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571-60-8 Usage

Chemical Properties

brown to greyish powder

Uses

1,4-Dihydroxynaphthalene is frequently used in organic synthesis as a reagent. In particular, it is used in the synthesis of a pH independent and cell permeant fluorescent dye, a hydroxyl regioisomeric 3'',4''-benzorhodol, which can be used as a fluorescent chemosensor and biomarker for biological applications.

Check Digit Verification of cas no

The CAS Registry Mumber 571-60-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 1 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 571-60:
(5*5)+(4*7)+(3*1)+(2*6)+(1*0)=68
68 % 10 = 8
So 571-60-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H8O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6,11-12H

571-60-8 Well-known Company Product Price

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  • Sigma-Aldrich

  • (76149)  1,4-Dihydroxynaphthalene  analytical standard

  • 571-60-8

  • 76149-50MG

  • 458.64CNY

  • Detail
  • Aldrich

  • (70430)  1,4-Dihydroxynaphthalene  technical, ≥90% (HPLC)

  • 571-60-8

  • 70430-10G

  • 1,222.65CNY

  • Detail

571-60-8SDS

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 naphthalene-1,4-diol

1.2 Other means of identification

Product number -
Other names 1,4-Naphthalenediol

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:571-60-8 SDS

571-60-8Synthetic route

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With acetic acid; zinc Ambient temperature; sonication, less than 5 min;100%
With hydrogen; palladium 10% on activated carbon under 2585.81 Torr; for 6h;100%
With sodium dithionite In diethyl ether; water at 20℃; for 1h;100%
3-mercaptopropionic acid ethyl ester
5466-06-8

3-mercaptopropionic acid ethyl ester

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

2-[2-(ethoxycarbonyl)ethyl]thio-1,4-naphthoquinone
234112-67-5

2-[2-(ethoxycarbonyl)ethyl]thio-1,4-naphthoquinone

Conditions
ConditionsYield
In ethanol at 20℃; Substitution;A n/a
B 93%
1,4-diacetoxynaphthalene
5697-00-7

1,4-diacetoxynaphthalene

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

1-acetoxy-4-hydroxynaphthalene
70662-30-5

1-acetoxy-4-hydroxynaphthalene

Conditions
ConditionsYield
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 2.5h; Hydrolysis; deacetylation;A n/a
B 89%
1-methoxy-1,3-butadiene
10034-09-0

1-methoxy-1,3-butadiene

p-benzoquinone
106-51-4

p-benzoquinone

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With [O=P(2-py)3W(CO)(NO)2](BF4)2 In water at 20℃; for 1.5h; Diels-Alder reaction;85%
butyraldehyde
123-72-8

butyraldehyde

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

1-(1,4-dihydroxynaphthalen-2-yl)butan-1-one
72827-02-2

1-(1,4-dihydroxynaphthalen-2-yl)butan-1-one

Conditions
ConditionsYield
In acetone Irradiation; Inert atmosphere; Flow reactor; Green chemistry;A 7 %Spectr.
B 83%
With 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide for 16h; Friedel Crafts acylation; Irradiation; Inert atmosphere; chemoselective reaction;A n/a
B 40%
In acetone; iso-butanol for 14.5h; Friedel-Crafts Acylation; Irradiation; Green chemistry;
Hepta<2.2.2>starphen-5,6,11,12,17,18-hexaol
96722-19-9

Hepta<2.2.2>starphen-5,6,11,12,17,18-hexaol

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

Hepta<2.2.2>starphen-5,18:6,11:12,17-trichinon
6880-74-6

Hepta<2.2.2>starphen-5,18:6,11:12,17-trichinon

C

5,12,17,18-Tetrahydroxyhepta<2.2.2>starphen-6,11-chinon
96722-21-3

5,12,17,18-Tetrahydroxyhepta<2.2.2>starphen-6,11-chinon

Conditions
ConditionsYield
With [1,4]naphthoquinone In acetic acid at 100℃; for 0.0833333h; Yield given;A n/a
B n/a
C 80%
With [1,4]naphthoquinone In acetic acid at 100℃; for 0.0833333h; Yields of byproduct given;A n/a
B n/a
C 80%
2-formylthiophenol
29199-11-9

2-formylthiophenol

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

12-hydroxy-12H-benzo[b]thioxanthene-6,11-dione

12-hydroxy-12H-benzo[b]thioxanthene-6,11-dione

B

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
In ethanol at 20℃; for 4h;A 65%
B n/a
3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With iodosylbenzene; racemic (salen)Mn(III) In acetonitrile at 0℃; for 3h;63%
3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

