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602-38-0

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602-38-0 Usage

Chemical Properties

Light yellow to Yellow to Orange powder to crystal.

Uses

1,8-Dinitronaphthalene (cas# 602-38-0) is a compound useful in organic synthesis.

Application

The reduction of 1,8-dinitronaphthalene to diaminonaphthalene is an important organic synthesis unit reaction and an important way to prepare diaminonaphthalene, and its product diaminonaphthalene is an important pigment intermediate. Diaminonaphthalene mainly includes 1,5-diaminonaphthalene and 1,8-diaminonaphthalene.

Preparation

Separation of dinitronaphthalene: Crude mixtures of dinitronaphthalene (5 g, from Table-3 run 8) was placed together with 50 mL acetone in a 100 mL flask, stirred and heated to reflux. The suspension was refluxing for 2 h and then cooled to 30 oC by stirred and filtered quickly. The precipitate was recrystallized by acetone and 1,5-dinitronaphthalene as light yellow crystals (1.725 g) was got. Then the filter liquor was concentrated to one-thirds of original volume, filtered, the precipitate was recrystallized by toluene and 1,8- dinitronaphthalene as light yellow crystals (1.987 g) was got. 1, 5-Dinitronaphthalene: m.p. 215-216 oC, 1H NMR (400 MHz, CDCl3): δ = 7.84 (t, 2H), 8.33 (d, 2H), 8.81 (d, 2H). 1, 8-Dinitronaphthalene: m.p. 172-173 oC, 1H NMR (400 MHz, CDCl3): δ = 7.98 (t, 2H), 8.51 (dd, 4H). Zeolite-Assisted Regioselective Synthesis of Dinitronaphthalene

Definition

ChEBI: 1,8-dinitronaphthalene is a dinitronaphthalene carrying nitro groups at positions 1 and 8.

General Description

1,8-dinitronaphthalene appears as yellow crystals. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,8-Dinitronaphthalene is sensitive to heat and shock.

Fire Hazard

Flash point data for 1,8-Dinitronaphthalene is not available, however 1,8-Dinitronaphthalene is probably combustible.

Purification Methods

Crystallise it from *benzene. [Beilstein 5 H 559, 5 II 455, 5 III 1608.]

Check Digit Verification of cas no

The CAS Registry Mumber 602-38-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 2 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 602-38:
(5*6)+(4*0)+(3*2)+(2*3)+(1*8)=50
50 % 10 = 0
So 602-38-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H6N2O4/c13-11(14)8-5-1-3-7-4-2-6-9(10(7)8)12(15)16/h1-6H

602-38-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,8-dinitronaphthalene

1.2 Other means of identification

Product number -
Other names Naphthalene,1,8-dinitro

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:602-38-0 SDS

602-38-0Synthetic route

Naphthalene-1,8-dicarboxylic acid
518-05-8

Naphthalene-1,8-dicarboxylic acid

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

Conditions
ConditionsYield
With nitronium tetrafluoborate; silver carbonate In N,N-dimethyl acetamide at 90℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;81%
naphthalene
91-20-3

naphthalene

A

1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

B

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

C

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
With nitric acid at 64.84℃; for 3h; Catalytic behavior; Reagent/catalyst;A 78.5%
B 10.6%
C 6.2%
With nitric acid In acetic acid at 64.84℃; for 3h; Catalytic behavior; Solvent;A 22.5%
B 42.5%
C 32.6%
With phosphotungstic acid; nitric acid at 64.84℃; for 3h; Catalytic behavior; Reagent/catalyst;A 31.5%
B 36.7%
C 28.5%
With nitric acid In dichloromethane for 12h; Reflux; regioselective reaction;
naphthalene
91-20-3

naphthalene

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
With nitric acid at 64.84℃; for 3h; Catalytic behavior; Reagent/catalyst;A 49.2%
B 48.5%
With nitric acid
With nitric acid Erwaermen des Reaktionsgemischs mit konz. Schwefelsaeure;
naphthalene
91-20-3

naphthalene

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

Conditions
ConditionsYield
With sulfuric acid; nitric acid
With Nitrogen dioxide
1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

