56047-23-5

Basic information

• Product Name: 4-CHLOROPHTHALIC ACID MONOSODIUM SALT
• Synonyms: 2-benzenedicarboxylicacid,4-chloro-monosodiumsalt;4-CHLOROPHTHALIC ACID MONOSODIUM SALT;4-CHLOROPHTHALIC ACID SODIUM SALT;4-CHLORO-2-CARBOXYBENZOIC ACID MONOSODIUM SALT;4-CHLORO-1,2-DICARBOXYBENZENE MONOSODIUM SALT;MONOSODIUM 4-CHLOROPHTHALATE;SODIUM 4-CHLOROPHTHALATE;SODIUM HYDROGEN 4-CHLOROPHTHALATE
• CAS NO: 56047-23-5
• Molecular Formula: C₈H₄ClO₄*Na
• Molecular Weight: 222.56
• EINECS: 259-963-2
• Mol File: 56047-23-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 399.5 °C at 760 mmHg
• Flash Point: 195.4 °C
• Appearance: white to light tan powder.
• Density: g/cm³
• Vapor Pressure: 4.22E-07mmHg at 25°C
• Water Solubility: Soluble in water
• CAS DataBase Reference: 4-CHLOROPHTHALIC ACID MONOSODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROPHTHALIC ACID MONOSODIUM SALT(56047-23-5)
• EPA Substance Registry System: 4-CHLOROPHTHALIC ACID MONOSODIUM SALT(56047-23-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36
• Safety Statements: 26-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 56047-23-5(Hazardous Substances Data)

Usage

Chemical Properties

white to tan to beige crystalline powder

InChI:InChI=1/C8H5ClO4/c9-4-1-2-5(7(10)11)6(3-4)8(12)13/h1-3H,(H,10,11)(H,12,13)/p-2

Synthetic route

phthalic anhydride (85-44-9) → monosodique de l'acide chloro-4 phtalique (56047-23-5)

Conditions	Yield
Stage #1: phthalic anhydride With sodium chlorate; sodium hydroxide In water at 28 - 30℃; for 17h; Stage #2: With hydrogenchloride In water at 30℃; pH=Ca. 5.5;

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chlorophthalic anhydride (118-45-6)

Conditions	Yield
With thionyl chloride for 2h; Heating;	70%
With sulfuric acid In acetic anhydride for 3h; Heating;
With thionyl chloride for 2h; Reflux;

ethanol (64-17-5) + monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chlorodiethylphthalate (38717-95-2)

Conditions	Yield
With hydrogenchloride at 80℃; for 48h; Esterification;	62%

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chloro-2-hydroxy-1(H)-isoindole-1,3-dione (173962-58-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / HCl(g) / 48 h / 80 °C 2: hydroxylamine; KOH / methanol / 8 h / -70 °C / RT, 72 h View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chloro-2-methylsulfonyloxy-1(H)-isoindole-1,3-dione

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / HCl(g) / 48 h / 80 °C 2: hydroxylamine; KOH / methanol / 8 h / -70 °C / RT, 72 h 3: 48 percent / NaHCO3 / H2O / 3 h / 0 °C View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chloro-2-isopropylsulfonyloxy-1(H)-isoindole-1,3-dione

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / HCl(g) / 48 h / 80 °C 2: hydroxylamine; KOH / methanol / 8 h / -70 °C / RT, 72 h 3: 56 percent / NaHCO3 / H2O / 3 h / 0 °C View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chlorophthalimide (7147-90-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / thionylchloride / 2 h / Heating 2: 98 percent / urea / 0.67 h / Heating View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / Reflux 2: formamide / 1 h / 150 °C View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 6-chlorophthalide (19641-29-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 83 percent / NaBH4 / methanol View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 5-chloro-1H-indene-1,3(2H)-dione (22018-96-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 2 h / Heating 3: 1.) SOCl2 / 1.) reflux; 2.) benzene, reflux, 1.5 h 4: Na / reflux 2 h, then r.t., 15 h View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → chloro-4 phtalate acide d'ethyle