3-[(1,4-dioxo-1,4-dihydronaphthalene-2-yl)thio]propionic acid
65726-66-1

3-[(1,4-dioxo-1,4-dihydronaphthalene-2-yl)thio]propionic acid

Conditions
ConditionsYield
Stage #1: 3-mercaptopropionic acid; [1,4]naphthoquinone In ethanol at 20℃; for 24h;
Stage #2: With lead dioxide In chloroform at 20℃; for 4h;
A n/a
B 52%
[(R)-1-(3,4-Dimethoxy-phenyl)-ethyl]-(4-methoxy-naphthalen-1-yl)-amine
293307-92-3

[(R)-1-(3,4-Dimethoxy-phenyl)-ethyl]-(4-methoxy-naphthalen-1-yl)-amine

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

1-(R)-(3,4-dimethoxyphenyl)ethylamine
100570-24-9

1-(R)-(3,4-dimethoxyphenyl)ethylamine

Conditions
ConditionsYield
Stage #1: [(R)-1-(3,4-Dimethoxy-phenyl)-ethyl]-(4-methoxy-naphthalen-1-yl)-amine With ammonium cerium(IV) nitrate In water; acetonitrile Oxidation; C-N bond cleavage;
Stage #2: With sodium tetrahydroborate In water; acetonitrile Reduction;
A n/a
B 47%
quinoclamine
2797-51-5

quinoclamine

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

N-(naphthoquinonyl)-N-(3-chloro-1,4-naphthoquinonyl)amine

N-(naphthoquinonyl)-N-(3-chloro-1,4-naphthoquinonyl)amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; pH=12;A n/a
B 41%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With oxygen; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 83℃; under 760.051 Torr; Diels-Alder Cycloaddition; Reflux;41%
(3-methyl-2-butenyl)trifluorosilane
114067-34-4

(3-methyl-2-butenyl)trifluorosilane

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

deoxylapachol
3568-90-9

deoxylapachol

C

2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone
82214-84-4

2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 1h;A 38%
B 28%
C 32%
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

deoxylapachol
3568-90-9

deoxylapachol

C

2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone
82214-84-4

2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions
ConditionsYield
With (3-methyl-2-butenyl)trifluorosilane; tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 1h;A 38%
B 28%
C 32%
Dodecanal
112-54-9

Dodecanal

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

1-(1,4-dihydroxynaphthalen-2-yl)-dodecan-1-one
875243-46-2

1-(1,4-dihydroxynaphthalen-2-yl)-dodecan-1-one

Conditions
ConditionsYield
In acetone Irradiation; Inert atmosphere; Flow reactor; Green chemistry;A 7 %Spectr.
B 32%
With 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide for 16h; Friedel Crafts acylation; Irradiation; Inert atmosphere; chemoselective reaction;
ethylaluminum dichloride
563-43-9

ethylaluminum dichloride

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

4-ethoxy-1-naphthol
27294-38-8

4-ethoxy-1-naphthol

Conditions
ConditionsYield
In toluene at -78℃; for 2h;A 26%
B 44 % Spectr.
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

4-ethoxy-1-naphthol
27294-38-8

4-ethoxy-1-naphthol

Conditions
ConditionsYield
With ethylaluminum dichloride In toluene at -78℃; for 2h;A 26%
B 44 % Spectr.
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

2-chloro-1,4-dihydroxynaphthalene
73661-09-3

2-chloro-1,4-dihydroxynaphthalene

Conditions
ConditionsYield
With (Z)-3-methyl-2-butenyltrichlorosilane In formamide for 24h; Ambient temperature;A 23%
B 18%
2-vinylthiophene
1918-82-7

2-vinylthiophene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

4,5,6,11-tetrahydro-6,11-dioxoanthra<2,1-b>thiophene
80090-37-5

4,5,6,11-tetrahydro-6,11-dioxoanthra<2,1-b>thiophene

Conditions
ConditionsYield
In toluene for 48h; Heating;A n/a
B 22%
naphthalene
91-20-3

naphthalene

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

α-naphthol
90-15-3

α-naphthol

Conditions
ConditionsYield
With peroxygenase; dihydrogen peroxide In acetonitrile at 20℃; for 0.416667h; pH=3; pH-value; Enzymatic reaction;A 15.4%
B 6.7%
2-vinyl-4-methylthiophene
84548-65-2

