3,4-DIMETHOXYBENZYL BROMIDE Chemical Properties

Melting point:

56-58℃

Boiling point:

273℃

Density 

1.384

Flash point:

116℃

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

CDCl3;

form 

Solid

color 

Off-white

InChI

InChI=1S/C9H11BrO2/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-5H,6H2,1-2H3

InChIKey

AKPSLMUFDIXDJJ-UHFFFAOYSA-N

SMILES

C1(OC)=CC=C(CBr)C=C1OC

3,4-DIMETHOXYBENZYL BROMIDE Usage And Synthesis

Uses

Reagent used in the dimethoxybenzyl alkylations.

Uses

3,4-DIMETHOXYBENZYL BROMIDE used in the dimethoxybenzyl alkylations.

Preparation

3,4-Dimethoxybenzyl Bromide is synthesized from commercially available 3,4-dimethoxybenzyl alcohol and PBr3 or HBr.^[2-3]

General Description

3,4-Dimethoxybenzyl Bromide (DMBBr) is used as a reagent for introduction of 3,4-dimethoxybenzyl protecting group, which can be cleaved selectively under conditions of benzylic oxidation.^[1]

Synthesis

The general procedure for the synthesis of 3,4-dimethoxybenzyl bromide from 3,4-dimethoxybenzyl alcohol: 3,4-dimethoxybenzyl alcohol (1 mmol) was dissolved in anhydrous benzene (15 mL) under anhydrous conditions, phosphorus tribromide (0.5 mL) was added and the reaction was stirred at room temperature. Upon completion of the reaction, the target product 3,4-dimethoxybenzyl bromide was obtained in quantitative yield by conventional post-treatment steps.

storage

3,4-Dimethoxybenzyl Bromide reactions are usually carried out in polar solvents such as THF or DMF. The reagent is quite unstable and is best prepared fresh or stored at low temperature under nitrogen. It is a lachrymator.

References

1. (a) Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. T 1986, 42, 3021. (b) Oikawa, Y.; Tanaka, T.; Horita, K.; Yoshioka, T.; Yonemitsu, O. TL 1984, 25, 5393.
2. Lakhlifi, T.; Sedqui, A.; Laude, B.; Dinh An, N.; Vebrel, J. CJC 1991, 69, 1156.
3. Coote, S. J.; Davies, S. G.; Middlemiss, D.; Naylor, A. JCS(P1) 1989, 2223.

3,4-DIMETHOXYBENZYL BROMIDE(21852-32-4)Related Product Information

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• AKOS 230-05
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• BIS-3,4-DIMETHOXYSTILBENE DIBROMIDE
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• 2,3-DIBROMO-3-(4-ETHOXY-3-METHOXYPHENYL)-1-(2-NITROPHENYL)PROPAN-1-ONE