101251-09-6

Basic information

• Product Name: 4-Acetamidophenylboronic acid
• Synonyms: P-ACETAMIDOPHENYLBORONIC ACID;TIMTEC-BB SBB000202;4-ACETAMIDOBENZENEBORONIC ACID;4-ACETAMINOPHENYLBORONIC ACID;4-ACETAMIDOPHENYLBORONIC ACID;4-ACETAMIDBENZENEBORONIC ACID;4-ACETYLAMINOPHENYLBORONIC ACID;4-Acetamidophenylboronic acid, 97+%
• CAS NO: 101251-09-6
• Molecular Formula: C₈H₁₀BNO₃
• Molecular Weight: 178.98
• Product Categories: Amines;blocks;BoronicAcids;Boronic acids;Aryl;Boronic Acids;Boronic Acids and Derivatives
• Mol File: 101251-09-6.mol

Chemical Properties

• Melting Point: 215-220 °C(lit.)
• Appearance: Gray-tan/Powder
• Density: 1.23 g/cm³
• Refractive Index: 1.553
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility: 85 g/L (70 ºC)
• CAS DataBase Reference: 4-Acetamidophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Acetamidophenylboronic acid(101251-09-6)
• EPA Substance Registry System: 4-Acetamidophenylboronic acid(101251-09-6)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 101251-09-6(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
4-Acetamidophenylboronic acid is used as a reactant for the synthesis of TpI2 kinase inhibitors, which are important in the development of treatments for various diseases.
2. Used in Chemical Research:
4-Acetamidophenylboronic acid is used as a reactant in the biological evaluation of modulators of the survival motor neuron protein, contributing to the understanding of motor neuron diseases and potential therapeutic interventions.
3. Used in Organic Synthesis:
4-Acetamidophenylboronic acid is used as a reactant in cross-coupling reactions with conjugated dienes, terminal alkenes, or diazoesters, enabling the synthesis of a wide range of organic compounds with diverse applications.
4. Used in Inorganic Chemistry:
4-Acetamidophenylboronic acid is used as a reactant in the synthesis of tetrabutylammonium trifluoroborates, which are useful in various chemical reactions and processes.
5. Used in Catalysis:
4-Acetamidophenylboronic acid is used as a reactant in rhodium-catalyzed cyanation reactions, which are important for the synthesis of various nitrogen-containing compounds.
6. Used in Cancer Treatment:
4-Acetamidophenylboronic acid is used in the synthesis of potent chrom-4-one inhibitors of the DNA-dependent protein kinase, which are utilized in radiotherapy and chemotherapy for cancer treatment.

InChI:InChI=1/C8H10BNO3/c1-6(11)10-8-4-2-7(3-5-8)9(12)13/h2-5,12-13H,1H3,(H,10,11)

Upstream product

• 89415-43-0 (4-aminophenyl)boronic acid 
• 64-19-7 acetic acid 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 103-88-8 4-bromoacetanilide 
• 214360-60-8 N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide 
• 13675-18-8 tetrahydroxydiboron 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 24067-17-2 4-nitrophenylboronic acid 
• 75-36-5 acetyl chloride 

Downstream Products

• 53811-38-4 5-(4-acetylamino-phenyl)-furan-2-carbaldehyde 
• 874347-86-1 C₂₂H₂₄N₂O₅ 
• 337535-54-3 N-(4'-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-propyl][1,1'-biphenyl]-4-yl)acetamide 
• 945756-13-8 N-[4-(2-chloropyrimidin-4-yl)phenyl]acetamide 
• 945756-28-5 C₁₂H₉Cl₂N₃O 
• 945756-15-0 N-(4-(2-chloro-5-methylpyrimidin-4-yl)phenyl)acetamide 
• 1032373-91-3 4'-acetylamino-6-aminobiphenyl-3-carboxylic acid (4-dibenzylaminophenyl)amide 
• 1033575-65-3 2-(2-chlorophenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (4'-acetylaminobiphenyl-4-yl)amide 
• 1040281-04-6 N-[4-(3,9-diamino-8-chloro-5,6-dihydrobenzo[f]quinazolin-1-yl)phenyl]acetamide 
• 1032597-37-7 N-methoxy-(4-acetamidobenzyl)cyclohexanecarboxamide 

Relevant articles and documents

Susceptibility to hydrolysis of phenylboronic pinacol esters at physiological pH

Boronic acids and their esters are highly considered compounds for the design of new drugs and drug delivery devices, particularly as boron-carriers suitable for neutron capture therapy. However, these compounds are only marginally stable in water. Hydrol

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.

A method of preparing 4-aminophenylboronic acid derivatives

The invention belongs to the technical field of medicine intermediates, and particularly relates to a method of preparing 4-aminophenylboronic acid derivatives. According to the method, 4-nitrophenylboronic acid is adopted as a raw material and subjected

Sequential one-pot access to molecular diversity through aniline aqueous borylation

On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

Synthesis and biological activity of new 4-(Pyridin-4-yl)-(3-methoxy-5- methylphenyl)- 1H-pyrazoles derivatives as ROS Receptor tyrosine kinase inhibitors

A series of new 4-(pyridin-4-yl)-(3-methoxy-5-methylphenyl)-1H-pyrazoles (6a-k & 7a-l) has been rationally designed based on the structure of the lead compound KIST301080, a selective ROS receptor tyrosine kinase inhibitor, in order to study the activity of ROS of this new class of inhibitors. The compounds were synthesized and screened against ROS kinase, where compound 6h showed moderate inhibitory activity with an IC50 value of 6.25 μM. The study emphasized the importance of the acetonitrile group at the pyrazole ring and also the importance of having a hydrogen bond donor on the distal phenyl ring linked to the pyridine moiety.

Heterocyclic compounds

The invention concerns pharmaceutically useful compounds of the formula I, in which A1, A2, A3, A4, B1, m, Ar, W, X, Y, Z and R1 have any of the meanings defined herein, and their pharmaceutically acceptable salts, and pharmaceutical compositions containing them. The novel compounds possess endothelin receptor antagonist activity and are useful, for example, in the treatment of diseases or medical conditions in which elevated or abnormal levels of endothelin play a significant causative role. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.