25834-16-6

Basic information

• Product Name: 1,3-Isobenzofurandione, 4,7-dibromo-
• Synonyms: 4,7-dibromoisobenzofuran-1,3-dione;3,6-dibromophthalicaci;6-Dibromophthalic anhydride;3,6-Dibromophthalic anhydride;3,6-DibromophthalicAnhydride>1,3-Isobenzofurandione, 4,7-dibromo;4,7-dibromo-1,3-dihydro-2-benzofuran-1,3-dione
• CAS NO: 25834-16-6
• Molecular Formula: C₈H₂Br₂O₃
• Molecular Weight: 305.90768
• Mol File: 25834-16-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 207.0 to 212.0 °C
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 1,3-Isobenzofurandione, 4,7-dibromo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Isobenzofurandione, 4,7-dibromo-(25834-16-6)
• EPA Substance Registry System: 1,3-Isobenzofurandione, 4,7-dibromo-(25834-16-6)

Safety Data

• Hazardous Substances Data: 25834-16-6(Hazardous Substances Data)

Usage

General Description

1,3-Isobenzofurandione, 4,7-dibromo- is a chemical compound with the molecular formula C8H2Br2O3. It is a dibromo derivative of isobenzofuran-1,3-dione and is commonly used in the synthesis of various organic compounds. It is a yellow solid that is sparingly soluble in water but soluble in organic solvents. 1,3-Isobenzofurandione, 4,7-dibromo- is used in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. It has also shown potential for use as a precursor in the development of new materials and polymers due to its unique chemical structure and reactivity. However, it is important to handle and use this compound with caution due to its potential hazards and toxicity.

Synthetic route

3,6-dibromophthalic acid → 4,7-dibromoisobenzofuran-1,3-dione (25834-16-6)

Conditions	Yield
With acetic anhydride for 1h; Reflux;	69%
durch Sublimation;

phthalic anhydride (85-44-9) → 4,7-dibromoisobenzofuran-1,3-dione (25834-16-6)

Conditions	Yield
With fuming sulphuric acid; bromine; iodine at 60℃; for 24h;	31%
With fuming sulphuric acid; bromine; iodine at 60℃; for 24h; Sealed tube;	30%
With bromine; iodine In oleum (30 % free SO3) at 60℃; for 24h;	22%

1,4-dibromonaphthalene (83-53-4) → 4,7-dibromoisobenzofuran-1,3-dione (25834-16-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid 2: durch Sublimation View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; potassium permanganate / water / 2.25 h / Reflux 2.1: potassium hydroxide; dihydrogen peroxide / 2.5 h / 0 - 20 °C 2.2: pH 3 - 4 3.1: acetic anhydride / 1 h / Reflux View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → N-hydroxy-3,6-dibromophthalimide (1219795-55-7)

Conditions	Yield
With pyridine; hydroxylamine hydrochloride at 20 - 95℃; for 5h; Inert atmosphere;	99%

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + benzylamine (100-46-9) → 2-benzyl-4,7-dibromoisoindoline-1,3-dione (1610046-75-7)

Conditions	Yield
With acetic acid at 20℃; for 20h;	97%
With acetic acid at 130℃; for 20h;	96%
With acetic acid for 16h; Reflux;	93%

n-Dodecylamine (124-22-1) + 4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → 4,7-dibromo-2-dodecylisoindoline-1,3-dione (1159905-88-0)

Conditions	Yield
In acetic acid for 2h; Inert atmosphere; Reflux;	94%
With acetic acid for 3h; Reflux; Inert atmosphere;	85%
In acetic acid Reflux; Inert atmosphere;

2-Ethylhexylamine (104-75-6) + 4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → N-(2-ethylhexyl)-3,6-dibromophthalimide (863027-98-9)

Conditions	Yield
With acetic acid at 120℃; for 2h; Inert atmosphere;	93%
In acetic acid for 2h; Inert atmosphere; Reflux;	90%
In acetic acid

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + n-Octylamine (111-86-4) → 4,7-dibromooctylisoindoline-1,3-dione

