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98-80-6

Basic Information
CAS No.: 98-80-6
Name: Phenylboronic acid
Article Data: 195
Molecular Structure:
Molecular Structure of 98-80-6 (Phenylboronic acid)
Formula: C6H7BO2
Molecular Weight: 121.931
Synonyms: Phenyldihydroxyborane;Borophenylic acid;Phenylboronic Acid (PBA);1/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9;Dihydroxyphenylborane;Boric acid, phenyl-;boronic acid, phenyl-;4-16-00-01654 (Beilstein Handbook Reference);Usaf bo-2;Dihydroxy(phenyl)borane;Kyselina fenylborita [Czech];Acide phenylborique [French];T-500;Acide phenylborique;Benzeneboronic acid;Phenyl boronic acid;Phenylboronic acid 98%;phenyl-Boronic acid;Boronic acid,phenyl-;
EINECS: 202-701-9
Density: 1.139 g/cm3
Melting Point: 216-219 °C(lit.)
Boiling Point: 265.856 °C at 760 mmHg
Flash Point: 114.586 °C
Solubility: water: 10 g/L (20 °C )
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn,IrritantXi,DangerousN
Risk Codes: 22-36/37/38-20/21/22
Safety: 22-24/25-36/37/39-26-36
PSA: 40.46000
LogP: -0.63360
Synthetic route
24388-23-6

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

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;
556-97-8

1-chloro-3,5-dimethylbenzene

A

17057-88-4

3,5-dimethylbiphenyl

B

98-80-6

phenylboronic acid

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

tetrahydroxydiboron

98-04-4

phenyltrimethylammonium iodide

98-80-6

phenylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;98%

potassium phenyltrifluoborate

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;
13061-96-6

dihydroxy-methyl-borane

24388-23-6

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

98-80-6

phenylboronic acid

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

tributylphenylstannane

98-80-6

phenylboronic acid

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

diisopropopylaminoborane

100-58-3

phenylmagnesium bromide

98-80-6

phenylboronic acid

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

diisopropopylaminoborane

100-58-3

phenylmagnesium bromide

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%
55124-35-1

diisopropylamine borane

100-58-3

phenylmagnesium bromide

98-80-6

phenylboronic acid

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

Sb2O4B2(C6H5)8

64-19-7

acetic acid

A

diacetoxotriphenylantimony

B

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%
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Specification

Phenylboronic acid is white powder and is commonly used in organic synthesis. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis. With the CAS NO.98-80-6, Phenylboronic acid is soluble in most polar organic solvents and is poorly soluble in hexanes and carbon tetrachloride. And it is also named as benzeneboronic acid.

Physical properties about Phenylboronic acid are: (1)ACD/LogP: 1.237; (2)ACD/LogD (pH 5.5): 1.24; (3)ACD/LogD (pH 7.4): 1.21; (4)ACD/BCF (pH 5.5): 5.12; (5)ACD/BCF (pH 7.4): 4.77; (6)ACD/KOC (pH 5.5): 112.04; (7)ACD/KOC (pH 7.4): 104.39; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.534; (12)Molar Refractivity: 33.288 cm3; (13)Molar Volume: 107.063 cm3; (14)Polarizability: 13.197 10-24cm3; (15)Surface Tension: 41.4830017089844 dyne/cm; (16)Density: 1.139 g/cm3; (17)Flash Point: 114.586 °C; (18)Enthalpy of Vaporization: 53.224 kJ/mol; (19)Boiling Point: 265.856 °C at 760 mmHg; (20)Vapour Pressure: 0.00400000018998981 mmHg at 25°C

Preparation of Phenylboronic acid: There are numerous methods to synthesize phenylboronic acid. One of the most common synthesis uses phenylmagnesium bromide and trimethyl borate to form the ester PhB(OMe)2, which is then hydrolyzed to the product.
PhMgBr + B(OMe)3 → PhB(OMe)2 + MeOMgBr
PhB(OMe)2 + H2O → PhB(OH)2 + MeOH

Uses of Phenylboronic acid: Phenylboronic acid is used in numerous cross coupling reactions. Phenylboronic acid is also used in biology schemes as receptors and sensors for carbohydrates, antimicrobial agents and enzyme inhibitors, neutron capture therapy for cancer, transmembrane transport, and bioconjugation and labeling of proteins and cell surface.

When you are using this chemical, please be cautious about it as the following:
1. Do not breathe dust;
2. Avoid contact with skin and eyes;
3. Wear suitable protective clothing, gloves and eye/face protection;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H;
(2)InChIKey=HXITXNWTGFUOAU-UHFFFAOYSA-N;
(3)Smilesc1c(cccc1)B(O)O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 450mg/kg (450mg/kg)   Bulletin de l'Academie Nationale de Medicine Vol. 135, Pg. 314, 1951.
 
guinea pig LDLo intraperitoneal 284mg/kg (284mg/kg)   Bulletin de l'Academie Nationale de Medicine Vol. 135, Pg. 314, 1951.
 
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 221mg/kg (221mg/kg)   Acta Physiologica Polonica. Vol. 12, Pg. 173, 1961.
 
rabbit LDLo oral 600mg/kg (600mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rabbit LDLo skin 4500mg/kg (4500mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rat LD50 oral 740mg/kg (740mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.

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