ChemicalBook > CAS DataBase List > 3-(Hydroxymethyl)phenylboronic acid

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
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
512834
Product name
3-(Hydroxymethyl)phenylboronic acid
Packaging
10g
Price
$314
Updated
2025/07/31
TCI Chemical
Product number
H1244
Product name
3-(Hydroxymethyl)phenylboronic Acid (contains varying amounts of Anhydride)
Packaging
1g
Price
$20
Updated
2025/07/31
TCI Chemical
Product number
H1244
Product name
3-(Hydroxymethyl)phenylboronic Acid (contains varying amounts of Anhydride)
Packaging
5g
Price
$45
Updated
2025/07/31
TRC
Product number
H972548
Product name
3-(Hydroxymethyl)phenylboronic acid
Packaging
5g
Price
$55
Updated
2021/12/16
TRC
Product number
H972548
Product name
3-(Hydroxymethyl)phenylboronic acid
Packaging
50g
Price
$165
Updated
2021/12/16
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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

Hebei Chuanghai Biotechnology Co., Ltd
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
Nanjing Fred Technology Co., Ltd
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
Henan Fengda Chemical Co., Ltd
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

87199-15-3, 3-(Hydroxymethyl)phenylboronic acidRelated Search:

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