Product Name

  • Name

    4,5-DICHLOROPHTHALIC ANHYDRIDE

  • EINECS 213-386-2
  • CAS No. 942-06-3
  • Article Data34
  • CAS DataBase
  • Density 1.715 g/cm3
  • Solubility
  • Melting Point 185-187 °C(lit.)
  • Formula C8H2Cl2O3
  • Boiling Point 313 °C at 760 mmHg
  • Molecular Weight 217.008
  • Flash Point 144.8 °C
  • Transport Information
  • Appearance Light grey to pale blue powder
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 942-06-3 (4,5-DICHLOROPHTHALIC ANHYDRIDE)
  • Hazard Symbols IrritantXi
  • Synonyms Phthalicanhydride, 4,5-dichloro- (6CI,7CI,8CI);4,5-Dichlorophthalic anhydride;5,6-Dichloro-1,3-isobenzofurandione;5,6-Dichloro-2-benzofuran-1,3-dione;1,3-isobenzofurandione, 5,6-dichloro-;4,5-Dichlorophthalic Anhydride;5,6-Dichloro-1,3-Dihydro-2-Benzofuran-1,3-Dione;
  • PSA 43.37000
  • LogP 2.30400

Synthetic route

4,5-dichlorophthalic acid
56962-08-4

4,5-dichlorophthalic acid

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

Conditions
ConditionsYield
With acetyl chloride for 2h; Reflux;100%
With acetic anhydride for 2h; Heating;97%
With acetic anhydride at 165℃; for 5h;96%
4,5-dichlorotetrahydrophthalic anhydride

4,5-dichlorotetrahydrophthalic anhydride

1,2,4-Trichlorobenzene
120-82-1

1,2,4-Trichlorobenzene

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

Conditions
ConditionsYield
99.6%
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

Conditions
ConditionsYield
With alkaline solution; chlorine in Gegenwart von Antimon-Salzen;
phthalic anhydride
85-44-9

phthalic anhydride

A

4-chlorophthalic anhydride
118-45-6

4-chlorophthalic anhydride

B

3-chlorophthalic anhydride
117-21-5

3-chlorophthalic anhydride

C

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

D

4,6-dichloroisobenzofuran-1,3-diketone
51971-64-3

4,6-dichloroisobenzofuran-1,3-diketone

Conditions
ConditionsYield
With chlorine at 390℃; Product distribution; var. temp, var. conc. of Cl2;
With chlorine at 420℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With chlorine at 390℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
...Expand
phthalic anhydride
85-44-9

phthalic anhydride

sulfuric acid
7664-93-9

sulfuric acid

iodine
7553-56-2

iodine

chlorine
7782-50-5

chlorine

A

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

B

3,6-dichlorophthalic anhydride
4466-59-5

3,6-dichlorophthalic anhydride

C

3,4-dichlorophthalic anhydride
56962-07-3

3,4-dichlorophthalic anhydride

Conditions
ConditionsYield
at 40 - 60℃;
...Expand
4,5-dichlorotetrahydrophthalic anhydride

4,5-dichlorotetrahydrophthalic anhydride

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

Conditions
ConditionsYield
With bromine In 1,2,3-trichlorobenzene
4,5-dichlorophthalic acid
56962-08-4

4,5-dichlorophthalic acid

A

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

B

6,7-dichlorobenzo[d][1,2]dioxine-1,4-dione

6,7-dichlorobenzo[d][1,2]dioxine-1,4-dione

Conditions
ConditionsYield
With sodium percarbonate In dichloromethane for 24h; Inert atmosphere; Overall yield = 56 %; Overall yield = 12 g;
methanol
67-56-1

methanol

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

4,5-dichloro-2-methoxycarbonyl benzoic acid
145303-69-1

4,5-dichloro-2-methoxycarbonyl benzoic acid

Conditions
ConditionsYield
With sodium methylate100%
for 18h; Reflux;87%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

4,5-dichlorophthalimide
15997-89-4

4,5-dichlorophthalimide

Conditions
ConditionsYield
With formamide at 180 - 190℃;100%
With formamide for 3h; Heating;98%
With formamide for 0.0666667h; microwave irradiation;96%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

4,5-dichloro-2-methoxycarbonyl benzoic acid
145303-69-1

4,5-dichloro-2-methoxycarbonyl benzoic acid

Conditions
ConditionsYield
Stage #1: 4,5-dichlorophthalic anhydride With sodium methylate In methanol for 12h; Heating / reflux;
Stage #2: With hydrogenchloride In methanol; water		99.5%
Stage #1: 4,5-dichlorophthalic anhydride With sodium methylate In methanol for 12h; Heating / reflux;
Stage #2: With hydrogenchloride In methanol; water		99.5%
In methanol
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

4,5-dichlorobenzene-1,2-dimethanol
24006-92-6

4,5-dichlorobenzene-1,2-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;98%
With lithium aluminium tetrahydride In tetrahydrofuran for 2.5h; Reflux;81%
With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Cooling with ice; Reflux;57%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