2-vinyl-4-methylthiophene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

6,11-dihydro-1-methyl-6,11-dioxoanthra<2,1-b>thiophene
84548-67-4

6,11-dihydro-1-methyl-6,11-dioxoanthra<2,1-b>thiophene

C

4,5,6,11-tetrahydro-1-methyl-6,11-dioxoanthra<2,1-b>thiophene
84641-98-5

4,5,6,11-tetrahydro-1-methyl-6,11-dioxoanthra<2,1-b>thiophene

Conditions
ConditionsYield
In toluene for 48h; Heating;A n/a
B 10%
C 5%
α-naphthol
90-15-3

α-naphthol

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
((2-O-C6H4CN)2CH2C(CH3)2)Cu for 12h;A 4.8%
B 6.9%
1,4-dioxane
123-91-1

1,4-dioxane

1,1-Bisethylene
7478-69-5

1,1-Bisethylene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

2-[2,2-bis-(4-dimethylamino-phenyl)-vinyl]-[1,4]naphthoquinone

2-[2,2-bis-(4-dimethylamino-phenyl)-vinyl]-[1,4]naphthoquinone

Conditions
ConditionsYield
at 70℃; unter Lichtausschluss;
α-naphthol
90-15-3

α-naphthol

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With sodium hydroxide; dipotassium peroxodisulfate
With sodium hydroxide; ammonium peroxydisulfate
With CYP175A1; dihydrogen peroxide In aq. phosphate buffer at 50℃; for 1h; pH=7.5; Kinetics; Enzymatic reaction;
α-naphthol
90-15-3

α-naphthol

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

1,2-Dihydroxynaphthalene
574-00-5

1,2-Dihydroxynaphthalene

Conditions
ConditionsYield
With sodium metabisulfite; sodium hydroxide; ozone weiteres Reagens: Sauerstoff;
2-diazo-1,2-naphthoquinone
879-15-2

2-diazo-1,2-naphthoquinone

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With sulfuric acid
4-amino-1-naphthalenesufonic acid
84-86-6

4-amino-1-naphthalenesufonic acid

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

α-naphthol
90-15-3

α-naphthol

C

1-hydroxy-4-naphthalenesulfonate
84-87-7

1-hydroxy-4-naphthalenesulfonate

Conditions
ConditionsYield
at 220 - 300℃; im Autoklaven;
4-amino-1-naphthalenesufonic acid
84-86-6

4-amino-1-naphthalenesufonic acid

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With sodium hydroxide at 220 - 300℃; unter Druck;
1,4-diacetoxynaphthalene
5697-00-7

1,4-diacetoxynaphthalene

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

Conditions
ConditionsYield
With sodium hydroxide; ethanol Kochen des Reaktionsgemisches mit konz. wss. HCl und SnCl2;
Multi-step reaction with 5 steps
1: sodium tetrahydroborate / methanol
2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
3: sodium hydroxide / ethanol / 3 h / 0 °C
4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 0.33 h / 120 °C / Microwave irradiation; Inert atmosphere
5: dihydrogen peroxide
View Scheme
hydroxynaphthylamine
607-30-7

hydroxynaphthylamine

A

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

B

4-amino-1-naphthol
2834-90-4

4-amino-1-naphthol

Conditions
ConditionsYield
With ethanol; sulfuric acid
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Heating;100%
With dihydrogen peroxide; bis-(tributyltin oxide) dioxochromium(VI) In benzene at 50℃; for 1.5h;100%
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Product distribution; Heating; effect of various chromium(VI) based oxidants;100%
[2-(2-thyenyl)ethyl]amine
30433-91-1

[2-(2-thyenyl)ethyl]amine

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

2-((thiophen-2-yl)ethylamino)naphthalene-1,4-dione

2-((thiophen-2-yl)ethylamino)naphthalene-1,4-dione

Conditions
ConditionsYield
With cerium(III) chloride heptahydrate; triethylamine In ethanol at 20℃; Further stages;100%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

benzoyl chloride
98-88-4

benzoyl chloride

1,4-dibenzoyloxy naphthalene
7437-73-2

1,4-dibenzoyloxy naphthalene

Conditions
ConditionsYield
In dichloromethane at 35℃; Flow reactor;99%
With pyridine at 0 - 20℃; for 16h; Reflux;86%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

methacryloyl anhydride
760-93-0

methacryloyl anhydride

1,4-dimethacryloyloxynaphthalene

1,4-dimethacryloyloxynaphthalene

Conditions
ConditionsYield
With dmap In dichloromethane at 35℃; Flow reactor;99%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

