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81-86-7 Usage

Uses

4-Bromo-1,8-naphthalic Anhydride is used as a starting material in the synthesis of a fluorescent probe for the detection of copper ions in living human LO-2 cell lines.

Check Digit Verification of cas no

The CAS Registry Mumber 81-86-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 1 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 81-86:
(4*8)+(3*1)+(2*8)+(1*6)=57
57 % 10 = 7
So 81-86-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H5BrO3/c13-9-5-4-8-10-6(9)2-1-3-7(10)11(14)16-12(8)15/h1-5H

81-86-7 Well-known Company Product Price

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  • Aldrich

  • (324248)  4-Bromo-1,8-naphthalicanhydride  95%

  • 81-86-7

  • 324248-5G

  • 466.83CNY

  • Detail

81-86-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Bromo-1,8-naphthalic Anhydride

1.2 Other means of identification

Product number -
Other names 1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-bromo-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:81-86-7 SDS

81-86-7Synthetic route

1,8-Naphthalic anhydride
81-84-5

1,8-Naphthalic anhydride

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
Stage #1: 1,8-Naphthalic anhydride With bromine; potassium hydroxide In water at 0 - 60℃; for 18h;
Stage #2: With sulfuric acid In water at 20℃; Reflux;
94%
With bromine; potassium hydroxide In water at 60℃; for 6h;80%
With bromine; potassium hydroxide In water at 60℃; for 6h;77%
5-bromoacenaphthene
2051-98-1

5-bromoacenaphthene

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
With sodium dichromate In water; acetic acid for 12h; Oxidation; Heating;80%
With sodium dichromate; acetic acid for 5h; Reflux;80%
With sodium dichromate; acetic acid for 3h; Reflux;80%
7-bromophenalenone
75839-72-4

7-bromophenalenone

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
With chromium(VI) oxide In acetic acid at 80℃; for 1h;13%
4-sulfo-naphthalene-1,8-dicarboxylic acid
26848-63-5

4-sulfo-naphthalene-1,8-dicarboxylic acid

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
With phosphorus pentabromide at 190 - 200℃;
4-bromo-naphthalene-1,8-dicarboxylic acid
7267-05-2

4-bromo-naphthalene-1,8-dicarboxylic acid

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
With acetic anhydride
5-bromoacenaphthene
2051-98-1

5-bromoacenaphthene

sulfuric acid
7664-93-9

sulfuric acid

chromic acid

chromic acid

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

5-bromoacenaphthene
2051-98-1

5-bromoacenaphthene

acetic acid
64-19-7

acetic acid

chromic acid

chromic acid

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

1,5-dibromo-acenaphthene
25132-44-9

1,5-dibromo-acenaphthene

Na2Cr2O7

Na2Cr2O7

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

5-bromoacenaphthylene-1,2-dione
26254-35-3

5-bromoacenaphthylene-1,2-dione

sulfuric acid
7664-93-9

sulfuric acid

water
7732-18-5

water

NaN3

NaN3

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

ethanol
64-17-5

ethanol

5-bromoacenaphthylene-1,2-dione
26254-35-3

5-bromoacenaphthylene-1,2-dione

sulfuric acid
7664-93-9

sulfuric acid

NaN3

NaN3

A

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

B

4-bromo-naphthalene-1,8-dicarboxylic acid imide

4-bromo-naphthalene-1,8-dicarboxylic acid imide

1,2-diethylidene-5-bromo-acenaphthene

1,2-diethylidene-5-bromo-acenaphthene

acetic acid
64-19-7

acetic acid

Na2Cr2O7

Na2Cr2O7

A

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

B

5-bromoacenaphthylene-1,2-dione
26254-35-3

5-bromoacenaphthylene-1,2-dione

4-hydroxy-1H-phenalene-1-one
39981-72-1

4-hydroxy-1H-phenalene-1-one

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.29 g / ammonium acetate / 2 h / 130 - 140 °C
2: 1)nitrosylsulfuric acid, sodium nitrite, 2) cuprous bromide, 48percent hydrobromic acid / 1) acetic acid, 1 - 5 deg C, 20 min, 2) 1 - 5 deg C, 20 min
3: 13 percent / CrO3 / acetic acid / 1 h / 80 °C
View Scheme
7-aminophenalenone
75839-70-2

