4-Bromobenzaldehyde

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4-Bromobenzaldehyde
4-bromobenzaldehyde.png
4-bromobenzaldehyde 3D.png
4-bromobenzaldehyde sample.jpg
Names
Preferred IUPAC name
4-Bromobenzaldehyde
Other names
p-Bromobenzaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.013.060 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-365-0
PubChem CID
UNII
  • InChI=InChI = 1S/C7H5BrO/c8-7-3-1-6(5-9)2-4-7/h1-5H Yes check.svgY
    Key: ZRYZBQLXDKPBDU-UHFFFAOYSA-N Yes check.svgY
  • C1=CC(=CC=C1C=O)Br
Properties
C7H5BrO
Molar mass 185.020 g·mol−1
Appearancewhite solid
Odor almond
Melting point 57 °C (135 °F; 330 K) [1]
Boiling point 255–258 °C (491–496 °F; 528–531 K) [1]
Hazards
GHS labelling: [2]
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H302, H315, H319, H334, H335
P233, P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, P501
Related compounds
Related compounds
 3-Bromobenzaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Bromobenzaldehyde, or p-bromobenzaldehyde, is an organobromine compound with the formula BrC6H4CHO. It is one of three isomers of bromobenzaldehyde. [3] It displays reactivity characteristic of benzaldehyde and an aryl bromide.

Contents

Preparation

4-Bromobenzaldehyde may be prepared in the laboratory in two steps by oxidation 4-bromotoluene. [4] In the first step, two bromine atoms are added to the methyl group of 4-bromotoluene by free radical bromination to form 4-bromobenzal bromide. In the second step, the dibrominated methyl group is hydrolyzed with calcium carbonate, then steam distilled to collect 4-bromobenzaldehyde.

Reactions

Owing to the bromoaryl group, 4-bromobenzaldehyde participates in various cross coupling reactions, such as Suzuki coupling. [5] In a Sonogashira coupling it couples with trimethylsilylacetylene to form 4-((trimethylsilyl)ethynyl)benzaldehyde, precursor to 4-ethynylbenzaldehyde. [6]

Applications

  1. CIX [32787-79-4] (page 266) [7] Patent: [8]
  2. OKY-1581 (CD) [9] [10]
  3. Atazanavir

References

  1. 1 2 "4-Bromobenzaldehyde". ChemSpider . Retrieved 21 October 2023.
  2. ↑ "4-Bromobenzaldehyde". pubchem.ncbi.nlm.nih.gov.
  3. ↑ PubChem. "4-Bromobenzaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-22.
  4. ↑ Coleman, G. H.; Honeywell, G. E. (1937). "p-Bromobenzaldehyde". Organic Syntheses . 17: 20. doi:10.15227/orgsyn.017.0020.
  5. ↑ Huff, Bret E.; Koenig, Thomas M.; Mitchell, David; Staszak, Michael A. (1998). "Synthesis of Unsymmetrical Biaryls Using a Modified Suzuki Cross-Coupling: 4-Biphenylcarboxaldehyde". Organic Syntheses. 75: 53. doi:10.15227/orgsyn.075.0053.
  6. ↑ Xu, X.; Cai, P.; Chen, H.; Zhou, H.-C.; Huang, N. (28 September 2022). "Three-Dimensional Covalent Organic Frameworks with she Topology". Journal of the American Chemical Society . 144 (40): 18511–18517. doi:10.1021/jacs.2c07733. PMID   36170014. S2CID   252566430.
  7. ↑ Ryley, John F.; Betts, Michael J. (1973). "Chemotherapy of Chicken Coccidiosis". 11: 221–293. doi:10.1016/S1054-3589(08)60459-7.
  8. ↑ Robert J Ferlauto, U.S. patent 3,577,553 (1971 to Smith Kline and French Laboratories Ltd, SmithKline Beecham Corp).
  9. ↑ Hillier, K.; Serradell, MN; Blancafort, P.; Castaer, J.; OKY-1581. Drugs Fut 1982, 7, 6, 399.
  10. ↑ Tadao Tanouchi, Masanori Kawamura, & Masaki Hayashi, U.S. patent 4,271,170 (1981 to Kissei Pharmaceutical Co Ltd, Ono Pharmaceutical Co Ltd).
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