4053-08-1

Basic information

• Product Name: 4-Chloro-1,8-naphthalic anhydride
• Synonyms: 6-Chloro-1H,3H-benzo[de]isochromene-1,3-dione;6-chloro-1h,3h-naphtho(1,8-cd)pyran-1,3-dione;4-Chloronaphthalene-1,8-Naphthalic Anhydride;4-CHLORO-1 8-NAPHTHALIC ANHYDRIDE TECH;6-Chlorobenzo[de]isochromene-1,3-dione;4-CHLORO-1,8-NAPHTHALENEDICARBOXYLIC ANHYDRIDE;4-CHLORO-1,8-NAPHTHALIC ANHYDRIDE;4-chloronaphthalene-1,8-dicarboxylic anhydride
• CAS NO: 4053-08-1
• Molecular Formula: C₁₂H₅ClO₃
• Molecular Weight: 232.62
• EINECS: 223-760-7
• Product Categories: Intermediates of Dyes and Pigments;Building Blocks;Carbonyl Compounds;Carboxylic Acid Anhydrides;Chemical Synthesis;Organic Building Blocks;API Intermediate
• Mol File: 4053-08-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 202-206 °C (dec.)
• Boiling Point: 332.56°C (rough estimate)
• Flash Point: 208.3 °C
• Appearance: beige to brown powder
• Density: 1.3447 (rough estimate)
• Vapor Pressure: 2.53E-08mmHg at 25°C
• Refractive Index: 1.4530 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly), Methanol (Slightly, Sonicated)
• Water Solubility: Hydrolyzes in water.
• Sensitive: Moisture Sensitive
• BRN: 178072
• CAS DataBase Reference: 4-Chloro-1,8-naphthalic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-1,8-naphthalic anhydride(4053-08-1)
• EPA Substance Registry System: 4-Chloro-1,8-naphthalic anhydride(4053-08-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: QL6127295
• TSCA: Yes
• Hazardous Substances Data: 4053-08-1(Hazardous Substances Data)

Usage

Chemical Properties

beige to brown powder

Uses

4-Chloro-1,8-naphthalic anhydride is used in dyes and pigments. It is also used in agrochemical, pharmaceutical.

InChI:InChI=1/C12H5ClO3/c13-9-5-4-8-10-6(9)2-1-3-7(10)11(14)16-12(8)15/h1-5H

Synthetic route

5-chloroacenaphthene (5209-33-6) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Conditions	Yield
With copper(II) acetate dihydrate; manganese(II) acetate dihydrate; oxygen; acetic acid; potassium bromide at 100℃;	93%
Multi-step reaction with 4 steps 1: Pb3O4 2: aq. NaOH / methanol 3: HCl / diethyl ether 4: Na2Cr2O7, AcOH View Scheme

1,8-Naphthalic anhydride (81-84-5) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Conditions	Yield
With sodium hydroxide; phosphoric acid; chlorine for 3h; Ambient temperature;	82%
With hydrogenchloride; potassium permanganate; phosphoric acid; sodium hydroxide In water at 20℃; for 3h;	40%

5-chloroacenaphthene (5209-33-6) → p-chloro-1,8-naphthalicanhydride (4053-08-1) + 5-chloro-acenaphthene-1,2-dione (13383-81-8)

Conditions	Yield
With sodium dichromate; acetic acid at 120℃;

4-chloro-naphthalene-1,8-dicarboxylic acid (13577-46-3) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Conditions	Yield
at 120 - 125℃;
With acetic acid
With acetic acid
at 120 - 125℃;

acenaphthene (83-32-9) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Conditions	Yield
With chloroform; chlorine Behandeln des entstandenen 5-Chlor-acenaphthen mit Natriumdichromat und Eisessig;

2,5-Dichloracenaphthen (31996-06-2) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Conditions	Yield
With sodium dichromate; acetic acid