Conditions
ConditionsYield
With sulfuric acid; potassium nitrate at 0℃;
With sulfuric acid; nitric acid at 0 - 35℃;
With sulfuric acid; nitric acid
1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
With nitric acid
With sulfuric acid; nitric acid at 0℃; Trennung der beiden Isomere durch Umkrystallisieren aus Pyridin;
With sulfuric acid; nitric acid at 0℃;
1-amino-4,5-dinitronaphthalene
90765-71-2

1-amino-4,5-dinitronaphthalene

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

Conditions
ConditionsYield
With sulfuric acid; acetic acid Diazotization.Behandlung der Diazoniumsalz-Loesung mit Cu2O und Aethanol;
4,5-dinitro-[1]naphthoic acid
99972-07-3

4,5-dinitro-[1]naphthoic acid

copper diacetate
142-71-2

copper diacetate

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

naphthalene
91-20-3

naphthalene

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

1,7‑dinitronaphthalene
24824-25-7

1,7‑dinitronaphthalene

C

1,6-dinitronaphthalene
607-46-5

1,6-dinitronaphthalene

D

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
With cupric nitrate trihydrate supported on K 10 montmorillonite clay; nitric acid; acetic anhydride In tetrachloromethane for 3h; Ambient temperature; Yield given. Yields of byproduct given;
naphthalene
91-20-3

naphthalene

A

1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

B

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

C

2,4-dinitronaphthalene
606-37-1

2,4-dinitronaphthalene

D

2-nitronaphthalene
581-89-5

2-nitronaphthalene

E

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
With Nitrogen dioxide; ozone In dichloromethane at -25℃; for 0.0833333h; Product distribution; Mechanism; other methylnaphthalenes; also with HNO3/Ac2O system and with methanesulfonic acid; var. temp. and reaction times;
naphthalene
91-20-3

naphthalene

nitric acid
7697-37-2

nitric acid

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

naphthalene
91-20-3

naphthalene

NO2

NO2

A

1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

B

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

C

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

8-nitro-naphthalene-carboxylic acid-(1)

8-nitro-naphthalene-carboxylic acid-(1)

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

Conditions
ConditionsYield
With nitric acid
diazotized 1.8-dinitro-2-amino-naphthalene

diazotized 1.8-dinitro-2-amino-naphthalene

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

Conditions
ConditionsYield
With ethanol
1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

sulfuric acid
7664-93-9

sulfuric acid

nitric acid
7697-37-2

nitric acid

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
Product distribution;
1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

HNO3+H2SO4

HNO3+H2SO4

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

sulfuric acid
7664-93-9

sulfuric acid

KNO3

KNO3

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
at 0℃;
1-naphthalenesulfonic acid
85-47-2

1-naphthalenesulfonic acid

nitric acid
7697-37-2

nitric acid

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

Conditions
ConditionsYield
at -10℃;
8-nitro-1-naphthalenecarboxylic acid
2216-13-9

8-nitro-1-naphthalenecarboxylic acid

nitric acid
7697-37-2

nitric acid

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

1-naphthalenecarboxylic acid
86-55-5

1-naphthalenecarboxylic acid

nitric acid
7697-37-2

nitric acid

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

4,5-dinitro-[1]naphthoic acid
99972-07-3

4,5-dinitro-[1]naphthoic acid

sulfuric acid
7664-93-9

sulfuric acid

2-amino-1,8-dinitronaphthalene
64574-28-3

2-amino-1,8-dinitronaphthalene

sodium nitrite

sodium nitrite

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

Conditions
ConditionsYield
Kochen des entstandenen Diazoniumsulfats mit Alkohol;
quinoline
91-22-5

quinoline

4,5-dinitro-[1]naphthoic acid
99972-07-3

4,5-dinitro-[1]naphthoic acid

copper-powder

copper-powder

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

naphthalene
91-20-3

naphthalene

nitric acid
7697-37-2

nitric acid

A

1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

B

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

C

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

naphthalene
91-20-3

naphthalene

A

1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

B

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

C

2,4-dinitronaphthalene
606-37-1

2,4-dinitronaphthalene

D

2,3-dinitronaphthalene
1875-63-4

2,3-dinitronaphthalene

Conditions
ConditionsYield
With sodium nitrate; silver nitrate; potassium nitrate; potassium hexacyanoferrate(III) at 160℃; for 1h; Further byproducts.;
naphthalene
91-20-3

