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6-Cyano-2-naphthol
Cas No: 52927-22-7
No Data 1 Kilogram 10 Metric Ton/Month HANGZHOU YUNUO CHEMICAL CO.,LTD Contact Supplier
6-Cyano-2-naphthol
Cas No: 52927-22-7
No Data No Data No Data CHANGZHOU HANGYU PHARMACEUTICAL TECHNOLOGY CO., LTD Contact Supplier
6-Cyano-2-naphthol
Cas No: 52927-22-7
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality 6-Cyano-2-Naphthol supplier in China
Cas No: 52927-22-7
No Data No Data Metric Ton/Day Simagchem Corporation Contact Supplier
High Quality 99% 52927-22-7 6-Cyano-2-naphthol (Nafamostat mesylate Manufacturer
Cas No: 52927-22-7
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
6-Cyano-2-naphthol
Cas No: 52927-22-7
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
2-Cyano-6-hydroxynaphthalene
Cas No: 52927-22-7
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
6-Cyano-2-naphthol
Cas No: 52927-22-7
USD $ 1.0-1.0 / Kilogram 1 Kilogram 2000 Metric Ton/Year Henan Sinotech Import&Export Corporation Contact Supplier
6-Cyano-2-naphthol
Cas No: 52927-22-7
USD $ 0.9-1.0 / Kilogram 1 Kilogram 1000 Kilogram/Month LIDE PHARMACEUTICALS LIMITED Contact Supplier
6-Cyano-2-naphthol 52927-22-7
Cas No: 52927-22-7
USD $ 7.0-7.0 / Gram 1 Gram 1 Metric Ton/Day Henan Tianfu Chemical Co., Ltd. Contact Supplier

52927-22-7 Usage

Uses

Intermediate of Nafamostat mesilate (N210000).

Chemical Properties

Brown Crystalline Solid
InChI:InChI=1/C11H7NO/c12-7-8-1-2-10-6-11(13)4-3-9(10)5-8/h1-6,13H

52927-22-7SDS

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 6-Cyano-2-naphthol

1.2 Other means of identification

Product number -
Other names 6-Hydroxy-2-Naphthonitrile

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:52927-22-7 SDS

52927-22-7Synthetic route

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate
939822-86-3

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 6h; Electrolysis; Green chemistry;94%
2-cyano-6-methoxynaphthalene
67886-70-8

2-cyano-6-methoxynaphthalene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
91%
With tetrachlorosilane; borontrifluoride acetic acid; lithium iodide In toluene; acetonitrile at 70℃; for 10h;83%
With boron tribromide In dichloromethane at -78 - 20℃; for 16h; Inert atmosphere;69%
With sodium cyanide In dimethyl sulfoxide at 160 - 170℃; for 12h;62%
With boron tribromide
trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
145369-29-5

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 9h; Electrolysis; Green chemistry;91%
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With CuCN In N,N-dimethyl-formamide at 160 - 170℃; for 3h;83%
56%
In ethanol; N,N-dimethyl-formamide
In ethanol; N,N-dimethyl-formamide
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

copper(l) cyanide

copper(l) cyanide

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 160 - 170℃; for 4h; Inert atmosphere;83%
In N,N-dimethyl-formamide at 135℃; for 18h;62%
In N,N-dimethyl-formamide at 150℃;60%
6-hydroxynaphthalene-2-carbaldehyde
78119-82-1

6-hydroxynaphthalene-2-carbaldehyde

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 1h;70%
6-acetoxy-[2]naphthonitrile
860363-16-2

6-acetoxy-[2]naphthonitrile

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With potassium hydroxide
acetate of α,α,α',α'-tetrabromo-3,4-xylenol
78119-72-9

acetate of α,α,α',α'-tetrabromo-3,4-xylenol

acrylonitrile
107-13-1

acrylonitrile

A

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

B

7-hydroxynaphthalene-2-carbonitrile
130200-58-7

7-hydroxynaphthalene-2-carbonitrile

Conditions
ConditionsYield
1) NaI, DMF; 2) hydrolysis; Yield given. Multistep reaction. Title compound not separated from byproducts;
benzoate of α,α,α',α'-tetrabromo-3,4-xylenol
78119-71-8

benzoate of α,α,α',α'-tetrabromo-3,4-xylenol

acrylonitrile
107-13-1

acrylonitrile

A

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

B

7-hydroxynaphthalene-2-carbonitrile
130200-58-7

7-hydroxynaphthalene-2-carbonitrile

Conditions
ConditionsYield
1) NaI, DMF; 2) NaOH, CH3OH; Yield given. Multistep reaction;
1) NaI, DMF; 2) NaOH, CH3OH; Yield given. Multistep reaction. Title compound not separated from byproducts;
6-bromonaphthalen-2-yl acetate
6343-72-2