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 2 h / Heating View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chlorodiethylphthalate (38717-95-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 2 h / Heating 3: 1.) SOCl2 / 1.) reflux; 2.) benzene, reflux, 1.5 h View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → chloro-5 (dihydro-1,4 pyridinylidene-4)-2 indanedione-1,3 (111983-50-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 57.1 percent / molecular sieves 3 Angstroem / diphenyl ether / 24 h / Heating View Scheme
Multi-step reaction with 3 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 83 percent / NaBH4 / methanol 3: 62.3 percent / NaOMe, ethyl propionate / methanol / 5 h / Heating View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → chloro-5 (dimethyl-2,6 4 H-pyrannylidene-4)-2 indanedione-1,3

Conditions	Yield
Multi-step reaction with 5 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 2 h / Heating 3: 1.) SOCl2 / 1.) reflux; 2.) benzene, reflux, 1.5 h 4: Na / reflux 2 h, then r.t., 15 h 5: 38.1 percent / acetic anhydride / 24 h / Heating View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 5-Chloro-2-(1-ethyl-1H-pyridin-4-ylidene)-indan-1,3-dione (111983-51-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 57.1 percent / molecular sieves 3 Angstroem / diphenyl ether / 24 h / Heating 3: 89.2 percent / 50percent NaH / dimethylsulfoxide / 8 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 83 percent / NaBH4 / methanol 3: 62.3 percent / NaOMe, ethyl propionate / methanol / 5 h / Heating 4: 89.2 percent / 50percent NaH / dimethylsulfoxide / 8 h / Ambient temperature View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → (chloro-5 isopropyl-1 dihydro-1,4 pyridinylidene-4)-2 indanedione-1,3 (111983-53-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 2 h / Heating 3: 1.) SOCl2 / 1.) reflux; 2.) benzene, reflux, 1.5 h 4: Na / reflux 2 h, then r.t., 15 h 5: 1.) 10N NaOH; 2.) O2, air / 1.) MeOH, r.t., 8 d View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → chloro-5 (isopropyl-1 dimethyl-2,6 dihydro-1,4 pyridinylidene-4)-2 indanedione-1,3

Conditions	Yield
Multi-step reaction with 6 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 2 h / Heating 3: 1.) SOCl2 / 1.) reflux; 2.) benzene, reflux, 1.5 h 4: Na / reflux 2 h, then r.t., 15 h 5: 38.1 percent / acetic anhydride / 24 h / Heating 6: 36 percent / acetonitrile / 0.5 h / Heating View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 5-Chloro-2-[1-(2-methoxy-ethyl)-1H-pyridin-4-ylidene]-indan-1,3-dione (111983-52-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 57.1 percent / molecular sieves 3 Angstroem / diphenyl ether / 24 h / Heating 3: 92 percent / 50percent NaH / dimethylsulfoxide / 8 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 83 percent / NaBH4 / methanol 3: 62.3 percent / NaOMe, ethyl propionate / methanol / 5 h / Heating 4: 92 percent / 50percent NaH / dimethylsulfoxide / 8 h / Ambient temperature View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 5-Chloro-2-[1-(2-piperidin-1-yl-ethyl)-1H-pyridin-4-ylidene]-indan-1,3-dione (111983-54-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 57.1 percent / molecular sieves 3 Angstroem / diphenyl ether / 24 h / Heating 3: 59.9 percent / 50percent NaH / dimethylsulfoxide / 8 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: H2SO4 / acetic anhydride / 3 h / Heating 2: 83 percent / NaBH4 / methanol 3: 62.3 percent / NaOMe, ethyl propionate / methanol / 5 h / Heating 4: 59.9 percent / 50percent NaH / dimethylsulfoxide / 8 h / Ambient temperature View Scheme

pyrographite (7440-44-0) + monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chlorophthalic acid (89-20-3)

