1,3-Bis(3-aminophenoxy)benzene Chemical Properties

Melting point:

108°C

Boiling point:

479.9±30.0 °C(Predicted)

Density 

1.243

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Water Solubility 

Insoluble in water

solubility 

Slightly soluble in methanol

form 

powder to crystal

pka

4.29±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C18H16N2O2/c19-13-4-1-6-15(10-13)21-17-8-3-9-18(12-17)22-16-7-2-5-14(20)11-16/h1-12H,19-20H2

InChIKey

DKKYOQYISDAQER-UHFFFAOYSA-N

SMILES

C1(OC2C=CC=C(N)C=2)=CC=CC(OC2C=CC=C(N)C=2)=C1

CAS DataBase Reference

10526-07-5(CAS DataBase Reference)

EPA Substance Registry System

Benzenamine, 3,3'-[1,3-phenylenebis(oxy)]bis- (10526-07-5)

Safety Information

Risk Statements 

20/21/22

Safety Statements 

26-36/37/39

HS Code 

29222990

1,3-Bis(3-aminophenoxy)benzene Usage And Synthesis

Chemical Properties

1,3-Bis(3-aminophenoxy)benzene, also known as TIMTEC-BB SBB008356, is a Light yellow to yellow solid. It has slight solubility in methanol but is insoluble in water. To maintain its stability, it is recommended to store it in a cool and dark place. However, it is incompatible with oxidizing agents and should not be stored or handled near them to avoid any hazardous reactions.

Uses

1,3-Bis(3-aminophenoxy)benzene is an intermediate compound used in the production of synthetic materials, such as PI (polyimide) films and polyimide materials.

Preparation

1,3-Bis(3-aminophenoxy)benzene is a reactive monomer commonly utilized in the synthesis of polyurethane coatings. This compound is processed at 200 degrees Celsius and has a viscosity of 1.5-2.0 centipoise at 25 degrees Celsius. Its chemical structure consists of three amine groups that are ether linked to a benzene ring with one hydroxyl group on the phenoxy side chain. The monomer can be synthesized via acylation reaction or polymerization process, typically through heating with a catalyst. The resulting product is thermally stable and resistant to heat up to 250 degrees Celsius.

Application

1,3-Bis(3-aminophenoxy)benzene (APB) is a diamine intermediate compound that can be used as a raw material for organic synthesis or as a component of polymer monomers. Studies have shown that APB reacts with p-benzoquinone to synthesise a novel oligomeric compound. The polymer also adheres to metals and becomes non-wetting when cured with heat. With a moisture absorption of only 0.1% by weight, it is a potential moisture barrier insulator for electronic components^[1].

Synthesis

In the 500mL four neck flasks that have agitator, reflux exchanger and dean stark trap, add the 3-amino phenol of 71.5g (0.655mol), 49 quality % aqueous sodium hydroxide solutions, 250gDMI and the 50g toluene of 53.5g (0.655mol).Flask contents is heated to 180 ℃ and stir and to feed nitrogen simultaneously, and azeotropic is removed toluene and water.Subsequently, the flask inclusion is cooled to room temperature and transfers in the 600mL autoclave that has agitator.
Subsequently, add 1 of 34g (0.298mol), 3-two fluorobenzene; Seal this reactor; To wherein being blown into nitrogen; After this, autoclave is heated to 200 ℃; And order is reflected to be carried out under 200 ℃ 53 hours.After this, cool off this autoclave, by the reaction mixture of high efficiency liquid chromatography (after this abbreviating HPLC as) analysis part.The result is 1,3-Bis(3-aminophenoxy)benzene is 82% (with respect to 1,3-two fluorobenzene).

References

[1] K. KALEEM; S. E; F Chertok. Quinone–amine polymers. II.? 1,3-bis(3-aminophenoxy) benzene-p-benzoquinone oligomers[J]. Journal of Polymer Science Part A: Polymer Chemistry, 1989. DOI:10.1002/pola.1989.080270312.

1,3-Bis(3-aminophenoxy)benzene(10526-07-5)Related Product Information

• 3-Aminophenol
• 4,4'-Bis(4-aminophenoxy)biphenyl
• 4,4'-DIAMINOBIPHENYL-2,2'-DICARBOXYLIC ACID
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• 4,4'-(HEXAFLUOROISOPROPYLIDENE)BIS[(4-AMINOPHENOXY)BENZENE]
• 1,3-DIPHENOXYBENZENE
• 1,3-Bis(3-aminophenoxy)benzene
• 3-PHENOXYPHENOL
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