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13922-41-3

Basic Information
CAS No.: 13922-41-3
Name: 1-Naphthaleneboronic acid
Molecular Structure:
Molecular Structure of 13922-41-3 (1-Naphthaleneboronic acid)
Formula: C10H9BO2
Molecular Weight: 171.99
Synonyms: NSC78936;a-Naphthaleneboronic acid;a-Naphthylboronic acid;1-Naphthylboric acid;1-Naphthaleneboronicacid (6CI,7CI,8CI);Boronic acid, 1-naphthalenyl- (9CI);(1-Naphthalenyl)boronic acid;
EINECS: 604-119-4
Density: 1.21 g/cm3
Melting Point: 208-214 °C(lit.)
Boiling Point: 381.9 °C at 760 mmHg
Flash Point: 184.8 °C
Solubility: 2.5 g/100 mL in water
Appearance: Off-white to pink beige powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
Transport Information:
PSA: 40.46000
LogP: 0.51960
Synthetic route
90-11-9

1-Bromonaphthalene

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%
121-43-7

Trimethyl borate

90-11-9

1-Bromonaphthalene

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;
5419-55-6

Triisopropyl borate

90-11-9

1-Bromonaphthalene

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%
5419-55-6

Triisopropyl borate

90-11-9

1-Bromonaphthalene

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%
688-71-1

tri-n-propyl borate

90-11-9

1-Bromonaphthalene

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%
67-56-1

methanol

131765-96-3

dicyclohexylamine borane complex

90-11-9

1-Bromonaphthalene

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%
67-56-1

methanol

55124-35-1

diisopropylamine borane

90-11-9

1-Bromonaphthalene

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%
90-11-9

1-Bromonaphthalene

22092-92-8

diisopropopylaminoborane

A

magnesium bromide diisopropylaminoborohydride

B

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%
90-11-9

1-Bromonaphthalene

22092-92-8

diisopropopylaminoborane

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%
90-11-9

1-Bromonaphthalene

73183-34-3

bis(pinacol)diborane

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%
121-43-7

Trimethyl borate

90-11-9

1-Bromonaphthalene

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%
972-09-8

1-(tributylstannyl)naphthalene

13922-41-3

1-Naphthylboronic acid

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

triethyl borate

90-11-9

1-Bromonaphthalene

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;
13675-18-8

tetrahydroxydiboron

90-14-2

1-Iodonaphthalene

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%
703-55-9

1-naphthylmagnesiumbromide

13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With boric acid triisopropyl ester In diethyl ether39%
4250-53-7

(1-naphthyl)dichloroborane

13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With water
13195-76-1

triisobutyl borate

703-55-9

1-naphthylmagnesiumbromide

13922-41-3

1-Naphthylboronic acid

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

Trimethyl borate

703-55-9

1-naphthylmagnesiumbromide

13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
Grignard reaction;
4250-53-7

(1-naphthyl)dichloroborane

13922-41-3

1-Naphthylboronic acid

7519-87-1

tris(1-naphthyl)boroxine

13922-41-3

1-Naphthylboronic acid

1-naphthylboronic acid dimethyl ester

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;
607-51-2

di-[1]naphthyl-mercury

13922-41-3

1-Naphthylboronic acid

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

3-hydroxyphenylboronic acid

13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With sulfuric acid; water
6962-78-3

Tri-naphthalen-1-yl-borane

13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With hydrogen bromide treatment with HBr, hydrolysis;;
With HBr treatment with HBr, hydrolysis;;
102024-92-0

(amino)di-1-naphthylborane

A

91-20-3

naphthalene

B

13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With water hot water;
With H2O hot water;
95561-70-9

(1-C10H7)2BNH-i-C4H9

A

13922-41-3

1-Naphthylboronic acid

B

78-81-9

isobutylamine

Conditions
ConditionsYield
With water heating;
With water heating;
102310-91-8

(1-C10H7)2BNHCH3

A

91-20-3

naphthalene

B

13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With water In water heating;
With water In water heating;
126508-82-5

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

13922-41-3

1-Naphthylboronic acid

Conditions
ConditionsYield
With water
With H2O
696-62-8

para-iodoanisole

13922-41-3

1-Naphthylboronic acid

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%
16932-45-9

1-bromo-2,6-dimethoxybenzene

13922-41-3

1-Naphthylboronic acid

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;
13922-41-3

1-Naphthylboronic acid

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

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

1-bromo-2-methoxynaphthalene

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%
7507-86-0

2-bromo-5-methoxy-benzaldehyde

13922-41-3

1-Naphthylboronic acid

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;
13922-41-3

1-Naphthylboronic acid

99-91-2

para-chloroacetophenone

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%
13922-41-3

1-Naphthylboronic acid

84539-35-5

(3-bromopyridin-4-yl)-dimethyl-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%
104-92-7