7-aminophenalenone

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1)nitrosylsulfuric acid, sodium nitrite, 2) cuprous bromide, 48percent hydrobromic acid / 1) acetic acid, 1 - 5 deg C, 20 min, 2) 1 - 5 deg C, 20 min
2: 13 percent / CrO3 / acetic acid / 1 h / 80 °C
View Scheme
acenaphthene
83-32-9

acenaphthene

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform; bromine
2: glacial acetic acid; sodium dichromate / 50 - 70 °C / Behandeln des Reaktionsprodukts in Wasser
View Scheme
Multi-step reaction with 3 steps
1: Br2
2: Na2Cr2O7, AcOH / Heating
3: Ac2O
View Scheme
Multi-step reaction with 2 steps
1: sodium dichromate / acetic acid / 8 h / 75 °C
2: bromine; potassium hydroxide / water / 6 h / 60 °C
View Scheme
1,2,4,5,6-pentabromo-1,2,4,5-tetrahydro-acenaphthylene
15735-20-3

1,2,4,5,6-pentabromo-1,2,4,5-tetrahydro-acenaphthylene

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Na2Cr2O7, AcOH / Heating
2: Ac2O
View Scheme
5-bromoacenaphthene
2051-98-1

5-bromoacenaphthene

acetic acid
64-19-7

acetic acid

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
With oxygen
With sodium dichromate at 120℃; for 5h;
5-bromoacenaphthylene-1,2-dione
26254-35-3

5-bromoacenaphthylene-1,2-dione

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
With potassium hydrogensulfate In ethanol for 18h; Reflux;
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

N-butylamine
109-73-9

N-butylamine

4-bromo-N-butylnaphthalimide
92874-17-4

4-bromo-N-butylnaphthalimide

Conditions
ConditionsYield
In ethanol at 78℃; for 4h;100%
In ethanol for 26h; Reflux;100%
for 3h; Reflux;94.5%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

3-dimethylaminopropiononitrile
1738-25-6

3-dimethylaminopropiononitrile

4-(N,N-dimethylamino)-1,8-naphthalic anhydride
77976-79-5

4-(N,N-dimethylamino)-1,8-naphthalic anhydride

Conditions
ConditionsYield
In i-Amyl alcohol under 760.051 Torr; for 12h; Inert atmosphere; Heating;100%
In i-Amyl alcohol at 132℃; for 16h;100%
In i-Amyl alcohol Reflux;100%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

2-(6-bromo-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N,N-dimethylethanamine
182344-65-6

2-(6-bromo-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N,N-dimethylethanamine

Conditions
ConditionsYield
In ethanol for 4h; Reflux;100%
In ethanol for 1h; Inert atmosphere; Reflux;95%
In 1,4-dioxane for 4h; Reflux;95%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

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

1,2-diamino-benzene

4-bromobenzo[d,e]benzo[4,5]-imidazo[2,1-a]isoquinolin-7-one
26559-73-9

4-bromobenzo[d,e]benzo[4,5]-imidazo[2,1-a]isoquinolin-7-one

Conditions
ConditionsYield
With acetic acid Reflux;100%
With acetic acid for 4h; Reflux;99%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Propargylamine
2450-71-7

Propargylamine

6-bromo-2-(prop-2-yn-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
1236253-27-2

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

Conditions
ConditionsYield
In 1,4-dioxane99%
In ethanol at 70℃; for 3h;94%
In ethanol at 70℃; for 3h; Inert atmosphere;94%
4-(3-Aminopropyl)morpholine
123-00-2

4-(3-Aminopropyl)morpholine

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

6-bromo-2-(3-morpholinopropyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

6-bromo-2-(3-morpholinopropyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
In ethanol at 90℃; for 12h;99%
In ethanol at 60℃; for 6h;87%
In ethanol Reflux;78.4%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

dimethyl 4-(11ʹ-aminoundecanyl)-3,5-dioxatricyclo[5.2.1.02,6]decane-8-endo-9-exo-dicarboxylate hydrogen chloride

dimethyl 4-(11ʹ-aminoundecanyl)-3,5-dioxatricyclo[5.2.1.02,6]decane-8-endo-9-exo-dicarboxylate hydrogen chloride

dimethyl 4-[11ʹ-(6ʺ-bromo-1ʺ,3ʺ-dioxo-1H-benzo[de]isoquinoline-2(3H))undecyl]-3,5-dioxatricyclo[5.2.1.02,6]decane-8-endo-9-exo-dicarboxylate

dimethyl 4-[11ʹ-(6ʺ-bromo-1ʺ,3ʺ-dioxo-1H-benzo[de]isoquinoline-2(3H))undecyl]-3,5-dioxatricyclo[5.2.1.02,6]decane-8-endo-9-exo-dicarboxylate

Conditions
ConditionsYield
With triethylamine In ethanol at 100℃; for 0.75h; Microwave irradiation;99%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

