| Identification | More | [Name]
Phenylboronic acid | [CAS]
98-80-6 | [Synonyms]
AKOS BRN-0133
BENZENEBORONIC ACID
BENZENEBORONIC ACID/ANHYDRIDE
BIO-FARMA BF001405
BORONIC ACID, PHENYL-
DIHYDROXYPHENYLBORANE
PHENYLBORIC ACID
PHENYLBORON DIHYDROXIDE
PHENYLBORONIC ACID
RARECHEM AH PB 0250
acidephenylborique
borophenylicacid
kyselinafenylborita
phenyboronic
phenyl-boronicaci
phenyldihydroxyborane
t-500
usafbo-2
Phenyboronic acid Benzenebcronic acid
Benzenebcronic acid | [EINECS(EC#)]
202-701-9 | [Molecular Formula]
C6H7BO2 | [MDL Number]
MFCD00002103 | [Molecular Weight]
121.93 | [MOL File]
98-80-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
216-219 °C(lit.)
| [Boiling point ]
265.9±23.0 °C(Predicted) | [density ]
1.13±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
8.83(at 25℃) | [color ]
White to off-white | [Water Solubility ]
10 g/L (20 ºC) | [Sensitive ]
Hygroscopic | [Detection Methods]
HPLC,NMR | [Merck ]
14,1068 | [BRN ]
970972 | [Stability:]
Hygroscopic | [InChIKey]
HXITXNWTGFUOAU-UHFFFAOYSA-N | [Uses]
Phenyihoronic 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. | [CAS DataBase Reference]
98-80-6(CAS DataBase Reference) | [EPA Substance Registry System]
98-80-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi,N | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
CY8575000
| [Hazard Note ]
Harmful | [TSCA ]
Yes | [HazardClass ]
IRRITANT, MOISTURE SENSITIVE | [HS Code ]
29310095 | [Toxicity]
LD50 orl-rat: 740 mg/kg 14KTAK -,693,64 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Characteristics]
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.
| [Definition]
ChEBI: Phenylboronic acid is a member of boronic acids. It is functionally related to a boronic acid. | [Synthesis Reference(s)]
Organic Syntheses, Coll. Vol. 4, p. 68, 1963
The Journal of Organic Chemistry, 49, p. 5237, 1984 DOI: 10.1021/jo00200a045 | [General Description]
Phenylboronic acid (PBA) is an organoboronic acid. It behaves as a molecular receptor that can attach to compounds containing cis-diol group. Microwave-assisted Suzuki coupling of aryl chlorides with phenylboronic acid in the presence of Pd/C (catalyst) and water (solvent) has been described. Palladium-catalyzed cross-coupling reaction of phenylboronicacid with haloarenes to afford biaryls has been reported. | [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. |
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