4-Chloro-1,8-naphthalic anhydride supplier

Name
4-Chloro-1,8-naphthalic anhydride
EINECS 223-760-7
CAS No. 4053-08-1
Article Data12
CAS DataBase
Density 1.565 g/cm³
Solubility Hydrolyzes in water.
Melting Point 202-206 °C (dec.)
Formula C₁₂H₅ClO₃
Boiling Point 450.9 °C at 760 mmHg
Molecular Weight 232.623
Flash Point 208.3 °C
Transport Information
Appearance beige to brown powder
Safety 24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Naphthalicanhydride, 4-chloro- (7CI,8CI);4-Chloro-1,8-naphthalenedicarboxylic anhydride;4-Chloronaphthalic anhydride;
PSA 43.37000
LogP 2.80380

Synthetic route

: 5209-33-6
5-chloroacenaphthene

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

Conditions

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

: 81-84-5
1,8-Naphthalic anhydride

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

Conditions

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%

: 5209-33-6
5-chloroacenaphthene

A: 4053-08-1
p-chloro-1,8-naphthalicanhydride

B: 13383-81-8
5-chloro-acenaphthene-1,2-dione

Conditions

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

: 13577-46-3
4-chloro-naphthalene-1,8-dicarboxylic acid

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

Conditions

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

: 83-32-9
acenaphthene

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

Conditions

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

: 31996-06-2
2,5-Dichloracenaphthen

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

Conditions

Conditions	Yield
With sodium dichromate; acetic acid

: 52083-08-6
4-hydroxy-1,8-naphthalic anhydride

: 10026-13-8, 874483-75-7
phosphorus pentachloride

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

Conditions

Conditions	Yield
at 190 - 200℃;

: 31996-05-1
5-Chloracenaphthen-2-ol

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

Conditions

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

: 31996-04-0
5-Chloracenaphthen-2-ol-acetat

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 479-27-6
naphthalene-1,8-diamine

: C22H11ClN2O

Conditions

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

: 110-91-8
morpholine

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 108-91-8
cyclohexylamine

: N-cyclohexyl-4-(morpholin-4-yl)-1,8-naphthalimide

Conditions

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

...Expand

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 95-54-5
1,2-diamino-benzene

: 3-chlorobenzimidazo<2,1-a>benzisoquinolin-7-one

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 60-32-2
6-aminohexanoic acid

: 181373-34-2
6-(6-chloro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)hexanoic acid

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 141-43-5
ethanolamine

: 4022-36-0
6-chloro-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

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%

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 108-00-9
N,N-dimethylethylenediamine

: 96807-71-5
6-chloro-2-(2-(dimethylamino)ethyl)-1H-benzo-[de]isoquinoline-1,3(2H)-dione

Conditions

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;

: 107-10-8
propylamine

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 39061-34-2
6-chloro-2-propyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

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%

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 506-59-2
N,N-dimethylammonium chloride

: 75-31-0
isopropylamine

: 4-dimethylamino-N-isopropyl-1,8-naphthalic imide

Conditions

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

...Expand

: 110-91-8
morpholine

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 75-31-0
isopropylamine

: N-isopropyl-4-(morpholin-4-yl)-1,8-naphthalimide

Conditions

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

...Expand

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 2450-71-7
Propargylamine

: 6-chloro-2-(prop-2-yn-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 123-30-8
4-amino-phenol

: 6-chloro-2-(4-hydroxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 52871-22-4
3-nitro-4-chloro-1,8-naphthalene dicarboxylic acid anhydride

Conditions

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℃;

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 106-45-6
para-thiocresol

: 114289-28-0
4-(4-methylphenyl)thio-1,8-naphthalic anhydride

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 41382-15-4
2-hydroxy-6-chlorobenzo[de]isoquinoline-1,3-dione

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 108-42-9
3-chloro-aniline

: 58226-81-6
6-chloro-2-(3-chlorophenyl)-1H-benz[de]isoquinolin-1,3(2H)dione

Conditions

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

: 2508-29-4
5-hydroxypentylamine

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 330649-49-5
N-(5'-Hydroxypentyl)-4-chloronaphthalene-1,8-dicarboximide

Conditions

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%

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 68-11-1
mercaptoacetic acid

: 847780-09-0
(1,3-dioxo-1H,3H-benzo[de]isochromen-6-ylsulfanyl)-acetic acid

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 109-85-3
2-methoxyethylamine

