57351-99-2

Basic information

• Product Name: 5-Methyl-3-isoxazolecarbonitrile
• Synonyms: 3-Cyano-5-methylisoxazole;5-Methyl-3-isoxazolecarbonitrile;5-Methylisoxazole-3-carbonitrile 97%;5-Methylisoxazole-3-carbonitrile ,97%;5-methyl-3-isoxazolecarbonitrile(SALTDATA: FREE)
• CAS NO: 57351-99-2
• Molecular Formula: C₅H₄N₂O
• Molecular Weight: 108.09806
• Mol File: 57351-99-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 249.4 °C at 760 mmHg
• Flash Point: 104.6 °C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 0.023mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: 2-8°C
• PKA: -6.83±0.50(Predicted)
• CAS DataBase Reference: 5-Methyl-3-isoxazolecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-3-isoxazolecarbonitrile(57351-99-2)
• EPA Substance Registry System: 5-Methyl-3-isoxazolecarbonitrile(57351-99-2)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 23-26-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• Hazardous Substances Data: 57351-99-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liquid

InChI:InChI=1/C5H4N2O/c1-4-2-5(3-6)7-8-4/h2H,1H3

Upstream product

• 89322-78-1 5-methy-3-isoxazolecarboxaldehyde oxime 
• 615-79-2 ethyl 2,4-diketopentanoate 
• 3209-72-1 ethyl 5-methylisoxazole-3-carboxylate 
• 39499-34-8 5-methyl-3-isoxazolyl chloride 
• 3445-52-1 5-methyl-isoxazole-3-carbothioic acid amide 

Downstream Products

• 154016-48-5 (5-methyl-3-isoxazolyl)methylamine 
• 77358-26-0 5-methyl-isoxazole-3-carbothioic acid amide 
• 24068-54-0 3-acetyl-5-methylisoxazole 
• 84654-34-2 5-Methylsulfanylmethyl-isoxazole-3-carbonitrile 
• 13600-36-7 5-(5-methyl-isoxazol-3-yl)-1H-tetrazole 
• 90585-88-9 5-Methyl-isoxazol-carbonsaeure-(3)-amidoxim 

Relevant articles and documents

Structure-Based Drug Design of Mineralocorticoid Receptor Antagonists to Explore Oxosteroid Receptor Selectivity

The mineralocorticoid receptor (MR) is a nuclear hormone receptor involved in the regulation of body fluid and electrolyte homeostasis. In this study we explore selectivity triggers for a series of nonsteroidal MR antagonists to improve selectivity over other members of the oxosteroid receptor family. A biaryl sulfonamide compound was identified in a high-throughput screening (HTS) campaign. The compound bound to MR with pKi=6.6, but displayed poor selectivity over the glucocorticoid receptor (GR) and the progesterone receptor (PR). Following X-ray crystallography of MR in complex with the HTS hit, a compound library was designed that explored an induced-fit hypothesis that required movement of the Met852 side chain. An improvement in MR selectivity of 11- to 79-fold over PR and 23- to 234-fold over GR was obtained. Given the U-shaped binding conformation, macrocyclizations were explored, yielding a macrocycle that bound to MR with pKi=7.3. Two protein–ligand X-ray structures were determined, confirming the hypothesized binding mode for the designed compounds.

DERIVATIVES OF 6,7-DIHYDRO-5H-IMIDAZO[1,2-α]IMIDAZOLE-3- CARBOXYLIC ACID AMIDES

Derivatives of 6,7-dihydro-5H-imidazo[1,2-α]imidazole-3-carboxylic acid amide exhibit good inhibitory effect upon the interaction of CAMs and Leukointegrins and are thus useful in the treatment of inflammatory disease.

Selective cyclooxygenase-2 inhibitors: Heteroaryl modified 1,2-diarylimidazoles are potent, orally active antiinflammatory agents

A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2.3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no GI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.