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Phenylboronic acid
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High purity and quality Phenylboronic acid
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98-80-6 Usage

Safety Profile

Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.Mildly toxic by skin contact. When heated to decomposition it emitsacrid smoke and irritating fumes.

Uses

Phenylboronic Acid is a compound used in organic synthesis of various pharmaceutical goods. Phenylboronic acid (PBA) and its derivatives can bind sugars and other diol compounds to form cyclic boronate esters. These esters bear negative charges. Due to this reaction, sugars can be detected by means of electrochemical and optical techniques. PBA modified electrodes have been constructed as reagentless electrochemical sensors. There, PBA is absorbed on the electrode surface either as a self- assembled monolayer film ore a polymer thin film. Basically, for optical detection techniques for the detection of sugars, PBA is modified with a chromophore that should change its properties on reaction with a sugar. Reaction of Phenylboronic acid with a sugar

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 68, 1963The Journal of Organic Chemistry, 49, p. 5237, 1984 DOI: 10.1021/jo00200a045

Chemical Properties

white to light yellow crystal powder

Uses

Reagent used for? ;Rhodium-catalyzed intramolecular amination1 ? ;Pd-catalyzed direct arylation2 ? ;Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles3 ? ;Palladium-catalyzed stereoselective Heck-type reaction4 ? ;Highly effective Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water5 Reagent used in Preparation of? ;Ni(II) pincer complex and Pd(II) pyridoxal hydrazone metallacycles as catalysts for the Suzuki-Miyaura cross-coupling reactions6,7? ;N-type polymers for all-polymer solar cells8 ?

Uses

suzuki reaction

Uses

Phenylboronic acid and its derivatives form complexes with polyol compounds such as saccharides and poly(vinyl alcohol) (PVA). Glucose-sensitive hydrogels can be prepared by using phenylhoronic acid as a ligand for target glucose. For example. a copolymer with phenylboronic acid moieties was synthesized by copolymerization of 4V-vinyl-2-pyrrolidone (NVP) and 3-(acryl- amide)phcnylhoronic acid (PBA). The complexes between the NVP-PBA copolymer and PVA enable us to construct glucose-sensitive insulin release systems because the complexes dissociated in response to the glucose concentration. This phenylboronic acid is soluble in water and the coupling reaction can even be carried out in water. It is compatible with many organic substituents such as esters, ketones, alcohols, etc. which would prohibit the use of Grignard reagents in coupling reactions.
InChI:InChI=1/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H

98-80-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (B0857)  Phenylboronic Acid (contains varying amounts of Anhydride)   98-80-6 5g 80.00CNY Detail
TCI America (B0857)  Phenylboronic Acid (contains varying amounts of Anhydride)   98-80-6 25g 230.00CNY Detail
TCI America (B0857)  Phenylboronic Acid (contains varying amounts of Anhydride)   98-80-6 250g 1,280.00CNY Detail
Alfa Aesar (A14257)  Benzeneboronic acid, 98+%    98-80-6 10g 234.0CNY Detail
Alfa Aesar (A14257)  Benzeneboronic acid, 98+%    98-80-6 50g 930.0CNY Detail
Alfa Aesar (A14257)  Benzeneboronic acid, 98+%    98-80-6 250g 3414.0CNY Detail

98-80-6SDS

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 phenylboronic acid

1.2 Other means of identification

Product number -
Other names Boronic acid,phenyl

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:98-80-6 SDS

98-80-6Synthetic route

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With potassium hydrogen difluoride In methanol at 20℃; for 0.25h;
Stage #2: With lithium hydroxide In acetonitrile at 20℃; for 20h;
100%
With hydrogenchloride In water at 20℃; for 15h;100%
With polystyrene boronic acid; trifluoroacetic acid In acetonitrile for 18h; Heating;98%
Multi-step reaction with 2 steps
1: diethyl ether / 0.5 h / 20 °C
2: hydrogenchloride / water / 0.33 h
View Scheme
With dimyristoylphosphatidylcholine; water In dimethyl sulfoxide at 20℃; for 168h;
1-chloro-3,5-dimethylbenzene
556-97-8