Conditions	Yield
With sulfuric acid In water
With sulfuric acid In water

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-(5-chloro-1,3-dioxo-2-isoindolinyl)-3-(4-chlorophenyl)butanoic acid (1221962-70-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / Reflux 2: sodium acetate / acetic acid / 20 h / Reflux View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → N-[(5-chloro-1,3-dioxo-2-isoindolinyl)methyl]-N-(4-chlorophenyl)glycine (1221962-71-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 2 h / Reflux 2.1: formamide / 1 h / 150 °C 3.1: ethanol 3.2: 3 h / Reflux View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4-chloro-phthaloyl dichloride (62366-66-9)

Conditions	Yield
With phosphorus pentachloride at 180℃; for 3h;

monosodique de l'acide chloro-4 phtalique (56047-23-5) → (R)-3-(5-chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (849106-72-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus pentachloride / 3 h / 180 °C 2: pyridine / 2.5 h / 80 °C View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → (R)-3-(5-chloro-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (849106-73-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphorus pentachloride / 3 h / 180 °C 2: pyridine / 2.5 h / 80 °C 3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 1.5 h / 0 °C View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 3,3',4,4'-biphenyltetracarboxylic anhydride (2420-87-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; palladium on activated charcoal / water / 6 h / Reflux 1.2: 6 h / Reflux 2.1: hydrogenchloride / water / 7 h / Reflux 3.1: 24 h / 120 - 250 °C / Heating View Scheme

monosodique de l'acide chloro-4 phtalique (56047-23-5) → sodium [1,1'-biphenyl]-3,3',4,4'-tetracarboxylate

Conditions	Yield
Stage #1: monosodique de l'acide chloro-4 phtalique With palladium on activated charcoal; sodium hydroxide In water for 6h; Reflux; Stage #2: With hydroxyammonium sulfate In water for 6h; Reflux;

monosodique de l'acide chloro-4 phtalique (56047-23-5) → 4,4'-biphthalic acid (22803-05-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; palladium on activated charcoal / water / 6 h / Reflux 1.2: 6 h / Reflux 2.1: hydrogenchloride / water / 7 h / Reflux View Scheme

Upstream product

• 85-44-9 phthalic anhydride 

Downstream Products

• 118-45-6 4-chlorophthalic anhydride 
• 38717-95-2 4-chlorodiethylphthalate 
• 7147-90-2 4-chlorophthalimide 
• 89-20-3 4-chlorophthalic acid 
• 1221962-70-4 4-(5-chloro-1,3-dioxo-2-isoindolinyl)-3-(4-chlorophenyl)butanoic acid 
• 1221962-71-5 N-[(5-chloro-1,3-dioxo-2-isoindolinyl)methyl]-N-(4-chlorophenyl)glycine 
• 2420-87-3 3,3',4,4'-biphenyltetracarboxylic anhydride 
• 22803-05-0 4,4'-biphthalic acid 

Relevant articles and documents

Preparation method of 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride

The invention discloses a preparation method of 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride. The method includes the reactions of: (1) chlorination reaction: taking phthalic anhydride as the rawmaterial, adding a mixed solution of sodium hypochlorite aqueous solution and sodium hydroxide aqueous solution dropwise, carrying out chlorination reaction, and adjusting the pH value to generate 4-chlorophthalic acid monosodium salt; (2) coupling and hydrolysis: carrying out coupling reaction and hydrolysis reaction on the 4-chlorophthalic acid monosodium salt in the presence of a catalyst and acocatalyst under an alkaline condition to generate 3, 3', 4, 4'-biphenyltetracarboxylic acid sodium salt, wherein the catalyst is a palladium-carbon catalyst or a nickel-palladium-carbon catalyst, and the cocatalyst is hydroxylamine sulfate or hydroxylamine hydrochloride; and (3) acidification into 3, 3', 4, 4'-biphenyltetracarboxylic acid, and then drying and dehydration, thus obtaining 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride. The method provided by the invention adopts phthalic anhydride as the raw material for reaction with sodium hypochlorite to synthesize 3, 3', 4, 4'-biphenyltetracarboxylic dianhydride, is low in production cost, avoids the use of potassium permanganate oxidation, simplifies the production process, and has small pollution, and high yield.