7127-19-7

Basic information

• Product Name: 4,5-DIHYDRO-2-PHENYLOXAZOLE
• Synonyms: 4,5-DIHYDRO-2-PHENYLOXAZOLE;(4,5-DIHYDRO-2-OXAZOLYL)BENZENE;2-PHENYL-2-OXAZOLINE;4,5-DIHYDRO-2-PHENYLOXAZOLE 98+%;2-Phenyl-4,5-dihydrooxazole;(4,5-Dihydro-2-oxazolyl)benzene 2-Phenyl(2-oxazoline);2-Phenyl-2-oxazoline 99%;2-phenyl-4,5-dihydro-1,3-oxazole
• CAS NO: 7127-19-7
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Oxazolines/Oxazolidines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 7127-19-7.mol

Chemical Properties

• Melting Point: 12 °C(lit.)
• Boiling Point: 75 °C0.3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.118 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00644mmHg at 25°C
• Refractive Index: n20/D 1.567(lit.)
• Storage Temp.: Refrigerator
• PKA: 4.69±0.50(Predicted)
• CAS DataBase Reference: 4,5-DIHYDRO-2-PHENYLOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIHYDRO-2-PHENYLOXAZOLE(7127-19-7)
• EPA Substance Registry System: 4,5-DIHYDRO-2-PHENYLOXAZOLE(7127-19-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 7127-19-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 19, p. 1221, 1982 DOI: 10.1002/jhet.5570190548

InChI:InChI=1/C9H9NO/c1-2-4-8(5-3-1)9-10-6-7-11-9/h1-5H,6-7H2

Upstream product

• 72047-82-6 chloroethyl benzimidate 
• 60779-46-6 1-benzoylamino-2-(toluene-4-sulfonyloxy)-ethane 
• 141-52-6 sodium ethanolate 
• 7646-66-4 N-benzoylaziridine 
• 92-83-1 xanthene 
• 64-19-7 acetic acid 
• 74-88-4 methyl iodide 
• 868-85-9 Dimethyl phosphite 
• 609-08-5 Diethyl methylmalonate 
• 613-31-0 9,10-dihydroanthracene 
• 2722-34-1 2-phenylthiazoline 
• 18838-10-3 N-(2-hydroxyethyl)-benzamide 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 1943-83-5 2-chloroethyl isothiocyanate 

Downstream Products

• 55065-04-8 S-2-(N-benzoylamino)ethyl benzothioathe 
• 16180-99-7 2-benzamidoethyl benzoate 
• 37056-16-9 N-(2-chloro-ethyl)-4-nitro-dibenzamide 
• 26385-07-9 N-(2-chloro-ethyl)-benzamide 
• 88186-35-0 4,5-dihydro-2-(3-nitrophenyl)oxazole 
• 106059-18-1 benzoic acid 2-isothiocyanato-ethyl ester 
• 82495-98-5 N-(2-Hydroxy-ethyl)-benzimidic acid tert-butyl ester 
• 3690-53-7 Bencainamide 
• 114521-93-6 2-(isobutylideneamino)ethyl benzoate 
• 94615-65-3 (5R,6R)-6-Phenoxy-5-phenyl-4-oxa-1-aza-bicyclo[3.2.0]heptan-7-one 
• 20662-88-8 2-phenyloxazole 
• 55-21-0 benzamide 
• 100-47-0 benzonitrile 
• 939-56-0 benzoyloxyacetonitrile 

Relevant articles and documents

Synthesis of (fluoroalkyl)amines by deoxyfluorination of amino alcohols

Deoxyfluorination of amino alcohols was achieved using N,N-diethyl-α, α-difluorobenzylamine (DFBA) to furnish N-benzoyl(fluoroalkyl)amines selectively. Georg Thieme Verlag Stuttgart.

Synthesis of organochalcogens stabilized by intramolecular non-bonded interactions of sterically unhindered 2-phenyl-2-oxazoline

The synthesis and characterization of low-valent organoselenium and -sulfur compounds incorporating sterically unhindered 2-phenyl-2-oxazoline are described. Organylselenenyl halides, RSeX (X = Cl, Br, I) were prepared from diselenide and the benzyl selenide derivative was synthesized by the reaction of in situ generated lithium arylselenolate, OxSe-Li+ (Ox = 2-phenyl-2-oxazoline) with benzyl chloride. These compounds in general show strong Se...N intramolecular interactions as compared with the substituted oxazoline analogues. Bis[2-(2-oxazolinylphenyl)] disulfide and [2-(2-oxazolinyl)phenyl]benzyl sulfide were synthesized by the ortho-lithiation method and characterized by 1H and 13C NMR spectroscopy. The S...N intramolecular interactions were confirmed by single crystal X-ray crystallography.

