1,5-diacetoxynaphthalene
A
1,5-dihydroxynaphthalene
B
5-hydroxynaphthalen-1-yl acetate
Conditions | Yield |
---|---|
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 2.5h; Hydrolysis; deacetylation; | A 60% B 40% |
1,5-dimethoxynaphthalene
A
5-methoxynaphthalen-1-ol
B
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
With Cyclohexyl iodide In N,N-dimethyl-formamide for 2.5h; Heating; | A 43% B 44% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -20℃; for 0.5h; Mechanism; Product distribution; | A 17.5% B 25.5% |
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -20℃; for 0.5h; | A 17.5% B 25.5% |
Conditions | Yield |
---|---|
With sodium hydrogensulfite alkal. Verseifung des entstandenen Sulfits; |
Conditions | Yield |
---|---|
With potassium carbonate beim Schmelzen; | |
With potassium carbonate at 200℃; | |
With sodium hydroxide at 220 - 260℃; beim Schmelzen; |
1-aminonaphthalene-5-sulfonic acid
A
5-amino-1-naphthol
B
1-hydroxynaphthalene-5-sulphonic acid
C
1,5-dihydroxynaphthalene
D
1-amino-naphthalene
Conditions | Yield |
---|---|
at 220 - 300℃; im Autoklaven; |
Conditions | Yield |
---|---|
With sodium hydroxide at 220 - 300℃; unter Druck; |
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
beim Erhitzen; |
Conditions | Yield |
---|---|
at 300℃; | |
at 220 - 260℃; |
Conditions | Yield |
---|---|
Behandeln des Reaktionsprodukts mit Alkali; |
naphthalene
A
1,4-Dihydroxynaphthalene
B
α-naphthol
C
2,7-Dihydroxynaphthalene
D
1,8-dihydroxynaphthalene
E
1,5-dihydroxynaphthalene
F
β-naphthol
Conditions | Yield |
---|---|
With n-butyllithium; potassium tert-butylate Product distribution; multistep reaction; isomer distribution as a function of the solvent and conditions (THF only monosubstitution), also after reaction with Me2SO4; |
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
With potassium carbonate at 300℃; | |
With potassium carbonate at 220 - 260℃; |
Conditions | Yield |
---|---|
at 200℃; beim Schmelzen; | |
beim Schmelzen; |
Conditions | Yield |
---|---|
at 220 - 260℃; beim Schmelzen; |
5-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-3-sulfonic acid
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
In chloroform at 24.85℃; Equilibrium constant; |
4-acetylamino-8-amino-naphthalene-1-sulfonic acid
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: NaOH-solution 2: sodium disulfite / man behandelt das Produkt mit Natronlauge 3: hydrochloric acid 4: NaHSO3 / alkal. Verseifung des entstandenen Sulfits View Scheme |
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: zinc dust; hydrochloric acid / 30 °C 2: NaOH-solution 3: sodium disulfite / man behandelt das Produkt mit Natronlauge 4: hydrochloric acid 5: NaHSO3 / alkal. Verseifung des entstandenen Sulfits View Scheme |
4,8-diamino-naphthalene-1-sulfonic acid
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium disulfite / man behandelt das Produkt mit Natronlauge 2: hydrochloric acid 3: NaHSO3 / alkal. Verseifung des entstandenen Sulfits View Scheme |
8-amino-4-hydroxy-naphthalene-1-sulfonic acid
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrochloric acid 2: NaHSO3 / alkal. Verseifung des entstandenen Sulfits View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: HNO3+H2SO4 2: zinc dust; hydrochloric acid / 30 °C 3: NaOH-solution 4: sodium disulfite / man behandelt das Produkt mit Natronlauge 5: hydrochloric acid 6: NaHSO3 / alkal. Verseifung des entstandenen Sulfits View Scheme |
