89808-75-3

Basic information

• Product Name: 5-(2-NITROPHENYL)-1,3-OXAZOLE
• Synonyms: 5-(2-NITROPHENYL)-1,3-OXAZOLE;BUTTPARK 154\16-89;5-(2-NITROPHENYL)OXAZOLE;2-(1,3-Oxazol-5-yl)nitrobenzene
• CAS NO: 89808-75-3
• Molecular Formula: C₉H₆N₂O₃
• Molecular Weight: 190.16
• Mol File: 89808-75-3.mol

Chemical Properties

• Boiling Point: 334.3 °C at 760 mmHg
• Flash Point: 156 °C
• Appearance: /
• Density: 1.333 g/cm³
• Vapor Pressure: 0.000251mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: 2-8°C
• PKA: -0.08±0.10(Predicted)
• CAS DataBase Reference: 5-(2-NITROPHENYL)-1,3-OXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-NITROPHENYL)-1,3-OXAZOLE(89808-75-3)
• EPA Substance Registry System: 5-(2-NITROPHENYL)-1,3-OXAZOLE(89808-75-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 89808-75-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Chemical Research:
5-(2-Nitrophenyl)-1,3-oxazole is used as a synthetic intermediate for the development of biologically active compounds. Its unique structure and reactivity make it a valuable component in the creation of new pharmaceuticals and other bioactive substances.
Used in Organic Synthesis:
In the field of organic synthesis, 5-(2-Nitrophenyl)-1,3-oxazole is employed as a key building block for the assembly of complex organic molecules. Its presence in the synthesis process can influence the properties and reactivity of the final products, contributing to the advancement of organic chemistry.
Used in Analytical Chemistry:
5-(2-Nitrophenyl)-1,3-oxazole may also find applications in analytical chemistry, potentially serving as a reagent or a component in assays and tests for detecting or quantifying specific substances, due to its distinctive chemical properties.

InChI:InChI=1/C9H6N2O3/c12-11(13)8-4-2-1-3-7(8)9-5-10-6-14-9/h1-6H

Upstream product

• 552-89-6 2-nitro-benzaldehyde 
• 288-42-6 oxazol 
• 577-19-5 2-nitrophenyl bromide 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 

Downstream Products

• 774238-36-7 2-(oxazol-5-yl)aniline 
• 959977-81-2 4-bromo-5-(2-nitrophenyl)oxazole 

Relevant articles and documents

Design, synthesis and biological evaluation of imidazole and oxazole fragments as HIV-1 integrase-LEDGF/p75 disruptors and inhibitors of microbial pathogens

We describe here the synthesis of libraries of novel 1-subtituted-5-aryl-1H-imidazole, 5-aryl-4-tosyl-4,5-dihydro-1,3-oxazole and 5-aryl-1,3-oxazole fragments via microwave (MW)-assisted cycloaddition of para-toluenesulfonylmethyl isocyanide (TosMIC) to imines and aldehydes. The compounds obtained were biologically evaluated in an AlphaScreen HIV-1 IN-LEDGF/p75 inhibition assay with six imidazole-based compounds (16c, 16f, 17c, 17f, 20a and 20d) displaying more than 50% inhibition at 10 μM, with IC50 values ranging from 7.0 to 30.4 μM. Additionally the hypothesis model developed predicts all active scaffolds except 20d to occupy similar areas as the N-heterocyclic (A) moiety and two aromatic rings (B and C) of previously identified inhibitor 5. These results indicate that the identified compounds represent a viable starting point for their use as templates in the design of next generation inhibitors targeting the HIV-1 IN and LEDGF/p75 protein-protein interaction. In addition, the in vitro antimicrobial properties of these fragments were tested by minimum inhibitory concentration (MIC) assays showing that compound 16f exhibited a MIC value of 15.6 μg/ml against S. aureus, while 17f displayed a similar MIC value against B. cereus, suggesting that these compounds could be further developed to specifically target those microbial pathogens.

Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts

Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C?H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C?H bond functionalization steps. The Ru-catalyzed C?H arylation of the aryl unit of 2-aryloxazoles is also described. (Figure presented.).

Synthesis of 4-substituted oxazolo[4,5-c]quinolines by direct reaction at the C-4 position of oxazoles

A facile synthesis of 4-aryl substituted oxazolo[4,5-c]quinolines has been described via a modified Pictet-Spengler method and using Cu(TFA)2 as a catalyst. The developed methodology directly functionalizes the C-4 position of oxazoles without

A Mild and convenient synthesis of 4-tosyl-4,5-dihydrooxazoles

A facile and mild synthesis of 4-tosyl-4,5-dihydrooxazoles is described. The reaction between tosyl methyl isocyanide (TosMIC) and cinnamic or aromatic aldehydes is catalyzed by triethylamine, affording trans-5-styryl- or 5-aryl-4-tosyl-4,5-dihydrooxazole

HYDRAZONE DERIVATIVE

A compound represented by the following formula (I): wherein R1 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R2 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R3 represents hydrogen, etc.; Ar represents a divalent group derived from aromatic hydrocarbon, etc.; X represents a single bond, linear or branched alkylene having from 1 to 3 carbon atoms which may have a substituent, etc.; and G represents halogen, a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc., a salt thereof or a solvate thereof; and an agent for inhibiting aggregation and/or deposition of an amyloid protein or an amyloid-like protein, which comprises the compound, a salt thereof or a solvate thereof

A solid-phase equivalent of van Leusen's TosMIC, and its application in oxazole synthesis

Polystyrene-SH resin, prepared from Merrifield resin in two steps, was converted to polystyrene-SO2-CH2-NC in three steps. This resin functions as a solid-phase equivalent of p-tolylsulfonylmethyl isocyanide (TosMIC). Thus, reaction with aromatic aldehydes and tetrabutylammonium hydroxide as base yields 5-aryloxazoles.