naphthalene

A

1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

B

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

C

2-nitronaphthalene
581-89-5

2-nitronaphthalene

D

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
With nitric acid In dichloromethane for 12h; Reflux; regioselective reaction;
With nitric acid In acetonitrile for 12h; Reflux; regioselective reaction;
With nitric acid In hexane for 2.3h; Reflux; regioselective reaction;
With nitric acid In nitrobenzene at 90℃; for 24h; Solvent; Temperature; Time; regioselective reaction;
1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

2,4-dinitronaphthalene
606-37-1

2,4-dinitronaphthalene

C

1,4-dinitronaphthalene
6921-26-2

1,4-dinitronaphthalene

D

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
With nickel(II) acetate tetrahydrate; Nitrogen dioxide In acetonitrile at 100℃; for 3h; Temperature; Time; Reagent/catalyst; Sealed tube; regioselective reaction;
1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

A

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

B

2,4-dinitronaphthalene
606-37-1

2,4-dinitronaphthalene

C

1,7‑dinitronaphthalene
24824-25-7

1,7‑dinitronaphthalene

D

1,4-dinitronaphthalene
6921-26-2

1,4-dinitronaphthalene

E

1,6-dinitronaphthalene
607-46-5

1,6-dinitronaphthalene

F

2,3,5-trinitronaphthalene
87185-24-8

2,3,5-trinitronaphthalene

G

1,5-dinitronaphthalene
605-71-0

1,5-dinitronaphthalene

Conditions
ConditionsYield
With oxygen; acetic anhydride; Nitrogen dioxide at 35℃; under 3750.38 Torr; for 4h; Catalytic behavior; Mechanism; Reagent/catalyst; Time; Temperature; Pressure;
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

1-amino-5,6,7,8-tetrahydronaphthalene
2217-41-6

1-amino-5,6,7,8-tetrahydronaphthalene

Conditions
ConditionsYield
With hydrogen In methanol at 150℃; under 15001.5 Torr; for 6h; Temperature; Solvent; Pressure; Autoclave;97.4%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

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

naphthalene-1,8-diamine

Conditions
ConditionsYield
With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate; sodium hydroxide In ethanol; water at 65 - 90℃; pH=8 - 12; Solvent; Temperature; Autoclave; Industrial scale;96.46%
With hydrogen; palladium on activated charcoal In methanol at 25℃; for 5h;95%
With sodium tetrahydroborate In water at 20℃; for 0.266667h; Catalytic behavior;92%
caprinaldehyde
112-31-2

caprinaldehyde

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

2-nonyl-1H-perimidine
13925-64-9

2-nonyl-1H-perimidine

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;85%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

2-(4-methylphenyl)-1H-perimidine
25110-47-8

2-(4-methylphenyl)-1H-perimidine

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Autoclave; chemoselective reaction;84%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

benzaldehyde
100-52-7

benzaldehyde

2-phenylperimidine
15666-84-9

2-phenylperimidine

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;83%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

para-acetamidobenzaldehyde
122-85-0

para-acetamidobenzaldehyde

acetic acid-[4-(1H-perimidin-2-yl)-anilide]

acetic acid-[4-(1H-perimidin-2-yl)-anilide]

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;82%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

C18H14N2

C18H14N2

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;81%
3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

C20H24N2

C20H24N2

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;81%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2-(4-chlorophenyl)-1H-perimidine
28478-19-5

2-(4-chlorophenyl)-1H-perimidine

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;80%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

LDN-0045024

LDN-0045024

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;80%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-stilbenecarboxaldehyde
32555-96-7

4-stilbenecarboxaldehyde

C25H18N2

C25H18N2

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;79%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-(Methylthio)benzaldehyde
3446-89-7

