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13922-41-3

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13922-41-3 Usage

Chemical Properties

Off-white to pink beige powder. soluble in methanol. Insoluble in water.

Uses

Different sources of media describe the Uses of 13922-41-3 differently. You can refer to the following data:
1. 1-Naphthaleneboronic acid is a useful synthetic intermediate. It is a reagent used to synthesize potassium aryltrifluoroborates which is a convenient precursor of arylboron difluoride lewis acids. It is also useful in the synthesis of polyaromatic hydrocarbons utilizing the Suzuki reaction.
2. Naphthalene-1-boronic acid can be used:Methyl 5-bromo-2-(naphthalene-1-yl)benzoate, which is a starting material for the preparation of 9-anthracene-spirobenzofluorene host materials.A bifunctional polymer used for the hydrolysis of cellulose.9-(Naphthalene-1-yl)anthracene, which is a key intermediate for the preparation of anthracene derived molecular glass having blue emission.1-Naphthaleneboronic acid can also be as a substrate in fluorometric boronic acid based saccharide sensors based on the Suzuki homocoupling reactions.

Precautions

Incompatible with oxidizing agents. Store in a cool, dry condition in a well sealed container. Store at room temperature.

Check Digit Verification of cas no

The CAS Registry Mumber 13922-41-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,9,2 and 2 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13922-41:
(7*1)+(6*3)+(5*9)+(4*2)+(3*2)+(2*4)+(1*1)=93
93 % 10 = 3
So 13922-41-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H9BO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7,12-13H

13922-41-3 Well-known Company Product Price

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  • TCI America

  • (N0630)  1-Naphthaleneboronic Acid (contains varying amounts of Anhydride)  

  • 13922-41-3

  • 1g

  • 195.00CNY

  • Detail
  • TCI America

  • (N0630)  1-Naphthaleneboronic Acid (contains varying amounts of Anhydride)  

  • 13922-41-3

  • 5g

  • 575.00CNY

  • Detail
  • TCI America

  • (N0630)  1-Naphthaleneboronic Acid (contains varying amounts of Anhydride)  

  • 13922-41-3

  • 25g

  • 1,920.00CNY

  • Detail
  • Alfa Aesar

  • (B21219)  1-Naphthaleneboronic acid, 97%   

  • 13922-41-3

  • 1g

  • 272.0CNY

  • Detail
  • Alfa Aesar

  • (B21219)  1-Naphthaleneboronic acid, 97%   

  • 13922-41-3

  • 5g

  • 569.0CNY

  • Detail
  • Alfa Aesar

  • (B21219)  1-Naphthaleneboronic acid, 97%   

  • 13922-41-3

  • 25g

  • 2215.0CNY

  • Detail

13922-41-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Naphthylboronic Acid

1.2 Other means of identification

Product number -
Other names 1-Naphthaleneboronic Acid

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:13922-41-3 SDS

13922-41-3Synthetic route

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: 1-Bromonaphthalene With tert.-butyl lithium In tetrahydrofuran at 78℃; for 0.75h;
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 4h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; ethyl acetate at 20℃;
96%
Stage #1: 1-Bromonaphthalene With diisobutylaluminium hydride; magnesium; lithium chloride In tetrahydrofuran; toluene at 20℃; for 15h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
86%
Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran for 2h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
74%
Trimethyl borate
121-43-7

Trimethyl borate

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5h; Inert atmosphere;
84%
With n-butyllithium In tetrahydrofuran N2; BuLi dropping into org. compd. soln. at -78°C, mixt. keeping 3 h, B-compd. soln. addn. dropwise at -78°C, mixt. allowing to warm to room temp. overnight , stirring 1 h with 10% HCl, extn. (Et2O); org. extracts washing (water), drying, solvent vac. removal;
Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Schlenk technique;
Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; Schlenk technique;
Triisopropyl borate
5419-55-6

Triisopropyl borate

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: Triisopropyl borate; 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water; toluene at 20℃; for 1h;
83%
With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere;83%
With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere;83%
Triisopropyl borate
5419-55-6

