34052-90-9

Usage

Uses

Used in Epoxy Resin Production:
1,3-Bis(4,5-dihydro-2-oxazolyl)benzene is used as a crosslinking agent for improving the mechanical and thermal properties of epoxy resins, making them more durable and heat-resistant.
Used in Adhesives Manufacturing:
In the adhesives industry, 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene is used as a component to enhance the bonding strength and heat resistance of adhesive formulations.
Used in Coatings Industry:
1,3-Bis(4,5-dihydro-2-oxazolyl)benzene is utilized as an additive in coatings to improve their mechanical properties and resistance to thermal degradation.
Used in Composite Materials:
This chemical compound is used in the production of composite materials to increase their overall strength and heat resistance, making them suitable for various high-performance applications.
Used as a UV Stabilizer in Plastics and Polymers:
1,3-Bis(4,5-dihydro-2-oxazolyl)benzene is employed as a UV stabilizer to protect plastics and polymers from the degrading effects of ultraviolet radiation, thereby extending their service life.
Used as a Flame Retardant in Plastics and Polymers:
In the plastics and polymers industry, 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene is used as a flame retardant to reduce the flammability of materials and improve their fire safety characteristics.
It is important to handle 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene with care due to its potential harmful effects if ingested or inhaled, and its ability to cause skin and eye irritation.

InChI:InChI=1/C12H12N2O2/c1-2-9(11-13-4-6-15-11)8-10(3-1)12-14-5-7-16-12/h1-3,8H,4-7H2

Synthetic route

benzene-1,3-dicarbonitrile (626-17-5) + ethanolamine (141-43-5) → 1,3-bis(4,5-dihydrooxazol-2-yl)benzene (34052-90-9)

Conditions	Yield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium acetate In neat (no solvent) at 100℃; for 16h; Glovebox; Inert atmosphere;	92%
With tris(trifluoroacetato)bismuth(III) for 10h; Heating;	88%
With sulfur; cobalt(II) nitrate In neat (no solvent) at 110℃; for 0.133333h; Time; Microwave irradiation;	84%

Isophthalaldehyde (626-19-7) + ethanolamine (141-43-5) → 3-(4,5-dihydro-oxazol-2-yl)-benzaldehyde + 1,3-bis(4,5-dihydrooxazol-2-yl)benzene (34052-90-9)

Conditions	Yield
With pyridinium hydrobromide perbromide at 20℃; for 39h;	A 10% B 83%

Isophthalaldehyde (626-19-7) + ethanolamine (141-43-5) → 1,3-bis(4,5-dihydrooxazol-2-yl)benzene (34052-90-9)

Conditions	Yield
Stage #1: Isophthalaldehyde; ethanolamine With potassium carbonate In tert-butyl alcohol at 20℃; for 0.5h; Inert atmosphere; Stage #2: With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione In tert-butyl alcohol at 50℃; for 24h; Inert atmosphere;	73%

3-(4,5-Dihydrooxazol-2-yl)benzonitrile + ethanolamine (141-43-5) → 1,3-bis(4,5-dihydrooxazol-2-yl)benzene (34052-90-9)

Conditions	Yield
With sodium acetate at 100℃;

benzene-1,3-dicarbonitrile (626-17-5) → 1,3-bis(4,5-dihydrooxazol-2-yl)benzene (34052-90-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate / 100 °C 2: sodium acetate / 100 °C View Scheme

1,3-bis(4,5-dihydrooxazol-2-yl)benzene (34052-90-9) → 1,3-bis(2-oxazolinyl)benzene (101614-49-7)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 12h; Molecular sieve;	74%

silver tetrafluoroborate (14104-20-2) + 1,3-bis(4,5-dihydrooxazol-2-yl)benzene (34052-90-9) → Ag4(1,3-di(2-oxazolinyl)benzene)4(BF4)4

Conditions	Yield
In methanol; acetonitrile mixt. of 1,3-bis(oxazolin-2-yl)benzene and AgBF4 (1:1) in CH3OH stirred for 5 min, several drops of CH3CN added until soln. is clear; soln. filtered, crystn. by diffusion of Et2O into filtrate at room temp.for several d; elem. anal.;	66%

Upstream product

• 626-19-7 Isophthalaldehyde 
• 141-43-5 ethanolamine 
• 626-17-5 benzene-1,3-dicarbonitrile 

Downstream Products

• 101614-49-7 1,3-bis(2-oxazolinyl)benzene 

Relevant academic research and scientific papers

A 2 - substituted oxazoline or 2 - substituted piperazine synthetic method (by machine translation)

The invention discloses a method for synthesizing 2 - substituted oxazoline or 2 - substituted oxazine new method, by nitrile and amino ethanol or 3 - amino - 1 - propanol as raw material, in the absence of solvent, can be used for the recycling of the sulfur to induce synthesis of 2 - substituted oxazoline and 2 - substituted piperazine. The method of the invention has low cost, simple reaction process, mild reaction conditions, the reaction time is short, the yield and the like, is suitable for the industrial generation. (by machine translation)

Copper N-Heterocyclic Carbene Complexes As Active Catalysts for the Synthesis of 2-Substituted Oxazolines from Nitriles and Aminoalcohols

The reaction between nitriles and aminoalcohols to access 2-substituted oxazolines was investigated. Using copper-NHC complexes, various nitriles were successfully converted into the corresponding oxazolines, under milder and less wasteful conditions than those of previously reported methods.

