56962-08-4

Basic information

• Product Name: 4,5-DICHLOROPHTHALIC ACID
• Synonyms: 4,5-dichloro-2-benzenedicarboxylicacid;DICHLOROPHTHALIC ACID;AKOS 92369;4,5-DICHLOROPHTHALIC ACID;RARECHEM AL BO 0785;4 5-DICHLOROPHTHALIC ACID 97%(HPLC);4,5-Dichlorophthalicacid,99%;4,5-DICHLOROPHTHALIC ACID 99%
• CAS NO: 56962-08-4
• Molecular Formula: C₈H₄Cl₂O₄
• Molecular Weight: 235.02
• EINECS: 260-478-3
• Product Categories: C8;Carbonyl Compounds;Carboxylic Acids;Carboxylic Acid Monomers;Monomers;Polymer Science
• Mol File: 56962-08-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 198-200 °C (dec.)(lit.)
• Boiling Point: 422.1°Cat760mmHg
• Flash Point: 209.1°C
• Appearance: /
• Density: 1.698g/cm³
• Vapor Pressure: 7.05E-08mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.35±0.10(Predicted)
• CAS DataBase Reference: 4,5-DICHLOROPHTHALIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DICHLOROPHTHALIC ACID(56962-08-4)
• EPA Substance Registry System: 4,5-DICHLOROPHTHALIC ACID(56962-08-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26
• WGK Germany: 3
• Hazardous Substances Data: 56962-08-4(Hazardous Substances Data)

Usage

Purification Methods

Crystallise the acid from water. It has been purified by converting to the anhydride, reacting it with boiling EtOH to form the monoethyl ester (m 133-134o) and hydrolysing it back to the diacid (see next entry). [Beilstein 9 III 4205.]

InChI:InChI=1/C8H4Cl2O4/c9-5-1-3(7(11)12)4(8(13)14)2-6(5)10/h1-2H,(H,11,12)(H,13,14)

Synthetic route

benzene-1,2-dicarboxylic acid (88-99-3) → 4-chlorophthalic acid (89-20-3) + 4,5-dichlorophthalic acid (56962-08-4)

Conditions	Yield
With sodium hydroxide; chlorine

dichloromaleic acid anhydride (1122-17-4) + 2,3-dichlorobuta-1,3-diene (1653-19-6) → 4,5-dichlorophthalic acid (56962-08-4)

Conditions	Yield
(i), (ii) aq. NaOH; Multistep reaction;

2-Amino-6,7-dichloro-9-oxofluoren-1-carbonsaeure (27979-29-9) → 4,5-dichlorophthalic acid (56962-08-4)

Conditions	Yield
With potassium dichromate; sulfuric acid

2-methyl-4,5-dichloroacetophenone (53803-91-1) + KMnO4 → 4,5-dichlorophthalic acid (56962-08-4)

chlorine (7782-50-5) + benzene-1,2-dicarboxylic acid (88-99-3) + diluted NaOH-solution → 4-chlorophthalic acid (89-20-3) + 4,5-dichlorophthalic acid (56962-08-4)

chlorine (7782-50-5) + benzene-1,2-dicarboxylic acid (88-99-3) + KOH-solution → 4-chlorophthalic acid (89-20-3) + 4,5-dichlorophthalic acid (56962-08-4)

water (7732-18-5) + chlorine (7782-50-5) + benzene-1,2-dicarboxylic acid (88-99-3) → 4-chlorophthalic acid (89-20-3) + 4,5-dichlorophthalic acid (56962-08-4) + 3,6-dichlorophthalic acid (16110-99-9) + 3,4-dichloro-phthalic acid (56962-06-2)

Conditions	Yield
at 45℃; zuletzt unter Zusatz von wss. Natronlauge;

4.5-dichloro-o-xylene → 4,5-dichlorophthalic acid (56962-08-4)

Conditions	Yield
With nitric acid at 180℃; im Rohr;

aqueous disodium phthalate → 4,5-dichlorophthalic acid (56962-08-4)

Conditions	Yield
With chlorine

x.x-dichloro-1.2-dimethyl-benzene → 4,5-dichlorophthalic acid (56962-08-4)

Conditions	Yield
With nitric acid at 200℃; im geschlossenen Rohr;

1,2-dichloro-4,5-dimethyl-benzene (20824-80-0) + nitric acid (7697-37-2) → 4,5-dichlorophthalic acid (56962-08-4)

Conditions	Yield
at 180℃; im Rohr;

6,7-dichloro-[1]naphthol + chromic acid → 4,5-dichlorophthalic acid (56962-08-4)

4,5-dichlorophthalic acid dimethyl ester (106727-86-0) → 4,5-dichlorophthalic acid (56962-08-4)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 0.0833333h;

methanol (67-56-1) + 4,5-dichlorophthalic acid (56962-08-4) → 4,5-dichlorophthalic acid dimethyl ester (106727-86-0)