dimethyl sulfate
77-78-1

dimethyl sulfate

1,4-dimethoxynaphthalene
10075-62-4

1,4-dimethoxynaphthalene

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; water Flow reactor;97%
With barium dihydroxide; hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide92%
With potassium carbonate In acetone for 1h; Reflux;89%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

ethanol
64-17-5

ethanol

4-ethoxy-1-naphthol
27294-38-8

4-ethoxy-1-naphthol

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;97%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

benzene
71-43-2

benzene

2-phenyl[1,4]naphthoquinone
2348-77-8

2-phenyl[1,4]naphthoquinone

Conditions
ConditionsYield
With palladium(II) acetylacetonate; dimethyl sulfoxide; silver carbonate; Trimethylacetic acid at 140℃; for 24h; Catalytic behavior; Reagent/catalyst; Sealed tube;97%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

diethylene glycol
111-46-6

diethylene glycol

4-(1,4,7-Trioxaheptyl)-1-naphthol
135664-65-2

4-(1,4,7-Trioxaheptyl)-1-naphthol

Conditions
ConditionsYield
With hydrogenchloride96%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

1-thiopropane
107-03-9

1-thiopropane

1,4-bis(1-propylthio)naphthalene

1,4-bis(1-propylthio)naphthalene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 1h; Heating;96%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

1,4-bis(2-mercapto-1-ethylthio)naphthalene

1,4-bis(2-mercapto-1-ethylthio)naphthalene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 1h; Heating;96%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

acetyl chloride
75-36-5

acetyl chloride

1,4-diacetoxynaphthalene
5697-00-7

1,4-diacetoxynaphthalene

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;96%
methanol
67-56-1

methanol

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

A

4-methoxynaphth-1-ol
84-85-5

4-methoxynaphth-1-ol

B

1,4-dimethoxynaphthalene
10075-62-4

1,4-dimethoxynaphthalene

Conditions
ConditionsYield
With hydrogenchloride for 0.25h; Mechanism;A 95%
B 2%
With hydrogenchloride for 0.25h;A 95%
B 2%
With boron trifluoride
propan-1-ol
71-23-8

propan-1-ol

1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

4-Propoxy-[1]naphthol
85-13-2

4-Propoxy-[1]naphthol

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;95%
With hydrogenchloride
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

isopropyl alcohol
67-63-0

isopropyl alcohol

4-isopropyloxynaphth-1-ol
41426-37-3

4-isopropyloxynaphth-1-ol

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;95%
With boron trifluoride at 80℃;
With hydrogenchloride
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

1,3-diphenyl-benzo[c]thiophene-5,6-dicarbaldehyde
64218-57-1

1,3-diphenyl-benzo[c]thiophene-5,6-dicarbaldehyde

1,3-Diphenylnaphthaceno<2,3-c>thiophene-6,11-quinone
84165-86-6

1,3-Diphenylnaphthaceno<2,3-c>thiophene-6,11-quinone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform for 4h; Heating;95%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

2-chloro-ethanol
107-07-3

2-chloro-ethanol

4-(2-chloroethoxy)-1-naphthol
73661-04-8

4-(2-chloroethoxy)-1-naphthol

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;95%
With hydrogenchloride94%
With hydrogenchloride at 20℃; for 7h; Inert atmosphere;91%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

N-Boc-1,3-diaminopropane
75178-96-0

N-Boc-1,3-diaminopropane

tert-butyl 3-(4-hydroxynaphth-1-ylamino)propylcarbamate
1191288-43-3

tert-butyl 3-(4-hydroxynaphth-1-ylamino)propylcarbamate

Conditions
ConditionsYield
In toluene at 120℃; for 1h;95%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

acetic anhydride
108-24-7

acetic anhydride

1,4-diacetoxynaphthalene
5697-00-7

1,4-diacetoxynaphthalene

Conditions
ConditionsYield
With pyridine at 20℃; for 1h;94%
With pyridine at 20℃; for 5h;83%
In pyridine at 20℃; for 1h;54%
With zinc(II) chloride
With sodium acetate
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

4-Isobutoxy-1-naphthol
73661-02-6

4-Isobutoxy-1-naphthol

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;94%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

