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

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Name

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

EINECS 213-386-2
CAS No. 942-06-3 Density 1.715 g/cm3
PSA 43.37000 LogP 2.30400
Solubility N/A 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 N/A 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;

Article Data 34

1,3-Isobenzofurandione,5,6-dichloro- Synthetic route

56962-08-4

4,5-dichlorophthalic acid

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

120-82-1

1,2,4-Trichlorobenzene

942-06-3

4,5-dichlorophthalic anhydride

Conditions
ConditionsYield
99.6%
88-99-3

benzene-1,2-dicarboxylic acid

942-06-3

4,5-dichlorophthalic anhydride

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

phthalic anhydride

A

118-45-6

4-chlorophthalic anhydride

B

117-21-5

3-chlorophthalic anhydride

C

942-06-3

4,5-dichlorophthalic anhydride

D

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;
85-44-9

phthalic anhydride

7664-93-9

sulfuric acid

7553-56-2

iodine

7782-50-5

chlorine

A

942-06-3

4,5-dichlorophthalic anhydride

B

4466-59-5

3,6-dichlorophthalic anhydride

C

56962-07-3

3,4-dichlorophthalic anhydride

Conditions
ConditionsYield
at 40 - 60℃;

4,5-dichlorotetrahydrophthalic anhydride

942-06-3

4,5-dichlorophthalic anhydride

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

4,5-dichlorophthalic acid

A

942-06-3

4,5-dichlorophthalic anhydride

B

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;
67-56-1

methanol

942-06-3

4,5-dichlorophthalic anhydride

145303-69-1

4,5-dichloro-2-methoxycarbonyl benzoic acid

Conditions
ConditionsYield
With sodium methylate100%
for 18h; Reflux;87%
942-06-3

4,5-dichlorophthalic anhydride

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%
942-06-3

4,5-dichlorophthalic anhydride

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

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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