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

1,2-diamino-benzene

3-bromo-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one
26559-67-1

3-bromo-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one

Conditions
ConditionsYield
With aluminum oxide for 0.15h; microwave irradiation;98%
With acetic acid at 95℃; for 4h; Inert atmosphere;90%
With acetic acid for 6h; Reflux;87%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

2-(2-Aminoethoxy)ethanol
929-06-6

2-(2-Aminoethoxy)ethanol

2-[2-(2-hydroxy-ethoxy)-ethyl]-6-[2-(2-hydroxy-ethoxy)-ethylamino]-benzo[de]isoquinoline-1,3-dione
903499-39-8

2-[2-(2-hydroxy-ethoxy)-ethyl]-6-[2-(2-hydroxy-ethoxy)-ethylamino]-benzo[de]isoquinoline-1,3-dione

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 110℃; for 2h;98%
hexan-1-amine
111-26-2

hexan-1-amine

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

6-bromo-2-hexyl-1H-benzo[de]isoquinoline-1,3 (2H)-dione
101721-89-5

6-bromo-2-hexyl-1H-benzo[de]isoquinoline-1,3 (2H)-dione

Conditions
ConditionsYield
In ethanol Reflux;98%
In ethanol at 90℃; for 15h;92%
In ethanol at 78℃; for 5h;90%
2-Ethylhexylamine
104-75-6

2-Ethylhexylamine

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

6-bromo-2-(2-ethylhexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
1193092-32-8

6-bromo-2-(2-ethylhexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
In ethanol for 24h; Reflux;98%
In ethanol at 110℃; Inert atmosphere;95.01%
In ethanol for 4h; Reflux;85%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

2-ethynyl-6-methoxynaphthalene
129113-00-4

2-ethynyl-6-methoxynaphthalene

4-(6-methoxynaphthalen-2-ylethynyl)-1,8-naphthalenedicarboxylic anhydride

4-(6-methoxynaphthalen-2-ylethynyl)-1,8-naphthalenedicarboxylic anhydride

Conditions
ConditionsYield
With copper(l) iodide; bis(triphenylphosphine)platinum(II) dichloride; triethylamine; triphenylphosphine In toluene for 14h; Sonogashira Cross-Coupling; Reflux; Inert atmosphere;98%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

3-dimethylaminopropiononitrile
1738-25-6

3-dimethylaminopropiononitrile

A

4-(N,N-dimethylamino)-1,8-naphthalic anhydride
77976-79-5

4-(N,N-dimethylamino)-1,8-naphthalic anhydride

B

dimethylaminopropionitrile hydrobromide

dimethylaminopropionitrile hydrobromide

C

acrylonitrile
107-13-1

acrylonitrile

Conditions
ConditionsYield
In i-Amyl alcohol at 132℃; for 12h;A 97.7%
B n/a
C n/a
4-(2-AMINOETHYL)MORPHOLINE
2038-03-1

4-(2-AMINOETHYL)MORPHOLINE

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

6-bromo-2-(2-morpholinoethyl)-1H-benzo[de]isoquinoline1,3 (2 H)-dione
182344-68-9

6-bromo-2-(2-morpholinoethyl)-1H-benzo[de]isoquinoline1,3 (2 H)-dione

Conditions
ConditionsYield
In ethanol at 80℃; for 2h;97.2%
In ethanol at 80℃; for 1h;95%
In ethanol at 80℃; for 5h;94%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

dimethyl amine
124-40-3

dimethyl amine

4-(N,N-dimethylamino)-1,8-naphthalic anhydride
77976-79-5

4-(N,N-dimethylamino)-1,8-naphthalic anhydride

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate In water; N,N-dimethyl-formamide Reflux;97%
With copper(II) sulfate In water; N,N-dimethyl-formamide for 2.5h; Reflux;90%
With copper(ll) sulfate pentahydrate In water; N,N-dimethyl-formamide for 3h; Reflux;88%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

2,5-Dimethyl-1,4-phenylenediamine
6393-01-7

2,5-Dimethyl-1,4-phenylenediamine

C20H15BrN2O2
1163177-02-3

C20H15BrN2O2

Conditions
ConditionsYield
In ethanol for 12h; Inert atmosphere; Reflux;97%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

6-azido-1H,3H-benzo[de]isochromene-1,3-dione
1262149-88-1

6-azido-1H,3H-benzo[de]isochromene-1,3-dione

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 20℃; for 12h;97%
With sodium azide In N,N-dimethyl-formamide for 12h;96%
With sodium azide In N,N-dimethyl-formamide at 55℃; for 1h;95.1%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

1-((2R,3R,4S,5R)-3-(6-aminohexylamino)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

1-((2R,3R,4S,5R)-3-(6-aminohexylamino)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