6-bromonaphthalen-2-yl acetate

copper(I) cyanide
544-92-3

copper(I) cyanide

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With pyridine; copper(II) sulfate In N,N-dimethyl-formamide
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

copper(I) cyanide
544-92-3

copper(I) cyanide

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone at 160℃; for 3h; Substitution;
2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With boron tribromide demethylation;
3,4-dimethylphenyl benzoate
3845-63-4

3,4-dimethylphenyl benzoate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / bromosuccinimide, azoisobutyronitrile / CCl4 / 12 h / Heating; Irradiation
2: 91 percent / NBS, azoisobutyronitrile / CCl4 / 12 h / Heating
3: 1) NaI, DMF; 2) NaOH, CH3OH
View Scheme
Multi-step reaction with 2 steps
1: 88.5 percent / bromosuccinimide, azoisobutyronitrile / CCl4 / 25 h / Heating; Irradiation
2: 1) NaI, DMF; 2) NaOH, CH3OH
View Scheme
benzoate of α,α,α'-tribromo-3,4-xylenol

benzoate of α,α,α'-tribromo-3,4-xylenol

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / NBS, azoisobutyronitrile / CCl4 / 12 h / Heating
2: 1) NaI, DMF; 2) NaOH, CH3OH
View Scheme
6-bromonaphthalen-2-yl acetate
6343-72-2

6-bromonaphthalen-2-yl acetate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper (II)-sulfate; pyridine / 180 - 190 °C
2: methanol. KOH-solution
View Scheme
1-methyl-pyrrolidin-2-one
872-50-4

1-methyl-pyrrolidin-2-one

6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

iron(III) chloride

iron(III) chloride

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With hydrogenchloride; CaCl2 In water
C11H9NO2
1123760-79-1

C11H9NO2

A

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

B

6-cyano-1-naphthol
91059-47-1

6-cyano-1-naphthol

Conditions
ConditionsYield
With perchloric acid In water at 25℃; for 10h; Kinetics; Concentration;
β-naphthol
135-19-3

β-naphthol

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: bromine / acetic acid
1.2: 3 h / Reflux
2.1: N,N-dimethyl-formamide / 4 h / 160 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; tin; bromine / 3 h / Reflux
2: N,N-dimethyl-formamide / 4 h / 160 - 170 °C / Inert atmosphere
View Scheme
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C
1.2: 2 h / 20 °C
2.1: sodium azide; trifluorormethanesulfonic acid / acetonitrile / 1 h / 0 - 20 °C
3.1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C
4.1: toluene-4-sulfonic acid / toluene / 16 h / Reflux
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
6.1: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
6-Methoxy-2-hydroxymethylen-1-tetralon
16252-53-2

6-Methoxy-2-hydroxymethylen-1-tetralon

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium azide; trifluorormethanesulfonic acid / acetonitrile / 1 h / 0 - 20 °C
2: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C
3: toluene-4-sulfonic acid / toluene / 16 h / Reflux
4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
5: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
1-hydroxy-2-cyano-6-methoxy-1,2,3,4-tetrahydronaphthalene
606494-99-9

1-hydroxy-2-cyano-6-methoxy-1,2,3,4-tetrahydronaphthalene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / toluene / 16 h / Reflux
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
3: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile
34093-07-7

6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C
2: toluene-4-sulfonic acid / toluene / 16 h / Reflux
3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
4: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
6-methoxy-3,4-dihydronaphthalene-2-carbonitrile
79215-28-4

6-methoxy-3,4-dihydronaphthalene-2-carbonitrile

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C
2: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere
View Scheme
6-Hydroxy-2-naphthoic acid
16712-64-4

6-Hydroxy-2-naphthoic acid

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 70 °C
2.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 25 °C
3.1: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 - 25 °C
3.2: 16 h / 25 °C
View Scheme
6-hydroxynaphthalene-2-carboxamide
62529-01-5

6-hydroxynaphthalene-2-carboxamide

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Stage #1: 6-hydroxynaphthalene-2-carboxamide With trifluoroacetic anhydride In tetrahydrofuran at 0 - 25℃; for 0.5h;
Stage #2: With pyridine In tetrahydrofuran at 25℃; for 16h;
C11H7ClO2

