chlorobenzoate (17264-74-3) → (2-Chloro-phenyl)-(3-hydroxy-phenyl)-methanone (62810-53-1)

Conditions	Yield
(i) nBuLi, (ii) /BRN= 4033718/, (iii) (demethylation); Multistep reaction;

4-Nitrophenacyl bromide (99-81-0) + sodium 2-chlorobenzoate (17264-74-3) → 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate

Conditions	Yield
In water; acetone at 35℃; Rate constant;

sodium 2-chlorobenzoate (17264-74-3) + C9H8O3(2-)*2Na(1+) (117571-38-7) → 2-[2-(Carboxymethyl)-5-methylphenoxy]benzoic acid (117570-83-9)

Conditions	Yield
With Tris(3,6-dioxaheptyl)amine; copper(l) chloride In 1,4-dioxane Heating;

sodium 2-chlorobenzoate (17264-74-3) + C9H8O3(2-)*2Na(1+) (118537-92-1) → 2-(2-Carboxymethyl-3-methyl-phenoxy)-benzoic acid (118537-80-7)

Conditions	Yield
With Tris(3,6-dioxaheptyl)amine; copper(l) chloride In 1,4-dioxane Heating;

sodium 2-chlorobenzoate (17264-74-3) + sodium 5-chloro-2-methylphenolate (40495-68-9) → 2-(5-chloro-2-methyl-phenoxy)-benzoic acid (107517-48-6)

Conditions	Yield
With Tris(3,6-dioxaheptyl)amine; copper(l) chloride In 1,4-dioxane Heating;

sodium 2-chlorobenzoate (17264-74-3) + sodium 3-chloro-2-methylphenolate (118537-93-2) → 2-(3-Chloro-2-methyl-phenoxy)-benzoic acid (43160-03-8)

Conditions	Yield
With Tris(3,6-dioxaheptyl)amine; copper(l) chloride In 1,4-dioxane Heating;

sodium 2-chlorobenzoate (17264-74-3) + Sodium; 2-allyl-4-chloro-phenolate (118537-91-0) → 2-(2-Allyl-4-chloro-phenoxy)-benzoic acid (117571-27-4)

Conditions	Yield
With Tris(3,6-dioxaheptyl)amine; copper(l) chloride In various solvent(s) Heating;

sodium 2-chlorobenzoate (17264-74-3) + Sodium; 2-allyl-4-methoxy-phenolate (118537-90-9) → 2-(2-Allyl-4-methoxy-phenoxy)-benzoic acid (117571-26-3)

Conditions	Yield
With Tris(3,6-dioxaheptyl)amine; copper(l) chloride In various solvent(s) Heating;

sodium 2-chlorobenzoate (17264-74-3) → 2-Chlorobenzyl alcohol (17849-38-6)

Conditions	Yield
With borane In tetrahydrofuran for 10h; Ambient temperature;	100 % Chromat.

sodium 2-chlorobenzoate (17264-74-3) + ethyl bromoacetate (105-36-2) → (2-chloro-benzoyloxy)-acetic acid ethyl ester

Conditions	Yield
In water; acetone at 30 - 40℃; Rate constant;

sodium 2-chlorobenzoate (17264-74-3) + α-bromoacetophenone (70-11-1) → 2-(2-chlorobenzoyloxy)-1-phenylethanone (55153-25-8)

Conditions	Yield
In water; acetone at 35℃; Rate constant;
sodium dodecyl-sulfate In water; acetone at 35℃; Rate constant; no or varying amounts of NaLS;

Upstream product

• 824-78-2 4-nitrophenol sodium salt 
• 118-91-2 ortho-chlorobenzoic acid 

Downstream Products

• 824-78-2 4-nitrophenol sodium salt 
• 118-91-2 ortho-chlorobenzoic acid 
• 36882-17-4 sodium 2-(diphenylphosphino)benzoate 
• 14686-63-6 4-hydroxy-9H-xanthen-9-one 
• 5396-28-1 4-methylxanthen-9-one 
• 1450824-36-8 4-(2-(2-chlorophenylformyloxyl)ethoxy)-3-phenylfuran-2(5H)-one 
• 1292847-91-6 3-methyl-2-(pyridin-2-yl)phenyl 2-chlorobenzoate 
• 17261-28-8 ortho-diphenylphosphinobenzoic acid 

Relevant articles and documents

Electronic and steric effects: How do they work in ionic liquids? the case of benzoic acid dissociation

(Figure Presented) The need to have a measure of the strength of some substituted benzoic acids in ionic liquid solution led us to use the protonation equilibrium of sodium p-nitrophenolate as a probe reaction, which was studied by means of spectrophotometric titration at 298 K. In order to evaluate the importance of electronic effect of the substituents present on the aromatic ring, both electron-withdrawing and -donor substituents were taken into account. Furthermore, to have a measure of the importance of the steric effect of the substituents both para- and ortho-substituted benzoic acids were analyzed. The probe reaction was studied in two ionic liquids differing for the ability of the cation to give hydrogen bond and π-π interactions, namely [bm 2im][NTf2] and [bmpyrr][NTf2]. Data collected show that benzoic acids are less dissociated in ionic liquid than in water solution. Furthermore, the equilibrium constant values seem to be significantly affected by both the nature of ionic liquid cation and the structure of the acid. In particular, the ortho-steric effect seems to operate differently in water and in the aromatic ionic liquid, determining in this solvent medium a particular behavior for ortho-substituted benzoic acids.