140373-17-7

Basic information

• Product Name: Benzeneethanol, beta-amino-4-fluoro- (9CI)
• Synonyms: Benzeneethanol, beta-amino-4-fluoro- (9CI);2-amino-2-(4-fluorophenyl)ethanol(SALTDATA: FREE);b-AMino-4-fluorobenzeneethanol;2-Amino-2-(4-fluorophenyl)
• CAS NO: 140373-17-7
• Molecular Formula: C₈H₁₀FNO
• Molecular Weight: 155.1695032
• Product Categories: HALIDE
• Mol File: 140373-17-7.mol

Chemical Properties

• Boiling Point: 287.4±25.0 °C(Predicted)
• Appearance: /
• Density: 1.208±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 12.48±0.10(Predicted)
• CAS DataBase Reference: Benzeneethanol, beta-amino-4-fluoro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanol, beta-amino-4-fluoro- (9CI)(140373-17-7)
• EPA Substance Registry System: Benzeneethanol, beta-amino-4-fluoro- (9CI)(140373-17-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 140373-17-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
Benzeneethanol, beta-amino-4-fluoro(9CI) is utilized as a building block for the synthesis of drug candidates due to its unique molecular structure. Its presence in the molecular framework can contribute to the development of new therapeutic agents with improved pharmacological properties.
Used in the Development of New Materials:
Benzeneethanol, beta-amino-4-fluoro(9CI)'s specific chemical properties make it a valuable component in the creation of new materials. Its fluorine substitution and beta-amino alcohol structure can enhance the properties of materials, such as their stability, reactivity, or selectivity, depending on the application.
Used in Chemical Intermediates:
Benzeneethanol, beta-amino-4-fluoro(9CI) can also serve as a key intermediate in the synthesis of more complex organic compounds. Its unique structure allows for further functionalization and modification, enabling the development of a wide range of chemical products with diverse applications.

Upstream product

• 18511-62-1 4-fluorostyrene oxide 
• 7589-27-7 2-(4-Fluorophenyl)ethanol 
• 405-99-2 para-fluorostyrene 
• 866886-40-0 2-azido-2-(4-fluorophenyl)ethan-1-ol 
• 7292-73-1 (2RS)-N-(p-fluorophenyl)glycine 

Downstream Products

• 1617545-45-5 2-[6-(3-chloro-phenyl)-pyrazin-2-ylamino]-2-(4-fluoro-phenyl)-ethanol 
• 1418283-52-9 N-[1-(4-fluorophenyl)-2-hydroxyethyl]-2-(2,4-dichlorophenoxy)propanamide 
• 403-31-6 4-fluoro-2-hydroxy-acetophenone 
• 224434-01-9 (S)-1-(4-fluorophenyl)-2-hydroxyethylamine 
• 130632-07-4 (E)-1-(4-fluorophenyl)-N-(4-methoxyphenyl)methanimine 
• 1637437-41-2 C₁₄H₁₂FIN₄O 
• 69776-89-2 4-(4-fluorophenyl)-oxazolidine-2-one 
• 1239363-29-1 3-[6-chloro-4-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl]-4-(4-fluorophenyl)oxazolidin-2-one 
• 1239361-87-5 (S)-1-{2-[1-(4-fluorophenyl)indolylethylamino]-6-(aminopyrazine-2-ylamino)pyrimidinecarboxylic-4-yl}-3-methylazetidin-3-ol 
• 1273550-37-0 5-(4-fluoro-phenyl)-thiomorpholine-3-thione 
• 1273550-36-9 5-(4-fluoro-phenyl)-thiomorpholin-3-one 
• 1273550-35-8 [2-tert-butoxycarbonylamino-2-(4-fluoro-phenyl)-ethylsulfanyl]-acetic acid methyl ester 
• 1273550-34-7 [1-(4-fluoro-phenyl)-2-iodo-ethyl]-carbamic acid tert-butyl ester 
• 1273647-83-8 3-(4-fluoro-phenyl)-5-methylsulfanyl-3,6-dihydro-2H-[1,4]thiazine 

Relevant articles and documents

Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions

The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.

Catalytic β C-H amination: Via an imidate radical relay

The first catalytic strategy to harness imidate radicals for C-H functionalization has been developed. This iodine-catalyzed approach enables β C-H amination of alcohols by an imidate-mediated radical relay. In contrast to our first-generation, (super)stoichiometric protocol, this catalytic method enables faster and more efficient reactivity. Furthermore, lower oxidant concentration affords broader functional group tolerance, including alkenes, alkynes, alcohols, carbonyls, and heteroarenes. Mechanistic experiments interrogating the electronic nature of the key 1,5 H-atom transfer event are included, as well as probes for chemo-, regio-, and stereo-selectivity.

