4-METHOXYBENZENEDIAZONIUM TETRAFLUOROBORATE Chemical Properties

Melting point:

142-144 °C(lit.)

storage temp. 

-20°C

form 

powder to crystal

color 

White to Orange to Green

Water Solubility 

Decompose in water

λmax

315nm(CHCl3)(lit.)

BRN 

3579591

InChI

InChI=1S/C7H7N2O.BF4/c1-10-7-4-2-6(9-8)3-5-7;2-1(3,4)5/h2-5H,1H3;/q+1;-1

InChIKey

CNKRQRKNUIYISU-UHFFFAOYSA-M

SMILES

[B-](F)(F)(F)F.C1(OC)=CC=C([N+]#N)C=C1

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

10-21

HazardClass 

8

PackingGroup 

III

HS Code 

29270000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

4-METHOXYBENZENEDIAZONIUM TETRAFLUOROBORATE Usage And Synthesis

Chemical Properties

grey-brown powder

Uses

4-Methoxybenzenediazonium tetrafluoroborate has been used in the preparation of azo coupled cyclic β-enaminones.

General Description

Interaction of 4-methoxybenzenediazonium tetrafluoroborate with synthetic DOPA-melanin and its precursors has been studied using EPR spectroscopy and spin-trapping technique.

Synthesis

The general procedure for the synthesis of tetrafluoroborate-4-methoxybenzenediazonium ortho ester from hydrofluoric acid, boric acid and p-aminoanisole was as follows: first, a mixture of aqueous hydrofluoric acid (2.08 g, 104 mmol, 17.2 eq.), boric acid (2.29 g, 26.0 mmol, 4.3 eq.), and water (5 mL) was added to p-aminomethyl ether (6.0 mmol). After stirring for 5 minutes, sodium nitrite (765 mg, 11.1 mmol, 1.9 eq.) was added in portions over 3 minutes at room temperature. After 15 minutes of reaction, the precipitate formed was filtered, washed with ether (5 mL) and subsequently suspended in acetonitrile (10 mL), filtered again and dissolved in acetonitrile (4 mL). Finally, after the addition of ether, the precipitate formed was filtered and dried under reduced pressure to give pure n-phenyl tetrafluoroborate-4-methoxy diazepine.

References

[1] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 1494 - 1502

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