Conditions	Yield
With thionyl chloride for 18h;	100%
With thionyl chloride at 0 - 25℃; for 49h; Inert atmosphere;	97%
With thionyl chloride at 20℃; for 72h;	94%

4,5-dichlorophthalic acid (56962-08-4) → 4,5-dichlorophthalic anhydride (942-06-3)

Conditions	Yield
With acetyl chloride for 2h; Reflux;	100%
With acetic anhydride for 2h; Heating;	97%
With acetic anhydride at 165℃; for 5h;	96%

4,5-dichlorophthalic acid (56962-08-4) → 4,5-dichlorobenzene-1,2-dimethanol (24006-92-6)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;	100%
With lithium aluminium tetrahydride In tetrahydrofuran -78 to 0 deg C, 2 h; reflux, overnight;	88%
Stage #1: 4,5-dichlorophthalic acid With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 20℃; Reflux; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 0℃;	88%

4,5-dichlorophthalic acid (56962-08-4) → 4,5-dichlorophthalimide (15997-89-4)

Conditions	Yield
With formamide at 140 - 180℃; for 4h;	93%
With urea at 235℃;	81%
Multi-step reaction with 2 steps 1: Ac2O / Heating 2: 96 percent / formamide / 0.07 h / microwave irradiation View Scheme

chloro-trimethyl-silane (75-77-4) + 4,5-dichlorophthalic acid (56962-08-4) → 5,6-dichloro-4,7-bis(trimethylsilyl)isobenzofuran-1,3-dione (1352879-94-7)

Conditions	Yield
Stage #1: chloro-trimethyl-silane; 4,5-dichlorophthalic acid With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: With toluene	92%

4,5-dichlorophthalic acid (56962-08-4) → 4,5-dichlorobenzene-1,2-dioyl dichloride (171614-40-7)

Conditions	Yield
With phosphorus pentachloride at 160℃; for 4.5h; Inert atmosphere;	90%
With phosphorus pentachloride for 2h; Heating;	88%
With thionyl chloride for 18h; Reflux;
With thionyl chloride; N,N-dimethyl-formamide at 80℃;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 3.5h; Inert atmosphere; Reflux;

pentan-1-ol (71-41-0) + 4,5-dichlorophthalic acid (56962-08-4) → dipentyl 4,5-dichlorophthalate (1030871-30-7)

Conditions	Yield
With sulfuric acid In toluene for 15h; Heating;	90%

n-Octylamine (111-86-4) + 4,5-dichlorophthalic acid (56962-08-4) → 5,6-dichloro-2-octylisoindole-1,3-dione

Conditions	Yield
With niobium(V) oxide In hexane for 18h; Inert atmosphere; Reflux; Microwave irradiation;	88%

cobalt(II) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) + 1,2-bis(imidazole-1-ylmethyl)benzene (42032-51-9) → Co(2+)*C8H2Cl2O4(2-)*C14H14N4

Conditions	Yield
With potassium hydroxide In ethanol; water at 120℃; for 72h; Sealed tube;	83.4%

cobalt(II) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) + 1,3-bis(imidazol-1-ylmethyl)benzene (69506-92-9) → Co(2+)*C8H2Cl2O4(2-)*C14H14N4

Conditions	Yield
With potassium hydroxide In ethanol; water at 120℃; for 72h; Sealed tube;	82%

cadmium(II) nitrate tetrhydrate + 4,5-dichlorophthalic acid (56962-08-4) + 1,2-bis(imidazole-1-ylmethyl)benzene (42032-51-9) → Cd(2+)*C8H2Cl2O4(2-)*C14H14N4

Conditions	Yield
With potassium hydroxide In ethanol; water at 120℃; for 72h; Sealed tube;	81.2%

4,5-dichlorophthalic acid (56962-08-4) → 2-carbamoyl-4,5-dichlorobenzoic acid (110568-92-8)

Conditions	Yield
In tetrahydrofuran; water	80%

4,4'-bis-(1H-imidazol-1-yl)biphenyl (855766-92-6) + cobalt(II) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) + water (7732-18-5) → 2Co(2+)*2C8H2Cl2O4(2-)*C18H14N4*2H2O

Conditions	Yield
With potassium hydroxide In ethanol at 120℃; for 72h; Sealed tube;	80%

4,5-dichlorophthalic acid (56962-08-4) + 4-fluoroaniline (371-40-4) → C14H6Cl2FNO2

Conditions	Yield
With SiO2-try-Nb In water; isopropyl alcohol at 110℃; for 14h; Sealed tube; Green chemistry;	79%

cadmium(II) nitrate tetrhydrate + 4,5-dichlorophthalic acid (56962-08-4) + water (7732-18-5) + 1,3-bis(imidazol-1-ylmethyl)benzene (69506-92-9) → Cd(2+)*C8H2Cl2O4(2-)*C14H14N4*H2O

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 72h; Sealed tube;	78.6%

2-(n-butyl)octanol (3913-02-8) + 4,5-dichlorophthalic acid (56962-08-4) → bis(2-butyloctyl)-4,5-dichlorophthalate (1030871-33-0)

