Conditions | Yield |
---|---|
With trifluoroacetyl peroxide In dichloromethane at -5 - 5℃; for 4h; | 85% |
naphthalene
A
1-Nitronaphthalene
B
1,8-dinitronaphthalene
C
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid | |
With Nitrogen dioxide at 100℃; |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at -60 - -50℃; |
Conditions | Yield |
---|---|
With nitric acid | |
With sulfuric acid; nitric acid Erwaermen des Reaktionsprodukts auf 80-90grad; | |
With sulfuric acid; nitric acid | |
With sulfuric acid; nitric acid Erwaermen des Reaktionsprodukts auf 80-90grad; |
Conditions | Yield |
---|---|
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℃; |
Conditions | Yield |
---|---|
With hydrogenchloride Diazotization.Versetzen der neutralisierten Diazoniumsalz-Loesung mit Na3 und Behandlung des gebildeten Diazonium-hexanitrocobaltats(III) mit NaNO2,Cu2O und CuSO4; |
2-amino-1,5-dinitronaphthalene
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
ueber die Diazonium-Verbindung; |
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
With (decomposition) In methanol; dimethyl sulfoxide at 24.9℃; Equilibrium constant; Rate constant; |
naphthalene
A
1,8-dinitronaphthalene
B
1,7-dinitronaphthalene
C
1,6-dinitronaphthalene
D
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
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
A
1-Nitronaphthalene
B
1,8-dinitronaphthalene
C
2,4-dinitronaphthalene
D
2-nitronaphthalene
E
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
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; |
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
With nitric acid |
naphthalene
nitric acid
A
1,8-dinitronaphthalene
B
1,5-dinitronaphthalene
naphthalene
A
1-Nitronaphthalene
B
1,8-dinitronaphthalene
C
1,5-dinitronaphthalene
naphthalene
A
1-Nitronaphthalene
B
2,4-dinitronaphthalene
C
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
at -60 - -50℃; |
1-Nitronaphthalene
sulfuric acid
nitric acid
A
1,8-dinitronaphthalene
B
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
Product distribution; |
1-Nitronaphthalene
sulfuric acid
A
1,8-dinitronaphthalene
B
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
at 0℃; |
5-nitro-1-naphthoic acid
nitric acid
A
4,5-dinitro-[1]naphthoic acid
C
1,5-dinitronaphthalene
3-nitro-benzenesulfonic acid-(1,5-dinitro-[2]naphthylamide)
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2SO4 / 50 °C 2: ueber die Diazonium-Verbindung View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine 2: acetic acid; HNO3 3: H2SO4 / 50 °C 4: ueber die Diazonium-Verbindung View Scheme |
3-nitro-benzenesulfonic acid-(5-nitro-[2]naphthylamide)
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; HNO3 2: H2SO4 / 50 °C 3: ueber die Diazonium-Verbindung View Scheme |
naphthalene
nitric acid
A
1-Nitronaphthalene
B
1,8-dinitronaphthalene
C
1,5-dinitronaphthalene
naphthalene
A
1-Nitronaphthalene
B
1,8-dinitronaphthalene
C
2-nitronaphthalene
D
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
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
A
1,8-dinitronaphthalene
B
2,4-dinitronaphthalene
C
1,4-dinitronaphthalene
D
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
With nickel(II) acetate tetrahydrate; Nitrogen dioxide In acetonitrile at 100℃; for 3h; Temperature; Time; Reagent/catalyst; Sealed tube; regioselective reaction; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; diphenyl ditelluride In ethanol; benzene at 55℃; for 15h; | 92% |
With iodophosphorus; water | |
With sulfuric acid; acetic acid elektrolytische Reduktion an Bleikathoden; |
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In various solvent(s) 1) 4 h, room temperature, 2) 1 h, 50 deg C; | 92% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid for 3h; cooling; | 91% |
