1,3-Bis(4,5-dihydro-2-oxazolyl)benzene Chemical Properties

Melting point:

147-151°C

Boiling point:

403.5±28.0 °C(Predicted)

Density 

1.45

Flash point:

208°C

storage temp. 

Sealed in dry,Room Temperature

Water Solubility 

Insoluble in water

form 

powder to crystal

pka

4.78±0.50(Predicted)

color 

White to Light yellow to Light red

InChI

InChI=1S/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

InChIKey

HMOZDINWBHMBSQ-UHFFFAOYSA-N

SMILES

C1(C2=NCCO2)=CC=CC(C2=NCCO2)=C1

CAS DataBase Reference

34052-90-9(CAS DataBase Reference)

EPA Substance Registry System

Oxazole, 2,2'-(1,3-phenylene)bis[4,5-dihydro- (34052-90-9)

Safety Information

Risk Statements 

22

Safety Statements 

22-24/25

HS Code 

2934.99.4400

1,3-Bis(4,5-dihydro-2-oxazolyl)benzene Usage And Synthesis

Uses

Dioxazoline is an important organic reaction intermediate. It is a compound containing a five-membered heterocycle with two carbon, nitrogen, and oxygen atoms and a carbon-nitrogen double bond. Because of its highly reactive chemical properties, it can undergo ring-opening reactions with carboxyl groups, acid anhydrides, amino groups, epoxy groups, thiol groups, phenolic hydroxyl groups, isocyanate groups, etc. at certain temperatures. Therefore, dioxazoline is often used as a chain extender or cross-linking agent for polymers.

Definition

Bisoxazoline is an essential organic reaction intermediate. It is a five-membered heterocyclic compound containing two carbons, nitrogen, oxygen and a carbon-nitrogen double bond. Because of its active chemical properties, it can undergo ring-opening reactions with carboxyl, anhydride, amino, epoxy, thiol, phenolic hydroxyl, isocyanate, etc., at a certain temperature. Therefore, bisoxazoline can often be used as a chain extender or cross-linking agent for polymers.

Synthesis

GENERAL METHOD: A mixture of isophthalonitrile (0.5 mmol), 2-aminoethanol (0.65 mmol, 0.040 g), Co(NO3)2 (0.02 mmol, 0.036 g), and sulfur (0.05 mmol, 0.0016 g) was stirred for an appropriate period of time at 90 °C, or reacted under microwave radiation (90 °C, 800 W) for the corresponding Time. For the synthesis of monooxazolines, a mixture of isophthalonitrile (0.5 mmol), 2-aminoethanol (0.65 mmol, 0.040 g), Co(NO3)2 (0.02 mmol, 0.036 g) and sulfur (0.05 mmol, 0.0016 g) was stirred for 3 h at 90 °C or reacted under microwave radiation conditions (90 °C, 800 W) for 3 min . For the synthesis of bisoxazoline, isophthalonitrile (0.5 mmol), 2-aminoethanol (2.6 mmol, 0.159 g), Co(NO3)2 (0.02 mmol, 0.036 g), and sulfur (0.05 mmol, 0.0016 g) were stirred for 10 hr at 110 °C or reacted under microwave radiation conditions (110 °C, 800 W) for 8 minutes. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, ethyl acetate (6 mL) was added and the catalyst was separated by filtration. After concentration under reduced pressure, the residue was purified by silica gel column chromatography to afford the pure product 1,3-bis(4,5-dihydrooxazol-2-yl)benzene (5a-r).

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 9910 - 9914
[2] Synlett, 2005, # 18, p. 2747 - 2750
[3] Tetrahedron, 2013, vol. 69, # 32, p. 6591 - 6597
[4] Monatshefte fur Chemie, 2009, vol. 140, # 12, p. 1489 - 1494
[5] Journal of the Serbian Chemical Society, 2012, vol. 77, # 9, p. 1181 - 1189,9

1,3-Bis(4,5-dihydro-2-oxazolyl)benzene(34052-90-9)Related Product Information

• Chlorodiphenylphosphine
• Diphenylsilane
• Diphenylphosphine
• Oxazoline
• Xylene
• tert-Butylchlorodiphenylsilane
• Dichlorodiphenylsilane
• Chlorodimethylphenylsilane
• Benzene
• 4-bromo-1-methylpyrazole-3-carboxy acid
• 5-HYDROXY-1-METHYL-1H-PYRAZOLE-3-CARBOXYLIC ACID METHYL ESTER
• 2,5-DIBROMO-3-AMINOPYRIDINE
• 4,5-Dihydrooxazole, 2-vinyl-
• 1-methyl-1H-pyrazol-4-amine
• 1,4-BIS(4,5-DIHYDRO-2-OXAZOLYL)BENZENE
• 3-METHYL-BENZIMIDIC ACID ETHYL ESTER
• 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene
• 1,3-BIS(4,5-DIHYDRO-2-OXAZOLYL)BENZENE=2,2'-(1,3-PHENYLEN)BIS-2-OXAZOLINE