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104-92-7 - 4-Bromoanisole, 99% - 4-Methoxybromobenzene - A11824 - Alfa Aesar

A11824 4-Bromoanisole, 99%

CAS Number
104-92-7
Synonyms
4-Methoxybromobenzene

Size Price ($) Quantity Availability
100g 32.37
500g 109.18
2500g 389.70
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4-Bromoanisole, 99%

MDL
MFCD00000097
EINECS
203-252-1

Chemical Properties

Formula
C7H7BrO
Formula Weight
187.04
Melting point
10-13°
Boiling Point
98-99°/10mm
Flash Point
94°(201°F)
Density
1.494
Refractive Index
1.5640
Solubility
Immiscible with water.

Applications

4-Bromoanisole finds application as an intermediate in synthetic chemistry. It is used in the preparation of aryl 1,3-diketones and ethyl 4-methoxycinnamate. It is a used as a brominating reagent. Further, it is used in Suzuki coupling reaction with phenylboronic acid as well as in Heck reaction.

Notes

Incompatible with strong oxidizing agents and strong acids.

Literature References

Nucleophilic displacement of Br can be effected with Na alkoxides in NMP in the presence of CuBr: Tetrahedron, 48, 3633 (1992).

For formation of the Grignard, conversion to the stannane and Stille coupling with an aryl triflate, catalyzed by trans-Dichlorobis(triphenyl­phosphine)­palladium(II)­, 10491, see: Org. Synth. Coll., 9, 553 (1998).

Moore, J. N.; Laskay, N. M.; Duque, K. S.; Kelley, S. P.; Rogers, R. D.; Shaughnessy, K. H. Synthesis of 4-sulfonatobenzylphosphines and their application in aqueous-phase palladium-catalyzed cross-coupling. J. Organomet. Chem. 2015, 777, 16-24.

Semmes, J. G.; Bevans, S. L.; Mullins, C. H.; Shaughnessy, K. H. Arylation of diethyl malonate and ethyl cyanoacetate catalyzed by palladium/di-tert-butylneopentylphosphine. Tetrahedron Lett. 2015, 56 (23), 3447-3450.

GHS Hazard and Precautionary Statements

Hazard Statements: H303

May be harmful if swallowed.

Precautionary Statements: P312

Call a POISON CENTER or doctor/physician if you feel unwell.

Other References

Merck
14,1427
Beilstein
1237590
Harmonized Tariff Code
2909.30
TSCA
Yes
RTECS
BZ8501000

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