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.

Valine amide carbamate derivative containing propargyloxy group and application thereof

The invention relates to a valine amide carbamate derivative containing a propargyloxy group and a pharmaceutically acceptable salt thereof, belonging to the field of botanical bactericides. The valine amide carbamate derivative has a general formula (I) as shown in the specification, and the substituent R in the general formula (I) is as defined in the specification. The invention also relates to a preparation method for the compound as shown in the general formula (I), an intermediate specially prepared for development of the compound and application of the compound to prevention and treatment of plant diseases.

Potent and Selective Inhibitors of Histone Deacetylase-3 Containing Chiral Oxazoline Capping Groups and a N-(2-Aminophenyl)-benzamide Binding Unit

A novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamide unit. Among several new inhibitors of this type exhibiting Class I selectivity and potent inhibition of HDAC3-NCoR2, in vitro assays for the inhibition of HDAC1, HDAC2, and HDAC3-NCoR2 by N-(2-aminophenyl)-benzamide 15k gave respective IC50 values of 80, 110, and 6 nM. Weak inhibition of all other HDAC isoforms (HDAC4, 5, 6, 7, and 9: IC50 > 100000 nM; HDAC8: IC50 = 25000 nM; HDAC10: IC50 > 4000 nM; HDAC11: IC50 > 2000 nM) confirmed the Class I selectivity of 15k. 2-Aminoimidazolinyl, 2-thioimidazolinyl, and 2-aminooxazolinyl units were shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)-benzamides previously reported, but the 2-aminooxazolinyl unit was the most potent in inhibiting HDAC3-NCoR2. Many of the new HDAC inhibitors showed higher solubilities and lower binding to human serum albumin than that of Mocetinostat. Increases in histone H3K9 acetylation in the human cell lines U937 and PC-3 was observed for all three oxazolinyl inhibitors evaluated; those HDAC inhibitors also lowered cyclin E expression in U937 cells but not in PC-3 cells, indicating underlying differences in the mechanisms of action of the inhibitors on those two cell lines.

Formal aromatic C-H insertion for stereoselective isoquinolinone synthesis and studies on mechanistic insights into the C-C bond formation

(Chemical Equation Presented) Formal aromatic C-H insertion of rhodium(II) carbenoid was intensively investigated to develop a new methodology and probe its mechanism. Contrasting with the previously proposed direct C-H insertion, the mechanism was revealed to be electrophilic aromatic substitution, which was supported by substituent effects on the aromatic ring and a secondary deuterium kinetic isotope effect. Various isoquinolinones were synthesized intramolecularly via six-membered ring formation with high regioand diastereoselectivity, while averting the common Buchner-type reaction. Intermolecularly, dirhodium catalyzed formal aromatic C-H insertion on electron-rich aromatics was also achieved.

PYRAZOLE DERIVATIVES AS INHIBITORS OF RECEPTOR TYROSYNE KINASES

Compounds of formula (I): and their use in the inhibition of Trk activity are described.

Novel diarylsulfonylurea derivatives as potent antimitotic agents

Novel diarylsulfonylurea derivatives have been synthesized and identified as potent inhibitors of tubulin polymerization and cancer cell proliferation. Furthermore, these compounds were also efficacious against multidrug-resistant cancer cells. A novel series of diarylsulfonylurea derivatives were synthesized and evaluated for interaction with tubulin and for cytotoxicity against human cancer cell lines. These derivatives demonstrated good inhibitory activity against tubulin polymerization, which was well correlated with promising antiproliferative activity as well as G2/M phase cell cycle arrest. Furthermore, several compounds were also efficacious against multidrug-resistant cancer cells, which are resistant to many other known microtubule inhibitors.

3-[3-(piperidin-1-yl)propyl]indoles as highly selective h5-HT(1D) receptor agonists

Several 5-HT(ID/1B) receptor agonists are now entering the marketplace as treatments for migraine. This paper describes the development of selective h5-HT(1D)receptor agonists as potential antimigraine agents which may produce fewer side effects. A series of 3-[3-(piperidin-1-yl)propyl]indoles has been synthesized which has led to the identification of 80 (L-772,405), a high- affinity h5-HT(1D) receptor full agonist having 170-fold selectivity for h5- HT(1D) receptors over h5-HT(1B) receptors. L-772,405 also shows very good selectivity over a range of other serotonin and nonserotonin receptors and has excellent bioavailability following subcutaneous administration in rats. It therefore constitutes a valuable tool to delineate the role of h5-HT(1D) receptors in migraine. Molecular modeling and physical properties have been utilized to postulate the binding conformation of these compounds in the receptor cavity.