Conditions	Yield
With sulfuric acid In toluene Heating;	78%

5,5'-dimethyl-2,2'-bipyridine (1762-34-1) + cobalt(II) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) → Co(2+)*C8H2Cl2O4(2-)*C12H12N2

Conditions	Yield
With potassium hydroxide In ethanol; water at 120℃; for 72h; Sealed tube;	76%

octanol (111-87-5) + 4,5-dichlorophthalic acid (56962-08-4) → dioctyl 4,5-dichlorophthalate (1030871-31-8)

Conditions	Yield
With sulfuric acid In toluene Heating;	75%

neodymium(III) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) → [Nd2(H2O)(4,5-dichlorophthalate)3]n

Conditions	Yield
With sodium hydroxide In methanol; water at 170℃; for 96h; pH=6.0; High pressure; Autoclave;	75%

1-dodecyl alcohol (112-53-8) + 4,5-dichlorophthalic acid (56962-08-4) → didodecyl 4,5-dichlorophthalate (1030871-32-9)

Conditions	Yield
With sulfuric acid In toluene Heating;	72%

2,3-dimethylpyrazine (5910-89-4) + 4,5-dichlorophthalic acid (56962-08-4) → C6H8N2*C8H4Cl2O4

Conditions	Yield
In ethanol; water for 0.333333h;	72%

copper(II) choride dihydrate + 4,5-dichlorophthalic acid (56962-08-4) + urea (57-13-6) → 2,3,9,10,16,17,23,24-octachloro-copper phthalocyanine (28451-28-7)

Conditions	Yield
With ammonium molibdate at 100 - 220℃;	70%

samarium(III) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) → [Sm2(H2O)(4,5-dichlorophthalate)3]n

Conditions	Yield
With sodium hydroxide In methanol; water at 170℃; for 96h; pH=6.0; High pressure; Autoclave;	70%

4,5-dichlorophthalic acid (56962-08-4) + (S)-1-phenyl-ethylamine (2627-86-3) → (S)-N-[1-(phenyl)ethyl]-4,5-dichlorophthalimide (1407490-00-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;	69%

europium(III) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) → [Eu2(H2O)(4,5-dichlorophthalate)3]n

Conditions	Yield
With sodium hydroxide In methanol; water at 170℃; for 96h; pH=6;	67%

terbium(III) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) → [Tb2(H2O)(4,5-dichlorophthalate)3]n

Conditions	Yield
With sodium hydroxide In methanol; water at 170℃; for 96h; pH=6.0; High pressure; Autoclave;	67%

propylamine (107-10-8) + 4,5-dichlorophthalic acid (56962-08-4) → N-propyl-4,5-dichlorophthalimide (1407489-99-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; Inert atmosphere;	62%

1-pentadecylamine (2570-26-5) + 4,5-dichlorophthalic acid (56962-08-4) → N-pentadecyl-4,5-dichlorophthalimide (1407489-98-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;	59%

4,4'-bipyridine (553-26-4) + cadmium(II) nitrate tetrhydrate + 4,5-dichlorophthalic acid (56962-08-4) + water (7732-18-5) → Cd(2+)*C8H2Cl2O4(2-)*4H2O*C10H8N2

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 72h; Sealed tube;	55%

1H-imidazole (288-32-4) + cobalt(II) nitrate hexahydrate + 4,5-dichlorophthalic acid (56962-08-4) → C28H20Cl4Co2N8O8

Conditions	Yield
With potassium hydroxide In ethanol; water at 120℃; for 72h; Sealed tube;	53%

Upstream product

• 7732-18-5 water 
• 7782-50-5 chlorine 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 106727-86-0 4,5-dichlorophthalic acid dimethyl ester 
• 53803-91-1 2-methyl-4,5-dichloroacetophenone 
• 27979-29-9 2-Amino-6,7-dichloro-9-oxofluoren-1-carbonsaeure 
• 1122-17-4 dichloromaleic acid anhydride 
• 1653-19-6 2,3-dichlorobuta-1,3-diene 
• 20824-80-0 1,2-dichloro-4,5-dimethyl-benzene 
• 7697-37-2 nitric acid 

Downstream Products

• 171614-40-7 4,5-dichlorobenzene-1,2-dioyl dichloride 
• 168893-61-6 2-(3-Amino-1H-1,2,4-triazol-5-yl)-4,5-dichlorobenzoic acid 
• 110568-92-8 2-carbamoyl-4,5-dichlorobenzoic acid 
• 1182369-39-6 3-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate 
• 93296-41-4 5,6-dichloro-1H-indene-1,3(2H)-dione 
• 872181-18-5 (4,5-dichloro-2-methoxymethoxymethylphenyl)methanol 
• 872181-19-6 2-(4,5-dichloro-2-methoxymethoxymethylbenzyloxy)-6-fluorobenzonitrile 
• 942-06-3 4,5-dichlorophthalic anhydride 

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