Triisopropyl borate

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

water
7732-18-5

water

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: Triisopropyl borate; 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere;
Stage #2: water With hydrogenchloride In tetrahydrofuran; hexane; toluene at 20℃; for 1h;
83%
tri-n-propyl borate
688-71-1

tri-n-propyl borate

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: tri-n-propyl borate; 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water; toluene at 20℃; for 1h;
83%
methanol
67-56-1

methanol

dicyclohexylamine borane complex
131765-96-3

dicyclohexylamine borane complex

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: dicyclohexylamine borane complex; 1-Bromonaphthalene With magnesium In tetrahydrofuran at 70℃;
Stage #2: methanol In tetrahydrofuran at 0℃; for 1h;
Stage #3: With hydrogenchloride; water In methanol at 20℃; for 1h;
82%
methanol
67-56-1

methanol

diisopropylamine borane
55124-35-1

diisopropylamine borane

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 1-Bromonaphthalene In tetrahydrofuran at 70℃;
Stage #3: methanol Further stages;
80%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

diisopropopylaminoborane
22092-92-8

diisopropopylaminoborane

A

magnesium bromide diisopropylaminoborohydride

magnesium bromide diisopropylaminoborohydride

B

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: diisopropopylaminoborane With iodine; magnesium at 25℃; Barbier Coupling Reaction; Reflux; Inert atmosphere;
Stage #2: 1-Bromonaphthalene at 65℃; for 4.083h;
Stage #3: With hydrogenchloride In water at 25 - 65℃; for 0.416667h;
A n/a
B 79%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

diisopropopylaminoborane
22092-92-8

diisopropopylaminoborane

water
7732-18-5

water

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: 1-Bromonaphthalene; diisopropopylaminoborane With magnesium In tetrahydrofuran at 65℃; for 4h; Inert atmosphere;
Stage #2: water With hydrogenchloride In tetrahydrofuran at 65℃; for 0.25h; Barbier Coupling Reaction; Inert atmosphere;
79%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate In toluene at 110 - 120℃; Inert atmosphere;76.3%
Trimethyl borate
121-43-7

Trimethyl borate

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

water
7732-18-5

water

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 0.166667h; Inert atmosphere;
Stage #3: water With hydrogenchloride In tetrahydrofuran for 0.333333h;
73.1%
1-(tributylstannyl)naphthalene
972-09-8

1-(tributylstannyl)naphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With borane; water In tetrahydrofuran for 4h; Heating;68%
triethyl borate
150-46-9

triethyl borate

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: triethyl borate In tetrahydrofuran; hexane at -78℃; for 6h;
62.24%
Stage #1: 1-Bromonaphthalene With iodine; magnesium In tetrahydrofuran at 75℃; for 17h;
Stage #2: triethyl borate In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; Cooling with acetone-dry ice;
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1-Iodonaphthalene
90-14-2

1-Iodonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tributyl-amine; water In acetonitrile at 25℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;48%
1-naphthylmagnesiumbromide
703-55-9

1-naphthylmagnesiumbromide

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With boric acid triisopropyl ester In diethyl ether39%
(1-naphthyl)dichloroborane
4250-53-7

(1-naphthyl)dichloroborane

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With water
triisobutyl borate
13195-76-1

triisobutyl borate

1-naphthylmagnesiumbromide
703-55-9

1-naphthylmagnesiumbromide

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With diethyl ether und anschliessenden Hydrolyse;
Trimethyl borate
121-43-7

Trimethyl borate

1-naphthylmagnesiumbromide
703-55-9

1-naphthylmagnesiumbromide

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Grignard reaction;
(1-naphthyl)dichloroborane
4250-53-7

(1-naphthyl)dichloroborane

water
7732-18-5

water

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

tris(1-naphthyl)boroxine
7519-87-1

tris(1-naphthyl)boroxine

water
7732-18-5

water

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-naphthylboronic acid dimethyl ester

1-naphthylboronic acid dimethyl ester

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; hexane at 5 - 20℃;1.5 g
With hydrogenchloride; water In tetrahydrofuran for 4h;3.74 g
With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; pH=3 - 5;
di-[1]naphthyl-mercury
607-51-2

di-[1]naphthyl-mercury

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trichloride / 120 - 150 °C
2: water
View Scheme
3-hydroxyphenylboronic acid
87199-18-6

