Product Name

  • Name

    6-methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione

  • EINECS 221-895-6
  • CAS No. 3271-05-4
  • Article Data8
  • CAS DataBase
  • Density 1.335g/cm3
  • Solubility
  • Melting Point 197-201 °C
  • Formula C14H11 N O3
  • Boiling Point 431.7°Cat760mmHg
  • Molecular Weight 241.246
  • Flash Point 214.9°C
  • Transport Information
  • Appearance
  • Safety Low toxicity by ingestion and intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 3271-05-4 (6-methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione)
  • Hazard Symbols
  • Synonyms Naphthalimide,4-methoxy-N-methyl- (7CI,8CI); 4-Methoxy-N-methyl-1,8-naphthalimide;4-Methoxynaphthalene-1,8-dicarboxylic methylimide; C.I. 56190; C.I. FluorescentBrightener 162; C.I. Fluorescent Brightening Agent 162; Fluorescent Brightener162; Fluorescent Brightening Agent 162; Mikawhite AT; Mikawhite AT CONC;N-Methyl-4-methoxy-1,8-naphthalimide
  • PSA 48.30000
  • LogP 1.49830

Synthetic route

methanol
67-56-1

methanol

4-nitro-N-methyl-1,8-naphthalimide
39061-36-4

4-nitro-N-methyl-1,8-naphthalimide

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
With potassium carbonate sonication;97%
sodium methylate
124-41-4

sodium methylate

4-chloro-N-methyl-1,8-naphthalimide
4118-33-6

4-chloro-N-methyl-1,8-naphthalimide

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
copper(II) sulfate In methanol for 12h; Heating;86%
4-bromo-N-methyl-1,8-naphthalimide
4116-90-9

4-bromo-N-methyl-1,8-naphthalimide

sodium methylate
124-41-4

sodium methylate

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate In methanol Reflux;81%
With copper(ll) sulfate pentahydrate In methanol Reflux;
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 8 h / 80 °C
2: copper(ll) sulfate pentahydrate / methanol / Reflux
View Scheme
Multi-step reaction with 2 steps
1: ethanol / 55 °C
2: copper(ll) sulfate pentahydrate / methanol / Reflux
View Scheme
6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

6-hydroxy-2-methyl-1H-benz[d,e]isoquinoline-1,3(2H)-dione
784-03-2

6-hydroxy-2-methyl-1H-benz[d,e]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
With hydrogen iodide for 3h; Heating;81%
With pyridine hydrochloride at 190℃; for 0.583333h; demethylation;45%
With hydrogen iodide In water at 130℃; Inert atmosphere;
With hydrogen iodide at 140℃;
6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

2,3,6-trimethylfuro<2,3-b><1>naphtho<4a,7a-e,f>pyrida-5,7-dione
146774-97-2

2,3,6-trimethylfuro<2,3-b><1>naphtho<4a,7a-e,f>pyrida-5,7-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / 57percent HI / 3 h / Heating
2: K2CO3 / butan-2-one / 72 h / Heating
3: 53 percent / 98percent H2SO4 / 10 h / Ambient temperature
View Scheme
6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

2-methyl-6-(2'-oxobutan-3'-yl)-naphtho<3a,9a-c,d>pyrida-1,3-dione
146774-96-1

2-methyl-6-(2'-oxobutan-3'-yl)-naphtho<3a,9a-c,d>pyrida-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / 57percent HI / 3 h / Heating
2: K2CO3 / butan-2-one / 72 h / Heating
View Scheme
6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

2-methyl-6-acetoxy-5-acetyl-naphtho<3a,9a-c,d>pyrida-1,3-dione
146774-98-3

2-methyl-6-acetoxy-5-acetyl-naphtho<3a,9a-c,d>pyrida-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / 57percent HI / 3 h / Heating
2: K2CO3 / butan-2-one / 72 h / Heating
3: 53 percent / 98percent H2SO4 / 10 h / Ambient temperature
4: 84 percent / O2, TPP / CH2Cl2 / 0.5 h / -10 °C / Irradiation
View Scheme
6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

6-hydroxy-2-methyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5-carbaldehyde

6-hydroxy-2-methyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogen iodide / water / 130 °C / Inert atmosphere
2.1: trifluoroacetic acid / 10 h / 0 - 120 °C
2.2: 2 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogen iodide / 140 °C
2.1: trifluoroacetic acid / 120 °C / Cooling with ice
2.2: Heating
View Scheme
6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

C20H12N2O3S

C20H12N2O3S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen iodide / water / 130 °C / Inert atmosphere
2.1: trifluoroacetic acid / 10 h / 0 - 120 °C
2.2: 2 h / Reflux
3.1: dihydrogen peroxide; hydrogenchloride / ethanol; water / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogen iodide / 140 °C
2.1: trifluoroacetic acid / 120 °C / Cooling with ice
2.2: Heating
3.1: hydrogenchloride; dihydrogen peroxide / ethanol; water / 0.5 h / 20 °C
View Scheme

6-Methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione Chemical Properties

Molecular Formula: C14H11NO3
Molar mass: 241.242 g/mol
EINECS: 221-895-6
Density: 1.335 g/cm3
Flash Point: 214.9 °C
Index of Refraction: 1.662
Boiling Point: 431.7 °C at 760 mmHg
Vapour Pressure: 1.18E-07 mmHg at 25°C
Structure of 4-Methoxy-N-methylnaphthalimide (3271-05-4):

SMILES: O=C2c1c3c(c(OC)cc1)cccc3C(=O)N2C 
InChI: InChI=1/C14H11NO3/c1-15-13(16)9-5-3-4-8-11(18-2)7-6-10(12(8)9)14(15)17/h3-7H,1-2H3 
InChIKey: CNUWYNDMLFVRBU-UHFFFAOYAR 
Std. InChI: InChI=1S/C14H11NO3/c1-15-13(16)9-5-3-4-8-11(18-2)7-6-10(12(8)9)14(15)17/h3-7H,1-2H3 
Std. InChIKey: CNUWYNDMLFVRBU-UHFFFAOYSA-N

6-Methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione Toxicity Data With Reference

1.    

bfa-rat:sat 12600 mg/kg/7D-C

     AECTCV    Archives of Environmental Contamination and Toxicology. 16 (1987),119.
2.    

orl-rat LDLo:15 g/kg

     ESKHA5    Eisei Shikenjo Hokoku. Bulletin of the National Hygiene Sciences.(101)(1983),152.
3.    

ipr-mus LD50:7700 mg/kg

     OKEHDW    Osaka-furitsu Koshu Eisei Kenkyusho Kenkyu Hokoku, Koshu Eisei Hen. Research Reports of the Osaka Prefectural Institute of Public Health, Public Health Section. 20 (1982),95.

6-Methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione Consensus Reports

Reported in EPA TSCA Inventory.

6-Methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione Safety Profile

Low toxicity by ingestion and intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

6-Methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione Specification

 4-Methoxy-N-methylnaphthalimide (3271-05-4) also can be called 4-Methoxy-1,8-naphthalic acid-N-methylimide ; 6-Methoxy-2-methyl-1H-benz(de)isoquinoline-1,3(2H)-dione ; 1H-Benz[de]isoquinoline-1,3(2H)-dione, 6-methoxy-2-methyl- ; and Naphthalimide, 4-methoxy-N-methyl- .

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