C11H7ClO2

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 25 °C
2.1: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 - 25 °C
2.2: 16 h / 25 °C
View Scheme
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 8h; Suzuki-Miyaura Coupling; High pressure; Inert atmosphere;
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

6-(aminomethyl)naphthalen-2-ol
199387-77-4

6-(aminomethyl)naphthalen-2-ol

Conditions
ConditionsYield
With ammonia; hydrogen; nickel In methanol; water100%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

D-cysteine hydrochloride
32443-99-5

D-cysteine hydrochloride

(S)-2-(6-hydroxynaphthalen-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
122364-82-3

(S)-2-(6-hydroxynaphthalen-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 80℃; for 5h;100%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

benzyl bromide
100-39-0

benzyl bromide

6-(benzyloxy)-2-cyanonaphthalene
66217-29-6

6-(benzyloxy)-2-cyanonaphthalene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;100%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

4-Methylbenzyl bromide
104-81-4

4-Methylbenzyl bromide

6-((4-methylbenzyl)oxy)-2-naphthonitrile

6-((4-methylbenzyl)oxy)-2-naphthonitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;98%
1-Bromopentane
110-53-2

1-Bromopentane

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

6-(pentyloxy)-2-naphthonitrile

6-(pentyloxy)-2-naphthonitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;98%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

(Z)-tert-butyl (3-methyl-5-oxo-1-phenyl-1H-pyrazol-4(5H)-ylidene) carbamate

(Z)-tert-butyl (3-methyl-5-oxo-1-phenyl-1H-pyrazol-4(5H)-ylidene) carbamate

tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-phenyl-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-phenyl-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 1h; stereoselective reaction;98%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

(Z)-tert-butyl (3-methyl-5-oxo-1-(p-tolyl)-1H-pyrazol-4(5H)-ylidene) carbamate

(Z)-tert-butyl (3-methyl-5-oxo-1-(p-tolyl)-1H-pyrazol-4(5H)-ylidene) carbamate

tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-(p-tolyl)-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-(p-tolyl)-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 1h; stereoselective reaction;98%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

6-p-tolyl-2-naphthonitrile
944042-22-2

6-p-tolyl-2-naphthonitrile

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With potassium phosphate; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere;
Stage #2: 4-methylphenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere;
97%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

5-benzhydryl-6-hydroxy-2-naphthonitrile

5-benzhydryl-6-hydroxy-2-naphthonitrile

Conditions
ConditionsYield
With stannic bromide In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation; Inert atmosphere;97%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
145369-29-5

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 48h;95%
With triethylamine In dichloromethane at 20℃;93%
With pyridine In dichloromethane at 20℃;79.1%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

2,5,8,11-tetraoxatridecan-13-ol tosylate
62921-76-0

2,5,8,11-tetraoxatridecan-13-ol tosylate

tetraethylene glycol methyl 6-cyano-2-naphthyl ether

tetraethylene glycol methyl 6-cyano-2-naphthyl ether

Conditions
ConditionsYield
With potassium hydroxide In 1,2-dimethoxyethane at 80℃; for 16h; Williamson etherification;95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate
939822-86-3

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;95%
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;95%
Stage #1: 6-cyano-2-naphthol With triethylamine In dichloromethane at 0℃; for 0.166667h;
Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 4h;
90%
With dmap; triethylamine In dichloromethane at 20℃;
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

4-methoxycarbonylphenylboronic acid
99768-12-4

4-methoxycarbonylphenylboronic acid

methyl 4-(2-cyanonaphthalen-6-yl)benzoate
1290542-49-2

methyl 4-(2-cyanonaphthalen-6-yl)benzoate

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With potassium phosphate; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere;
Stage #2: 4-methoxycarbonylphenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere;
95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

6-(diphenylphosphoryl)-2-naphthonitrile
1378042-96-6

6-(diphenylphosphoryl)-2-naphthonitrile

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With potassium carbonate; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In acetonitrile at 100℃; for 3h; Inert atmosphere;
Stage #2: Diphenylphosphine oxide With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In acetonitrile at 100℃; for 18h; Inert atmosphere;
95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

[(1,10-phenanthroline)2Cu][O2CCF2Cl]

[(1,10-phenanthroline)2Cu][O2CCF2Cl]

6-(difluoromethoxy)-2-naphthonitrile
1261682-37-4

6-(difluoromethoxy)-2-naphthonitrile

Conditions
ConditionsYield
With sodium hydroxide; phenol In N,N-dimethyl-formamide at 75℃; for 4h; Sealed tube; Inert atmosphere;95%
di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