3-hydroxyphenylboronic acid

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With sulfuric acid; water
Tri-naphthalen-1-yl-borane
6962-78-3

Tri-naphthalen-1-yl-borane

water
7732-18-5

water

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With hydrogen bromide treatment with HBr, hydrolysis;;
With HBr treatment with HBr, hydrolysis;;
(amino)di-1-naphthylborane
102024-92-0

(amino)di-1-naphthylborane

A

naphthalene
91-20-3

naphthalene

B

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With water hot water;
With H2O hot water;
(1-C10H7)2BNH-i-C4H9
95561-70-9

(1-C10H7)2BNH-i-C4H9

A

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

B

isobutylamine
78-81-9

isobutylamine

Conditions
ConditionsYield
With water heating;
With water heating;
(1-C10H7)2BNHCH3
102310-91-8

(1-C10H7)2BNHCH3

A

naphthalene
91-20-3

naphthalene

B

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With water In water heating;
With water In water heating;
1,2-bis(1-naphthyl)diborane(6)
126508-82-5

1,2-bis(1-naphthyl)diborane(6)

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With water
With H2O
para-iodoanisole
696-62-8

para-iodoanisole

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(4-methoxyphenyl)naphthalene
27331-33-5

1-(4-methoxyphenyl)naphthalene

Conditions
ConditionsYield
With potassium phosphate; tetrabutylammomium bromide In 1,4-dioxane; water at 120℃; for 1.5h; Suzuki Coupling; Inert atmosphere;100%
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
With sodium carbonate; trisphosphine-based palladium In water at 100℃; for 3h; Suzuki-Miyaura cross-coupling;98%
1-bromo-2,6-dimethoxybenzene
16932-45-9

1-bromo-2,6-dimethoxybenzene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(2,6-dimethoxyphenyl)naphthalene
173300-93-1

1-(2,6-dimethoxyphenyl)naphthalene

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); C31H27FeOP In toluene at 70℃; for 24h; Reagent/catalyst; Time; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Sealed tube;100%
With barium dihydroxide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water for 2h; Heating;92%
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; C30H25FeP In toluene at 100℃; for 24h; Suzuki-Miyaura Coupling; Sealed tube;78%
With barium dihydroxide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water Heating;
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

4,6-Dibromo-2,3,7-trimethoxy-cyclohepta-2,4,6-trienone
199609-54-6

4,6-Dibromo-2,3,7-trimethoxy-cyclohepta-2,4,6-trienone

2,3,7-Trimethoxy-4,6-di-naphthalen-1-yl-cyclohepta-2,4,6-trienone

2,3,7-Trimethoxy-4,6-di-naphthalen-1-yl-cyclohepta-2,4,6-trienone

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 100℃; for 16h;100%
1-bromo-2-methoxynaphthalene
3401-47-6

1-bromo-2-methoxynaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 20℃; for 24h; Suzuki-Miyaura reaction; Inert atmosphere; Micellar solution;100%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate In tetrahydrofuran at 20℃; Suzuki coupling; Inert atmosphere;100%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); C31H27FeOP In toluene at 70℃; for 24h; Reagent/catalyst; Time; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Sealed tube;100%
2-bromo-5-methoxy-benzaldehyde
7507-86-0

2-bromo-5-methoxy-benzaldehyde

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

5-methoxy-2-(naphthalen-1-yl)benzaldehyde
199117-07-2

5-methoxy-2-(naphthalen-1-yl)benzaldehyde

Conditions
ConditionsYield
With cesium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 18h; Suzuki reaction; Heating;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; 1,2-dimethoxyethane; water at 100℃; for 12h;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 12h;
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

para-chloroacetophenone
99-91-2

para-chloroacetophenone

1-(4-naphthalen-1-ylphenyl)ethanone

1-(4-naphthalen-1-ylphenyl)ethanone

Conditions
ConditionsYield
With C38H53Cl2N2O2PPd*CH2Cl2; tetrabutylammomium bromide; potassium hydroxide In water at 80℃; for 6h; Suzuki-Miyaura Coupling; Schlenk technique;100%
With potassium phosphate; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; trisodium tris(3-sulfophenyl)phosphine; zinc In 1,4-dioxane; water at 50℃;99%
With potassium fluoride; 18-crown-6 ether; bis-phenanthrylimidazolium chloride; palladium diacetate In tetrahydrofuran at 50℃; for 3h; Suzuki-Miyaura coupling;99%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

