3-(Hydroxymethyl)phenylboronic acid
- Product Name
- 3-(Hydroxymethyl)phenylboronic acid
- CAS No.
- 87199-15-3
- Chemical Name
- 3-(Hydroxymethyl)phenylboronic acid
- Synonyms
- PACR-012;RARECHEM AH PB 0189;3-Boronobenzyl alcohol;(3-Boronophenyl)methanol;3-hydroxymethylboronic acid;3-(hydroxyMethyl)phenylboronic;3-HydroMethylphenylboronicacid;3-(HYDROXYMETHYL)PHENYLBORONIC ACID;m-(Hydroxymethyl)phenylboronic Acid;3-(HYDROXYMETHYL)BENZENEBORONIC ACID
- CBNumber
- CB1185434
- Molecular Formula
- C7H9BO3
- Formula Weight
- 151.96
- MOL File
- 87199-15-3.mol
3-(Hydroxymethyl)phenylboronic acid Property
- Melting point:
- 95-99 °C (lit.)
- Boiling point:
- 380.5±44.0 °C(Predicted)
- Density
- 1.25±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- pka
- 8.31±0.10(Predicted)
- form
- powder to crystal
- color
- White to Almost white
- Water Solubility
- Soluble in water.
- BRN
- 8832019
- InChI
- InChI=1S/C7H9BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,9-11H,5H2
- InChIKey
- HGTDLKXUWVKLQX-UHFFFAOYSA-N
- SMILES
- B(C1=CC=CC(CO)=C1)(O)O
- CAS DataBase Reference
- 87199-15-3(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 37/39-26-36-24/25
- WGK Germany
- 3
- HazardClass
- IRRITANT
- HS Code
- 29319090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 512834
- Product name
- 3-(Hydroxymethyl)phenylboronic acid
- Packaging
- 10g
- Price
- $314
- Updated
- 2025/07/31
- Product number
- H1244
- Product name
- 3-(Hydroxymethyl)phenylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 1g
- Price
- $20
- Updated
- 2025/07/31
- Product number
- H1244
- Product name
- 3-(Hydroxymethyl)phenylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 5g
- Price
- $45
- Updated
- 2025/07/31
- Product number
- H972548
- Product name
- 3-(Hydroxymethyl)phenylboronic acid
- Packaging
- 50g
- Price
- $165
- Updated
- 2021/12/16
- Product number
- H972548
- Product name
- 3-(Hydroxymethyl)phenylboronic acid
- Packaging
- 5g
- Price
- $55
- Updated
- 2021/12/16
3-(Hydroxymethyl)phenylboronic acid Chemical Properties,Usage,Production
Chemical Properties
Off-white Cryst
Uses
suzuki reaction
Uses
Reactant used for copper-mediated trifluoromethylation, copper-catalyzed transformations from arylboronic acids in water, Mitsunobu, Suzuki, and amidation reactions with hydroxyphenylamino bromopyrazinecarboxylate. Reactant involved in the synthesis of biologically active molecules including Mycobacterium tuberculosis H37Rv chorismate mutase inhibitors via Suzuki coupling reactions, HIV protease inhibitors with antiviral activity against drug-resistant viruses, Pyrrole derivatives for use as PDE4B inhibitors.
Synthesis
5419-55-6
103978-12-7
87199-15-3
The general procedure for the synthesis of 3-hydroxymethylphenylboronic acid from triisopropyl borate and ((3-bromobenzyl)oxy)(tert-butyl)dimethylsilane is as follows: Example 3B: Synthesis of 3-(hydroxymethyl)phenylboronic acid Example 3A (150 mg, 0.498 mmol) was dissolved in THF (2.49 mL) and the solution was cooled to -78 °C. Under stirring, n-butyllithium (431.1 μL, 0.647 mmol) was slowly added and stirred continuously for 30 hours at this temperature. Subsequently, triisopropyl borate (231 μL, 0.996 mmol) was added and stirring was continued for 20 minutes. After that, the reaction mixture was slowly warmed up to room temperature and stirring was continued for 2.5 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed sequentially with water and brine, then dried with anhydrous sodium sulfate, filtered, and concentrated under vacuum. The resulting crude product was dissolved in HPLC solvent B (90:10:0.1 MeCN:H2O:TFA) and stirred at room temperature for 1 hour. Afterwards, the solution was concentrated in vacuum and purified by preparative liquid chromatography (using an Axia Luna 5μ C18 30×100 mm column with a 10-minute gradient, 20 to 100% B, A = 10:90:0.1 MeCN:H2O:TFA, B = 90:10:0.1 MeCN:H2O:TFA) to give Example 3B (57 mg, yield 75%). 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm: 7.75 (1H, s), 7.67 (1H, d, J = 7.28 Hz), 7.40-7.48 (1H, m), 7.30-7.40 (1H, m), 4.60 (2H, s).
References
[1] Patent: WO2014/201073, 2014, A1. Location in patent: Paragraph 00214
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 1, p. 67 - 72
3-(Hydroxymethyl)phenylboronic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 3-(Hydroxymethyl)phenylboronic acid manufacturers
- Product
- 3-(Hydroxymethyl)phenylboronic acid 87199-15-3
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-07
- Product
- 3-(Hydroxymethyl)phenylboronic acid 87199-15-3
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1 ton
- Release date
- 2023-12-20
- Product
- 3-(Hydroxymethyl)phenylboronic acid 87199-15-3
- Price
- US $34.00-1.20/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-04-08