1-chloro-3,5-dimethylbenzene

A

3,5-dimethylbiphenyl
17057-88-4

3,5-dimethylbiphenyl

B

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With cesium fluoride; Pd(dba)2 In tolueneA n/a
B 99%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;98%
water
7732-18-5

water

potassium phenyltrifluoborate

potassium phenyltrifluoborate

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With montmorillonite K10 at 25℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature;97%
With 1H-imidazole; iron(III) chloride at 20℃; for 0.25h; Catalytic behavior; Solvent; Reagent/catalyst; Time; Inert atmosphere;87%
With glass or Cs2CO3 In tetrahydrofuran; water Kinetics; hydrolysis at 55°C in THF/H2O in the presence of glass powder or Cs2CO3; not isolated;
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; Reagent/catalyst; Solvent;97%
tributylphenylstannane
960-16-7

tributylphenylstannane

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With borane; water In tetrahydrofuran for 1h; Heating;96%
diisopropopylaminoborane
22092-92-8

diisopropopylaminoborane

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
at -78 - -45℃;95%
diisopropopylaminoborane
22092-92-8

diisopropopylaminoborane

water
7732-18-5

water

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: diisopropopylaminoborane; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: water With hydrogenchloride In tetrahydrofuran at 0℃; for 0.583333h; Inert atmosphere;
95%
diisopropylamine borane
55124-35-1

diisopropylamine borane

water
7732-18-5

water

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: diisopropylamine borane; phenylmagnesium bromide In tetrahydrofuran at 20℃;
Stage #2: water In tetrahydrofuran; methanol
95%
Sb2O4B2(C6H5)8
244109-23-7

Sb2O4B2(C6H5)8

acetic acid
64-19-7

acetic acid

A

diacetoxotriphenylantimony

diacetoxotriphenylantimony

B

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
excess acid addn. to soln. of Sb-compd., refluxing (3 h), volatile products collecting in cooled trap; products sepn. by ether;A 94%
B 92%
Trimethyl borate
121-43-7

Trimethyl borate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Temperature; Concentration; Flow reactor;93.9%
bromobenzene
108-86-1

bromobenzene

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;92%
With [{Pd(μ-Cl){κ2-P,C-P(iPr)2(OC6H3-2-Ph)}}2]; sodium acetate In dichloromethane; water at 40℃; for 6h; Inert atmosphere;
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 80℃; for 4h; Miyaura Borylation Reaction; Schlenk technique; Inert atmosphere; Sealed tube;
dicyclohexylamine borane complex
131765-96-3

dicyclohexylamine borane complex

water
7732-18-5

water

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: dicyclohexylamine borane complex; phenylmagnesium bromide In tetrahydrofuran at 20℃;
Stage #2: With methanol In tetrahydrofuran
Stage #3: water In tetrahydrofuran
92%
benzene
71-43-2

benzene

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With bis(pinacol)diborane; Ir(o-O-C6H4-CH=N=CH2Ph)(cod) at 80℃; for 21h; Product distribution; Further Variations:; Solvents;91%
Stage #1: benzene With Pinacolborane; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(l) dimer at 80℃; for 24h;
Stage #2: With sodium periodate In tetrahydrofuran; water for 0.5h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 17h;
Multi-step reaction with 2 steps
1: Pd
2: H2O
View Scheme
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

benzene
71-43-2

benzene

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With tetra-2-pyridinylpyrazine; [Ir(I)(salicylidenebenzyliminato)(1,5-cyclooctadiene)] In dichloromethane; benzene under Ar; mixt. was heated at 80°C for 21 h in mixt. of 3 ml benzene and 2 ml each CH2Cl2 and ionic liquid TBPD (tributyltetradecylphosphonium dodecylbenzenesulfonate) as solvent; solvent was removed under reduced pressure, Et2O was added, after 10% aq. HCl was added, mixt. stirred for 4 h, organic layer dried with MgSO4, solvent was removed under reduced pressure, residue was chromd. (flash chromy, SiO2); NMR;91%
With tetra-2-pyridinylpyrazine; [Ir(I)(salicylidenebenzyliminato)(1,5-cyclooctadiene)] In benzene under Ar; soln. of Ir complex and pyridinylpyrazine was prepared, pinacolato soln. was added, mixt. was then heated at 80°C for 21 h; solvent was removed under reduced pressure, Et2O was added, after 10% aq. HCl was added, mixt. stirred for 4 h, organic layer dried with MgSO4, solvent was removed under reduced pressure, residue was chromd. (flash chromy, SiO2); NMR;70%
With tetra-2-pyridinylpyrazine; [Ir(I)(salicylidenebenzyliminato)(1,5-cyclooctadiene)] In benzene High Pressure; under Ar; soln. of Ir complex and pyridinylpyrazine was prepared in glove box, pinacolato soln. and prepared catalyst and ligand soln. were placed in autoclave, mixt. was then heated at 100°C for 40 h; solvent was removed under reduced pressure, Et2O was added, after 10% aq. HCl was added, mixt. stirred for 4 h, organic layer dried with MgSO4, solvent was removed under reduced pressure, residue was chromd. (flash chromy, SiO2); NMR;67%
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