(3-bromopyridin-4-yl)-dimethyl-amine
84539-35-5

(3-bromopyridin-4-yl)-dimethyl-amine

dimethyl(3-naphthyl(4-pyridyl))amine

dimethyl(3-naphthyl(4-pyridyl))amine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Arylation; cross-coupling; Suzuki reaction; Heating;100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(4-methoxyphenyl)naphthalene
27331-33-5

1-(4-methoxyphenyl)naphthalene

Conditions
ConditionsYield
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water; acetonitrile at 50℃; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox;100%
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water; acetonitrile at 50℃; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox;100%
With C38H53Cl2N2O2PPd*CH2Cl2; tetrabutylammomium bromide; potassium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique;100%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

(R)-Nα-benzyloxycarbonyl-(1-bromo-2-napthyl)alanine methyl ester
445417-44-7

(R)-Nα-benzyloxycarbonyl-(1-bromo-2-napthyl)alanine methyl ester

(R)-Nα-benzyloxycarbonyl-[1-(1-naphthyl)-2-naphthyl]alanine methyl ester

(R)-Nα-benzyloxycarbonyl-[1-(1-naphthyl)-2-naphthyl]alanine methyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; benzene at 80℃; for 36h; Suzuki cross coupling;100%
With water; tetrakis(triphenylphosphine) palladium(0) In benzene at 80℃; for 36h; Suzuki cross-coupling;100%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1,1'-bisnaphthalene
604-53-5

1,1'-bisnaphthalene

Conditions
ConditionsYield
With 1-bromo-2-methylnaphtalene; bis[1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene]palladium(II) iodide; potassium tert-butylate In ethanol at 20℃; for 2h; Inert atmosphere;100%
With C54H74Cl2N4O2Pd2 In ethanol at 22℃; for 6h;98%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium diacetate; tetraethylammonium perchlorate; potassium carbonate In water; acetonitrile at 20℃; Inert atmosphere; Electrochemical reaction;97%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1,1'-bisnaphthalene
604-53-5

1,1'-bisnaphthalene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate In tetrahydrofuran at 20℃; for 6h; Suzuki coupling; Inert atmosphere;100%
With C64H76Br2N4O2Pd; potassium carbonate In N,N-dimethyl acetamide at 20 - 140℃; for 24h; Suzuki coupling; Inert atmosphere;99%
With potassium fluoride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 48h; Suzuki coupling;97%
2,6-dimethyl-1-chlorobenzene
6781-98-2

2,6-dimethyl-1-chlorobenzene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(2,6-dimethylphenyl)naphthalene
147424-62-2

1-(2,6-dimethylphenyl)naphthalene

Conditions
ConditionsYield
With (3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II); triethylamine In water at 23℃; for 24h; Suzuki-Miyaura reaction; Inert atmosphere; Micellar solution;100%
With naphthalene; Pd(η3-cinnamyl)(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Cl; potassium tert-butylate In tetrahydrofuran; methanol; isopropyl alcohol at 40℃; for 0.5h; Reagent/catalyst; Temperature; Time; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;99%
With potassium phosphate; C29H37O2P; palladium diacetate In toluene at 110℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;99%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

para-bromoacetophenone
99-90-1

para-bromoacetophenone

1-(4-naphthalen-1-ylphenyl)ethanone

1-(4-naphthalen-1-ylphenyl)ethanone

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate In toluene at 80℃; for 10h; Suzuki-Miyaura cross-coupling;100%
With potassium carbonate In ethanol; water at 20℃; for 4h; Suzuki-Miyaura reaction; Inert atmosphere;100%
With potassium phosphate; Pd[1,3,5,7-Me4-2,4,8-trioxa-6-Ph-6-phosphaadamantane]2*dba In toluene at 20℃; for 0.166667h; Suzuki cross-coupling;99%
2-amino-6-methyl-4-chloropyrimidine
5600-21-5

