40067-80-9

Basic information

• Product Name: 3-(TRIFLUOROMETHYL)BENZAMIDOXIME
• Synonyms: 3-(TRIFLUOROMETHYL)BENZAMIDOXIME;N-HYDROXY-3-TRIFLUOROMETHYL-BENZAMIDINE;N'-HYDROXY-3-(TRIFLUOROMETHYL)BENZENECARBOXIMIDAMIDE;3-(Trifluoromethyl)benzamidoxime 97%;3-(Trifluoromethyl)benzamidoxime97%;N'-Hydroxy-3-(trifluoromethyl)benzenecarboximidamide, 3-(N'-Hydroxycarbamimidoyl)benzotrifluoride;BenzenecarboxiMidaMide,N-hydroxy-3-(trifluoroMethyl)-
• CAS NO: 40067-80-9
• Molecular Formula: C₈H₇F₃N₂O
• Molecular Weight: 204.15
• Product Categories: pharmacetical;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Nitrogen Compounds;Organic Building Blocks;Oximes
• Mol File: 40067-80-9.mol

Chemical Properties

• Melting Point: 87-90 °C(lit.)
• Boiling Point: 306.6°Cat760mmHg
• Flash Point: 139.2°C
• Appearance: /
• Density: 1.4g/cm³
• PKA: 13.88±0.50(Predicted)
• CAS DataBase Reference: 3-(TRIFLUOROMETHYL)BENZAMIDOXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(TRIFLUOROMETHYL)BENZAMIDOXIME(40067-80-9)
• EPA Substance Registry System: 3-(TRIFLUOROMETHYL)BENZAMIDOXIME(40067-80-9)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-43-25
• Safety Statements: 26-36-45-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 40067-80-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
3-(TRIFLUOROMETHYL)BENZAMIDOXIME is used as a reagent in pharmaceutical research for the development of new drugs and pharmaceutical intermediates. Its unique chemical properties make it a valuable component in the synthesis of various medicinal compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(TRIFLUOROMETHYL)BENZAMIDOXIME serves as a building block for the production of other organic compounds. Its versatility in chemical reactions contributes to the creation of a wide range of chemical products.
Used in Disease Treatment:
3-(TRIFLUOROMETHYL)BENZAMIDOXIME is also known for its potential application in the treatment of various diseases and conditions. Its specific biological activity and interaction with biological targets make it a promising candidate for therapeutic use.

Upstream product

• 368-77-4 3-trifluoromethylbenzonitrile 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 368-83-2 3-(trifluoromethyl)benzaldehyde oxime 

Downstream Products

• 40067-76-3 3,3'-bis-(3-trifluoromethyl-phenyl)-5,5'-p-phenylene-bis-[1,2,4]oxadiazole 
• 40067-77-4 3,3'-bis-(3-trifluoromethyl-phenyl)-5,5'-m-phenylene-bis-[1,2,4]oxadiazole 
• 911048-35-6 (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid n-(N-hydroxy-3-trifluoromethylbenz-amidine) ester 
• 1402448-94-5 (Z)-dimethyl-(3-(trifluoromethyl)benzimidamidoxy)but-2-enedioate 
• 1402448-92-3 (E)-dimethyl-(3-(trifluoromethyl)benzimidamidoxy)but-2-enedioate 
• 1419611-66-7 5-(2,4-dichlorophenyl)-3-(3-(trifluoromethyl)phenyl)-1,2,4-oxadiazole 
• 360049-07-6 N²-(Ethoxycarbonyloxy)-3-trifluoromethylbenzamidine 

Relevant articles and documents

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators

Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing py

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Herein, we describe the preparation of pyridylpyrazole-4-carboxamides containing a 1,2,4-oxadiazole ring as novel anthranilic diamide derivatives and compare their insecticidal activities to that of chlorantraniliprole, a well-established potent insectici

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

KCNT1 INHIBITORS AND METHODS OF USE

The present invention is directed to, in part, compounds and compositions useful for preventing and/or treating a neurological disease or disorder, a disease or condition relating to excessive neuronal excitability, and/or a gain-of-function mutation in a gene (e.g., KCNT1). Methods of treating a neurological disease or disorder, a disease or condition relating to excessive neuronal excitability, and/or a gain-of-function mutation in a gene such as KCNT1 are also provided herein.

A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.

Novel 5-(quinuclidin-3-ylmethyl)-1,2,4-oxadiazoles to investigate the activation of the α7 nicotinic acetylcholine receptor subtype: Synthesis and electrophysiological evaluation

α7 nicotinic acetylcholine receptors (nAChRs) are relevant therapeutic targets for a variety of disorders including neurodegeneration, cognitive impairment, and inflammation. Although traditionally identified as an ionotropic receptor, the α7 subtype showed metabotropic-like functions, mainly linked to the modulation of immune responses. In the present work, we investigated the structure-activity relationships in a set of novel α7 ligands incorporating the 5-(quinuclidin-3-ylmethyl)-1,2,4-oxadiazole scaffold, i.e. derivatives 21a-34a and 21b-34b, aiming to identify the structural requirements able to preferentially trigger one of the two activation modes of this receptor subtype. The new compounds were characterized as partial and silent α7 nAChR agonists in electrophysiological assays, which allowed to assess the contribution of the different groups towards the final pharmacological profile. Overall, modifications of the selected structural backbone mainly afforded partial agonists, among them tertiary bases 27a-33a, whereas additional hydrogen-bond acceptor groups in permanently charged ligands, such as 29b and 31b, favored a silent desensitizing profile at the α7 nAChR.

Cobalt(III)-Catalyzed Oxadiazole-Directed C-H Activation for the Synthesis of 1-Aminoisoquinolines

Aromatic heterocycles have been identified as effective directing groups (DGs) in C-H functionalization but can be retained as undesired bulky substituents in the final products. Herein, we report a Co(III)-catalyzed 1-aminoisoquinoline synthesis strategy based on oxadiazole-directed aromatic C-H coupling with alkynes and a subsequent redox-neutral C-N cyclization reaction. This labile N-O bond-based protocol has allowed the toleration of a broad range of functional groups.

Oxadiazolone-Enabled Synthesis of Primary Azaaromatic Amines

Despite their tremendous synthetic and pharmaceutical utility, primary azaaromatic amines remain elusive for access based on a generally applicable C-H functionalization strategy. An oxadiazolone-enabled approach is reported for convenient entry into N-unsubstituted 1-aminoisoquinolines through Co(III)-catalyzed redox-neutral, step-, atom-, and purification-economic C-H functionalization with alkynes. A 15N labeling experiment reveals the effectiveness of both oxadiazolone N atoms as directing sites. The installed primary amine can be harnessed as a synthetically useful handle for attachment of divergent appendages.

Fragmentation of GW4064 led to a highly potent partial farnesoid X receptor agonist with improved drug-like properties

Abstract The ligand activated transcription factor farnesoid X receptor (FXR) is a crucial regulator of several metabolic and inflammatory pathways and its activation by agonistic ligands seems a valuable therapeutic approach for many disorders. Most known non-steroidal FXR agonists however, have limitations that hinder their clinical development and novel FXR ligands are required. Evaluation of the co-crystal structures of the widely used FXR agonist GW4064 and related compounds in complex with the FXR ligand binding domain indicated that their disubstituted isoxazole moiety is especially relevant for FXR activation. By investigation of GW4064-fragments missing the aromatic tail, we discovered a highly potent and soluble partial FXR agonist (14, ST-1892) as well as a fluorescent FXR ligand (15) as potential pharmacological tool.