benzene
71-43-2

benzene

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; benzene other Radiation; under Ar atm. mixt. HBpin, nano-Ir(0) cat. prepd by reduction (Ph3P)2Ir(H)(7,8-nido-C2B9H11), tetra-2-pyridinylpyrazine, benzene, CH2Cl2 and trihexyltetradecylphosphonium methylsulfonate was heated at 130°C for 1 h in microwave, hydrolysis aq.HCl; flash chromy.;91%
With hydrogenchloride In dichloromethane; benzene Sonication; under Ar atm. mixt. HBpin, nano-Ir(0) cat. prepd by reduction (Ph3P)2Ir(H)(7,8-nido-C2B9H11), tetra-2-pyridinylpyrazine, benzene, CH2Cl2 and trihexyltetradecylphosphonium methylsulfonate was heated at 80°C for4 h in ultrasonic, hydrolysis aq.HCl; flash chromy.;61%
With hydrogenchloride In dichloromethane; benzene High Pressure; under Ar atm. mixt. HBpin, nano-Ir(0) cat. prepd by reduction (Ph3P)2Ir(H)(7,8-nido-C2B9H11), tetra-2-pyridinylpyrazine, benzene, CH2Cl2 and trihexyltetradecylphosphonium methylsulfonate was heated at 180°C for 12 h, hydrolysis with aq.HCl; flash chromy.;50%
C22H27BN4O3

C22H27BN4O3

boric acid
11113-50-1

boric acid

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With acetic acid In water90%
methanol
67-56-1

methanol

bromobenzene
108-86-1

bromobenzene

diisopropylamine borane
55124-35-1

diisopropylamine borane

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: bromobenzene In tetrahydrofuran at 70℃;
Stage #3: methanol Further stages;
88%
potassium phenyltrifluoborate

potassium phenyltrifluoborate

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With iron(III) chloride; water In tetrahydrofuran at 20℃; for 0.5h;86%
With water; silica gel at 20℃; for 4h; Inert atmosphere;65%
In phosphate buffer pH=6.9 - 7.0; Kinetics;
With water In tetrahydrofuran at 55℃; Kinetics; Reagent/catalyst;
bromobenzene
108-86-1

bromobenzene

triethyl borate
150-46-9

triethyl borate

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;82.7%
With n-butyllithium In tetrahydrofuran
bromobenzene
108-86-1

bromobenzene

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: bromobenzene With triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 65℃;
Stage #2: With sodium hydroxide In tetrahydrofuran Further stages.;
82%
Stage #1: bromobenzene With Trimethyl borate In tetrahydrofuran at -20 - 0℃; Inert atmosphere;
Stage #2: With sulfuric acid In tetrahydrofuran at 0 - 10℃; for 10h; Inert atmosphere;
82.4%
Stage #1: bromobenzene With magnesium In tetrahydrofuran
Stage #2: With Trimethyl borate In tetrahydrofuran at -70℃;
82.4%
(S,S)-2-(phenyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane

(S,S)-2-(phenyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane

water
7732-18-5

water

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With 1H-imidazole; thionyl chloride In acetonitrile the B complex was obtained by a treatment of the boronic ester with SOCl2 and imidazole in the presence of borosilicate glass (the catalyst); this complex was hydrolized in aq. CH3CN;82%
5-(4-methoxyphenyl)-4,4-dimethyl-2-phenyl-[1,3,2]dioxaborolane

5-(4-methoxyphenyl)-4,4-dimethyl-2-phenyl-[1,3,2]dioxaborolane

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 8h;81%
Trimethyl borate
121-43-7

Trimethyl borate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

A

phenol
108-95-2

phenol

B

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran at -12℃; Temperature; Concentration; Flow reactor;A 7.9%
B 80.7%
iodobenzene
591-50-4

iodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: iodobenzene With diisopropopylaminoborane; triethylamine; triphenylphosphine; palladium dichloride In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere;
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;
80%
Multi-step reaction with 2 steps
2: H2O
View Scheme
Trimethyl borate
121-43-7