2-amino-6-methyl-4-chloropyrimidine

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

4-methyl-6-(naphthalen-1-yl)-pyrimidin-2-ylamine
92554-55-7

4-methyl-6-(naphthalen-1-yl)-pyrimidin-2-ylamine

Conditions
ConditionsYield
With potassium phosphate monohydrate; C66H84O10P2Pd In water; ethyl acetate; toluene at 45℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 100℃; for 14h; Suzuki-Miyaura cross-coupling;92%
5-bromopyrimidine
4595-59-9

5-bromopyrimidine

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

5-(naphthalen-1-yl)pyrimidine

5-(naphthalen-1-yl)pyrimidine

Conditions
ConditionsYield
With potassium phosphate monohydrate; C66H84O10P2Pd In water; toluene at 45℃; for 4.5h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With (3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II); potassium carbonate In ethanol at 40℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry;99%
With potassium carbonate In water; toluene at 90℃; for 0.5h; Suzuki-Miyaura Coupling;97%
4-bromo-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one
656800-67-8

4-bromo-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

3,5,6,7-tetrahydro-2-methyl-4-(1-naphthalenyl)-s-hydraindacen-1(2H)-one
656800-71-4

3,5,6,7-tetrahydro-2-methyl-4-(1-naphthalenyl)-s-hydraindacen-1(2H)-one

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 16h; Heating / reflux;100%
3-benzyl-2-chloro-6-p-tolylfuro[2,3-b]pyrazine
1011736-47-2

3-benzyl-2-chloro-6-p-tolylfuro[2,3-b]pyrazine

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

3-benzyl-2-(naphthalen-1-yl)-6-p-tolylfuro[2,3-b]pyrazine
1011736-54-1

3-benzyl-2-(naphthalen-1-yl)-6-p-tolylfuro[2,3-b]pyrazine

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Suzuki coupling; microwave irradiation;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Suzuki-Miyaura reaction; Microwave irradiation; regioselective reaction;100%
(mesityl)C((C4H2N)(C6H4)OH)((C4H3N)(C6H4)OH)
1162652-16-5

(mesityl)C((C4H2N)(C6H4)OH)((C4H3N)(C6H4)OH)

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

C40H31BN2O2
1171817-78-9

C40H31BN2O2

Conditions
ConditionsYield
In chloroform for 3h; Reflux;100%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

α-naphthol
90-15-3

α-naphthol

Conditions
ConditionsYield
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h;100%
With dihydrogen peroxide at 30℃; for 5h; Green chemistry;98%
With water; dihydrogen peroxide at 20℃; for 0.166667h; Green chemistry;97%
6-chloropyridin-2-amine
45644-21-1

6-chloropyridin-2-amine

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

6-naphthalen-1-yl-pyridin-2-ylamine
1028834-19-6

6-naphthalen-1-yl-pyridin-2-ylamine

Conditions
ConditionsYield
With potassium phosphate monohydrate; Ethyl 4-bromobenzoate; C52H49PRu; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 1.16667h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-chloro-7-methoxy-3,4-dihydronaphthalene-2-carboxaldehyde
77664-95-0

1-chloro-7-methoxy-3,4-dihydronaphthalene-2-carboxaldehyde

7-methoxy-3,4-dihydro-[1,1′-binaphthalene]-2-carbaldehyde

7-methoxy-3,4-dihydro-[1,1′-binaphthalene]-2-carbaldehyde

Conditions
ConditionsYield
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water at 45℃; for 1.5h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-bromo-2-isopropoxy-3-vinylbenzene

1-bromo-2-isopropoxy-3-vinylbenzene

1-(2-isopropoxy-3-vinylphenyl)naphthalene

1-(2-isopropoxy-3-vinylphenyl)naphthalene

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran; water for 3h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;100%
4-bromo-6-chloro-2-phenylbenzo[d]oxazole
1195791-48-0