2,6-diisopropylbenzenamine
24544-04-5

2,6-diisopropylbenzenamine

C20H19Cl2NO2

C20H19Cl2NO2

Conditions
ConditionsYield
With acetic acid at 120℃; for 8h;98%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

4-(4,5-Dichlorophthalimido)butanoic acid
144631-14-1

4-(4,5-Dichlorophthalimido)butanoic acid

Conditions
ConditionsYield
In xylene for 24h; Heating;96%
With acetic acid at 100℃; for 3h;96%
2-thienyl lithium
2786-07-4

2-thienyl lithium

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

2-(2-theonyl)-4,5-dichlorobenzoic acid
143746-69-4

2-(2-theonyl)-4,5-dichlorobenzoic acid

Conditions
ConditionsYield
96%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

5'-O-(4-4'-dimethoxytrityl)thymidine
40615-39-2

5'-O-(4-4'-dimethoxytrityl)thymidine

triethylamine
121-44-8

triethylamine

triethylammonium 5'-O-(4,4'-dimethoxytrityl)thymidine-3'-yl-(4,5-dichloro)phthalate

triethylammonium 5'-O-(4,4'-dimethoxytrityl)thymidine-3'-yl-(4,5-dichloro)phthalate

Conditions
ConditionsYield
With dmap In pyridine for 6h;96%
With pyridine; dmap at 20℃; for 6h;96%
...Expand
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

4-chlorophthalic acid
89-20-3

4-chlorophthalic acid

Conditions
ConditionsYield
With aq. NaOH; zinc95%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

3,4,5-Trimethoxyaniline
24313-88-0

3,4,5-Trimethoxyaniline

5,6-dichloro-2-(3,4,5-trimethoxyphenyl)isoindoline-1,3-dione
1293923-42-8

5,6-dichloro-2-(3,4,5-trimethoxyphenyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With acetic acid for 12h; Reflux;95%
3,4,5-trimethoxybenzylamine
18638-99-8

3,4,5-trimethoxybenzylamine

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

5,6-dichloro-2-(3,4,5-trimethoxybenzyl)isoindoline-1,3-dione

5,6-dichloro-2-(3,4,5-trimethoxybenzyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With acetic acid for 4h; Reflux;95%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

4-methoxy-aniline
104-94-9

4-methoxy-aniline

N-(p-methoxyphenyl)-4,5-dichlorophthalimide
93296-68-5

N-(p-methoxyphenyl)-4,5-dichlorophthalimide

Conditions
ConditionsYield
With acetic acid for 2h; Heating;93%
2-(aminoethyl)pyridine
2706-56-1

2-(aminoethyl)pyridine

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

5,6-dichloro-2-[2-(pyridin-2-yl)ethyl]isoindoline-1,3-dione
1335104-52-3

5,6-dichloro-2-[2-(pyridin-2-yl)ethyl]isoindoline-1,3-dione

Conditions
ConditionsYield
Stage #1: 2-(aminoethyl)pyridine; 4,5-dichlorophthalic anhydride With acetic acid for 6h; Reflux;
Stage #2: With sodium hydrogencarbonate		93%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

glycine
56-40-6

glycine

2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)acetic acid
111104-25-7

2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)acetic acid

Conditions
ConditionsYield
In xylene for 24h; Heating;92%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 40h;92%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 4h;92%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

L-cyclohexylalanine
27527-05-5

L-cyclohexylalanine

(S)-3-cyclohexyl-2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)propanoic acid
1416811-70-5

(S)-3-cyclohexyl-2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)propanoic acid

Conditions
ConditionsYield
With triethylamine In toluene Reflux; Dean-Stark;92%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

benzylamine
100-46-9

benzylamine

2-benzyl-5,6-dichloroisoindoline-1,3-dione
331420-68-9

2-benzyl-5,6-dichloroisoindoline-1,3-dione

Conditions
ConditionsYield
With acetic acid for 3h; Reflux; Inert atmosphere; Schlenk technique;92%
With acetic acid at 120℃; for 2h; Inert atmosphere; Schlenk technique;91%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

phenylhydrazine
100-63-0

phenylhydrazine

4,5-dichloro-1-phenyl-1,2-dihydropyridazine-3,6-dione

4,5-dichloro-1-phenyl-1,2-dihydropyridazine-3,6-dione

Conditions
ConditionsYield
With hydrogenchloride In water at 120℃; for 9h;92%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

pararosaniline
467-62-9

pararosaniline

4,4',4''-tris(4,5-dichlorophthalimido)tritanol
91898-84-9

4,4',4''-tris(4,5-dichlorophthalimido)tritanol

Conditions
ConditionsYield
With acetic anhydride In pyridine at 150℃; for 2h;91%
In pyridine at 80℃; for 1h; Yield given;
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

methylamine hydrochloride
593-51-1

methylamine hydrochloride

4,5-Dichloro-N-methylphthalimide
86611-81-6

4,5-Dichloro-N-methylphthalimide

Conditions
ConditionsYield
With sodium acetate In acetic acid for 1h; Heating;91%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

ethyl acetoacetate
141-97-9

ethyl acetoacetate

2-Ethoxycarbonyl-5,6-dichlorindan-1,3-dione
99979-36-9

2-Ethoxycarbonyl-5,6-dichlorindan-1,3-dione

Conditions
ConditionsYield
With acetic anhydride; triethylamine for 24h;91%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

