Chemistry:4-Bromobenzaldehyde
From HandWiki
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| Names | |
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| Preferred IUPAC name
4-Bromobenzaldehyde | |
| Other names
p-Bromobenzaldehyde
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
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PubChem CID
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| Properties | |
| C7H5BrO | |
| Molar mass | 185.020 g·mol−1 |
| Appearance | white 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 pictograms |  
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| GHS Signal word | Danger |
| H302, H315, H319, H334, H335 | |
| P233, P260, P261, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P270, P271, P280, P284, P301+317Script error: No such module "Preview warning".Category:GHS errors, P302+352, P304+340, P305+351+338, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P330, P332+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P342+316Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P403, P403+233, P405, P501 | |
| Related compounds | |
Related compounds
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3-Bromobenzaldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
4-Bromobenzaldehyde, or p-bromobenzaldehyde, is an isomer of bromobenzaldehyde.[3]
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]
References
- ↑ 1.0 1.1 "4-Bromobenzaldehyde". https://www.chemspider.com/Chemical-Structure.63906.html.
- ↑ "4-Bromobenzaldehyde" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/70741#section=Safety-and-Hazards.
- ↑ PubChem. "4-Bromobenzaldehyde" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/4-Bromobenzaldehyde.
- ↑ Coleman, G. H.; Honeywell, G. E. (1937). "p-BROMOBENZALDEHYDE". Organic Syntheses 17: 20. doi:10.15227/orgsyn.017.0020.
- ↑ 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.
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