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ChemicalBook--->CAS DataBase List--->25487-66-5

25487-66-5

25487-66-5 Structure

25487-66-5 Structure
IdentificationMore
[Name]

3-Carboxyphenylboronic acid
[CAS]

25487-66-5
[Synonyms]

3-BORONOBENZOIC ACID
3-CARBOXYBENZENEBORONIC ACID
3-CARBOXYPHENYLBORONIC ACID
3-(DIHYDROXYBORANE)BENZOIC ACID
3-(DIHYDROXYBORONYL)BENZOIC ACID
3-(DIHYDROXYBORYL)BENZOIC ACID
AKOS BRN-0007
M-CARBOXYPHENYLBORONIC ACID
RARECHEM AH PB 0148
3-borono-benzoicaci
m-borono-benzoicaci
m-carboxy-benzeneboronicaci
m-carboxybenzeneboronicacid
3-Carboxypenylboronic Acid
3-Carboxyphenylboronicacid,min.97%
3-CARBOXYBENZENEBORONIC ACID 98%
3-Carboxyphenylboronic Acid (contains varying amounts of Anhydride)
3-Carboxyphenylboronic acid ,98%
3-Carboxyphenylboronic acid, min. 97%
(3-Formyloxyphenyl)boronicacid
[EINECS(EC#)]

607-734-6
[Molecular Formula]

C7H7BO4
[MDL Number]

MFCD00036833
[Molecular Weight]

165.94
[MOL File]

25487-66-5.mol
Chemical PropertiesBack Directory
[Appearance]

off-white crystalline powder
[Melting point ]

243-247 °C (lit.)
[Boiling point ]

434.5±47.0 °C(Predicted)
[density ]

1.40±0.1 g/cm3(Predicted)
[storage temp. ]

0-6°C
[solubility ]

DMSO (Slightly), Methanol (Slightly), Water (Slightly)
[form ]

Crystalline Powder
[pka]

4.21±0.10(Predicted)
[color ]

Off-white
[Water Solubility ]

2.5 g/100 mL
[Detection Methods]

HPLC,NMR
[BRN ]

2967400
[InChI]

InChI=1S/C7H7BO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,11-12H,(H,9,10)
[InChIKey]

DBVFWZMQJQMJCB-UHFFFAOYSA-N
[SMILES]

C(O)(=O)C1=CC=CC(B(O)O)=C1
[CAS DataBase Reference]

25487-66-5(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi,Xn
[Risk Statements ]

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 ]

S37/39:Wear suitable 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 ]

2
[RTECS ]

CY8750000
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

29319099
[Toxicity]

mouse,LD50,intravenous,2560mg/kg (2560mg/kg),"Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
Raw materials And Preparation ProductsBack Directory
[Raw materials]

3-Cyanophenylboronic acid-->Potassium permanganate-->Carbon dioxide-->Boroxin, 2,4,6-tris(3-bromophenyl)--->3-Tolylboronic acid-->Ethylene glycol-->Hydrochloric acid-->Potassium hydroxide
[Preparation Products]

3-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID-->3-(3-PYRIDINYL)BENZOIC ACID-->3''-AMINO-2''-HYDROXY-BIPHENYL-3-CARBOXYLIC ACID-->(Z)-3-(5-((5-chloro-2-oxoindolin-3-ylidene)Methyl)furan-2-yl)benzoic acid-->3-(4-FLUOROPHENYL)BENZOIC ACID-->3-PYRIMIDIN-5-YL-BENZOIC ACID-->CX6258-->3-(6-Chloropyrimidin-4-yl)benzoic acid-->4-(3-Carboxyphenyl)benzoic acid-->3-(4-Methanesulfonylphenyl)benzoic acid
Hazard InformationBack Directory
[Chemical Properties]

3-Carboxyphenylboronic acid is off-white crystalline powder
[Uses]

3-Carboxyphenylboronic acid can be used as a substrate in the preparation of:
  • Biaryl derivatives by reacting with bromoaniline through the Suzuki-Miyaura coupling reaction.
  • Boronic acid-functionalized block copolymer.
  • 1H-Imidazo[1,2-a]quinoxaline derivatives.

[Uses]

3-Carboxyphenylboronic acid is used in Suzuki coupling chemistry.1,2,3
[Uses]

suzuki reaction
[Synthesis]

3-Cyanophenylboronic acid

150255-96-2

3-Carboxyphenylboronic acid

25487-66-5

1. Synthesis of 3-carboxyphenylboronic acid: 10 g (68 mmol) of 3-cyanophenylboronic acid was suspended in 40 mL of ethylene glycol with 15.26 g (272 mmol, 4 eq.) of potassium hydroxide powder, heated to 175 °C and maintained for 3 hours. After completion of the reaction, the reaction mixture was cooled and diluted with 60 mL of water. The pH was adjusted to 2-3 with 32% hydrochloric acid solution, colorless crystalline 3-carboxyphenylboronic acid was precipitated and the product was separated by filtration. The resulting crystals were washed with water and dried under mild vacuum at 35 °C. The final product was 10.04 g in mass. The final product was 10.04 g (60.5 mmol, 89% yield).

[References]

[1] Patent: US2009/286995, 2009, A1. Location in patent: Page/Page column 4
Spectrum DetailBack Directory
[Spectrum Detail]

3-Carboxyphenylboronic acid(25487-66-5)1HNMR
3-Carboxyphenylboronic acid(25487-66-5)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

3-Carboxyphenylboronic acid, 98%(25487-66-5)
[Alfa Aesar]

3-Carboxybenzeneboronic acid(25487-66-5)
[Sigma Aldrich]

25487-66-5(sigmaaldrich)
[TCI AMERICA]

3-Carboxyphenylboronic Acid  (contains varying amounts of Anhydride)(25487-66-5)
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