4-Acetamidophenylboronic acid

Base Information

• Chemical Name: 4-Acetamidophenylboronic acid
• CAS No.: 101251-09-6
• Molecular Formula: C8H10BNO3
• Molecular Weight: 178.983
• Hs Code.: 29319090
• European Community (EC) Number: 671-684-1
• DSSTox Substance ID: DTXSID50370427
• Nikkaji Number: J2.139.356H
• Wikidata: Q72434116
• Mol file: 101251-09-6.mol

Synonyms:4-Acetamidophenylboronic acid;101251-09-6;4-acetylaminophenylboronic acid;(4-acetamidophenyl)boronic Acid;4-acetamidophenyl boronic acid;p-(Acetylamino)phenylboronic acid;MFCD02179451;Boronic acid, [4-(acetylamino)phenyl]-;4-Acetamidobenzeneboronic acid;4-Acetylaminophenylboronic acid;4-Acetylaminophenylboronicacid;4-Acetamidophenyl-Boronic Acid;4-acetylaminophenyl boronic acid;Boronic acid, B-[4-(acetylamino)phenyl]-;SCHEMBL9162;4-acetoamidophenylboronic acid;p-acetamido-phenylboronic acid;4-acetamido-phenylboronic acid;4-acetaminophenyl boronic acid;4-(acetamido)phenylboronic acid;4-acetylamino-phenylboronic acid;(4-acetylaminophenyl)boronic acid;4-(acetylamino)phenylboronic acid;DTXSID50370427;4-(Acetylamino)phenylboranic acid;VYEWTHXZHHATTA-UHFFFAOYSA-N;(4-acetamido-phenyl)-boronic acid;AMY29964;BCP16827;CS-D1684;[4-(acetylamino)phenyl]boronic acid;[4-(acetylamino) phenyl]boronic acid;AKOS006222734;AB11156;NCGC00249515-01;AS-11604;Boronic acid,B-[4-(acetylamino)phenyl]-;SY002730;FT-0602234;A22122;EN300-3273853;Z1203161679

Chemical Property of 4-Acetamidophenylboronic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Melting Point: 215-220 °C(lit.)
• Refractive Index: 1.553
• PSA: 69.56000
• Density: 1.23 g/cm³
• LogP: -0.60220
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: 85 g/L (70 ºC)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 179.0753733
• Heavy Atom Count: 13
• Complexity: 178

Purity/Quality:

99% ^*data from raw suppliers

4-Acetamidophenyl boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)NC(=O)C)(O)O
• Uses: Reactant involved in:Synthesis of TpI2 kinase inhibitorsBiological evaluation of modulators of survival motor neuron proteinCross-coupling with conjugated dienes or terminal alkenes or diazoestersSynthesis of tetrabutylammonium trifluoroboratesRhosium-catalyzed cyanation 4-Acetamidophenylboronic Acid is used in the synthesis of potent chrom-4-one inhibitors of the DNA-Dependant protein kinase for use in radiotherapy and chemotherapy in cancer treatment.

Technology Process of 4-Acetamidophenylboronic acid

There total 8 articles about 4-Acetamidophenylboronic 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: 82.0%

(4-(1-(hydroxyimino)ethyl)phenyl)boronic acid → (4-acetylaminophenyl)boronic acid (101251-09-6)

Guidance literature:

(4-(1-(hydroxyimino)ethyl)phenyl)boronic acid; With fluorosulfonyl fluoride; triethylamine; In acetonitrile; at 20 ℃; for 1h;

With hydrogenchloride; In water; acetonitrile; at 20 ℃;

DOI:10.1002/ejoc.201900844

Reference yield: 78.2%

(4-aminophenyl)boronic acid (89415-43-0) + acetyl chloride (75-36-5) → (4-acetylaminophenyl)boronic acid (101251-09-6)

Guidance literature:

In chloroform; at 5 - 40 ℃; for 3h; Solvent; Temperature;

Reference yield: 31.0%

tetrahydroxydiboron (13675-18-8) + N-acetyl-p-phenylenediamine (122-80-5) → (4-acetylaminophenyl)boronic acid (101251-09-6)

Guidance literature:

N-acetyl-p-phenylenediamine; With hydrogenchloride; In water; at 20 ℃; for 0.0166667h;

With sodium nitrite; In water; at 0 ℃; for 0.25h;

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

DOI:10.1021/jo501665e

upstream raw materials:

(4-aminophenyl)boronic acid

acetic acid

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-bromoacetanilide

Downstream raw materials:

5-(4-acetylamino-phenyl)-furan-2-carbaldehyde

C₂₂H₂₄N₂O₅

N-[4-(2-chloropyrimidin-4-yl)phenyl]acetamide

N-methoxy-(4-acetamidobenzyl)cyclohexanecarboxamide

Refernces

• 1、 Zhang, Guofu,Zhao, Yiyong,Xuan, Lidi,Ding, Chengrong. "SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams". supporting information. p. 4911 - 4915. Retrieved 2019/07/31.
• 2、 Erb, William,Albini, Mathieu,Rouden, Jacques,Blanchet, Jrme. "Sequential one-pot access to molecular diversity through aniline aqueous borylation". . p. 10568 - 10580. Retrieved 2015/01/08.