4-Bromobenzaldehyde

4-Bromobenzaldehyde, or p-bromobenzaldehyde, is an organic compound with the formula BrC6H4COH.[3]

4-Bromobenzaldehyde
Names
Preferred IUPAC name
4-Bromobenzaldehyde
Other names
p-Bromobenzaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.013.060
EC Number
  • 214-365-0
UNII
  • InChI=InChI = 1S/C7H5BrO/c8-7-3-1-6(5-9)2-4-7/h1-5H checkY
    Key: ZRYZBQLXDKPBDU-UHFFFAOYSA-N checkY
  • C1=CC(=CC=C1C=O)Br
Properties
C7H5BrO
Molar mass 185.02 g/mol
Appearance white solid
Odor almond
Melting point 57 °C (135 °F; 330 K)[1]
Hazards
GHS labelling:[2]
GHS07: Exclamation markGHS08: Health hazard
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).
Infobox references

Preparation

4-Bromobenzaldehyde may be prepared in the laboratory in two steps starting from 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

The bromoaryl group of 4-bromobenzaldehyde may be coupled with trimethylsilylacetylene in a Sonogashira coupling to form 4-((trimethylsilyl)ethynyl)benzaldehyde, followed by removal of the trimethylsilyl group with base to form 4-ethynylbenzaldehyde.[5]

See also

References
  1. "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. 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.
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