5-chloro-2-methyl-4-nitroaniline
13852-51-2

5-chloro-2-methyl-4-nitroaniline

2-chloro-5-methyl-1,4-phenylenediamine
5307-03-9

2-chloro-5-methyl-1,4-phenylenediamine

Conditions
ConditionsYield
With sodium hydroxide In water; toluene94%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

butan-1-ol
71-36-3

butan-1-ol

4-Butoxy-[1]naphthol
73661-01-5

4-Butoxy-[1]naphthol

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;93%
With hydrogenchloride
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

4-sec-Butoxy-1-naphthol
73661-03-7

4-sec-Butoxy-1-naphthol

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;93%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

4-(2-Methoxyethoxy)-1-naphthol
70524-63-9

4-(2-Methoxyethoxy)-1-naphthol

Conditions
ConditionsYield
With hydrogenchloride for 0.25h;92%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

4-(1,4,7,10-Tetraoxadecyl)-1-naphthol
135664-66-3

4-(1,4,7,10-Tetraoxadecyl)-1-naphthol

Conditions
ConditionsYield
With hydrogenchloride92%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

bis[(2-pyridyl)methyl]amine
1539-42-0

bis[(2-pyridyl)methyl]amine

2-(bis(pyridin-2-ylmethyl)amino)naphthalene-1,4-dione

2-(bis(pyridin-2-ylmethyl)amino)naphthalene-1,4-dione

Conditions
ConditionsYield
With cerium(III) chloride heptahydrate; triethylamine In ethanol at 20℃; for 4h;92%
With cerium(III) chloride heptahydrate; triethylamine In ethanol at 20℃; for 6h;92%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

2-chloroethyl tosylate
80-41-1

2-chloroethyl tosylate

1,4-bis(2-chloroethoxy)naphthalene

1,4-bis(2-chloroethoxy)naphthalene

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; water for 4h; Reflux;90%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

naphthalene-1,4-diyl bis(trifluoromethanesulfonate)
152873-78-4

naphthalene-1,4-diyl bis(trifluoromethanesulfonate)

Conditions
ConditionsYield
In dichloromethane Flow reactor;89%
With pyridine at 20℃; for 2h; Cooling with ice;72.6%
With pyridine 1.) 0 deg C, 5 min, 2.) 0 deg C to r.t., 24 h; Yield given;

571-60-8Relevant articles and documents

Palladium-Catalyzed Dearomative syn-1,4-Carboamination

Okumura, Mikiko,Shved, Alexander S.,Sarlah, David

, p. 17787 - 17790 (2017)

A dearomative 1,4-carboamination of arenes has been achieved using arenophile cycloaddition and subsequent palladium-catalyzed substitution with nonstabilized lithium enolates. This protocol delivers products with exclusive syn-1,4-selectivity and can be also conducted in an asymmetric fashion. The method allows rapid dearomative difunctionalization of simple aromatic compounds into functional small molecules amenable to further diversification.

An Improved Synthesis of Balsaminone A

Daley, Sharna-Kay A.,Downer-Riley, Nadale K.

, p. 325 - 328 (2019)

A short and efficient synthesis of balsaminone A, a dinaphthofuran-1,4-dione, is described. The eight-step synthesis features two alternate pathways including a base-induced coupling reaction of 4-methoxy-1-naphthol and 2,3-dichloro-1,4-naphthoquinone, as well as a light-mediated cyclization of 1,1'-binaphthoquinone to afford the dinaphthofurandione core. Subsequent ortho formylation yielded a known precursor to balsaminone A, affording the natural product in 20-27% yield. This represents a moderate increase from the previous synthesis of 7.4% yield.

Synthesis of new vitamin K analogues as steroid and xenobiotic receptor (SXR) agonists: Insights into the biological role of the side chain part of vitamin K

Suhara, Yoshitomo,Watanabe, Masato,Motoyoshi, Sayaka,Nakagawa, Kimie,Wada, Akimori,Takeda, Kazuyoshi,Takahashi, Kazuhiko,Tokiwa, Hiroaki,Okano, Toshio

, p. 4918 - 4922 (2011)

Vitamin K2 has been demonstrated to induce gene expression related to bone formation through a nuclear steroid and xenobiotic receptor (SXR). We synthesized new vitamin K analogues with the same isoprene side chains symmetrically introduced at the 2 and 3 positions of 1,4-naphthoquinone and evaluated the transcriptional activity of the target gene. The transcriptional activity was related to the length of the side chain which allowed optimal interaction with ligand-binding domain of SXR.

