34052-90-9

Basic information

• Product Name: 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene
• Synonyms: 1,3-Bis(2-oxazolidinyl-2-yl)benzene;1,3-Bis(4,5-dihydrooxazol-2-yl)benzene;1,3-Bisdihydrooxazolylbenzene;2,2'-(1,3-phenylene)bis-2-oxazolin;2,2'-(1,3-PHENYLENE)BIS(2-OXAZOLINE);1,3-Phenylene-bis-oxazoline;1,3-PHENYLENBISOXAZOLINE;1,3-PBO
• CAS NO: 34052-90-9
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.24
• EINECS: 421-510-3
• Mol File: 34052-90-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 147-151°C
• Boiling Point: 403.5 °C at 760 mmHg
• Flash Point: 208°C
• Appearance: /
• Density: 1.45
• Vapor Pressure: 2.36E-06mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.78±0.50(Predicted)
• Water Solubility: Insoluble in water
• CAS DataBase Reference: 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene(34052-90-9)
• EPA Substance Registry System: 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene(34052-90-9)

Safety Data

• Statements: 22
• Safety Statements: 22-24/25
• Hazardous Substances Data: 34052-90-9(Hazardous Substances Data)

Usage

General Description

1,3-Bis(4,5-dihydro-2-oxazolyl)benzene is a chemical compound that is commonly used as a crosslinking agent in the production of epoxy resins. It is a white crystalline solid and is insoluble in water, but soluble in organic solvents. It is known for its ability to improve the mechanical and thermal properties of epoxy resins, making them more durable and heat-resistant. This chemical is also used in the manufacturing of adhesives, coatings, and composite materials. Additionally, it is used as a UV stabilizer and flame retardant in plastics and polymers. However, 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene should be handled with care, as it may be harmful if ingested or inhaled, and can cause irritation to the skin and eyes.

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

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

Downstream Products

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

Relevant articles and documents

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)

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.