1-Bromobenzocyclobutene

• CAT Number: M007172
• CAS Number: 21120-91-2
• Molecular Formula: C8H5Br
• Molecular Weight: 181.03
• Purity: ≥95%
• Synonyms: 1-BROMOBENZOCYCLOBUTENE;1-BroMobenzocyclobutene;7-BroMobicyclo[4.2.0]octa-1,3,5,7-tetraene;1-BrBCB 1-Bromobenzocyclobutene;1-Bromobenzocyclobutene 95%
• Storage: -20°C
• IUPAC Name: 7-bromobicyclo[4.2.0]octa-1,3,5-triene
• InChI: InChI=1S/C8H7Br/c9-8-5-6-3-1-2-4-7(6)8/h1-4,8H,5H2
• InChIKey: AYNXHFRDABNHRX-UHFFFAOYSA-N
• SMILES: C1C(C2=CC=CC=C21)Br

1-Bromobenzocyclobutene (CAS 21120-91-2) is a useful synthon. It has important applications in organometallic methodology. It may be used in the synthesis of five-membered zirconacycles and benzocyclobutenol and benzocyclobutenone.

Reference

1: Ramakrishna TV, Sharp PR. Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes. Org Lett. 2003 Mar 20;5(6):877-9. Erratum in: Org Lett. 2003 Jun 12;5(12):2193. PubMed PMID: 12633095.
2:DeCamp, Mark R., and Lori A. Viscogliosi. "1-Bromobenzocyclobutene: a convenient entry into the benzocyclobutene ring system." The Journal of Organic Chemistry 46.19 (1981): 3918-3920.
3:Cava, M. P., and K. Muth. "Condensed Cyclobutane Aromatic Compounds. IX. Benzocyclobutenol and Benzocyclobutenone." Journal of the American Chemical Society 82.3 (1960): 652-654.