Conditions | Yield |
---|---|
addn. of alkali; | |
addn. of alkali; |
A
5-methyl-2-hydroxyacetophenone
B
4-hydroxybutanoic acid
C
malic acid
D
2-hydroxyacrylic acid
E
1,5-dihydroxynaphthalene
F
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol
Conditions | Yield |
---|---|
With dihydrogen peroxide pH=3; Kinetics; Reagent/catalyst; Concentration; pH-value; |
Conditions | Yield |
---|---|
Stage #1: disodium 1,5-naphthalenedisulfonate With sodium hydroxide at 300 - 305℃; for 2h; Large scale; Stage #2: With sulfuric acid at 60℃; for 0.133333h; Temperature; Large scale; | 1020 kg |
Conditions | Yield |
---|---|
With air; C32H36Br2N4 In methanol; dichloromethane at 20℃; for 1h; Irradiation; | 100% |
With C39H50N7O2S(1+)*F6P(1-); N,N,N-trimethyl-N-propylammonium bis(trifluoromethanesulfonyl)imide at 25℃; for 3h; Kinetics; UV-irradiation; | 100% |
With C171H45BF2N4; oxygen In methanol; dichloromethane at 20℃; Kinetics; Quantum yield; Reagent/catalyst; | 99.9% |
1,5-dihydroxynaphthalene
magnesium methyl carbonate
1,5-dihydroxy-2,6-naphthalenedicarboxylic acid
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 180℃; under 25857.4 Torr; for 6h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Heating; | 100% |
With potassium carbonate In tetrahydrofuran; acetone Heating / reflux; | 92% |
Stage #1: 1,5-dihydroxynaphthalene With potassium carbonate In acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: allyl bromide In acetonitrile for 12h; Reflux; | 90% |
Conditions | Yield |
---|---|
With pyridine for 1h; | 99% |
With pyridine at 20℃; for 12h; Inert atmosphere; | 98% |
With pyridine at 0 - 100℃; for 8h; Inert atmosphere; | 98% |
1,5-dihydroxynaphthalene
2-(2-Chloroethoxy)ethanol
1,5-bis[2-(2-hydroxyethoxy)ethoxy]naphthalene
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 82℃; | 99% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere; | 75% |
With potassium carbonate In N,N-dimethyl-formamide Heating; | 67% |
allyl methyl carbonate
1,5-dihydroxynaphthalene
1,5-Di-2-propenoxynaphthalene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 25℃; for 24h; Condensation; | 99% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 70 - 140℃; for 0.183333h; Microwave irradiation; | 99% |
With sodium carbonate In acetonitrile at 120℃; for 24h; Schlenk technique; | 47% |
trifluoromethylsulfonic anhydride
1,5-dihydroxynaphthalene
naphthalene-1,5-diyl bis(trifluoromethanesulfonate)
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 0.25h; Inert atmosphere; Schlenk technique; | 98% |
With pyridine In dichloromethane at 0 - 20℃; for 8h; | 97% |
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With sodium dithionite; tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran; water at 20 - 30℃; Inert atmosphere; | 98% |
With potassium carbonate In acetone Inert atmosphere; Reflux; | 95.2% |
With potassium carbonate In acetone for 18h; Reflux; Inert atmosphere; | 88% |
1,5-dihydroxynaphthalene
1-chloro-3-hydroxypropane
1,5-bis(3-hydroxypropoxy)naphthalene
Conditions | Yield |
---|---|
Stage #1: 1,5-dihydroxynaphthalene With potassium carbonate In acetonitrile for 1h; Inert atmosphere; Reflux; Stage #2: 1-chloro-3-hydroxypropane With potassium iodide In acetonitrile for 24h; Inert atmosphere; Heating; | 98% |