With sulfuric acid; nitric acid | |
With sulfuric acid; nitric acid | |
Nitrierung; | |
With sulfuric acid; nitric acid |
Conditions | Yield |
---|---|
With sulfuric acid; potassium nitrate at 20 - 50℃; for 3h; | 85% |
chloromethyl tert-butyl sulfone
1,5-dinitronaphthalene
2-(tert-Butylsulfonylmethyl)-1,5-dinitronaphthalene
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 18 - 22℃; for 0.75h; | 83% |
1,5-dinitronaphthalene
4.8-dinitro-1-hydroxy-naphthalene
Conditions | Yield |
---|---|
With potassium hydroxide; Cumene hydroperoxide In water; dimethyl sulfoxide at 20℃; for 10h; Oxidation; | 83% |
trans-4-methoxy-3-buten-2-one
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
Stage #1: trans-4-methoxy-3-buten-2-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #3: 1,5-dinitronaphthalene In tetrahydrofuran; hexane at -78℃; for 4h; Reagent/catalyst; Inert atmosphere; | 82% |
1,5-dinitronaphthalene
A
4.8-dinitro-1-hydroxy-naphthalene
B
1.5-dinitro-2-hydroxy-naphthalene
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; potassium tert-butylate In ammonia at -33℃; | A 5% B 81% |
With tert.-butylhydroperoxide; sodium hydroxide In ammonia at -33℃; | A 61% B 22% |
With sodium hydroxide; Cumene hydroperoxide In dimethyl sulfoxide at 20℃; for 2h; Product distribution; Further Variations:; Reagents; Solvents; Oxidation; | A 30% B 5% |
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
With chlorosulfonic acid; iodine; chlorine | 81% |
Conditions | Yield |
---|---|
With hydrazine hydrate at 90℃; for 16h; | 80% |
With sodium sulfide; sodium hydrogencarbonate In methanol; water at 70℃; for 0.0833333h; Reflux; | 71% |
With sodiumsulfide nonahydrate; water In ethanol at 65℃; | 60% |
Conditions | Yield |
---|---|
With tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran for 16h; Cyclization; Condensation; Heating; | 78% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Heating; | 44% |
Conditions | Yield |
---|---|
Stage #1: cyclohexenone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #3: 1,5-dinitronaphthalene In tetrahydrofuran; hexane at -78℃; for 14h; Inert atmosphere; | 72% |
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
Stage #1: N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine; 1,5-dinitronaphthalene With trifluoroacetic acid In dichloromethane at 20℃; for 5.5h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In dichloromethane Saturated solution; diastereoselective reaction; | 66% |
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 5.5h; Inert atmosphere; | 66% |
1,5-dinitronaphthalene
5-amino-8-hydroxy-[1,4]naphthoquinone
Conditions | Yield |
---|---|
With sulfuric acid; sulfur trioxide; sulfur 1.) 1 h, 2.) 50 deg C, 10 min, 3.) room temp., 18 h; | 65% |
methanol
carbon monoxide
1,5-dinitronaphthalene
A
dimethyl 1,5-naphthalenedicarbamate
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; dodecacarbonyl-triangulo-triruthenium; montmorillonitebipyridynylpalladium(II) acetate (Pd-clay) In benzene at 180℃; under 53200 Torr; for 24h; | A 64% B 12% |
Conditions | Yield |
---|---|
With bis(acetylacetonato)palladium(II); 18-crown-6 ether; tripotassium phosphate "n" hydrate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane at 130℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; | 61% |
propylamine
1,5-dinitronaphthalene
1,5-dinitro-N-propylnaphthalen-2-amine
Conditions | Yield |
---|---|
With bis(pyridine)silver(I) permanganate In tetrahydrofuran at -15 - -12℃; for 2h; | 60% |
1,5-dinitronaphthalene
N-butylamine
N-butyl-1,5-dinitronaphthalen-2-amine
Conditions | Yield |
---|---|
With bis(pyridine)silver(I) permanganate In tetrahydrofuran at -15 - -12℃; for 2h; | 60% |
Conditions | Yield |
---|---|
Stage #1: 1,5-dinitronaphthalene With perhydrodibenzo-18-crown-6 In benzene for 2h; Stage #2: acetic anhydride | A 59.7% B 24.4% |