(+/-)-3-chloromethyl-2-hydroxymethyl-1-methyl-2,5-dihydropyrrolium chloride
112120-07-7

(+/-)-3-chloromethyl-2-hydroxymethyl-1-methyl-2,5-dihydropyrrolium chloride

(+/-)-6,7-O,O-(4,5-Dichlorophthaloyl)synthanecine A
117424-41-6

(+/-)-6,7-O,O-(4,5-Dichlorophthaloyl)synthanecine A

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Ambient temperature;91%
(2-aminomethylpyridine)
3731-51-9

(2-aminomethylpyridine)

4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

5,6-dichloro-2-(pyridin-2-yl-methyl)isoindoline-1,3-dione
332044-42-5

5,6-dichloro-2-(pyridin-2-yl-methyl)isoindoline-1,3-dione

Conditions
ConditionsYield
Stage #1: 2-(Aminomethyl)pyridine; 4,5-dichlorophthalic anhydride With acetic acid for 6h; Reflux;
Stage #2: With sodium hydrogencarbonate		91%
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

Conditions
ConditionsYield
With sodium acetate; acetic anhydride; acetic acid for 12h; Reflux;91%
With acetic acid for 4h; Reflux;

Conditions
ConditionsYield
In toluene at 120℃; for 5h;91%
With sulfuric acid In toluene at 120℃; for 5h;91%

Conditions
ConditionsYield
With sodium acetate; acetic acid for 12h; Reflux;91%

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In toluene Dean-Stark; Reflux;91%

Conditions
ConditionsYield
With aluminium trichloride; sodium chloride at 220℃; for 1.5h; Friedel-Crafts reaction;90%
With boric acid at 190℃; beim Behandeln das Reaktionsprodukt bei 150-165grad mit 94prozentiger Schwefelsaeure;
With aluminium trichloride; sodium chloride at 200 - 220℃;

Conditions
ConditionsYield
With acetic acid; hydrazine at 70℃; Inert atmosphere;90%
Stage #1: 4,5-dichlorophthalic anhydride With hydrazine hydrate Inert atmosphere;
Stage #2: With hydrogenchloride In water for 24h; Reflux; Inert atmosphere;		84%
With hydrazine In ethanol at 20℃; for 2h; Reflux;76%

1,3-Isobenzofurandione,5,6-dichloro- Specification

The 1,3-Isobenzofurandione,5,6-dichloro-, with the CAS registry number 942-06-3 and EINECS registry number 213-386-2, has the systematic name of 5,6-dichloro-2-benzofuran-1,3-dione. It is a kind of light grey to pale blue powder, and belongs to the following product categories: Anhydride Monomers; Monomers; Polymer Science. And the molecular formula of the chemical is C8H2Cl2O3.

The characteristics of 1,3-Isobenzofurandione,5,6-dichloro- are as followings: (1)ACD/LogP: 2.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.66; (4)ACD/LogD (pH 7.4): 2.66; (5)ACD/BCF (pH 5.5): 62.43; (6)ACD/BCF (pH 7.4): 62.43; (7)ACD/KOC (pH 5.5): 671.04; (8)ACD/KOC (pH 7.4): 671.04; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.638; (14)Molar Refractivity: 45.47 cm3; (15)Molar Volume: 126.4 cm3; (16)Polarizability: 18.02×10-24cm3; (17)Surface Tension: 63.7 dyne/cm; (18)Density: 1.715 g/cm3; (19)Flash Point: 144.8 °C; (20)Enthalpy of Vaporization: 55.4 kJ/mol; (21)Boiling Point: 313 °C at 760 mmHg; (22)Vapour Pressure: 0.00051 mmHg at 25°C.

Preparation of 1,3-Isobenzofurandione,5,6-dichloro-: This chemical can be prepared by 4,5-dichloro-phthalic acid. The reaction will need reagent acetic anhydride. The reaction time is 0.5 hours with heating, and the yield is about 92%. 

Uses of 1,3-Isobenzofurandione,5,6-dichloro-: It can react with methylamine; hydrochloride to produce 5,6-dichloro-2-methyl-isoindole-1,3-dione. This reaction will need reagent NaOAc, and the menstruum acetic acid. The reaction time is 1 hour with heating, and the yield is about 91%.  

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. 

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Clc1cc2C(=O)OC(=O)c2cc1Cl
(2)InChI: InChI=1/C8H2Cl2O3/c9-5-1-3-4(2-6(5)10)8(12)13-7(3)11/h1-2H
(3)InChIKey: ULSOWUBMELTORB-UHFFFAOYAF

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