Trimethyl borate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

A

chlorobenzene
108-90-7

chlorobenzene

B

phenol
108-95-2

phenol

C

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran at 22℃; Temperature; Concentration; Flow reactor;A 8.9%
B 5.7%
C 79.6%
bromobenzene
108-86-1

bromobenzene

chloro-bis(dimethylamino)borane
6562-41-0

chloro-bis(dimethylamino)borane

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With lithium In tetrahydrofuran at -10℃; Inert atmosphere;76%
borane
13283-31-3

borane

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
With water; phenylmagnesium bromide In tetrahydrofuran slow addn. of 10 mmol of the Grignard reagent to a stirred soln. of borane in THF (40 mmol); the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;;75%
With bromobenzene; water; magnesium In tetrahydrofuran a 2.0 M soln. of borane (40 mmol) in THF was added to flame dried Mg turnings (12 mmol) at 0°C; slow addn. of the aryl bromide (10 mmol)in THF; stirring at room temp. for 12-16 h; the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;;
Phenyl triflate
17763-67-6

Phenyl triflate

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: Phenyl triflate With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere;
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;
74%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-1,3,2-benzodioxaborole
5747-23-9

2-phenyl-1,3,2-benzodioxaborole

Conditions
ConditionsYield
at 80℃; for 1h;100%
for 0.166667h; Schlenk technique;96%
In dichloromethane; ethyl acetate at 20℃;81%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
2479-64-3

2-phenyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

Conditions
ConditionsYield
at 40℃; for 1h;100%
In toluene for 2h; Reflux;92%
In toluene stirring mixt. of diamine deriv. and phenylboric acid in toluene for 2 hat reflux; filtration, washing with petroleum ether, NMR;92%
2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-1,3,2-benzodioxaborole-4-ol
108880-02-0

2-phenyl-1,3,2-benzodioxaborole-4-ol

Conditions
ConditionsYield
at 40℃; for 2h;100%
mannitol
69-65-8

mannitol

phenylboronic acid
98-80-6

phenylboronic acid

(2R,3R,4R,5R)-1:2,3:4,5:6-O1:O2,O3:O4,O5:O6-tris(phenylboranato)-D-mannitol
6638-75-1, 62560-54-7

(2R,3R,4R,5R)-1:2,3:4,5:6-O1:O2,O3:O4,O5:O6-tris(phenylboranato)-D-mannitol

Conditions
ConditionsYield
at 20℃; for 1h;100%
phenylboronic acid
98-80-6

phenylboronic acid

triphenylboroxine
3262-89-3

triphenylboroxine

Conditions
ConditionsYield
at 110℃; for 6h;100%
at 110℃; for 6h; Inert atmosphere; Neat (no solvent);100%
Stage #1: phenylboronic acid With barium(II) hydroxide In water at 80℃; for 0.0833333h;
Stage #2: With Au38(SCH2CH2Ph)24 In toluene at 80℃; for 12h; Reagent/catalyst;
100%
anthranilic acid
118-92-3

anthranilic acid

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-1,2-dihydro-benzo[a][1,3,2]-oxazaborinin-4-one
42409-65-4

2-phenyl-1,2-dihydro-benzo[a][1,3,2]-oxazaborinin-4-one

Conditions
ConditionsYield
at 20℃; for 1h;100%
In toluene for 16h; Inert atmosphere; Dean-Stark; Reflux;93%
In toluene
In tetrahydrofuran for 24h; Reflux;72 %Spectr.
2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

phenylboronic acid
98-80-6

phenylboronic acid

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane
5123-13-7

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane

Conditions
ConditionsYield
With magnesium sulfate In diethyl ether at 25℃; for 20h; Inert atmosphere;100%
In tetrahydrofuran for 0.666667h; Inert atmosphere; Dean-Stark; Reflux;100%
With magnesium sulfate In diethyl ether at 20℃; for 20h;100%
N1,N1'-diphenyloxaldiamidrazone
3449-06-7