With caesium carbonate In acetonitrile Reflux; | 45% |
Conditions | Yield |
---|---|
With oxygen; rose bengal In water for 5h; Irradiation; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 18h; Reflux; | 97% |
With potassium carbonate In acetonitrile for 4h; Heating; | 71% |
1,5-dihydroxynaphthalene
ethyl 6-O-(tert-butyldiphenylsilyl)-4-O-methoxycarbonyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
Conditions | Yield |
---|---|
tris-(dibenzylideneacetone)dipalladium(0); 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 25℃; for 20h; | 97% |
1,5-dihydroxynaphthalene
4-nitro-benzoyl chloride
5-[(4-nitrobenzoyl)oxy]-1-naphthyl 4-nitrobenzoate
Conditions | Yield |
---|---|
With pyridine; dmap at 0 - 140℃; | 97% |
With sodium hydroxide In dichloromethane; water at 10℃; for 3h; Inert atmosphere; |
1,5-dihydroxynaphthalene
p-toluidine
5-hydroxy-4-(p-tolyl)-imino-1-naphthalenone
Conditions | Yield |
---|---|
With sodium periodate In methanol; ethanol at 20℃; for 1h; | 96% |
1,5-dihydroxynaphthalene
4-methoxy-benzaldehyde
malononitrile
3,9-Diamino-1,7-bis-(4-methoxy-phenyl)-1,7-dihydro-4,10-dioxa-chrysene-2,8-dicarbonitrile
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In ethanol at 80℃; | 96% |
1,5-dihydroxynaphthalene
Conditions | Yield |
---|---|
With K2CO3; HCl In N,N-dimethyl-formamide stirring stoich. amts. of Fe-complex and C10H6(OH)2 with excess of K2CO3 (N2-atmosphere, room temp., 16 h), filtration into 10% HCl (pptn.), dissoln. on addn. of Me2CO washings, concn., addn. of concd. aq. NH4PF6 (pptn.); collection (filtration), washing (cold water), drying (vac.), washing (Et2O), drying; elem. anal.; | 96% |
1,5-dihydroxynaphthalene
naphthalene-1,5-diylbis(dimethylphosphoramidite)
N3,N3,N16,N16-tetramethyl-2,4,15,17-tetraoxa-3,16-diphosphapentacyclo[20.4.0.05,10.09,14.018,23]hexacosa-1(22),5(10),6,8,11,13,18,20,23,25-decaene-3,16-diamine
Conditions | Yield |
---|---|
In acetonitrile Cyclization; | 95% |
In acetonitrile Cyclization; |
1,5-dihydroxynaphthalene
p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester
2-[2-(2-{2-[5-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-naphthalen-1-yloxy]-ethoxy}-ethoxy)-ethoxy]-ethanol
Conditions | Yield |
---|---|
With potassium carbonate; lithium bromide In acetonitrile for 24h; Heating; | 94% |
With potassium carbonate; lithium bromide In acetonitrile for 24h; Reflux; | 94% |
With potassium carbonate; lithium bromide In acetonitrile for 36h; Heating; | 90% |
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In ethanol at 80℃; | 94% |
1,5-dihydroxynaphthalene
chloroacetic acid ethyl ester
diethyl 2,2'-(naphthalene-1,5-diylbis(oxy))diacetate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 93% |
With potassium carbonate In acetonitrile for 12h; Reflux; | 79.1% |
1,5-dihydroxynaphthalene
4-chlorobenzaldehyde
malononitrile
2,8-diamino-4,10-bis(4-chlorophenyl)-3,9-dicyano-4H,10H-chromeno[8,7-h]chromene
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In ethanol at 80℃; | 93% |
With triethylamine In ethanol for 0.166667h; Heating; | 82% |
[1,3]-dioxolan-2-one
1,5-dihydroxynaphthalene
2,2'-(naphthalene-1,5-diylbis(oxy))bis(ethan-1-ol)
Conditions | Yield |
---|---|
With 18-crown-6 ether; Aliquat 336; potassium hydroxide In 1,4-dioxane Inert atmosphere; | 92% |
With 1,4-dioxane; methanol; N-benzyl-trimethylammonium hydroxide |
1,5-dihydroxynaphthalene