4-bromo-6-chloro-2-phenylbenzo[d]oxazole

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

C23H14ClNO

C23H14ClNO

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 2h; Reflux;100%
para-diiodobenzene
624-38-4

para-diiodobenzene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1,4-di(naphthalen-1-yl)benzene
64065-97-0

1,4-di(naphthalen-1-yl)benzene

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 80℃; for 4h; Suzuki-Miyaura Coupling;100%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

2-cyanomethylbenzoic acid methyl ester
5597-04-6

2-cyanomethylbenzoic acid methyl ester

3-(naphthalen-1-yl)isoquinolin-1-(2H)-one
130369-98-1

3-(naphthalen-1-yl)isoquinolin-1-(2H)-one

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium(II) trifluoroacetate; trifluoroacetic acid In tetrahydrofuran at 85℃; for 20h; Catalytic behavior; Reagent/catalyst; Solvent;99.4%
With [2,2]bipyridinyl; palladium(II) trifluoroacetate; trifluoroacetic acid In tetrahydrofuran at 80℃; for 24h; Schlenk technique;99%
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); zinc(II) chloride In 2-methyltetrahydrofuran at 120℃; for 48h; Schlenk technique;86%
N-(2-cyanophenyl)benzamide
40288-69-5

N-(2-cyanophenyl)benzamide

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

4-(naphthalen-1-yl)-2-phenylquinazoline

4-(naphthalen-1-yl)-2-phenylquinazoline

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium diacetate; trifluoroacetic acid In tetrahydrofuran at 90℃; for 16h; Reagent/catalyst; Solvent;99.4%
With [2,2]bipyridinyl; palladium diacetate; trifluoroacetic acid In tetrahydrofuran at 80℃; for 24h; Schlenk technique;91%
4'-bromobiphenyl-4-carbonitrile
57774-35-3

4'-bromobiphenyl-4-carbonitrile

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

4'-(naphthalen-1-yl)[1,1'-biphenyl]-4-carbonitrile

4'-(naphthalen-1-yl)[1,1'-biphenyl]-4-carbonitrile

Conditions
ConditionsYield
Stage #1: 4'-bromobiphenyl-4-carbonitrile; 1-Naphthylboronic acid With potassium carbonate In toluene Inert atmosphere;
Stage #2: With palladium diacetate; tri(m-tolyl)phosphine In toluene at 90℃;
99.3%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(3,5-dimethylphenyl)naphthalene
164172-87-6

1-(3,5-dimethylphenyl)naphthalene

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(1-(naphtho[2,3-b]furan-9-yl)naphthalen-2-yl)phosphine In toluene at 80℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;99%
With palladium diacetate; 5A molecular sieve; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 4h;73%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

diphenyliodonium tetrafluoroborate

diphenyliodonium tetrafluoroborate

1-phenylnaphthalene
605-02-7

1-phenylnaphthalene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 0.416667h; Ambient temperature;99%
With copper(l) iodide; sodium carbonate In 1,2-dimethoxyethane; water at 35℃; for 0.333333h;96%
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

potassium trifluoro(naphth-1-yl)borate
166328-07-0

potassium trifluoro(naphth-1-yl)borate

Conditions
ConditionsYield
Stage #1: 1-Naphthylboronic acid With potassium fluoride In water; acetonitrile at 21℃;
Stage #2: With L-Tartaric acid In tetrahydrofuran; water; acetonitrile
99%
With potassium hydrogen bifluoride In methanol; water at 20℃; Fluorination;94%
With potassium hydrogen bifluoride In methanol; water for 0.5h;81%

13922-41-3Relevant articles and documents

Oil-in-water microemulsion: An effective medium for triplet-triplet annihilated upconversion with efficient triplet acceptors

Ye, Changqing,Wang, Bao,Hao, Roukang,Wang, Xiaomei,Ding, Ping,Tao, Xutang,Chen, Zhigang,Liang, Zuoqin,Zhou, Yuyang

, p. 8507 - 8514 (2014)

