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2859-78-1 - 4-Bromoveratrole, 97% - 4-Bromo-1,2-dimethoxybenzene - 3,4-Dimethoxybromobenzene - A11133 - Alfa Aesar

A11133 4-Bromoveratrole, 97%

CAS Number
2859-78-1
Synonyms
4-Bromo-1,2-dimethoxybenzene
3,4-Dimethoxybromobenzene

Size Price ($) Quantity Availability
25g 51.87
100g 130.40
500g 468.80
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4-Bromoveratrole, 97%

MDL
MFCD00008381
EINECS
220-677-8

Chemical Properties

Formula
C8H9BrO2
Formula Weight
217.06
Boiling Point
255-256°
Flash Point
109°(228°F)
Density
1.510
Refractive Index
1.5730
Solubility
Soluble in benzene, ether, toluene.

Applications

4-Bromo-1,2-dimethoxybenzene is a metabolite of bromobenzene, with a catechol moiety in the substructure. It also has use as a redox shuttle additive, essentially a component in lithium batteries that consumes excess current during overcharge. And also used in the synthesis of the isoquinoline alkaloid (-)-mesembrine.

Notes

Store away from strong oxidizing agents. Keep container tightly closed. Store in cool, dry conditions in well sealed containers.

Literature References

Han Yu Xin.; Edward R. Biehl. Reaction of various nucleophiles with 2-bromo-p-xylene and 4-bromoveratrole via aryne reaction. J. Org. Chem. 1983, 48, (23), 4397-4399.

Timothy K. Beng.; Robert E. Gawley. Application of Catalytic Dynamic Resolution of N-Boc-2-lithiopiperidine to the Asymmetric Synthesis of 2-Aryl and 2-Vinyl Piperidines. Org. Lett. 1983, 13, (3), 394-397.

In the presence of sodamide, displacement by nucleophiles, e.g. anions of secondary amines or nitriles, occurs by an ortho-metallation-benzyne mechanism. The incoming nucleophile adds regioselectively such that the resulting anion is ortho-stabilized by methoxyl: J. Org. Chem., 48, 4397 (1983):

The derived Grignard reagent has been used in the synthesis of the isoquinoline alkaloid (-)-mesembrine: J. Org. Chem., 60, 6785 (1995).

Other References

Beilstein
2046884
Harmonized Tariff Code
2909.30
TSCA
Yes

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