Stereoselective [4+2] cycloaddition of singlet oxygen to naphthalenes controlled by carbohydrates

Bauch, Marcel,Fudickar, Werner,Linker, Torsten

, (2021/06/12)

Stereoselective reactions of singlet oxygen are of current interest. Since enantioselective photooxygenations have not been realized efficiently, auxiliary control is an attractive alternative. However, the obtained peroxides are often too labile for isolation or further transformations into enantiomerically pure products. Herein, we describe the oxidation of naphthalenes by singlet oxygen, where the face selectivity is controlled by carbohydrates for the first time. The synthesis of the precursors is easily achieved starting from naphthoquinone and a protected glucose derivative in only two steps. Photooxygenations proceed smoothly at low temperature, and we detected the corresponding endoperoxides as sole products by NMR. They are labile and can thermally react back to the parent naphthalenes and singlet oxygen. However, we could isolate and characterize two enantiomerically pure peroxides, which are sufficiently stable at room temperature. An interesting influence of substituents on the stereoselectivities of the photooxygenations has been found, ranging from 51:49 to up to 91:9 dr (diastereomeric ratio). We explain this by a hindered rotation of the carbohydrate substituents, substantiated by a combination of NOESY measurements and theoretical calculations. Finally, we could transfer the chiral information from a pure endoperoxide to an epoxide, which was isolated after cleavage of the sugar chiral auxiliary in enantiomerically pure form.

Single-atom cobalt-fused biomolecule-derived nitrogen-doped carbon nanosheets for selective oxidation reactions

Huang, Haitao,Wei, Qiao-Hua,Xia, Miao,Xie, Zailai,Zhang, Xuefei

, p. 14276 - 14283 (2021/07/13)

Non-noble metal single-atom catalysts hold great promise in selective oxidation reactions, although the progress is still unsatisfactory because of the synthesis challenge and the lack of mechanistic interpretations. Herein, we develop a biomolecule-based strategy to synthesize isolated Co single atom site catalysts by one-step pyrolysis of guanosine and Co precursors. Due to the abundant hydrogen bonding and π-π interaction of guanosine, the as-synthesized Co-N-C catalysts present a hierarchical porous two-dimensional (2D) nanostructure with an ultrahigh specific surface area, large pore volume, and high density of cobalt single atoms. Aberration-corrected electron microscopy and X-ray photoelectron spectroscopy reveal that Co species are present as isolated single sites and stabilized by nitrogen-doped carbon nanosheets. These characteristics make Co-GS-900 suitable as an efficient catalyst for selective oxidation of aromatic alkanes. For oxidation of ethylbenzene, Co-GS-900 exhibits a superior performancefwith 91% conversion and 98% selectivity of acetophenone.

Determining Proton-Coupled Standard Potentials and X-H Bond Dissociation Free Energies in Nonaqueous Solvents Using Open-Circuit Potential Measurements

Agarwal, Rishi G.,Mayer, James M.,Wise, Catherine F.

supporting information, p. 10681 - 10691 (2020/07/06)

Proton-coupled electron transfer (PCET) reactions are increasingly being studied in nonaqueous conditions, where the thermochemistry of PCET substrates is largely unknown. Herein, we report a method to obtain electrochemical standard potentials and calculate the corresponding bond dissociation free energies (BDFEs) of stable PCET reagents in nonaqueous solvents, using open-circuit potential (OCP) measurements. With this method, we measure PCET thermochemistry in acetonitrile and tetrahydrofuran for substrates with O-H and N-H bonds that undergo 1e-/1H+ and 2e-/2H+ redox processes. We also report corrected thermochemical values for the 1/2H2(g)/H?1M and H+/H? (CG) couples in several organic solvents. For 2e-/2H+ couples, OCP measurements provide the multielectron/multiproton standard potential and the average of the two X-H BDFEs. In contrast to traditional approaches for calculating BDFEs from electrochemical measurements, the OCP method directly measures the overall PCET reaction thermodynamics and avoids the need for a pKa scale in the solvent of interest. Consequently, the OCP approach yields more accurate thermochemical values and should be general to any solvent mixture compatible with electrochemical measurements. The longer time scale of OCP measurements enables accurate thermochemical measurements for redox couples with irreversible or distorted electrochemical responses by cyclic voltammetry, provided the PCET reaction is chemically reversible. Recommendations for successful OCP measurements and limitations of the approach are discussed, including the current inability to measure processes involving C-H bonds. As a straightforward and robust technique to determine nonaqueous PCET thermochemistry, these OCP measurements will be broadly valuable, with applications ranging from fundamental reactivity studies to device development.

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