ethyl acetoacetate
7-hydroxy-4-methyl-benzo[h]chromen-2-one
Conditions | Yield |
---|---|
With MnSb2O6-chitosan nanocomposite In neat (no solvent) at 80℃; for 0.5h; Pechmann Condensation; | 92% |
With silica supported boric trisulfuric anhydride In neat (no solvent) at 85℃; for 1.25h; Pechmann Condensation; | 90% |
With sulfuric acid In water at 20℃; for 24h; Condensation; | 87% |
1,5-dihydroxynaphthalene
ethyl bromoacetate
diethyl 2,2'-(naphthalene-1,5-diylbis(oxy))diacetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 21h; Reflux; | 92% |
With potassium carbonate; acetone; potassium iodide |
1,5-dihydroxynaphthalene
Hexamethylphosphorous triamide
naphthalene-1,5-diylbis(dimethylphosphoramidite)
Conditions | Yield |
---|---|
In acetonitrile at 20℃; Substitution; | 92% |
In acetonitrile Substitution; | |
In acetonitrile at 20℃; for 2h; | |
In acetonitrile |
Conditions | Yield |
---|---|
at 120℃; for 0.5h; | 92% |
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In ethanol at 80℃; | 92% |
1,5-dihydroxynaphthalene
toluene-4-sulfonic acid 2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl ester
2-{2-[2-(2-{2-[2-(5-{2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-naphthalen-1-yloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethanol
Conditions | Yield |
---|---|
With potassium carbonate; lithium bromide In acetonitrile for 36h; Heating; | 92% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; | 84% |
With potassium carbonate In acetone for 20h; Heating; | 47% |
With potassium carbonate; potassium iodide In acetonitrile for 36h; Heating; |
Conditions | Yield |
---|---|
With aluminum tri-bromide at 25℃; for 24h; | 92% |
IUPAC Name: Naphthalene-1,5-diol
Molecular Formula: C10H8O2
Molecular Weight: 160.17 g/mol
Canonical SMILES: c12c(c(ccc2)O)cccc1O
InChI: InChI=1/C10H8O2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6,11-12H
EINECS: 201-487-4
Classification Code: Mutation data
Product Categories: Intermediates of Dyes and Pigments; Naphthalene derivatives
XLogP3: 1.8
H-Bond Donor: 2
H-Bond Acceptor: 2
Surface Tension: 64.4 dyne/cm
Density: 1.33 g/cm3
Flash Point: 193.5 °C
Enthalpy of Vaporization: 64.73 kJ/mol
Boiling Point: 375.4 °C at 760 mmHg
Melting Point: 259-261 °C (dec.)(lit.)
Vapour Pressure of 1,5-Dihydroxy naphthalene (CAS NO.83-56-7): 3.62E-06 mmHg at 25 °C
1,5-Dihydroxy naphthalene (CAS NO.83-56-7) is used as oxidising colouring agents for hair dyeing.
1. | dlt-oin-oin-par 10 ppm | EVETBX Environmental Entomology. 2 (1973),1029. | ||
2. | dlt-oin-oin-skn 10 ppm | EVETBX Environmental Entomology. 2 (1973),1029. |
Reported in EPA TSCA Inventory.
Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: Xn, N, Xi
Risk Statements: 22-51/53-36-36/37/38
R22: Harmful if swallowed.
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R36: Irritating to eyes.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-61-39-29-26
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
S39: Wear eye / face protection.
S29: Do not empty into drains.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS of 1,5-Dihydroxy naphthalene (CAS NO.83-56-7): QJ4740000
1,5-Dihydroxy naphthalene (CAS NO.83-56-7), its Synonyms are 1,6-Naphthalenediol ; CI 76625 ; Durafur Developer E ; Oxidation Base ; 1,5-Naphthalenediol . It is gray powder.
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