Conditions	Yield
With acetic acid for 2h; Reflux; Inert atmosphere; Schlenk technique;	90%

hexadecylamine (143-27-1) + 4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → C24H35Br2NO2 (1613460-24-4)

Conditions	Yield
With acetic acid for 3h; Reflux; Inert atmosphere;	89%

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + methyl N-[5(6)-(4-aminophenylsulfanyl)benzimidazol-2-yl]carbamate (56073-96-2) → sodium; 3,6-dibromo-2-[4-(2-methoxycarbonylamino-1H-benzoimidazol-5-ylsulfanyl)-phenylcarbamoyl]-benzoate

Conditions	Yield
With sodium acetate; acetic acid at 40 - 45℃;	82%

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → 4,7-dibromoisoindoline-1,3-dione (866767-16-0)

Conditions	Yield
With urea In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 0.5h; Microwave irradiation;	62.5%

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + di-(n-octyl)methylamine (3241-20-1) → N-(1-Octyl-nonyl)-3,6-dibromo-phthalimide (890705-11-0)

Conditions	Yield
With acetic acid for 3h; Reflux; Inert atmosphere;	59%

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + cyclohexylamine (108-91-8) → 4,7-dibromo-2-cyclohexylisoindoline-1,3-dione (1387566-55-3)

Conditions	Yield
With acetic acid for 5h; Reflux;	48%

2-octyldodecylamine (62281-06-5) + 4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → 4,7-dibromo-2-(2-octyldodecyl)isoindoline-1,3-dione (1391835-88-3)

Conditions	Yield
With acetic acid for 4h; Reflux; Inert atmosphere;	38%

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + hydroquinone (123-31-9) → 1,4-dibromo-5,8-hydroxy-9,10-anthraquinone (42985-19-3)

Conditions	Yield
With aluminium trichloride; sodium chloride at 200 - 220℃;

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + N-methylene-glycine nitrile → N,N-(3,6-dibromo-phthaloyl)-glycine-nitrile (857802-04-1)

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + methyl N-[5(6)-(4-aminophenylsulfanyl)benzimidazol-2-yl]carbamate (56073-96-2) → 3,6-dibromo-N-[4-(2-methoxycarbonylamino-1H-benzoimidazol-5-ylsulfanyl)-phenyl]-phthalamic acid

Conditions	Yield
In dimethyl sulfoxide at 40 - 45℃;

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → N,N-(3,6-dibromo-phthaloyl)-glycine

Conditions	Yield
Multi-step reaction with 2 steps 2: hydrochloric acid; water / 60 °C View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → N,N-(3,6-dibromo-phthaloyl)-glycin-amide

Conditions	Yield
Multi-step reaction with 2 steps 2: hydrochloric acid; water View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → 4,4'-((1E,1'E)-(2-cyclohexyl-1,3-dioxoisoindoline-4,7-diyl)bis(ethene-2,1-diyl))dibenzaldehyde (1387566-56-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 5 h / Reflux 2: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → (2Z,2'Z)-3,3'-(((1E,1'E)-(2-cyclohexyl-1,3-dioxoisoindoline-4,7-diyl)bis(ethene-2,1-diyl))bis(4,1-phenylene))bis(2-(4-nitrophenyl)acrylonitrile) (1387566-54-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid / 5 h / Reflux 2: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere 3: sodium hydroxide / ethanol; N,N-dimethyl-formamide / 20 °C / Inert atmosphere View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → 4,7-dibromo-3-hydroxyisoindolin-1-one (1417569-16-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: urea / 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 150 °C / Microwave irradiation 2.1: zinc; copper(ll) sulfate pentahydrate; sodium hydroxide / water / 3.5 h / 0 - 20 °C 2.2: pH 7 View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → 5,8-dibromophthalazin-1(2H)-one (1417569-18-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: urea / 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 150 °C / Microwave irradiation 2.1: zinc; copper(ll) sulfate pentahydrate; sodium hydroxide / water / 3.5 h / 0 - 20 °C 2.2: pH 7 3.1: hydrazine hydrate / isopropyl alcohol / 1.5 h / 90 °C View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → C12H16Br2NO (1610046-78-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetic acid / 20 h / 20 °C 2.1: diethyl ether / 90 °C / Inert atmosphere 2.2: 15.25 h / Inert atmosphere; Reflux 3.1: acetic acid; bromine / acetonitrile; water / 0.5 h / 20 °C 3.2: 0.5 h / 0 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → 4,7-bis(4-pyridyl)-1,1,3,3-tetramethylisoindolin-2-yloxyl (1610046-79-1)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: acetic acid / 20 h / 20 °C 2.1: diethyl ether / 90 °C / Inert atmosphere 2.2: 15.25 h / Inert atmosphere; Reflux 3.1: acetic acid; bromine / acetonitrile; water / 0.5 h / 20 °C 3.2: 0.5 h / 0 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C 5.1: potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 12 h / 130 °C / Inert atmosphere; Sealed tube; Microwave irradiation View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → [Cu(4,7-bis(4-pyridyl)-1,1,3,3-tetramethylisoindolin-2-yloxyl)2(SiF6)]