N1,N1'-diphenyloxaldiamidrazone

phenylboronic acid
98-80-6

phenylboronic acid

2,3,2',3'-tetraphenyl-3,4,3',4'-tetrahydro-2H,2'H-[5,5']bi[1,2,4,3]triazaborolyl

2,3,2',3'-tetraphenyl-3,4,3',4'-tetrahydro-2H,2'H-[5,5']bi[1,2,4,3]triazaborolyl

Conditions
ConditionsYield
100%
In di-isopropyl ether
naphthalene-1,8-diamine
479-27-6

naphthalene-1,8-diamine

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
24341-81-9

2-phenyl-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

Conditions
ConditionsYield
at 0℃; for 1h;100%
With 1H-imidazole; iron(III) chloride In water; acetonitrile at 20℃; for 2h; Catalytic behavior; Temperature; Time; Inert atmosphere;93%
at 150℃; for 0.25h; Microwave irradiation; Sealed tube;90%
oxalodihydrazonic acid dianilide
29180-72-1

oxalodihydrazonic acid dianilide

phenylboronic acid
98-80-6

phenylboronic acid

3,4,3',4'-tetraphenyl-3,4,3',4'-tetrahydro-2H,2'H-[5,5']bi[1,2,4,3]triazaborolyl

3,4,3',4'-tetraphenyl-3,4,3',4'-tetrahydro-2H,2'H-[5,5']bi[1,2,4,3]triazaborolyl

Conditions
ConditionsYield
100%
In di-isopropyl ether
3-Chloropyridine
626-60-8

3-Chloropyridine

phenylboronic acid
98-80-6

phenylboronic acid

3-phenylpyridine
1008-88-4

3-phenylpyridine

Conditions
ConditionsYield
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In tert-Amyl alcohol for 12h; Solvent; Suzuki-Miyaura Coupling; Heating;100%
With cesiumhydroxide monohydrate; 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl; palladium diacetate In water; butan-1-ol at 25℃; for 0.25h; Solvent; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With potassium phosphate; catacxium A; palladium diacetate In toluene at 100℃; for 20h; Suzuki reaction;99%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylpyridine
1008-89-5

2-phenylpyridine

Conditions
ConditionsYield
With [Pd(N-(naphthyl)-salicylaldimine(-2H))(triphenylphosphine)]; sodium hydroxide at 120℃; for 24h; Reagent/catalyst; Suzuki Coupling;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;100%
With potassium phosphate; (PdCl2)(2-pyridyl)-6-isopropyl cis piperidine complex In water; N,N-dimethyl-formamide at 110℃; for 2h;99%
2-chloropyrazin
14508-49-7

2-chloropyrazin

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylpyrazine
29460-97-7

2-phenylpyrazine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; tricyclohexylphosphine; dichloro bis(acetonitrile) palladium(II) at 85 - 90℃; for 5h; Suzuki-Miyaura reaction;100%
With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h; Suzuki-Miyaura Coupling;99%
With 2-((3-sulfonatomesityl)-5-sulfonatoindenyl)dicyclohexylphosphinehydrate sodium salt; palladium diacetate; potassium carbonate In water at 100℃; for 24h; Suzuki-Miyaura Coupling;95%
5-bromopyrimidine
4595-59-9

5-bromopyrimidine

phenylboronic acid
98-80-6

phenylboronic acid

5-phenylpyrimidine
34771-45-4

5-phenylpyrimidine

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 6h; Suzuki-Miyaura cross-coupling reaction;100%
With potassium carbonate In ethanol; water at 30℃; for 1h; Suzuki-Miyaura Coupling;100%
With N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate; palladium dichloride In 1,4-dioxane; N,N-dimethyl-formamide at 90℃; for 6h; Suzuki coupling; Inert atmosphere;99%
chlorobenzene
108-90-7

chlorobenzene

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With Cs2O3; PCy3 adduct of cyclopalladated ferrocenylimine In 1,4-dioxane at 100℃; for 15h; Suzuki cross-coupling reaction;100%
With dichloro(cycloocta-1,5-diene)palladium (II); 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol); potassium carbonate In methanol for 0.166667h; Suzuki cross-coupling reaction; Microwave irradiation; Inert atmosphere;100%
With potassium carbonate In methanol at 100℃; for 0.0833333h; Suzuki-Miyaura Coupling; Microwave irradiation;100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium phosphate monohydrate; 4,4'-di-tBu-2,2'-dipyridylpalladium(II) dichloride In methanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling;100%
With potassium carbonate; palladium dichloride In water at 20 - 90℃; Suzuki coupling; Inert atmosphere;99%
With potassium carbonate In water at 90℃; for 0.25h; Suzuki reaction; Inert atmosphere;99%
2-bromo-5-nitrotoluene
7149-70-4

