1186127-13-8

Basic information

• Product Name: 2-(5-Oxazolyl)benzonitrile
• Synonyms: 2-(5-Oxazolyl)benzonitrile
• CAS NO: 1186127-13-8
• Molecular Formula: C₁₀H₆N₂O
• Molecular Weight: 170.16744
• Mol File: 1186127-13-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(5-Oxazolyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5-Oxazolyl)benzonitrile(1186127-13-8)
• EPA Substance Registry System: 2-(5-Oxazolyl)benzonitrile(1186127-13-8)

Safety Data

• Hazardous Substances Data: 1186127-13-8(Hazardous Substances Data)

Usage

General Description

2-(5-Oxazolyl)benzonitrile, also known as 5-Phenyl-2-oxazolecarbonitrile, is a chemical compound with the molecular formula C13H8N2O. It is a nitrile derivative with a phenyl group and an oxazole ring. 2-(5-Oxazolyl)benzonitrile is commonly used in the synthesis of pharmaceutical products and agrochemicals. It exhibits a wide range of biological activities, including antibacterial, antifungal, and anticancer properties. It is also used as a building block for the preparation of various organic intermediates. Additionally, 2-(5-Oxazolyl)benzonitrile is employed in research as a reagent for different chemical reactions and in the development of novel organic compounds.

Upstream product

• 288-42-6 oxazol 
• 2042-37-7 o-cyanobromobenzene 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 7468-67-9 o-formylbenzonitrile 
• 153657-11-5 2-diacetoxymethyl-benzonitrile 
• 1186127-11-6 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(triisopropylsilyl)-1,3-oxazole 

Downstream Products

• 1240321-89-4 (E)-2-(hex-2-en-2-yl)-5-phenyloxazole 
• 1240321-96-3 (E)-2-(hex-2-en-3-yl)-5-phenyloxazole 
• 1240321-80-5 (E)-5-(2-cyanophenyl)-2-(4-octen-4-yl)oxazole 
• 1240321-86-1 (E)-5-(2-cyanophenyl)-2-(1,8-chloro-4-octen-4-yl)oxazole 

Relevant articles and documents

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.).

Cobalt-catalyzed addition of azoles to alkynes

A ternary catalytic system consisting of a cobalt salt, a diphosphine ligand, and a Grignard reagent promotes syn-addition of an azole C(2)-H bond across an unactivated internal alkyne with high chemo-, regio-, and stereoselectivities under mild conditions. Mechanistic experiments suggest that the reaction involves oxidative addition of the oxazolyl C-H bond to the cobalt center, alkyne insertion into the Co-H bond, and reductive elimination of the resulting diorganocobalt species.