4-hydroxy-1,8-naphthalic anhydride (52083-08-6) + phosphorus pentachloride (10026-13-8, 874483-75-7) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Conditions	Yield
at 190 - 200℃;

5-Chloracenaphthen-2-ol (31996-05-1) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / diethyl ether 2: Na2Cr2O7, AcOH View Scheme

5-Chloracenaphthen-2-ol-acetat (31996-04-0) → p-chloro-1,8-naphthalicanhydride (4053-08-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH / methanol 2: HCl / diethyl ether 3: Na2Cr2O7, AcOH View Scheme

p-chloro-1,8-naphthalicanhydride (4053-08-1) + naphthalene-1,8-diamine (479-27-6) → C22H11ClN2O

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 150℃; for 4h;	98.9%

morpholine (110-91-8) + p-chloro-1,8-naphthalicanhydride (4053-08-1) + cyclohexylamine (108-91-8) → N-cyclohexyl-4-(morpholin-4-yl)-1,8-naphthalimide

Conditions	Yield
In dimethyl sulfoxide at 140℃; for 0.5h; Inert atmosphere; Microwave irradiation;	98%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + 1,2-diamino-benzene (95-54-5) → 3-chlorobenzimidazo<2,1-a>benzisoquinolin-7-one

Conditions	Yield
With acetic acid for 4h; Reflux;	98%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + 6-aminohexanoic acid (60-32-2) → 6-(6-chloro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)hexanoic acid (181373-34-2)

Conditions	Yield
In ethanol at 100℃; for 1h; Microwave irradiation;	97%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + ethanolamine (141-43-5) → 6-chloro-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (4022-36-0)

Conditions	Yield
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 140℃; for 0.333333h; Ionic liquid; In thick-walled sealed reaction vessel;	96%
In ethanol at 80℃; for 5h;	89.6%
In ethanol for 12h; Reflux;	87%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + N,N-dimethylethylenediamine (108-00-9) → 6-chloro-2-(2-(dimethylamino)ethyl)-1H-benzo-[de]isoquinoline-1,3(2H)-dione (96807-71-5)

Conditions	Yield
for 6h; Condensation; Heating;	95%
In chloroform at 20℃; for 0.333333h;	80%
In ethanol at 20℃; for 5h;	55%
In toluene for 2h; Heating;

propylamine (107-10-8) + p-chloro-1,8-naphthalicanhydride (4053-08-1) → 6-chloro-2-propyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (39061-34-2)

Conditions	Yield
In ethanol at 100℃; for 1h; Microwave irradiation;	94%
In ethanol for 24h; Inert atmosphere; Reflux;	78%
In water at 22 - 25℃; for 3h; sonication;	70%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + N,N-dimethylammonium chloride (506-59-2) + isopropylamine (75-31-0) → 4-dimethylamino-N-isopropyl-1,8-naphthalic imide

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 140℃; for 0.5h; Inert atmosphere; Microwave irradiation;	94%

morpholine (110-91-8) + p-chloro-1,8-naphthalicanhydride (4053-08-1) + isopropylamine (75-31-0) → N-isopropyl-4-(morpholin-4-yl)-1,8-naphthalimide

Conditions	Yield
In dimethyl sulfoxide at 140℃; for 0.5h; Inert atmosphere; Microwave irradiation;	94%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + Propargylamine (2450-71-7) → 6-chloro-2-(prop-2-yn-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions	Yield
In ethanol at 100℃; for 1h; Microwave irradiation;	94%
In ethanol for 24h; Schlenk technique; Inert atmosphere; Heating;	89.9%
In ethanol at 50℃; for 17h; Reflux; Inert atmosphere;	88%
In ethanol
In ethanol

p-chloro-1,8-naphthalicanhydride (4053-08-1) + 4-amino-phenol (123-30-8) → 6-chloro-2-(4-hydroxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions	Yield
With acetic acid for 10h; Reflux;	94%
In 2-ethoxy-ethanol at 145℃;	85%

p-chloro-1,8-naphthalicanhydride (4053-08-1) → 3-nitro-4-chloro-1,8-naphthalene dicarboxylic acid anhydride (52871-22-4)