DDQ-induced dehydrogenation of heterocycles for c-c double bond formation: Synthesis of 2-thiazoles and 2-oxazoles

Strong as an Ox: 2-Thiazoles and 2-oxazoles are formed by oxidation of 2-thiazolines and 2-oxazolines without requiring substituents at the C4 and C5 positions. DDQ plays an important role as the oxidant in this transformation and metal is unnecessary. This general procedure shows good functional group tolerance and provides a wide variety of 2-thiazoles and 2-oxazoles in moderate to excellent yields.

S-Co(II) cascade catalysis: Cyclocondensation of aromatic nitriles with alkamine

A solvent-free S/Co(NO3)2 cascade catalyzed cyclocondensation reaction of aromatic nitriles with 3-amino-1-propanol or 2-aminoethanol has been successfully developed under thermal and microwave conditions. By this two-component protocol, mono- and bis-oxazines and oxazolines were selectively synthesized both in good to excellent yields and short reaction times. This catalytic system exhibits excellent chemoselectivity, and can be reused at least seven times without significant loss of activity in subsequent reactions.

Trichloroisocyanuric acid as an efficient homogeneous catalyst for the chemoselective synthesis of 2-substituted oxazolines, imidazolines and thiazolines under solvent-free condition

Trichloroisocyanuric acid, as a commercially available and inexpensive catalyst, was used in a new, facile and efficient procedure for the synthesis of 2-oxazolines, 2-imidazolines and 2-thiazolines through the reaction of nitriles with 2-aminoethanol, ethylenediamine or 2-aminoethanethiol under solvent-free conditions.

An efficient oxidative conversion of aldehydes into 2-substituted 2-oxazolines using 1,3-diiodo-5,5-dimethylhydantoin

Various aromatic and aliphatic aldehydes were converted into the corresponding 2-aryl and 2-alkyl-2-oxazolines, respectively, in good to high yields by reaction with 2-aminoethanol and 1,3-diiodo-5,5-dimethylhydantoin. Moreover, chiral bis-2-oxazolines, which can be used as chiral ligands in asymmetric synthesis, could be also prepared in moderate yields by the reaction of dialdehydes with (R)-(-)-2-phenylglycinol under the same conditions. Georg Thieme Verlag Stuttgart.

Preparation of an improved sulfonated carbon-based solid acid as a novel, efficient, and reusable catalyst for chemoselective synthesis of 2-oxazolines and bis-oxazolines

A highly sulfonated carbon as an efficient, recyclable, nontoxic, and green solid acid catalyst was readily synthesized by simultaneous sulfonation, dehydration, and carbonization of sucrose in sulfuric acid and was characterized by FT-IR, TG-DTG, XRD, and CHNS analysis, neutralization potentiometric titration, and SEM techniques. This new catalyst was used for preparation of 2-oxazolines and bis-oxazolines by reaction of β-aminoethanol with nitriles under reflux conditions. Sonication of this system enhanced the catalytic activity of the carbon-based solid acid and led to higher product yields and shorter reaction times. Another advantage of the system under ultrasonic irradiation is the ability to carry out large-scale reactions. In two cases, the catalyst was reused several times without loss of its activity.

A convenient synthesis of oxazolines and imidazolines from aromatic aldehydes with pyridinium hydrobromide perbromide in water

Various 2-oxazolines were prepared from aromatic aldehydes and 2-aminoethanol with pyridinium hydrobromide perbromide in water at room temperature. 2-Imidazolines were also obtained in good yields from aromatic aldehydes and ethylenediamine under the same reaction conditions. Georg Thieme Verlag Stuttgart.

A novel and chemoselective synthesis of 2-aryloxazolines and bis-oxazolines catalyzed by Bi(III) salts

Different arylnitriles react with β-aminoalcohols in the presence of catalytic amounts of Bi(III) salts such as Bi(TFA)3, Bi(OTf) 3 and BiOClO4·XH2O producing the corresponding 2-aryl-oxazolines in high yields. Selective synthesis of mono- and bis-oxazolines from dicyanobenzenes and selective conversion of arylnitriles to their 2-oxazolines in the presence of alkylnitriles can be considered as noteworthy advantages of this method. Georg Thieme Verlag Stuttgart.

Method of preparation of phenylenebisoxazolines.

Preparation of 1,3- or 1,4-phenylene-bis-oxazolidines (I) by reacting a dicyanobenzene (II) with a 2-aminoalkanol (III) in presence of catalyst in which a mixture of catalyst, (III) and optionally solvent is treated at reaction temperature with (II). 1,3- or 1,4-phenylene-bis-oxazolidines of formula (I) are prepared by reacting a dicyanobenzene of formula (II) with a 2-aminoalkanol of formula NH 2-CR 1R 2-CR 3R 4-OH (III) in presence of catalyst. A mixture of catalyst, (III) and an optional solvent is treated at reaction temperature with (II): [Image] R 1to R 4hydrogen or 1-3C alkyl An independent claim is included for preparation of (I) by reacting (II) and (III) is presence of zinc 2-ethylhexanoate as catalyst.