: 6-chloro-2-(2-methoxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

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

: 2038-03-1
4-(2-AMINOETHYL)MORPHOLINE

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 6-chloro-2-(2-morpholinoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 109-55-7
1-amino-3-(dimethylamino)propane

: 4063-59-6
6-chloro-2-[3-(dimethylamino)propyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 60-24-2
2-hydroxyethanethiol

: 101139-75-7
6-[(2-hydroxyethyl)thio]-1H,3H-benzo[de]isochromene-1,3-dione

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 108-98-5
thiophenol

: 54470-29-0
4-phenylthio-1,8-naphthalic anhydride

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 108-91-8
cyclohexylamine

: 57601-49-7
6-chloro-2-cyclohexyl-1H-benz[de]isoquinolin-1,3(2H)dione

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 106-40-1
4-bromo-aniline

: 58226-87-2
2-(4-bromophenyl)-6-chloro-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 65710-34-1
glutamic acid diethyl ester hydrochloride

: C21H20ClNO6

Conditions

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%

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 65710-34-1
glutamic acid diethyl ester hydrochloride

: C21H21NO6

Conditions

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

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 156-87-6
propan-1-ol-3-amine

: 52821-21-3
4-chloronaphthalic acid N-(3-hydroxypropyl)imide

Conditions

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%

: 3731-52-0
3-Aminomethylpyridine

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 4-chloro-N-(3′-picolylamine)-1,8-naphthalimide

Conditions

Conditions	Yield
In ethanol Schlenk technique; Heating;	89%

: 4053-08-1
p-chloro-1,8-naphthalicanhydride

: 4403-71-8
(4-aminomethyl)aniline

: 1070270-91-5
2-(4-amino-benzyl)-6-chloro-benzo[de]isoquinoline-1,3-dione

Conditions

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

4-Chloro-1,8-naphthalic anhydride Chemical Properties

Molecular Structure of 1H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-chloro- (CAS NO.4053-08-1):

Molecular Formula: C₁₂H₅ClO₃
Molecular Weight: 232.62
CAS Registry Number: 4053-08-1
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 43.37 Å²
Index of Refraction: 1.715
Molar Refractivity: 58.41 cm³
Molar Volume: 148.6 cm³
Surface Tension: 66.9 dyne/cm
Density: 1.565 g/cm³
Flash Point: 208.3 °C
Enthalpy of Vaporization: 70.99 kJ/mol
Boiling Point: 450.9 °C at 760 mmHg
Vapour Pressure: 2.53E-08 mmHg at 25°C
EINECS: 223-760-7
Melting Point: 207-210 °C
Storage temp: 2-8 °C
Sensitive: Moisture Sensitive
BRN: 178072
Product Categories: Intermediates of Dyes and Pigments
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
Smiles
O=C1OC(=O)c2cccc3c2c1ccc3Cl

4-Chloro-1,8-naphthalic anhydride Toxicity Data With Reference

orl-rat LD50:3460 mg/kg

NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0535458 .

4-Chloro-1,8-naphthalic anhydride Consensus Reports

Reported in EPA TSCA Inventory.

4-Chloro-1,8-naphthalic anhydride Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of Cl⁻.
Safety information of 1H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-chloro- (CAS NO.4053-08-1):
Hazard Codes: Xi
Risk Statements:
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements:
24/25: Avoid contact with skin and eyes
WGK Germany: 2
RTECS: QL6127295

4-Chloro-1,8-naphthalic anhydride Specification

1H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-chloro- , with CAS number of 4053-08-1, can be called 1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro- ; 6-Chloro-1H,3H-benzo[de]isochromene-1,3-dione ; 4-Chloro-1,8-naphthalic anhydride ; 6-Chloro-1H,3H-naphtho(1,8-cd)pyran-1,3-dione . It is a beige to brown powder, 1H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-chloro- (CAS NO.4053-08-1) is used as synthetic dyes, pigments, fluorescent brighteners and other important raw materials.

Product Name

4-Chloro-1,8-naphthalic anhydride

Synthetic route

4-Chloro-1,8-naphthalic anhydride Chemical Properties

4-Chloro-1,8-naphthalic anhydride Toxicity Data With Reference

4-Chloro-1,8-naphthalic anhydride Consensus Reports

4-Chloro-1,8-naphthalic anhydride Safety Profile

4-Chloro-1,8-naphthalic anhydride Specification

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