1-bromo-4-methoxy-benzene

13922-41-3

1-Naphthylboronic acid

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%
13922-41-3

1-Naphthylboronic acid

445417-44-7

(R)-Nα-benzyloxycarbonyl-(1-bromo-2-napthyl)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%
13922-41-3

1-Naphthylboronic acid

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%
90-11-9

1-Bromonaphthalene

13922-41-3

1-Naphthylboronic acid

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%
6781-98-2

2,6-dimethyl-1-chlorobenzene

13922-41-3

1-Naphthylboronic acid

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%
13922-41-3

1-Naphthylboronic acid

99-90-1

para-bromoacetophenone

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%
5600-21-5

2-amino-6-methyl-4-chloropyrimidine

13922-41-3

1-Naphthylboronic acid

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%
4595-59-9

5-bromopyrimidine

13922-41-3

1-Naphthylboronic acid

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%
656800-67-8

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

13922-41-3

1-Naphthylboronic acid

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%
1011736-47-2

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

13922-41-3

1-Naphthylboronic acid

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%
1162652-16-5

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

13922-41-3

1-Naphthylboronic acid

1171817-78-9

C40H31BN2O2

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

1-Naphthylboronic acid

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%
45644-21-1

6-chloropyridin-2-amine

13922-41-3

1-Naphthylboronic acid

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%
13922-41-3

1-Naphthylboronic acid

77664-95-0

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

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%
13922-41-3

1-Naphthylboronic acid

1-bromo-2-isopropoxy-3-vinylbenzene

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%
1195791-48-0

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

13922-41-3

1-Naphthylboronic acid

C23H14ClNO

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

para-diiodobenzene

13922-41-3

1-Naphthylboronic acid

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%
13922-41-3

1-Naphthylboronic acid

5597-04-6

2-cyanomethylbenzoic acid methyl ester

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%
40288-69-5

N-(2-cyanophenyl)benzamide

13922-41-3

1-Naphthylboronic acid

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%
57774-35-3

4'-bromobiphenyl-4-carbonitrile

13922-41-3

1-Naphthylboronic acid

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%
556-96-7

5-bromo-1,3-xylene

13922-41-3

1-Naphthylboronic acid

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%
13922-41-3

1-Naphthylboronic acid

diphenyliodonium tetrafluoroborate

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%
13922-41-3

1-Naphthylboronic acid

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%
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    Chemical Names 1-Naphthaleneboronic acid CAS No 13922-41-3 MF C10H9BO2 MW 171.99 g/mol

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Specification

The 1-Naphthaleneboronic acid is an organic compound with the formula C10H9BO2. The IUPAC name of this chemical is naphthalen-1-ylboronic acid. With the CAS registry number 13922-41-3, it is also named as Boronic acid, B-1-naphthalenyl-. The product's categories are Blocks; Boronic Acids; Boronic Acid Series; Naphthalene Derivatives; Heterocyclic Compounds; Naphthalene; Organoborons; B (Classes of Boron Compounds). It is off-white to pink beige powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container, kept away from light and stored in thewell-ventilated and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.82; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 3; (6)Polar Surface Area: 18.46 Å2; (7)Index of Refraction: 1.638; (8)Molar Refractivity: 50.84 cm3; (9)Molar Volume: 141.3 cm3; (10)Polarizability: 20.15×10-24 cm3; (11)Surface Tension: 50.4 dyne/cm; (12)Density: 1.21 g/cm3; (13)Flash Point: 184.8 °C; (14)Enthalpy of Vaporization: 66.48 kJ/mol; (15)Boiling Point: 381.9 °C at 760 mmHg; (16)Vapour Pressure: 1.63E-06 mmHg at 25°C.

Preparation of 1-Naphthaleneboronic acid: It can be obtained by tributyl-naphthalen-1-yl-stannane. This reaction needs reagents BH3, H2O and solvent tetrahydrofuran by heating. The reaction time is 4 hours. The yield is 68%.

1-Naphthaleneboronic acid can be obtained by tributyl-naphthalen-1-yl-stannane

Uses of 1-Naphthaleneboronic acid: It is used as pharmaceutical intermediate. And it can react with 4-iodo-3,5-dimethyl-isoxazole to get 4-(1-naphthyl)-3,5-dimethylisoxazole. This reaction needs reagents (PPh3)2PdCl2, NaHCO3 and solvents 1,2-dimethoxy-ethane, H2O at temperature of 80 °C. The reaction time is 18 hours. The yield is 75%.

1-Naphthaleneboronic acid can react with 4-iodo-3,5-dimethyl-isoxazole to get 4-(1-naphthyl)-3,5-dimethylisoxazole

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:OB(O)c2cccc1ccccc12
2. InChI:InChI=1/C10H9BO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7,12-13H
3. InChIKey:HUMMCEUVDBVXTQ-UHFFFAOYAQ

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