4-(Methylthio)benzaldehyde

C18H14N2S

C18H14N2S

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;78%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

2-(4-methoxyphenyl)-1H-perimidine
25110-46-7

2-(4-methoxyphenyl)-1H-perimidine

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Catalytic behavior; Solvent; Temperature; Autoclave; chemoselective reaction;76%
5-Methylfurfural
620-02-0

5-Methylfurfural

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

2-(5-methyl-furan-2-yl)-1H-perimidine
43213-70-3

2-(5-methyl-furan-2-yl)-1H-perimidine

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;75%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

2-(4-fluorophenyl)-1H-perimidine
385387-32-6

2-(4-fluorophenyl)-1H-perimidine

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;74%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

C18H14N2

C18H14N2

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;72%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

2-(4-bromophenyl)-1H-perimidine
25163-64-8

2-(4-bromophenyl)-1H-perimidine

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Catalytic behavior; Temperature; Solvent; Autoclave; chemoselective reaction;72%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

C17H11ClN2

C17H11ClN2

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;71%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
128376-64-7

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

C23H23BN2O2

C23H23BN2O2

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;70%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

C17H11IN2

C17H11IN2

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;67%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

C18H11N3
862886-05-3

C18H11N3

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;66%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

4-[(trimethylsilyl)ethynyl]bezaldehyde
77123-57-0

4-[(trimethylsilyl)ethynyl]bezaldehyde

C22H20N2Si

C22H20N2Si

Conditions
ConditionsYield
With hydrogen In toluene at 130℃; under 45004.5 Torr; for 20h; Autoclave; chemoselective reaction;65%
propylamine
107-10-8

propylamine

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

A

4,5-dinitro-N-propylnaphthalen-1-amine
1137661-55-2

4,5-dinitro-N-propylnaphthalen-1-amine

B

1,8-dinitro-N-propylnaphthalen-2-amine
1137661-44-9

1,8-dinitro-N-propylnaphthalen-2-amine

Conditions
ConditionsYield
With silver(I) permanganate at 20℃;A 53%
B 35%
danishefsky's diene
54125-02-9

danishefsky's diene

1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

2-hydroxy-5-nitrophenanthrene

2-hydroxy-5-nitrophenanthrene

Conditions
ConditionsYield
In benzene at 150℃; for 72h;43%
In benzene at 150℃; for 80h; Inert atmosphere; Sealed tube; Heating;40%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

3,4,5,6-tetrachloro-1,8-dinitronaphthalene

3,4,5,6-tetrachloro-1,8-dinitronaphthalene

Conditions
ConditionsYield
With chlorosulfonic acid; iodine; chlorine40%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

cyclohexylamine
108-91-8

cyclohexylamine

N-cyclohexyl-1,8-dinitronaphthalen-2-amine
1137661-47-2

N-cyclohexyl-1,8-dinitronaphthalen-2-amine

Conditions
ConditionsYield
With silver(I) permanganate In tetrahydrofuran at 20℃;40%
1,8-dinitronaphthalene
602-38-0

1,8-dinitronaphthalene

N-butylamine
109-73-9

N-butylamine

A

N-butyl-1,8-dinitronaphthalen-2-amine
1137661-45-0

N-butyl-1,8-dinitronaphthalen-2-amine

B

N-butyl-4,5-dinitronaphthalen-1-amine
57091-57-3

N-butyl-4,5-dinitronaphthalen-1-amine

Conditions
ConditionsYield
With silver(I) permanganate at 20℃;A 32%
B 38%

602-38-0Relevant articles and documents

Regioselective nitration of naphthalene over HZSM-5-supported phosphotungstic acid

Liu, Pingle,Xiong, Wei,Wang, Xiaofei,Huang, Kun,Hao, Fang,Wang, Liangjie,Luo, He'An

, p. 4533 - 4543 (2015)

HZSM-5-supported phosphotungstic acid (PW) has been prepared and characterized. The results indicate that 5 wt% PW/HZSM-5 calcined at 773 K has the largest surface area and high dispersion of PW. It was confirmed that Keggin units are present inside the catalyst and that the proton of PW and the silanol of HZSM-5 interact via bridging structure. The catalytic properties of PW/HZSM-5 in the regioselective nitration of naphthalene to dinitronaphthalene were investigated. The best results, i.e. 48.5 % yield of 1,5-dinitronaphthalene, 49.2 % yield of 1,8-dinitronaphthalene, and the highest ratio of 1,5-dinitronaphthalene to 1,8-dinitronaphthalene, were obtained by use of 5 wt% PW/HZSM-5.