C19H21N3O5

C19H21N3O5

Conditions
ConditionsYield
With 1,3,4-triphenyl-1,2,4-triazolium hexafluorophosphate; potassium tert-butylate In chloroform at 20℃; for 4h; Inert atmosphere;95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

1-bromo-7-(4-bromophenylthio)heptane

1-bromo-7-(4-bromophenylthio)heptane

1-(4-bromophenylthio)-7-(6-cyano-2-naphthyloxy)heptane

1-(4-bromophenylthio)-7-(6-cyano-2-naphthyloxy)heptane

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 12h; Williamson Ether Synthesis; Reflux;95%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

6-cyanonaphthalen-2-yl methanesulfonate
939822-84-1

6-cyanonaphthalen-2-yl methanesulfonate

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With triethylamine In toluene at 0℃; for 0.166667h;
Stage #2: methanesulfonyl chloride In toluene at 20℃; for 12h;
93%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;91%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

allyl bromide
106-95-6

allyl bromide

6-(allyloxy)-2-naphthonitrile

6-(allyloxy)-2-naphthonitrile

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 70℃; for 4h;93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
1-bromo-butane
109-65-9

1-bromo-butane

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

6-(butyloxy)-2-naphthonitrile
66217-27-4

6-(butyloxy)-2-naphthonitrile

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;93%
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;93%
With potassium carbonate In acetonitrile at 80℃;93%
1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

2-(o-tolyl)naphtho[2,1-b]furan-7-carbonitrile

2-(o-tolyl)naphtho[2,1-b]furan-7-carbonitrile

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform; toluene at 80℃; for 2h; Inert atmosphere; Schlenk technique;93%
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
145369-29-5

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;93%
styrene
100-42-5

styrene

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

6-isocyano-1-(1-phenylethyl)naphthalen-2-ol

6-isocyano-1-(1-phenylethyl)naphthalen-2-ol

Conditions
ConditionsYield
With phosphorous acid In water; 1,2-dichloro-ethane at 100℃; for 18h; Schlenk technique; regioselective reaction;93%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

5-bromo-6-hydroxy-2-naphthonitrile
1192026-57-5

5-bromo-6-hydroxy-2-naphthonitrile

Conditions
ConditionsYield
With bromine; acetic acid at 20℃;92%
With bromine; acetic acid at 25℃; for 2.5h;
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere;
With pyridinium perbromide hydrobromide In acetonitrile at 0℃;
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere; Schlenk technique;
1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate
866562-23-4

1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate

6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

(R)-2-methylene-1-phenyl-1,2-dihydronaphtho[2,1-b]furan-7-carbonitrile

(R)-2-methylene-1-phenyl-1,2-dihydronaphtho[2,1-b]furan-7-carbonitrile

Conditions
ConditionsYield
With (S)-N-[(3,5-dimethylphenyl)(pyridin-2-yl)methylene]-1-[2-(diphenylphosphino)phenyl]ethanamine; copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine In methanol at -20℃; for 12h; Schlenk technique; Inert atmosphere; enantioselective reaction;92%
Stage #1: 1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate; 6-cyano-2-naphthol With (S)-N-[(3,5-dimethylphenyl)(pyridin-2-yl)methylene]-1-[2-(diphenylphosphino)phenyl]ethanamine; copper(II) acetate monohydrate In methanol for 1h; Inert atmosphere;
Stage #2: With N-ethyl-N,N-diisopropylamine In methanol for 24h; Inert atmosphere;
90%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

C10H9BrOS2

C10H9BrOS2

1-(3-bromobenzoyl)-2-(methylthio)-4,5-dioxo-4,5-dihydronaphtho[2,1-b]thiophene-8-carbonitrile

1-(3-bromobenzoyl)-2-(methylthio)-4,5-dioxo-4,5-dihydronaphtho[2,1-b]thiophene-8-carbonitrile

Conditions
ConditionsYield
Stage #1: 6-cyano-2-naphthol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) bis(trifluoromethanesulfonate) In acetic acid at 100℃; for 0.166667h;
Stage #2: C10H9BrOS2 In acetic acid at 100℃; for 4h; chemoselective reaction;
92%
6-cyano-2-naphthol
52927-22-7

6-cyano-2-naphthol

bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride
68641-49-6

bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride

6-cyanonaphthalen-2-yl bis(2-oxo-3-oxazolidinyl)phosphoramide
1231261-78-1

6-cyanonaphthalen-2-yl bis(2-oxo-3-oxazolidinyl)phosphoramide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;91%

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