2-bromo-5-nitrotoluene

phenylboronic acid
98-80-6

phenylboronic acid

2-methyl-4-nitrobiphenyl
91718-52-4

2-methyl-4-nitrobiphenyl

Conditions
ConditionsYield
With trans-dibromobis(1-butyl-3-methylimidazol-2-ylidene)palladium(II); sodium hydrogencarbonate In ethylene glycol at 110℃; for 1h; Catalytic behavior; Suzuki-Miyaura Coupling; Schlenk technique;100%
With tetrabutylammomium bromide; sodium carbonate In water at 100℃; for 2h; Suzuki coupling;99%
With sodium carbonate In 1,2-dimethoxyethane; water for 16h; Heating / reflux;86%
2-bromo-6-nitrotoluene
55289-35-5

2-bromo-6-nitrotoluene

phenylboronic acid
98-80-6

phenylboronic acid

2-nitro-6-phenyltoluene
107622-50-4

2-nitro-6-phenyltoluene

Conditions
ConditionsYield
With potassium carbonate; copper-palladium In N,N-dimethyl-formamide at 110℃; for 4h; Suzuki cross-coupling;100%
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol at 120℃; for 0.166667h; Suzuki cross-coupling; microwave irradiation;97%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100 - 102℃; Suzuki Coupling; Inert atmosphere;93%
phenylboronic acid
98-80-6

phenylboronic acid

3-Iodobenzoic acid
618-51-9

3-Iodobenzoic acid

3-phenylbenzoic acid
716-76-7

3-phenylbenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; palladium dichloride In water for 0.166667h; Product distribution; Ambient temperature; other reagents, reaction times;100%
With sodium hydroxide; palladium diacetate In water at 20℃; for 2h; Suzuki reaction;100%
With disodium hydrogenphosphate; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 In water at 120℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation;98%
bromochlorobenzene
106-39-8

bromochlorobenzene

phenylboronic acid
98-80-6

phenylboronic acid

4'-biphenyl chloride
2051-62-9

4'-biphenyl chloride

Conditions
ConditionsYield
With potassium carbonate In ethanol at 80℃; for 36h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With C28H38Cl2N2O6PdS2(2-)*2Na(1+); tetrabutylammomium bromide; potassium carbonate In water at 75℃; Suzuki coupling; Inert atmosphere;99%
With Br(1-)*C28H29BrN5O2Pd(1+); potassium carbonate In methanol; water at 100℃; for 3h; Suzuki-Miyaura coupling;99%
bromobenzene
108-86-1

bromobenzene

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With potassium carbonate; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 In xylene at 130℃; for 13h; Suzuki-Miyaura cross-coupling reaction;100%
With potassium phosphate; triphenylphosphine; Ni(II) complexes of bidentate carbene; phosphine ligand In toluene at 80℃; Suzuki cross-coupling;100%
With [PdCl2(2-ethyl-2-oxazoline)2]; potassium carbonate In toluene at 110℃; for 3h; Suzuki reaction;100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

phenylboronic acid
98-80-6

phenylboronic acid

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
With potassium carbonate; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 In xylene at 130℃; for 14h; Suzuki-Miyaura cross-coupling reaction;100%
With 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling;100%
With 1,4-diaza-bicyclo[2.2.2]octane; PEG-400; potassium carbonate; palladium diacetate at 110℃; for 2h; Suzuki-Miyaura cross-coupling reaction;100%
iodobenzene
591-50-4

iodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With potassium carbonate; copper-palladium In N,N-dimethyl-formamide at 110℃; Kinetics; Product distribution; Further Variations:; Catalysts; Reaction partners; Suzuki cross-coupling;100%
With sodium hydroxide; Pd-dodecanethiolate nanoparticles In tetrahydrofuran at 20℃; for 24h; Suzuki-Miyaura cross-coupling;100%
With sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate; 2C10H15N2(1+)*Cl4Pd(2-) In water at 110℃; for 12h; Conversion of starting material; Suzuki Coupling;100%
2-bromoanisole
578-57-4