Facile one-pot synthesis of 2-oxazoline

We developed a facile one-pot synthesis of 2-oxazolines from carboxylic acid and 2-chloroethyl isocyanate, involving amide bond formation and a following intramolecular cyclization using 4-dimethylaminopyridine as the catalyst. A large variety of functional groups are well tolerated by the mild reaction conditions to afford diverse 2-oxazolines in good to excellent yields. This reaction will keep the chirality of the isocyanate at position 1, the R2 substituted carbon. Microwave-assisted synthesis can further enhance the reaction yield and reduce the reaction time to 5 min. This method facilities the synthesis of 2-oxazolines for diverse applications, such as 2-oxazoline derived polymers and materials.

Synthesis of Nitrogen-Containing Heterocycles through Catalytic Dehydrative Cyclization Reactions

Re2O7 in hexafluoroisopropyl alcohol provides access to cationic intermediates from alcohols through the intermediacy of perrhenate esters. This manuscript describes the application of the system to the formation of a number of weakly basic heterocyclic systems through dehydration reactions and intramolecular nucleophilic addition. The influence of the substrate structure on the reaction rates and stereocontrol is discussed with respect to intermediate ion pairs.

Rhodium(III)-Catalyzed Oxidative Cyclization of Oxazolines with Cyclopropanols: Synthesis of Isoindolinones

The synthesis of C3-substituted isoindolin-1-ones from oxazolines and cyclopropanols has been achieved with oxazoline as a bifunctional nucleophilic directing group. The reaction proceeds by the cleavage of three chemical bonds and allows the formation of three new chemical bonds, a C-N bond, a C-C bond, and a C-O bond, in a single step.

Ultrasound-Accelerated, Concise, and Highly Efficient Synthesis of 2-Oxazoline Derivatives Using Heterogenous Calcium Ferrite Nanoparticles and Their DFT Studies

A rapid and operationally simple approach for synthesising biologically relevant 2-oxazoline derivatives has been developed through highly efficient ultrasound-promoted coupling reactions of thioamides and amino alcohols using calcium ferrite nanoparticles as heterogeneous catalysts. The major advantage of using ultrasound irradiation lies in the drastic reduction of reaction time as compared with conventional stirring. Furthermore, quantum chemical investigations for the synthesised 2-oxazoline derivatives have been carried out at the DFT/B3LYP/6-311 + G (d, p) level of theory to predict the optimized geometry. The molecular properties such as bond lengths, bond orders, Milliken charges, frontier molecular orbitals, global reactivity descriptors, molecular electrostatic potential map, and thermodynamic parameters of all the compounds have also been reported at the same level of theory.

Ruthenium-catalysedmeta-selective CAr-H bond alkylationviaa deaminative strategy

The use of aliphatic amines as alkylating reagents in organic synthesisviaC-N bond activation remains underdeveloped. We herein describe a novel ruthenium-catalysed and directing-group assisted protocol for the synthesis ofmeta-alkylated arenesviadual C-H and C-N activation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amines and amino acid species were used as alkyl radical precursors. This catalytic reaction could accommodate a broad range of functional groups and provide access to variousmeta-alkylated products.

Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4 H -1,3-thiazines

An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4 H -1,3-thiazines is developed via microwave-assisted ring closure of ω-thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an S N 2-type mechanism and features the advantages of very short reaction times, high yields and a predictable stereochemical outcome. The acyclic precursors are prepared in high overall yields by an improved diacylation-thionation-saponification sequence from commercially available ω-amino alcohols. The whole process is metal-free and operationally simple.

Benzyne-mediated trichloromethylation of chiral oxazolines

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Oxazolinyl-Assisted Ru(II)-Catalyzed C-H Allylation with Allyl Alcohols and Synthesis of 4-Methyleneisochroman-1-ones

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