92629-11-3

Basic information

• Product Name: 5-BROMO-2-PHENYLOXAZOLE
• Synonyms: 5-BROMO-2-PHENYLOXAZOLE;5-broMo-2-phenyl-1,3-oxazole
• CAS NO: 92629-11-3
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05404
• Mol File: 92629-11-3.mol

Chemical Properties

• Boiling Point: 308.3 °C at 760 mmHg
• Flash Point: 140.2 °C
• Appearance: /
• Density: 1.524±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00125mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.56±0.10(Predicted)
• CAS DataBase Reference: 5-BROMO-2-PHENYLOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-PHENYLOXAZOLE(92629-11-3)
• EPA Substance Registry System: 5-BROMO-2-PHENYLOXAZOLE(92629-11-3)

Safety Data

• Hazardous Substances Data: 92629-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-2-PHENYLOXAZOLE is used as a Δ5-desaturase inhibitor for the preparation of heterocyclic compounds. This application is significant in the development of pharmaceuticals, as Δ5-desaturase enzymes play a crucial role in the biosynthesis of certain fatty acids and other lipids, which are involved in various physiological processes and diseases.
In the preparation of heterocyclic compounds, 5-BROMO-2-PHENYLOXAZOLE serves as a key intermediate, enabling the synthesis of novel compounds with potential therapeutic properties. By inhibiting the Δ5-desaturase enzyme, these heterocyclic compounds can modulate lipid metabolism and potentially offer treatment options for various health conditions related to lipid imbalances.

InChI:InChI=1/C9H6BrNO/c10-8-6-11-9(12-8)7-4-2-1-3-5-7/h1-6H

Upstream product

• 20662-88-8 2-phenyloxazole 
• 7127-19-7 2-phenyl-1,3-oxazoline 
• 98-88-4 benzoyl chloride 
• 18838-10-3 N-(2-hydroxyethyl)-benzamide 
• 93-89-0 benzoic acid ethyl ester 
• 591-50-4 iodobenzene 

Downstream Products

• 35337-84-9 N-methoxycarbonyl benzamide 
• 4252-31-7 N-formylbenzamide 
• 4461-33-0 benzoyl isocyanate 
• 62921-42-0 5-(4-methoxyphenyl)-2-phenyl-1,3-oxazole 
• 861440-59-7 4-bromo-2-phenyloxazole 
• 92629-12-4 4,5-Dibromo-2-phenyloxazole 
• 7007-08-1 4-bromo-2,5-diphenyloxazole 
• 106833-83-4 methyl 2-phenyl-1,3-oxazole-5-carboxylate 
• 942070-80-6 C₁₅H₁₈BNO₃ 
• 1415610-06-8 2-Phenyl-5-(thiophen-2-yl)oxazole 
• 163303-25-1 4-(4-fluorophenyl)-5-(4-(methylsulfonyl)phenyl)-2-phenyloxazole 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS AS DELTA-5 DESATURASE INHIBITORS AND METHODS OF USE

The present disclosure provides compounds useful for the inhibition of Delta-5 Desaturase ("D5D"). The compounds have a general Formula (I): wherein the variables of Formula (I) are defined herein. This disclosure also provides pharmaceutical compositions comprising the compounds, uses of the compounds, and compositions for treatment of, for example, a metabolic or cardiovascular disorder. Further, the disclosure provides intermediates useful in the synthesis of compounds of Formula (I).

Widely Exploited, Yet Unreported: Regiocontrolled Synthesis and the Suzuki–Miyaura Reactions of Bromooxazole Building Blocks

An approach to synthesis of 2-, 4-, and 5-bromooxazoles is described. The method was optimized, and its scope was extended to all three isomeric parents, as well as various alkyl- and aryl-substituted bromooxazoles. It was found that direct regiocontrolled lithiation followed by reaction with electrophilic bromine source was common for all substrates and led exclusively to the target substituted 2-, 4- and 5-bromooxazoles on multigram scale. The utility of the multipurpose building blocks obtained in this work was demonstrated in the Suzuki–Miyaura cross-coupling reaction under parallel synthesis conditions.

Composite tetraheteroarylenes and related higher cyclic oligomers of heteroarenes produced by palladium-catalyzed direct coupling

Substantial research interests have been focused on cyclic π-conjugated molecules owing to their unique chemical and physical properties. By constructing hybrid aromatic arrays within these cyclic systems, new series of composite macrocycles would be prov

Versatile Photochemical Reactivity of Diverse Substituted 2-, 4- and 5-(o-Vinylstyryl)oxazoles

To study the effects of the position of the hexatrienyl moiety on the oxazole ring, novel substituted cis/trans-2/4/5-(2-vinylstyryl)oxazoles have been synthesized. These novel compounds were prepared by Wittig reaction from the diphosphonium salt of α,α′-o-xylenedibromide, formaldehyde and the corresponding 2-methyl-4-, 4-methyl-2-, 2-pheny-5- and 4-methyl-5-oxazolecarbaldehyde, respectively. Aldehydes were synthesized by using several synthetic approaches. By applying intramolecular photocycloaddition, 2-methyl-4-(2-vinylstyryl)oxazole afforded, as major product, fused oxazoline-benzobicyclo[3.2.1]octene with small quantities of 4-(1,2-dihydronaphthalen-2-yl)-2-methyloxazole, as electrocyclization product. Upon irradiation of 4-methyl-5-(2-vinylstyryl)oxazole, endo- and exo-benzobicyclo[2.1.1]hexene products were formed by [2+2] cycloaddition; this was the first instance of the 1,4-closure to the bicyclo[2.1.1]hexene skeleton in the 2-, 4-, and 5-oxazole-stilbene derivatives studied so far. Derivatives 2-phenyl-5- and 4-methyl-2-(2-vinylstyryl)oxazole did not react and gave only high-weight molecular products but were crucial as a comparison in the overall mechanistic study. We have found that, depending on the position of the hexatrienyl moiety in the oxazole ring, as well as on the position of the methyl/phenyl substituents, these new vinylstyryl-2/4/5-oxazole derivatives show diverse photochemical behavior.

Synthesis of 2-Aryl- and 5-Alkyl-2-aryloxazoles from 2-Aryl-5-bromooxazoles

2-Aryloxazoles, their 5-deuterio derivatives, and 5-alkyl-2-aryloxazoles are prepared in good yields from 2-aryl-5-bromooxazoles via halogen/metal exchange with butyllithium followed by treatment with water, methanol-O-d, or alkyl halides, respectively.

SYNTHESIS AND SOME ELECTROPHILIC SUBSTITUTION REACTIONS OF 2-PHENYLOXAZOLE

A new synthesis of 2-phenyloxazole that includes the preparation of 2-phenyloxazoline and aromatization of the latter by the action of nickel peroxide was developed.It was established that under conditions that exclude protonation electrophilic substituti