454-81-9

Basic information

• Product Name: 2-amino-alpha,alpha,alpha-trifluoro-p-creso
• Synonyms: 3-Amino-4-hydroxybenzotrifluoride 95%;T5394155;2-Hydroxy-5-(trifluoromethyl)aniline;4-(Trifluoromethyl)-2-aminophenol;2-amino-alpha,alpha,alpha-trifluoro-p-creso;3-AMINO-4-HYDROXYBENZOTRIFLUORIDE;5-Amino-2-trifluoromethyl-phenol;2-amino-4-(trifluoromethyl)phenol
• CAS NO: 454-81-9
• Molecular Formula: C₇H₆F₃NO
• Molecular Weight: 177.1238496
• Mol File: 454-81-9.mol

Chemical Properties

• Melting Point: 121-122 °C(Solv: benzene (71-43-2))
• Boiling Point: 234.5 °C at 760 mmHg
• Flash Point: 95.6 °C
• Appearance: /
• Density: 1.432 g/cm³
• Vapor Pressure: 0.0345mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.36±0.18(Predicted)
• CAS DataBase Reference: 2-amino-alpha,alpha,alpha-trifluoro-p-creso(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-alpha,alpha,alpha-trifluoro-p-creso(454-81-9)
• EPA Substance Registry System: 2-amino-alpha,alpha,alpha-trifluoro-p-creso(454-81-9)

Safety Data

• Hazardous Substances Data: 454-81-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-amino-alpha,alpha,alpha-trifluoro-p-creso is used as a key intermediate in the synthesis of benzoxazolone carboxamides, which are being studied for their potential as potent acid ceramidase inhibitors. These inhibitors are of interest in the development of treatments for various diseases, as they can modulate the levels of ceramide, a bioactive lipid molecule involved in cell signaling and apoptosis.
In the field of medicinal chemistry, understanding the structure-activity relationship (SAR) of compounds is crucial for optimizing their potency, selectivity, and pharmacokinetic properties. The use of 2-amino-alpha,alpha,alpha-trifluoro-p-creso in these studies allows researchers to explore the effects of its unique structural features on the biological activity of the resulting benzoxazolone carboxamides, ultimately contributing to the discovery of more effective therapeutic agents.

InChI:InChI=1/C7H6F3NO/c8-7(9,10)4-1-2-6(12)5(11)3-4/h1-3,12H,11H2

Upstream product

• 402-45-9 4-hydroxybenzotrifluoride 
• 400-99-7 2-nitro-4-trifluoromethylphenol 
• 7772-99-8 stannous chloride 
• 400-98-6 4-trifluoromethyl-2-nitroaniline 
• 121-17-5 2-chloro-3-nitro-5-trifluoromethylbenzene 

Downstream Products

• 19420-46-3 (2-hydroxy-5-trifluoromethyl-phenyl)-thiourea 
• 25761-42-6 1-(3,5-Bis-trifluoromethyl-phenyl)-3-(2-hydroxy-5-trifluoromethyl-phenyl)-urea 
• 185419-99-2 3,6-dichloro-N-(4-trifluoromethyl-2-hydroxyphenyl)pyridazine-4-carboxamide 
• 347-40-0 6-trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine 
• 921198-83-6 N-(2-hydroxy-5-(trifluoromethyl)phenyl)-4-nitrobenzamide 
• 160383-94-8 N-(1-naphthyl)-N'-(2-hydroxy-5-(trifluoromethyl)phenyl)-urea 
• 888731-86-0 2-chloro-N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide 
• 944356-81-4 2-bromo-N-(2-hydroxy-5-trifluoromethylphenyl)-3-methylbutyramide 
• 1192021-13-8 3-tert-butoxycarbonylamino-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide 
• 1192021-02-5 3-chloro-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide 
• 1192021-11-6 N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3-iodoisonicotinamide 
• 1282541-12-1 N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3-(methoxymethyl)isonicotinamide 
• 1192021-03-6 2-chloro-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide 
• 1413929-96-0 C₂₃H₁₆Cl₂F₃NO₅ 

Relevant articles and documents

2:1 versus 1:1 Coupling of Alkylacetylenes with Secondary Amines: Selectivity Switching in 8-Quinolinolato Rhodium Catalysis

Both 2:1 and 1:1 couplings of alkylacetylenes with secondary amines were achieved using 8-quinolinolato rhodium catalysts and CsF. The 2:1/1:1 selectivity was switched by choosing the reaction solvent. In DMA, an unprecedented 2:1 coupling reaction of alkylacetylenes with amines proceeded to give 2-aminodiene products. One-pot 2:1 coupling/reduction provided rapid access to various allylamines, while one-pot coupling/hydrolysis gave enones as products. In toluene, anti-Markovnikov hydroamination occurred under relatively mild conditions to give 1:1 coupling products.

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Synthesis of benzoxazoles via the copper-catalyzed hydroamination of alkynones with 2-aminophenols

We describe herein the synthetic method to benzoxazole derivatives via the copper-catalyzed hydroamination of alkynones with 2-aminophenols. The method produced a wide variety of functionalized benzoxazole derivatives in good yields. Preliminary mechanistic experiments revealed that the reaction would proceed through the copper-catalyzed hydroamination of alkynones and the sequential intramolecular cyclization of β-iminoketones/elimination of acetophenone promoted by the copper catalyst.

Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors

We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.

Novel benzoxazolone compound

PROBLEM TO BE SOLVED: To provide a therapeutic agent for diseases such as neuropathic pain, nociceptive pain, inflammatory pain, small diameter fiber neuropathy, erythromelalgia, paroxysmal extreme pain disorder, dysuria or multiple sclerosis. SOLUTION: There is provided a benzoxazolone compound represented by the formula (1) or a pharmaceutically acceptable salt. (1), where R1 and R2 are each independently H or C1-6 alkyl, where the alkyl may be substituted by hydroxy, C1-4 alkylsulfonyl, aminocarbonyl or 4 to 7-membered heterocycloalkyl, or the like, L is C1-6 alkylene, R3 is C1-6 alkyl, C3-7 cycloalkyl, where the cycloalkyl may be substituted by halogen or hydroxy or the like, C6-10 aryl, where the aryl may be substituted by halogen, C1-4 alkyl or C1-4 haloalkyl or the like, R4 is H, halogen or C1-4 alkyl. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

ONE POT PROCESS FOR THE CONVERSION OF AROYL CHLORIDES TO ACYL THIOUREAS

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HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND

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