ethylamine
1,5-dinitronaphthalene
N-ethyl-1,5-dinitronaphthalen-2-amine
Conditions | Yield |
---|---|
With bis(pyridine)silver(I) permanganate In tetrahydrofuran at -15 - -12℃; for 2h; | 59% |
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
1,5-dinitronaphthalene
Conditions | Yield |
---|---|
Stage #1: N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine; 1,5-dinitronaphthalene With trifluoroacetic acid In dichloromethane at 20℃; for 26h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In dichloromethane Saturated solution; diastereoselective reaction; | 57% |
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 26h; Inert atmosphere; | 57% |
1,5-dinitronaphthalene
A
5-nitro-[1]naphthylamine
B
1,5-diaminonaphthalene
Conditions | Yield |
---|---|
With sodium sulfide; ammonium hydroxide at 80℃; | A 54% B 34% |
With sodium sulfide; ammonium chloride In water at 80 - 85℃; for 4h; | A 54% B 34% |
With nickel; hydrazine hydrate In ethanol; 1,2-dichloro-ethane at 50 - 60℃; for 8h; | A 20.33% B 47.26% |
Conditions | Yield |
---|---|
With sulfuric acid; sulfur for 1h; Ambient temperature; | 50% |
With sulfuric acid; sulfur at 40℃; |
Conditions | Yield |
---|---|
In benzene at 150℃; for 72h; | 48% |
Conditions | Yield |
---|---|
With potassium hydroxide; hydroxylamine hydrochloride In methanol at 50℃; for 2h; | 46% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 12h; Ambient temperature; | 43% |
potassium methanolate
1,5-dinitronaphthalene
A
1-Methoxy-4,8-dinitronaphthalene
B
1,7-Dimethoxy-4,8-dinitronaphthalene
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 14h; Substitution; Methoxylation; | A 18% B 30% |
Chemical Name: 1,5-Dinitronaphthalene
IUPAC NAME: 1,5-Dinitronaphthalene
CAS No.: 605-71-0
EINECS: 210-095-2
RTECS: QJ4551000
RTECS Class: Mutagen
Molecular Formula: C10H6N2O4
Molecular Weight: 218.17 g/mol
Melting Point: 214 °C
Density: 1.481 g/cm3
Flash Point: 200.3 °C
Boiling Point: 389.8 °C at 760 mmHg
Following is the structure of 1,5-Dinitronaphthalene (CAS No.605-71-0):
Product Categories about 1,5-Dinitronaphthalene (CAS No.605-71-0) are Intermediates of Dyes and Pigments ; Naphthalene derivatives ; Nitro Compounds ; Nitrogen Compounds ; Organic Building Blocks
The chemical synonymous of 1,5-Dinitronaphthalene (CAS No.605-71-0) are 1,5-Dinitro-Naphthalen ; Naphthalene,1,5-Dinitro- ; 1,5-Dinitronaphthalene ; Labotest-Bb Lt00436936 ; 1,5-Dinitroaphthalene ; 1,5-Dinitronaphthalene98% ; 1,5-Dinitronaphthalene,Tech.90% ; 1,5-Dinitro Naphtalene
1. | mmo-sat 50 µg/plate | MUREAV Mutation Research. 91 (1981),321. | ||
2. | uns-bac-esc 5 µg/tube | EMMUEG Environmental and Molecular Mutagenesis. 18 (1991),41. | ||
3. | pic-esc 15,500 ng/well | MUREAV Mutation Research. 260 (1991),349. |
A suspected carcinogen. Mutation data reported. Mixtures with sulfur or sulfuric acid (used in commercial reactions) may explode if heated to 120°C. Initiation temperature depends on the quality of the dinitronaphthalene. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS.
Hazard Codes: Xi Xn
Risk Statements about 1,5-Dinitronaphthalene (CAS No.605-71-0):
R41:Risk of serious damage to the eyes.
R43:May cause sensitization by skin contact.
R68:Possible risk of irreversible effects.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements about 1,5-Dinitronaphthalene (CAS No.605-71-0):
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S29:Do not empty into drains.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
Attention:
1. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
2. Handling: Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation.
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
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