The oil-in-water (o/w) microemulsion containing bimolecular system of acceptor (9,10-dinaphthylanthracene) and sensitizer (Pd(ii)tetratolylporphyrin), i.e., upconverted o/w microemulsion, was firstly reported for the triplet-triplet annihilated upconversion (TTA-UC) by temperature effects. The correlation between structure/up-conversion performance of three 9,10-dinaphthylanthracenes doped with Pd(ii)tetratolylporphyrin were investigated. Under excitation at an ultralow power density at 60 mW cm-2, the up-converted o/w microemulsion emits green-to-blue upconversion and an efficiency (ΦUC) increase is accompanied by an increase in temperature. The maximum ΦUCvalue for the upconverted o/w microemulsion obtained was as high as 33.12%, which is comparable to its counterpart in a pure organic solvent. Very importantly, there is no need for the upconverted o/w microemulsion to deaerate, which is of critical importance for applications such as upconversion-powered photoelectrochemistry. To the best of our knowledge, the current study represents a simple approach to obtain high TTA-UC without degassing.

Synthesis and photophysical processes of a novel 1,10-phenanthroline-containing p-conjugated chromophores and Zn(II) chelated complex

Zhang, Caihong,Feng, Liheng,Chen, Zhaobin

, p. 1204 - 1207 (2007)

A novel 1,10-phenanthroline-containing p-conjugated chromophore, 3,8-di-(1-naphthyl)-1,10-phenanthroline, was synthesized by Suzuki reaction and its chelated complex was prepared. The UV-visible spectroscopy and photoluminescent (PL) properties were investigated. The results show that when the solution of the complex in THF located in low concentration range (-6 mol/L), the fluorescence emission exhibit only one emission band and the excimer is formed with gradual increase in concentration of the complex. The emission spectra of the complex show obvious solvent effect. In addition, the intermolecular action between the complex and fullerene (C60) were investigated. The fluorescence intensity of the complex is decreased and the maximal emission obvious red-shifted with the increasing of the concentration of C60, which suggests that the strong interactions between the complex and C60 happen in the excited state.

Synthesis and functional properties of symmetrically naphthyl-Based oligoarylenes with high glass-transition temperatures

Zhang, Xiaolinga,Sun, Kanga,Liu, Yurong,Xiong, Mojunb,Xia, Pingfanga,Li, Zhonghui,Cao, Zijian

, p. 1034 - 1040 (2010)

Symmetrically naphthyl-based π-conjugated oligoarylenes, OPP(4)Ph-TNp, OPP(4)An-TNp and OPP(4)OXTNp have successfully been synthesized by a divergent approach using Pd-catalyzed Suzuki cross-coupling reaction of diiodo- or dibromo-oligoarylene and arylboronic acid as a key step. Their optical, electrochemical and thermal properties have also been characterized. These newly synthesized naphthyl-based oligoarylenes show highly morphological (Tg 149-187 °C) and thermal (Tdec 509-597 °C) stabilities as well as exhibit potential applications in optoelectronic fields.

The synthesis and application of 2-acetyl-6-(1-naphthyl)-pyridine oxime as a new ligand for palladium precatalyst in suzuki coupling reaction

Zhou, Yongchang,Kijima, Tatsuro,Izumi, Taeko

, p. 116 - 118 (2009)

The synthesis of 2-acetyl-6-(1-naphthyl)-pyridine oxime ligand from 2,6-dibromopyridine and 1-bromo-naphthalene is described, and the new palladium(II) complex used as a Pd(0) precatalyst in the Suzuki cross-coupling reaction was studied. The results showed that the novel naphthalene pyridine oxime complex could serve as an efficient precatalyst.

Magnesiation of Aryl Fluorides Catalyzed by a Rhodium-Aluminum Complex

Fujii, Ikuya,Semba, Kazuhiko,Li, Qiao-Zhi,Sakaki, Shigeyoshi,Nakao, Yoshiaki

supporting information, p. 11647 - 11652 (2020/08/06)

We report the magnesiation of aryl fluorides catalyzed by an Al-Rh heterobimetallic complex. We show that the complex is highly reactive to cleave the C-F bonds across the polarized Al-Rh bond under mild conditions. The reaction allows the use of an easy-to-handle magnesium powder to generate a range of arylmagnesium reagents from aryl fluorides, which are conventionally inert to such metalation compared with other aryl halides.

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu

, p. 164 - 171 (2018/12/05)

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.

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