6-bromo-2-(6-((2R,3R,4S,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-ylamino)hexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

6-bromo-2-(6-((2R,3R,4S,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-ylamino)hexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
With pyridine; dmap In ethanol for 18h; Reflux; Inert atmosphere;97%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

2,2-Diphenylethylamine
3963-62-0

2,2-Diphenylethylamine

6-bromo-2-(2,2-diphenylethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

6-bromo-2-(2,2-diphenylethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
In ethanol at 80℃; for 18h; Inert atmosphere;97%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

Propargylamine
2450-71-7

Propargylamine

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

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

Conditions
ConditionsYield
Stage #1: 4-bromo-1,8-naphthalenedicarboxylic anhydride; Propargylamine In 1,4-dioxane for 5h; Reflux;
Stage #2: With sodium azide In N,N-dimethyl-formamide at 80℃; for 1.5h;
97%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

cyclohexylamine
108-91-8

cyclohexylamine

N-(cyclohexyl)-4-bromonaphthalene-1,8-dicarboxiimide
324035-44-1

N-(cyclohexyl)-4-bromonaphthalene-1,8-dicarboxiimide

Conditions
ConditionsYield
In ethanol for 12h; Heating;96%
In ethanol at 78℃; for 5h;80%
In ethanol at 90℃; for 15h;80%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

methylamine
74-89-5

methylamine

4-bromo-N-methyl-1,8-naphthalimide
4116-90-9

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

Conditions
ConditionsYield
With acetic acid at 100℃; for 2h; Inert atmosphere;96%
In water at 20℃;95%
In ethanol for 3h; Reflux;94%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

2,6-diisopropylbenzenamine
24544-04-5

2,6-diisopropylbenzenamine

6-bromo-2-(2,6-diisopropylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
187536-93-2

6-bromo-2-(2,6-diisopropylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
With propionic acid at 150℃; for 17h; Inert atmosphere;96%
With acetic acid at 120℃; for 72h;90%
With acetic acid for 96h; Reflux;85%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

2-[2-(2-methoxyethoxy)ethoxy]ethylamine
74654-07-2

2-[2-(2-methoxyethoxy)ethoxy]ethylamine

6-bromo-2-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-1H-benz[de]isoquinoline-1,3(2H)-dione
1562520-17-5

6-bromo-2-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-1H-benz[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
In methanol for 10h; Solvent; Inert atmosphere; Reflux;96%
In ethanol for 2h; Reflux;92%
In ethanol Reflux;90%
In ethanol Reflux;84%
3-aminobenzaldehyde ethylene acetal
6398-87-4

3-aminobenzaldehyde ethylene acetal

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

C19H10BrNO3

C19H10BrNO3

Conditions
ConditionsYield
Stage #1: 3-aminobenzaldehyde ethylene acetal; 4-bromo-1,8-naphthalenedicarboxylic anhydride With 1H-imidazole In chloroform for 7h; Reflux;
Stage #2: With toluene-4-sulfonic acid In acetone
96%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

1,4-diaminobutane
110-60-1

1,4-diaminobutane

2-(4-aminobutyl)-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione

2-(4-aminobutyl)-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
In ethanol at 20℃; for 3h;95.6%
In ethanol for 3h;
In ethanol at 80℃; for 2h;
3-(2-ethylhexoxy)propylamine
5397-31-9

3-(2-ethylhexoxy)propylamine

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

C23H28BrNO3

C23H28BrNO3

Conditions
ConditionsYield
In ethanol at 50℃; for 8h;95.6%
n-Dodecylamine
124-22-1

n-Dodecylamine

4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

6-bromo-2-dodecyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione

6-bromo-2-dodecyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione

Conditions
ConditionsYield
With pyridine for 1h; Reflux;95%
In ethanol for 8h; Reflux;94%
In ethanol Reflux;85%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

aniline
62-53-3

aniline

6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
84216-52-4

6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
With pyridine In methanol at 60℃; for 0.0833333h; Inert atmosphere;95%
With acetic acid for 24h; Inert atmosphere; Reflux;83%
In ethanol for 7h; Inert atmosphere; Reflux;83.3%
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

4-bromonaphthalene-1,8-dicarboximide
52559-36-1

4-bromonaphthalene-1,8-dicarboximide

Conditions
ConditionsYield
With ammonium hydroxide95%
With choline chloride; urea at 140℃; for 1h; Green chemistry;93%
With acetamide In methanol at 130℃; for 18h; glas tube;87%

81-86-7Relevant articles and documents

Naphthalimide-Based DNA-Coupled Hybrid Assembly for Sensing Dipicolinic Acid: A Biomarker for Bacillus anthracis Spores