Conditions

Yield

Multi-step reaction with 6 steps 1.1: acetic acid / 20 h / 20 °C 2.1: diethyl ether / 90 °C / Inert atmosphere 2.2: 15.25 h / Inert atmosphere; Reflux 3.1: acetic acid; bromine / acetonitrile; water / 0.5 h / 20 °C 3.2: 0.5 h / 0 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C 5.1: potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 12 h / 130 °C / Inert atmosphere; Sealed tube; Microwave irradiation 6.1: water; ethanol / 336 h View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) → 4,7-dibromo-1,1,3,3-tetramethylisophthalide (1610046-77-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic acid / 20 h / 20 °C 2.1: diethyl ether / 90 °C / Inert atmosphere 2.2: 15.25 h / Inert atmosphere; Reflux 3.1: acetic acid; bromine / acetonitrile; water / 0.5 h / 20 °C 3.2: 0.5 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid / 20 h / 130 °C 2.1: toluene; diethyl ether / 15 h / 120 °C / Inert atmosphere 3.1: acetic acid; bromine / acetonitrile; water / 1 h / 25 °C 3.2: 1 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid / 16 h / Reflux 2.1: toluene; diethyl ether / 1 h / 70 - 100 °C 3.1: bromine; acetic acid / acetonitrile; water / 0.5 h / 25 °C 3.2: 0.5 h / 0 - 25 °C View Scheme

4,7-dibromoisobenzofuran-1,3-dione (25834-16-6) + benzylamine (100-46-9) → 2-benzyl-4,7-dibromo-1,1,3,3-tetramethylisophthalide (1610046-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid / 20 h / 20 °C 2.1: diethyl ether / 90 °C / Inert atmosphere 2.2: 15.25 h / Inert atmosphere; Reflux View Scheme

Upstream product

• 83-53-4 1,4-dibromonaphthalene 
• 85-44-9 phthalic anhydride 

Downstream Products

• 1610046-76-8 2-benzyl-4,7-dibromo-1,1,3,3-tetramethylisophthalide 
• 1610046-75-7 2-benzyl-4,7-dibromoisoindoline-1,3-dione 
• 1387566-55-3 4,7-dibromo-2-cyclohexylisoindoline-1,3-dione 
• 1387566-54-2 (2Z,2'Z)-3,3'-(((1E,1'E)-(2-cyclohexyl-1,3-dioxoisoindoline-4,7-diyl)bis(ethene-2,1-diyl))bis(4,1-phenylene))bis(2-(4-nitrophenyl)acrylonitrile) 
• 1387566-56-4 4,4'-((1E,1'E)-(2-cyclohexyl-1,3-dioxoisoindoline-4,7-diyl)bis(ethene-2,1-diyl))dibenzaldehyde 
• 1159905-88-0 N-dodecyl-3,6-dibromophthalimide 
• 863027-98-9 N-(2-ethylhexyl)-3,6-dibromophthalimide 

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