4-Cyanophenylboronic acid
Description Reference- Product Name
- 4-Cyanophenylboronic acid
- CAS No.
- 126747-14-6
- Chemical Name
- 4-Cyanophenylboronic acid
- Synonyms
- SWF-108;AKOS BRN-0076;CAS:126747-14-6;CHEMBRDG-BB 3200965;RARECHEM AH PB 0209;4-Boronobenzonitrile;4-Cyanophenylboronic;4-cyanobboronic acid;4-Cyanophenylboric acid;4-Cyanophenylboronicaci
- CBNumber
- CB8283302
- Molecular Formula
- C7H6BNO2
- Formula Weight
- 146.94
- MOL File
- 126747-14-6.mol
4-Cyanophenylboronic acid Property
- Melting point:
- >350 °C (lit.)
- Boiling point:
- 355.9±44.0 °C(Predicted)
- Density
- 1.25±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO, Methanol (Slightly)
- pka
- 7.38±0.10(Predicted)
- form
- Powder
- color
- White to yellow
- BRN
- 6593772
- InChI
- InChI=1S/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H
- InChIKey
- CEBAHYWORUOILU-UHFFFAOYSA-N
- SMILES
- B(C1=CC=C(C#N)C=C1)(O)O
- CAS DataBase Reference
- 126747-14-6(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 22-24/25-37/39-26-36
- RIDADR
- UN3439
- WGK Germany
- 3
- Hazard Note
- Irritant
- HazardClass
- 6.1
- PackingGroup
- III
- HS Code
- 29163990
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.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
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
- 521418
- Product name
- 4-Cyanophenylboronic acid
- Purity
- ≥95%
- Packaging
- 1g
- Price
- $55.31
- Updated
- 2025/07/31
- Product number
- 521418
- Product name
- 4-Cyanophenylboronic acid
- Purity
- ≥95%
- Packaging
- 10g
- Price
- $373
- Updated
- 2025/07/31
- Product number
- C1778
- Product name
- 4-Cyanophenylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 1g
- Price
- $22
- Updated
- 2025/07/31
- Product number
- C1778
- Product name
- 4-Cyanophenylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 5g
- Price
- $51
- Updated
- 2025/07/31
- Product number
- C1778
- Product name
- 4-Cyanophenylboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 25g
- Price
- $150
- Updated
- 2025/07/31
4-Cyanophenylboronic acid Chemical Properties,Usage,Production
Description
4-Cyanophenylboronic acid can be used for palladium catalyzed Suzuki cross-coupling reactions to synthesize 6-acryl-2,4-diamino-pyrimidines and triazines. It is used as precursor in the synthesis of inhibitors such as Tpl2 kinase inhibitors and P2X7 antagonists used in the treatment of pain. It is also a reagent used for preparation of himbacine analogs as thrombin receptor antagonists and potential antiplatelet agents, trisulfonated calixarene upper-rim sulfonamido and their complexation with trimethyllysine epigenetic mark, antimalarial compounds via Suzuki cross-coupling, and deoxyuridine derivatives.
Reference
- G. Cooke, H. A. de Cremiers, V. M. Rotello, B. Tarbit, P. E. Vandersträten, Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions, Tetrahedron, 2001, vol. 57, pp. 2787-2789
- N. Ni, H. Chou, J. Wang, M. Li, C. Lu, P. C. Tai, B. Wang, Identification of boronic acids as antagonists of bacterial quorum sensing in Vibrio harveyi, Biochemical and Biophysical Research Communications, 2008, vol. 369, pp. 590-594
Chemical Properties
white to yellow powder
Uses
suzuki reaction
Uses
4-Cyanophenylboronic Acid is a reactant used in the synthesis of (AMG-8718), an inhibitor of β-site amyloid precursor protein cleaving enzyme (BACE1).
Uses
Intermediates of Liquid Crystals
Synthesis
623-00-7
126747-14-6
The general procedure for the synthesis of 4-cyanobenzeneboronic acid from 4-bromobenzonitrile was as follows: 4-bromobenzonitrile (91 g, 0.50 mol) was dissolved in THF (1.1 L) at room temperature, and activated 3?molecular sieves were added for drying. After completion of drying, the solution was filtered and cooled to -100 °C. A hexane solution of 1.6 M n-butyllithium (355 mL, 0.567 mol) was slowly added over 15 min while maintaining an internal temperature between -105 °C and -93 °C. Subsequently, trimethyl borate (81 g, 0.78 mol) was added to the reaction mixture over 3 min, at which time the reaction temperature briefly increased to -72 °C. The reaction mixture was re-cooled to -100 °C over 5 min, followed by a slow warming to room temperature over 2.3 h. The reaction temperature was then increased to -100 °C over 2.3 h. The reaction temperature was then increased to -100 °C over 3 min. Upon completion of the reaction, the reaction mixture was acidified to pH 2.2 with 4N HCl and diluted with CH2Cl2 (200 mL). After separation of the aqueous layer, the organic layer was washed with brine (2 x 200 mL), dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to give a light yellow solid. The solid was purified by dissolving in 1N NaOH and extracting with CH2Cl2/THF (1:1, 2 × 200 mL). The aqueous phase was again acidified to pH 2.2 with 4N HCl and extracted with CH2Cl2/THF (1:1, 500 mL). The organic extracts were combined and concentrated to give a crude solid (64.6 g), which was ground with ether (160 mL) and dried under vacuum to give 4-cyanobenzeneboronic acid (44.0 g, 59.9% yield) in white powder form.1H NMR (d6-acetone, 300 MHz) data were as follows: δ 8.03 (d, 2H, J = 8.1), 7.75 (d, 2H, J = 8.4) , 7.54 (s, 2H).
References
[1] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481
[2] Tetrahedron, 2002, vol. 58, # 29, p. 5779 - 5787
[3] Dyes and Pigments, 2011, vol. 88, # 3, p. 274 - 279
[4] Patent: US2004/6114, 2004, A1. Location in patent: Page 63
[5] Patent: US7034045, 2006, B1. Location in patent: Page/Page column 37
4-Cyanophenylboronic acid Preparation Products And Raw materials
Raw materials
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View Lastest Price from 4-Cyanophenylboronic acid manufacturers
- Product
- 4-Cyanophenylboronic acid 126747-14-6
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98
- Supply Ability
- 10000KGS
- Release date
- 2025-11-17
- Product
- 4-Cyanophenylboronic acid 126747-14-6
- 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
- Product
- 4-Cyanophenylboronic acid 126747-14-6
- Price
- US $35.00-25.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 Ton
- Release date
- 2023-10-30