4-Bromoanisole, 99%, Thermo Scientific Chemicals

Name: 4-Bromoanisole, 99%, Thermo Scientific Chemicals
SKU: ALFA11824.22

CAS: 104-92-7 | C7H7BrO | 187.036 g/mol

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Catalog number ALFA11824.22

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Specifications

Chemical Name or Material4-Bromoanisole

CAS104-92-7

Melting Point10°C to 13°C

Recommended StorageAmbient temperatures

Density1.494

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Immiscible with water.

Notes
Incompatible with strong oxidizing agents and strong acids.

RUO – Research Use Only

General 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(triphenyl phosphine) 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.