Conditions	Yield
With sulfuric acid; nitric acid for 1h; Ambient temperature;	93%
With nitric acid In sulfuric acid
With sulfuric acid; nitric acid at 20℃;

p-chloro-1,8-naphthalicanhydride (4053-08-1) + para-thiocresol (106-45-6) → 4-(4-methylphenyl)thio-1,8-naphthalic anhydride (114289-28-0)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide for 7h; Heating;	93%

p-chloro-1,8-naphthalicanhydride (4053-08-1) → 2-hydroxy-6-chlorobenzo[de]isoquinoline-1,3-dione (41382-15-4)

Conditions	Yield
With hydroxylamine hydrochloride; potassium carbonate In 1,4-dioxane for 24h; Reflux;	93%
With hydroxylamine hydrochloride In pyridine

p-chloro-1,8-naphthalicanhydride (4053-08-1) + 3-chloro-aniline (108-42-9) → 6-chloro-2-(3-chlorophenyl)-1H-benz[de]isoquinolin-1,3(2H)dione (58226-81-6)

Conditions	Yield
In acetic acid for 20h; Reflux;	93%

5-hydroxypentylamine (2508-29-4) + p-chloro-1,8-naphthalicanhydride (4053-08-1) → N-(5'-Hydroxypentyl)-4-chloronaphthalene-1,8-dicarboximide (330649-49-5)

Conditions	Yield
In toluene at 90℃; for 16h; Heating / reflux;	91.7%
Stage #1: 5-hydroxypentylamine; p-chloro-1,8-naphthalicanhydride In toluene Heating / reflux; Stage #2: With 1-methyl-pyrrolidin-2-one In toluene for 16h; Heating / reflux;	91.7%
In ethanol at 80 - 90℃; for 1h;	62.4%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + mercaptoacetic acid (68-11-1) → (1,3-dioxo-1H,3H-benzo[de]isochromen-6-ylsulfanyl)-acetic acid (847780-09-0)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide for 1h; Heating;	91%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + 2-methoxyethylamine (109-85-3) → 6-chloro-2-(2-methoxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions	Yield
In ethanol at 100℃; for 1h; Microwave irradiation;	91%
In ethanol for 12h; Reflux; Inert atmosphere;	79%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + p-chloro-1,8-naphthalicanhydride (4053-08-1) → 6-chloro-2-(2-morpholinoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions	Yield
With acetic acid In ethanol at 85℃; for 6h;	90%
In ethanol at 70℃; for 2.5h;	89%
In toluene

p-chloro-1,8-naphthalicanhydride (4053-08-1) + 1-amino-3-(dimethylamino)propane (109-55-7) → 6-chloro-2-[3-(dimethylamino)propyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione (4063-59-6)

Conditions	Yield
Condensation; Heating;	90%
In chloroform at 60℃; for 0.5h;	85%
In toluene for 4h; Reflux;

p-chloro-1,8-naphthalicanhydride (4053-08-1) + 2-hydroxyethanethiol (60-24-2) → 6-[(2-hydroxyethyl)thio]-1H,3H-benzo[de]isochromene-1,3-dione (101139-75-7)

Conditions	Yield
In 2-methoxy-ethanol for 6h; Heating;	90%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + thiophenol (108-98-5) → 4-phenylthio-1,8-naphthalic anhydride (54470-29-0)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide for 7h; Heating;	90%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + cyclohexylamine (108-91-8) → 6-chloro-2-cyclohexyl-1H-benz[de]isoquinolin-1,3(2H)dione (57601-49-7)

Conditions	Yield
In acetic acid for 46h; Reflux;	90%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + 4-bromo-aniline (106-40-1) → 2-(4-bromophenyl)-6-chloro-1H-benzo[de]isoquinoline-1,3(2H)-dione (58226-87-2)

Conditions	Yield
In acetic acid for 20h; Reflux;	90%
In acetic acid for 44h; Reflux;	77%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + glutamic acid diethyl ester hydrochloride (65710-34-1) → C21H20ClNO6

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 18h;	89.1%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 18h;	89.1%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 18h;	89.1%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + glutamic acid diethyl ester hydrochloride (65710-34-1) → C21H21NO6

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 18h;	89.1%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + propan-1-ol-3-amine (156-87-6) → 4-chloronaphthalic acid N-(3-hydroxypropyl)imide (52821-21-3)

Conditions	Yield
In ethanol for 2h; Heating / reflux;	89%
With triethylamine In ethanol for 12h; Reflux; Inert atmosphere; Schlenk technique;	75%
In 2-ethoxy-ethanol for 6h; Substitution; Heating;	64%

3-Aminomethylpyridine (3731-52-0) + p-chloro-1,8-naphthalicanhydride (4053-08-1) → 4-chloro-N-(3′-picolylamine)-1,8-naphthalimide

Conditions	Yield
In ethanol Schlenk technique; Heating;	89%

p-chloro-1,8-naphthalicanhydride (4053-08-1) + (4-aminomethyl)aniline (4403-71-8) → 2-(4-amino-benzyl)-6-chloro-benzo[de]isoquinoline-1,3-dione (1070270-91-5)

Conditions	Yield
With triethylamine In ethanol at 100℃; for 18h;	88%
In ethanol	66%
In ethanol

Upstream product

• 13577-46-3 4-chloro-naphthalene-1,8-dicarboxylic acid 
• 31996-04-0 5-Chloracenaphthen-2-ol-acetat 
• 31996-05-1 5-Chloracenaphthen-2-ol 
• 52083-08-6 4-hydroxy-1,8-naphthalic anhydride 
• 10026-13-8 phosphorus pentachloride 
• 31996-06-2 2,5-Dichloracenaphthen 
• 81-84-5 1,8-Naphthalic anhydride 
• 83-32-9 acenaphthene 
• 5209-33-6 5-chloroacenaphthene 

Downstream Products

• 38842-43-2 4-cyclohexylamino-N-cyclohexyl-1,8-naphthalic imide 
• 78153-38-5 4-diphenylamino-1,8-naphthalene anhydride 
• 19125-99-6 2-butyl-6-(butylamino)-1H-benz(de)isoquinoline-1,3(2H)-dione 
• 111669-59-1 4-(2-Nitrophenoxy)-1,8-naphthalic anhydride 
• 7267-05-2 4-bromo-naphthalene-1,8-dicarboxylic acid 
• 52821-24-6 N-(3-hydroxypropyl)imide of 4-(3'-hydroxypropyl)aminonaphthalic acid 
• 23204-36-6 3-hydroxy-1,8-naphthalic acid anhydride 
• 41382-35-8 4-((2-aminophenyl)thio)-1,8-naphthalic anhydride 
• 77616-95-6 6-chloro-1,3-dioxo-1H-benzo[de]isoquinoline-2(3H)-acetic acid 
• 77616-93-4 1,3-Dioxo-6-(phenylthio)-1H-benz[de]isoquinoline-2(3H)-acetic acid 
• 950781-06-3 6-chloro-2-(2-{[2-(6-chloro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl]disulfanyl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 47268-66-6 N-(3-dimethylaminopropyl)-4-methoxy-1,8-naphthalimide 
• 87223-13-0 6-morpholino-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 216852-15-2 4-chloro-N-(4-carboxyphenylmethyl)-1,8-naphthalimide 

Relevant articles and documents

The quest for highly fluorescent chromophores: Evaluation of 1H,3H-isochromeno[6,5,4-mna]xanthene-1,3-dione (CXD)

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