A simple approach for preparation of dinitronaphthalene compounds from the nitration reaction of 1-nitronaphthalene with NO2 as nitration reagent

You, Kuiyi,Zhou, Zhongcang,Jian, Jian,Deng, Renjie,Liu, Pingle,Ai, Qiuhong,Luo, He'An

, p. 8307 - 8315 (2015)

A simple method for the preparation of dinitronaphthalene from the nitration reaction of 1-nitronaphthalene with NO2 as nitration reagent under the mild conditions has been successfully developed in this work. The results indicated that Ni(CH3COO)2·4H2O catalyst shows better catalytic performances, and the conversion of 1-nitronaphthalene is 33.10 % with 34.10, 23.56, 19.30, and 3.56 % of the selectivity to 1,5-DNN, 1,3-DNN, 1,4-DNN, and 1,8-DNN, respectively, under the optimal reaction conditions. This is a mild, environmentally benign, and economical method for the preparation of dinitronaphthalene.

Highly selective catalytic nitration of 1-nitronaphthalene with NO2 to 1,5-dinitronaphthalene over solid superacid SO42?/ZrO2 promoted by molecular oxygen and acetic anhydride under mild conditions

Yan, Jiaqi,Ni, Wenjin,You, Kuiyi,Duan, Ting,Deng, Renjie,Chen, Yi,Zhao, Fangfang,Liu, Pingle,Luo, He’an

, p. 3569 - 3582 (2021/06/14)

A simple and efficient method for liquid-phase catalytic nitration of 1-nitronaphthalene with NO2 to 1,5-dinitronaphthalene under mild conditions has been developed. The results indicated that the sulfated zirconia (SO42?/ZrO2) as solid superacid catalyst exhibits superior catalytic performance with dioxygen and acetic anhydride. 93.8% conversion of 1-nitronaphthalene and 52.8% 1,5-dinitronaphthalene selectivity were achieved. Furthermore, the physicochemical properties of SO42?/ZrO2 were determined by XRD, Py-FT-IR, BET, FT-IR, Raman spectroscopy and ICP-OES technologies. The possible nitration reaction mechanism over SO42?/ZrO2 catalyst was proposed. The present work provides an easy-to-implement, mild and eco-friendly approach for the efficient preparation of valuable 1,5-dinitronaphthalene, which has extensive industrial application prospects.

Method for preparing diaminonaphthalene

-

Paragraph 0039-0041, (2017/08/29)

The invention provides a method for preparing diaminonaphthalene. The method comprises the following steps: carrying out a nitration reaction by adopting sulfuric acid, fuming nitric acid and naphthalene so as to obtain mixed dinitronaphthalene; adding a second organic solvent, the mixed dinitronaphthalene, a catalyst and activated carbon into a reaction kettle, raising the temperature to 60-65 DEG C, adding hydrazine hydrate, and reacting and separating so as to obtain second filtrate and second filter cake; separating and purifying the second filtrate so as to obtain a solid, namely 1,8-diaminonaphthalene; and separating and purifying the second filter cake so as to obtain 1,5-diaminonaphthalene. According to the preparation of the mixed dinitronaphthalene, the nitratlon reaction is carried out by adopting an organic solvent free method, the waste acid can be recycled, and the yield and treatment cost of the three wastes can be reduced. The mixed dinitronaphthalene is directly reduced, the separation cost is reduced, and the market competitiveness is improved for industrial production. By utilizing different physical properties of the mixed dinitronaphthalene in different organic solvents, 1,8-diaminonaphthalene and 1,5-diaminonaphthalene with high purity are separated.