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3271-05-4

Basic Information
CAS No.: 3271-05-4
Name: 6-methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione
Article Data: 8
Molecular Structure:
Molecular Structure of 3271-05-4 (6-methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione)
Formula: C14H11 N O3
Molecular Weight: 241.246
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
EINECS: 221-895-6
Density: 1.335g/cm3
Melting Point: 197-201 °C
Boiling Point: 431.7°Cat760mmHg
Flash Point: 214.9°C
Safety: Low toxicity by ingestion and intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.
PSA: 48.30000
LogP: 1.49830
Synthetic route
67-56-1

methanol

39061-36-4

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

3271-05-4

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

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

sodium methylate

4118-33-6

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

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%
4116-90-9

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

124-41-4

sodium methylate

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;
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

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
3271-05-4

6-methoxy-2-methyl-1H-benzo[de]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℃;
3271-05-4

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

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

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

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
3271-05-4

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

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
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Chemistry

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

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.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

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

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- .