3-Cyanophenylboronic acid
- Product Name
- 3-Cyanophenylboronic acid
- CAS No.
- 150255-96-2
- Chemical Name
- 3-Cyanophenylboronic acid
- Synonyms
- 1-p-Tolylpyrazole-4-boronic acid;2-Methyl-3-nitrophenylboronic acid, pinacol ester;4,4,5,5-Tetramethyl-2-(4-methyl-3-nitrophenyl)-1,3,2-dioxaborolane;2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;AKOS BRN-0075;CAS:150255-96-2;RARECHEM AH PB 0207;3-Cyanophenylboronic;3-boronobenzonitrile;Hydroxydip-tolylborane
- CBNumber
- CB7780990
- Molecular Formula
- C7H6BNO2
- Formula Weight
- 146.94
- MOL File
- 150255-96-2.mol
3-Cyanophenylboronic acid Property
- Melting point:
- 298 °C (dec.) (lit.)
- Boiling point:
- 347.4±44.0 °C(Predicted)
- Density
- 1.25±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- soluble in Methanol
- pka
- 7.17±0.10(Predicted)
- form
- solid
- color
- White to Light yellow
- BRN
- 6136720
- InChI
- InChI=1S/C7H6BNO2/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,10-11H
- InChIKey
- XDBHWPLGGBLUHH-UHFFFAOYSA-N
- SMILES
- B(C1=CC=CC(C#N)=C1)(O)O
- CAS DataBase Reference
- 150255-96-2(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi,C,Xn
- Risk Statements
- 36/37/38-34-36-41-37/38-22
- Safety Statements
- 26-37/39-45-36/37/39-22-39-36
- RIDADR
- UN3439
- WGK Germany
- 3
- Hazard Note
- Harmful/Irritant
- HazardClass
- 6.1
- PackingGroup
- III
- HS Code
- 29163990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 513016
- Product name
- 3-Cyanophenylboronic acid
- Purity
- ≥95.0%
- Packaging
- 1g
- Price
- $41.6
- Updated
- 2025/07/31
- Product number
- 513016
- Product name
- 3-Cyanophenylboronic acid
- Purity
- ≥95.0%
- Packaging
- 5g
- Price
- $190
- Updated
- 2025/07/31
- Product number
- C2031
- Product name
- 3-Cyanophenylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 5g
- Price
- $50
- Updated
- 2025/07/31
- Product number
- C2031
- Product name
- 3-Cyanophenylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 25g
- Price
- $143
- Updated
- 2025/07/31
- Product number
- C989728
- Product name
- 3-Cyanophenylboronic acid
- Packaging
- 100mg
- Price
- $45
- Updated
- 2021/12/16
3-Cyanophenylboronic acid Chemical Properties,Usage,Production
Chemical Properties
light orange powder
Uses
suzuki reaction
Uses
3-Cyanophenylboronic acid can be used:
- As an intermediate in the synthesis of piperidine-based MCH R1 antagonists.
- As a substrate in the Suzuki coupling reactions to prepare 4-aryl-1,8-naphthyridin-2(1H)-ones.
- As an intermediate in the synthesis of biaryl-based?phenylalanine?amino acid analogs, which are used as kainate receptors ligands.
- To prepare phenylimidazole-based?Ir(III) complexes for phosphorescent blue OLED applications.
Synthesis
5419-55-6
6952-59-6
150255-96-2
The general procedure for the synthesis of 3-cyanophenylboronic acid from triisopropyl borate and m-bromobenzonitrile was as follows: 20 g of 3-bromobenzonitrile was dissolved in 100 ml of anhydrous tetrahydrofuran (THF) and mixed with 37.6 ml of triisopropoxyborane under nitrogen protection. The reaction system was cooled to -78 °C, followed by the slow dropwise addition of 98.3 ml of 1.6 M n-butyllithium hexane solution under stirring for about 30 minutes. The reaction mixture was continued to be stirred at room temperature for 30 minutes, then cooled to 0°C and 220 ml of 4M sulfuric acid solution was added. The reaction solution was heated to reflux overnight, cooled again to 0°C, and 340 ml of 5M aqueous sodium hydroxide solution was added, followed by extraction with 200 ml of diethyl ether. The aqueous phase was separated and the pH was adjusted to 2 with 6 M hydrochloric acid and extracted twice with 300 ml ethyl acetate. The ethyl acetate layers were combined, dried with anhydrous magnesium sulfate (MgSO4) and the solvent was removed by distillation under reduced pressure. The resulting crude product was recrystallized by DMF-water system to give 11.6 g (72% yield) of 3-cyanophenylboronic acid as light yellow needle-like crystals. The product was characterized by 1H NMR (270 MHz, DMSO-d6): δ 8.5 (brs, 2H), 8.3-7.6 (m, 4H).
References
[1] Patent: EP1179527, 2002, A1. Location in patent: Page 19-20
[2] Patent: US6348478, 2002, B1. Location in patent: Page column 14
[3] Patent: US2012/295874, 2012, A1. Location in patent: Page/Page column 207
[4] Patent: US2002/45613, 2002, A1
[5] Patent: US6538137, 2003, B1
3-Cyanophenylboronic acid Preparation Products And Raw materials
Raw materials
Preparation Products
3-Cyanophenylboronic acid Suppliers
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View Lastest Price from 3-Cyanophenylboronic acid manufacturers
- Product
- (3-Cyanophenyl)boronic acid 150255-96-2
- Price
- US $3.00-9.00/KG
- Min. Order
- 0.1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2025-07-03
- Product
- 3-Cyanophenylboronic acid 150255-96-2
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 ton
- Release date
- 2024-12-06
- Product
- 3-Cyanophenylboronic acid 150255-96-2
- Price
- US $35.00-25.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 Ton
- Release date
- 2023-10-30