Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A11133 4-Bromoveratrole, 97%

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

Stock No. Size Price ($) Quantity Availability
A11133-14 25g 57.30
A11133-22 100g 155.00
A11133-36 500g 568.00
Add to Cart Bulk/Specialty Print Quote View Item

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
Storage & Sensitivity
Ambient temperatures.
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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P264b-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse.

Other References

Beilstein
2046884
Harmonized Tariff Code
2909.30
TSCA
Yes

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware