4-Cyanophenylboronic acid

Base Information

• Chemical Name: 4-Cyanophenylboronic acid
• CAS No.: 126747-14-6
• Molecular Formula: C7H6BNO2
• Molecular Weight: 146.941
• Hs Code.: 29163990
• European Community (EC) Number: 671-676-8
• DSSTox Substance ID: DTXSID20370217
• Nikkaji Number: J1.102.036D
• Wikidata: Q72458776
• ChEMBL ID: CHEMBL500339
• Mol file: 126747-14-6.mol

Synonyms:4-Cyanophenylboronic acid;126747-14-6;(4-cyanophenyl)boronic Acid;4-Cyanobenzeneboronic Acid;p-cyanophenylboronic acid;MFCD01318968;BORONIC ACID, (4-CYANOPHENYL)-;4-cyanophenyl boronic acid;4-cyano-phenyl-boronic acid;(4-cyano-phenyl)boronic acid;4-(dihydroxyboranyl)benzonitrile;4-cyanoplienylboronic acid;4-cyano phenylboronic acid;4-cyano-phenylboronic acid;4-cyanophenyl-boronic acid;D0AW4G;para-cyanophenylboronic acid;4-cyanobenzene boronic acid;SCHEMBL6016;4-cyano phenyl boronic acid;(4-cyanophenyl) boronic acid;(4-cyano-phenyl)-boronic acid;CHEMBL500339;B-(4-cyanophenyl)-boronic acid;BDBM26131;DTXSID20370217;BCP12932;CS-B0849;BBL101374;STL555170;AKOS004116072;AB08783;AC-1101;AS-2262;pound 4-Cyanophenyl pound(c)boronic acid;PD182141;SY005370;BORONIC ACID, B-(4-CYANOPHENYL)-;AM20060345;C1778;FT-0602412;EN300-59658;A805597;J-005431;J-515232;FMOC-3-AMINO-3-(4-CHLOROPHENYL)PROPIONICACID;Z915380662;4-Cyanophenylboronic Acid (contains varying amounts of Anhydride)

Chemical Property of 4-Cyanophenylboronic acid

Chemical Property:

• Appearance/Colour: white to yellow powder
• Vapor Pressure: 1.11E-05mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.559
• Boiling Point: 355.9 °C at 760 mmHg
• PKA: 7.38±0.10(Predicted)
• Flash Point: 169 °C
• PSA: 64.25000
• Density: 1.25 g/cm³
• LogP: -0.76192
• Storage Temp.: 0-60°C
• Solubility.: DMSO, Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 147.0491586
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

4-Cyanophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C#N)(O)O
• Recent ClinicalTrials: Study to Evaluate the Safety and Tolerability of AC-1101 Topical Gel in Patients With Granuloma Annulare
• 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.
• Uses: suzuki reaction 4-Cyanophenylboronic Acid is a reactant used in the synthesis of (AMG-8718), an inhibitor of β-site amyloid precursor protein cleaving enzyme (BACE1). Intermediates of Liquid Crystals

Technology Process of 4-Cyanophenylboronic acid

There total 22 articles about 4-Cyanophenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

4-(1,3,2-dioxaborinan-2-yl)benzonitrile (152846-62-3) → 4-cyanophenylboronic acid (126747-14-6)

Guidance literature:

With potassium carbonate; In methanol; water; mixt. stirred at 25°C for 10 h; filtration; MeOH removed in vac.; soln. cooled; acidified (HCl); crystn.; filtration; washed (H2O); IR; NMR; mass spectra;

DOI:10.1246/bcsj.62.3896

Reference yield: 76.0%

tetrahydroxydiboron (13675-18-8) + 4-Aminobenzonitrile (873-74-5) → 4-cyanophenylboronic acid (126747-14-6)

Guidance literature:

4-Aminobenzonitrile; With hydrogenchloride; sodium nitrite; In water; at 0 ℃; for 0.25h;

tetrahydroxydiboron; With sodium acetate; In water; at 20 ℃; for 0.333333h;

DOI:10.1002/chem.201402487

Reference yield: 74.0%

4-Chlorophenylboronic acid (1679-18-1) + dicyanozinc (557-21-1) → 4-cyanophenylboronic acid (126747-14-6)

Guidance literature:

With racemic 2-di-tert-butylphosphino-1,1'-binaphthyl; palladium(II) trifluoroacetate; zinc; In N,N-dimethyl acetamide; at 80 ℃; for 5h;

DOI:10.1021/ol070372d

upstream raw materials:

4-bromobenzenecarbonitrile

di-isopropyl 4-cyanophenylboronate

Triisopropyl borate

4-Chlorophenylboronic acid

Downstream raw materials:

4-(3-oxo-3H-inden-1-yl)-benzonitrile

4-(methylsulfonyl)benzonitrile

4'-methoxybiphenyl-4-carbonitrile

4-(2-methylsulfanylpyrimidin-4-yl)benzonitrile

Refernces

• 1、 Haddenham, Dustin,Bailey, Christopher L.,Vu, Chau,Nepomuceno, Gabby,Eagon, Scott,Pasumansky, Lubov,Singaram, Bakthan. "Lithium aminoborohydrides 17. Palladium catalyzed borylation of aryl iodides, bromides, and triflates with diisopropylaminoborane prepared from lithium diisopropylaminoborohydride". . p. 576 - 583. Retrieved 2011.
• 2、 Leermann, Timo,Leroux, Frederic R.,Colobert, Francoise. "Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges". . p. 4479 - 4481. Retrieved 2011.
• 3、 Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup. "Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source". . p. 10966 - 10972. Retrieved 2020/09/23.
• 4、 Yang, Xintuo,Pang, Xuehai,Fan, Lei,Li, Xinghai,Chen, Yuanwei. "Synthesis and evaluation of sulfonamide derivatives as potent Human Uric Acid Transporter 1 (hURAT1) inhibitors". supporting information. p. 1919 - 1922. Retrieved 2017/04/10.