Verma, Meenakshi,Kaur, Navneet,Singh, Narinder

, p. 6591 - 6600 (2018)

We have designed and synthesized a novel, water-soluble naphthalimide-histidine receptor (1) with excellent fluorescent properties. Functioning of the synthesized receptor was performed through developing their DNA-receptor hybrid assembly (DRHA), which has shown significant changes in the emission profile upon interactions with dipicolinic acid (DPA), a biomarker for Bacillus anthracis spores. DRHA showed fluorescence enhancement upon binding with DPA with the characteristic of internal charge transfer. It is notable that this assembly exhibited a significant limit of detection (12 nM) toward DPA. The mechanism of sensing was fully defined using ethidium bromide (EtBr) interaction studies as well as Fourier transform infrared spectroscopic analysis, which describes the binding mode of DRHA with DPA. This assembly selectively interacts with DPA over other anions, common cellular cations, and aromatic acids in aqueous media.

Naphthalimide-gold-based nanocomposite for the ratiometric detection of okadaic acid in shellfish

Chaudhary, Monika,Kaur, Navneet,Singh, Amanpreet,Singh, Narinder,Verma, Meenakshi

, p. 8405 - 8413 (2020)

Okadaic acid (OA) is one of the known marine biotoxins produced by various dinoflagellates and exists in seafood such as shellfish. The consumption of contaminated shellfish with OA leads to diarrheic shellfish poisoning (DSP), which results in the inhibition of protein phosphatase enzymes in humans. This poisoning can cause immunotoxicity and tumor promotion due to the accumulation of okadaic acid in more than the allowed limit in bivalve molluscs. The reported methods for the detection of okadaic acid include mouse bioassays, immunoassays, chromatography coupled with spectroscopic techniques, electrochemical sensors and immunosensors. We have developed a naphthalimide-gold-based nanocomposite for the detection of okadaic acid. Individually, the organic nanoparticles (ONPs) of synthesized naphthalimide-based receptors and gold-coated ONPs are less sensitive for detection. However, fabrication of the composite of Au?ONPs and ONPs enhance the sensing properties and selectivity. The composite shows a ratiometric response in the UV-Vis absorption spectrum and quenching in the fluorescence profile with a detection limit of 20 nM for OA in aqueous medium. In cyclic voltammetry, a shift was observed in the cathodic peak (-0.532 V to -0.618 V) as well as in the anodic peak (-0.815 V to -0.847 V) with the addition of okadaic acid. To study the quick binding of the composite with OA, a time response experiment was performed. Also, the developed sensor retains its sensing ability in the pH range of 5-9 and in high salt conditions. Our developed composite can be used for the detection of OA in real applications.

Synthesis and fluorescence quenching mechanism of novel naphthalimide derivative by nanographene oxide

Rouhani, Shohre,Seraj, Sanaz

, (2021/07/30)

Novel naphthalimide derivative with amine functional group was prepared, and its FTIR and 1H and 13C NMR spectral characteristics were reported. The fluorescence quenching of synthesized dye by nanographene oxide was studied using absorption and fluorescence measurements. From the stern-Volmer analysis, we observed that the quenching was mainly due to the dynamic mechanism. The CV plots indicate that the quenching also went through an electron transfer process. The binding constant (K) and the number of binding sites (n) were calculated based on the fluorescence quenching data. In addition, the free energy change (ΔG) for the electron transfer process was calculated.

Synthesis of naphthalimide-phenanthro[9,10-d]imidazole derivatives: In vitro evaluation, binding interaction with DNA and topoisomerase inhibition

Luxami, Vijay,Paul, Kamaldeep,Singh, Iqubal

, (2020/02/11)

The synthesis and characterization of a series of naphthalimide and phenanthro[9,10-d]imidazole conjugate is described. These compounds are evaluated in vitro for their cytotoxicity towards 60 human cancer cell lines. Derivative 16 shows excellent cytotoxic activity against these cancer cell lines with the range of growth inhibition from ?55.78 to 94.53. The most potent derivative (ethylpiperazine, 16) is further studied to evaluate the interaction with ct-DNA using absorption and emission spectroscopy as well as DNA viscosity measurement. The DNA binding studies indicate that compound 16 is significantly interacted with DNA through groove binding having binding constant value of 7.81 × 104 M?1 alongwith partial intercalation between the base pairs of DNA strands. Further, topoisomerase inhibition study suggests that compound 16 is induced apoptosis and inhibits human topoisomerase (Topo-IIα) as a possible intracellular target. Molecular docking study of compound 16 with ct-DNA shows good docking score.

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