2-bromoanisole

phenylboronic acid
98-80-6

phenylboronic acid

2-methoxy-1,1'-biphenyl
86-26-0

2-methoxy-1,1'-biphenyl

Conditions
ConditionsYield
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water at 50℃; for 24h; Solvent; Temperature; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox;100%
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water at 50℃; Reagent/catalyst; Solvent; Temperature; Suzuki Coupling; Inert atmosphere; Glovebox;100%
With sodium carbonate In water at 100℃; Suzuki-Miyaura reaction;99.1%
para-bromotoluene
106-38-7

para-bromotoluene

phenylboronic acid
98-80-6

phenylboronic acid

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

Conditions
ConditionsYield
With potassium phosphate; (η5-C5H5)Re(NO)(P(C6H5)3)(C(CH3)3)2; palladium diacetate In toluene at 100℃; for 1h; Suzuki cross-couplings reaction;100%
With N,N-dicyclohexyl-2-(dicyclohexylphosphanyl)benzenesulfonamide; tris(dibenzylideneacetone)dipalladium (0); caesium carbonate In 1,4-dioxane at 80℃; for 3h; Suzuki-Miyaura cross coupling;100%
With potassium phosphate; 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride; bis(η3-allyl-μ-chloropalladium(II)) In 1,4-dioxane at 80℃; for 12h; Product distribution; Further Variations:; Catalysts; Reagents; Solvents; Suzuki cross-coupling;100%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

phenylboronic acid
98-80-6

phenylboronic acid

2-methylbiphenyl
643-58-3

2-methylbiphenyl

Conditions
ConditionsYield
With [Pd(1-butylimidazole)2Cl2]; potassium hydroxide In water; isopropyl alcohol at 40℃; for 1h; Suzuki-Miyaura reaction; Under air;100%
With caesium carbonate In water; isopropyl alcohol at 80℃; for 3h; Suzuki-Miyaura reaction; Inert atmosphere;100%
With potassium hydroxide In propan-1-ol; water at 60℃; for 1h; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique;100%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

phenylboronic acid
98-80-6

phenylboronic acid

1-phenylnaphthalene
605-02-7

1-phenylnaphthalene

Conditions
ConditionsYield
With C31H26N6O4Pd; potassium carbonate In water at 100℃; for 3h; Suzuki-Miyaura coupling;100%
With potassium phosphate; 1,1'-bis(4-methoxyphenyl)-3,3'-methylene-diimidazoline-2,2'-diylidene-palladium(II)-dibromide In toluene at 40℃; for 2h; Reagent/catalyst; Temperature; Time; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With C16H21ClN2Pd; sodium carbonate In methanol at 85℃; for 1h; Reagent/catalyst; Suzuki-Miyaura Coupling;100%
2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

phenylboronic acid
98-80-6

phenylboronic acid

2-methoxy-6-phenylnaphthalene
59115-43-4

2-methoxy-6-phenylnaphthalene

Conditions
ConditionsYield
With potassium phosphate; (η5-C5H5)Re(NO)(P(C6H5)3)P(C6H5)2; palladium diacetate In toluene at 100℃; for 0.25h; Suzuki cross-couplings reaction;100%
With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In water at 70℃; for 1h;99%
With potassium fluoride; o-(dicyclohexylphosphino)diisopropylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 80℃; for 40h; Suzuki cross-coupling;98%
4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

phenylboronic acid
98-80-6

phenylboronic acid

methyl 4-phenylbenzoate
720-75-2

methyl 4-phenylbenzoate

Conditions
ConditionsYield
With potassium phosphate; second generation phosphine dendrimer-stabilized palladium In 1,4-dioxane for 20h; Suzuki coupling; Heating;100%
With potassium phosphate; silica gel; palladium In toluene at 110℃; for 5h; Suzuki-Miyaura reaction;100%
With potassium phosphate tribasic heptahydrate In 1,4-dioxane for 20h; Suzuki coupling; Reflux;100%
para-iodoanisole
696-62-8

para-iodoanisole

phenylboronic acid
98-80-6

phenylboronic acid

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate; palladium diacetate In acetone at 110℃; for 2h; Suzuki-Miyaura cross-coupling reaction;100%
With sodium hydroxide; Pd-dodecanethiolate nanoparticles In tetrahydrofuran at 20℃; for 17h; Suzuki-Miyaura cross-coupling;100%
With caesium carbonate; (1-adamantylisonitrile)2PdCl2 In 1,4-dioxane for 18h; Product distribution; Further Variations:; Catalysts; Suzuki-Miyaura reaction; Heating;100%
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