19312-06-2

Basic information

• Product Name: 4,4-DIMETHYL-2-PHENYL-2-OXAZOLINE
• Synonyms: 4,4-DIMETHYL-2-PHENYL-2-OXAZOLINE;4,4-Dimethyl-2-phenyl-4,5-dihydro-1,3-oxazole;4,4-Dimethyl-2-phenyl-2-oxazoline 96%
• CAS NO: 19312-06-2
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Oxazolines/Oxazolidines
• Mol File: 19312-06-2.mol
• Article Data: 52

Chemical Properties

• Melting Point: 20-24 °C(lit.)
• Boiling Point: 124 °C20 mm Hg(lit.)
• Flash Point: 217 °F
• Appearance: /
• Density: 1.025 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0555mmHg at 25°C
• Refractive Index: n20/D 1.5322(lit.)
• PKA: 4.82±0.70(Predicted)
• BRN: 132225
• CAS DataBase Reference: 4,4-DIMETHYL-2-PHENYL-2-OXAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-DIMETHYL-2-PHENYL-2-OXAZOLINE(19312-06-2)
• EPA Substance Registry System: 4,4-DIMETHYL-2-PHENYL-2-OXAZOLINE(19312-06-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 19312-06-2(Hazardous Substances Data)

Usage

Description

4,4-Dimethyl-2-phenyl-2-oxazoline is an organic compound belonging to the 2-aryl-2-oxazoline class. It has been tested as a ligand for the Suzuki coupling reaction of aryl bromides and arylboronic acids. 4,4-DIMETHYL-2-PHENYL-2-OXAZOLINE forms mildly hygroscopic complexes with ether solutions of [ZnX2] (X = Cl, Br, I), except for ZnI2, which does not form an isolable complex due to steric reasons.

Uses

Used in Chemical Synthesis:
4,4-Dimethyl-2-phenyl-2-oxazoline is used as a ligand in the Suzuki coupling reaction for the formation of ester-ammonium salts via the rupture of the oxazoline ring. This application is significant in the synthesis of various organic compounds and materials.
Used in Coordination Chemistry:
In coordination chemistry, 4,4-Dimethyl-2-phenyl-2-oxazoline is used to form complexes with zinc halides, such as [ZnX2(ox)2] (ox = 4,4-Dimethyl-2-phenyl-2-oxazoline), where X = Cl, Br, or I. These complexes are of interest in studying the coordination properties and potential applications of zinc halide complexes.

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 2032, 1960 DOI: 10.1021/ja01493a045Tetrahedron Letters, 27, p. 5269, 1986 DOI: 10.1016/S0040-4039(00)85187-4

InChI:InChI=1/C11H13NO/c1-11(2)8-13-10(12-11)9-6-4-3-5-7-9/h3-7H,8H2,1-2H3

Upstream product

• 109-72-8 n-butyllithium 
• 80762-49-8 2-(m-chlorophenyl)-4,4-dimethyl-4,5-dihydrooxazole 
• 108-86-1 bromobenzene 
• 118559-32-3 4,4-dimethyl-2-(tri-n-butylstannyl)-2-oxazoline 
• 93-58-3 benzoic acid methyl ester 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 100-39-0 benzyl bromide 
• 32664-13-4 2-(2-bromo-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 100-44-7 benzyl chloride 
• 66195-42-4 2-(2-iodophenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 20515-61-1 2-phenyl-4,4-dimethyloxazolidine 
• 30093-99-3 4,4-dimethyl-2-oxazoline 
• 100-47-0 benzonitrile 

Downstream Products

• 77765-22-1 o-(trideuteriomethyl)benzaldehyde 
• 61436-73-5 2-allylbenzoic acid 
• 209173-72-8 [2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-naphthalen-2-yl-methanol 
• 118559-28-7 2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzonitrile 
• 133341-93-2 4,4-dimethyl-2-[2-(prop-2-enyl)]phenyl-2-oxazoline 
• 82998-95-6 4,4-dimethyl-2-(3-nitrophenyl)-4,5-dihydrooxazole 
• 936-49-2 2-phenyl-2-imidazoline 
• 2722-34-1 2-phenylthiazoline 
• 25099-77-8 2-phenyl-1,4,5,6-tetrahydropyrimidine 
• 939-06-0 4-methyl-2-phenyl-Δ²-imidazoline 
• 79966-31-7 2-(2-benzothenyl)benzenecarboxylic acid 
• 683277-08-9 dibromobis(η1-N-(4,4-dimethyl-2-phenyl-2-oxazoline))zinc 
• 683277-07-8 dichlorobis(η1-N-(4,4-dimethyl-2-phenyl-2-oxazoline))zinc 

Relevant articles and documents

Arylation of Heterocycles via Rhodium-Catalyzed C-H Bond Functionalization

(Equation presented) A new method for the rhodium-catalyzed arylation of a variety of heterocycles has been developed. The reaction provided moderate to good yields of the arylated products. A preliminary mechanistic investigation of this reaction revealed the intermediacy of an isolable N-heterocyclic carbene complex.

Pd/Cu-Catalyzed C-H/C-H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates

A highly efficient method for the selective formal C-H/C-H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity, one-pot procedures, and the late-stage functionalization of complex molecules without the use of oxidants, offering a promising strategy for the transition-metal-catalyzed C-H arylation of azoles.

Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.