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4,4'-Dibromotriphenylamine

Product Name4,4'-Dibromotriphenylamine
CAS81090-53-1
MFC18H13Br2N
MW403.11
EINECS628-703-3
MOL File81090-53-1.mol

Chemical Properties

Melting point	69°C
Boiling point	470.7±30.0 °C(Predicted)
Density	1.593
Flash point	110 °C
storage temp.	Inert atmosphere,Room Temperature
pka	-4.29±0.50(Predicted)
form	Solid
color	Off-white
InChI	InChI=1S/C18H13Br2N/c19-14-6-10-17(11-7-14)21(16-4-2-1-3-5-16)18-12-8-15(20)9-13-18/h1-13H
InChIKey	KIGVOJUDEQXKII-UHFFFAOYSA-N
SMILES	C1(N(C2=CC=C(Br)C=C2)C2=CC=CC=C2)=CC=C(Br)C=C1

Safety Information

Hazard Codes	Xn
Risk Statements	36/37/38-43-22
Safety Statements	26-36/37/39-36/37
WGK Germany	3
HS Code	29214990
Storage Class	12 - Non Combustible Liquids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3

Usage And Synthesis

Description

4,4′-Dibromotriphenylamine is a brominated derivative of aniline, a primary aromatic amine. It is a synthetic reagent for proteomics research. It is also employed as a starting material in the synthesis of various compounds.

Uses

Polytriarylamine Semiconductors

Biological Functions

4,4′-Dibromotriphenylamine acts as an inhibitor of enzymes involved in metabolism, a substrate for certain enzymes, and a modulator of certain receptor systems.

Synthesis

603-34-9

81090-53-1

Step 1: Synthesis of 4,4'-dibromotriphenylamine 1. 12 g (50 mmol) of triphenylamine was dissolved in 250 mL of ethyl acetate in a 500 mL conical flask. 2. 18 g (100 mmol) of N-bromosuccinimide (NBS) was added to the above solution. 3. The reaction mixture was stirred at room temperature for 24 hours. 4. Upon completion of the reaction, the reaction mixture was washed with deionized water. 5. The mixture was dried by adding anhydrous magnesium sulfate to remove water. 6. The desiccant was removed by filtration and the filtrate was concentrated. 7. 7. 20 g of white solid product was obtained after drying in 99% yield.

References

[1] Patent: WO2009/72587, 2009, A1. Location in patent: Page/Page column 191
[2] Patent: WO2009/139358, 2009, A1. Location in patent: Page/Page column 90
[3] Journal of Materials Chemistry C, 2016, vol. 4, # 13, p. 2579 - 2586
[4] Journal of Materials Chemistry C, 2016, vol. 4, # 43, p. 10301 - 10308
[5] Journal of Materials Chemistry, 2012, vol. 22, # 23, p. 11629 - 11635

4,4'-Dibromotriphenylamine

Chemical Properties

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Usage And Synthesis

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