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469068

Sigma-Aldrich

1-Bromobenzocyclobutene

95%

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Empirical Formula (Hill Notation):
C8H7Br
CAS Number:
21120-91-2
Molecular Weight:
183.05
MDL number:
MFCD17976891
UNSPSC Code:
12352100
PubChem Substance ID:
24870555
NACRES:
NA.22

Quality Level

100

Assay

95%

refractive index

n20/D 1.59 (lit.)

bp

90 °C/10.5 mmHg (lit.)

density

1.45 g/mL at 25 °C (lit.)

SMILES string

BrC1Cc2ccccc12

InChI

1S/C8H7Br/c9-8-5-6-3-1-2-4-7(6)8/h1-4,8H,5H2

InChI key

AYNXHFRDABNHRX-UHFFFAOYSA-N

General description

1-Bromobenzocyclobutene is a useful synthon. It has important applications in organometallic methodology. Reaction between cycloheptatriene, bromoform, potassium carbonate and 18-crown-6 at 140°C yields 1-bromobenzocyclobutene.

Application

1-Bromobenzocyclobutene may be used in the synthesis of following compounds:
  • five-membered zirconacycles
  • benzocyclobutenol and benzocyclobutenone
  • 2,3-dimethoxyprotoberberinium bromide, via reaction with 3,4-dihydro-6,7-dimethoxyisoquinoline

WGK

WGK 3

Flash Point(F)

204.8 °F

Flash Point(C)

96.00 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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1-Bromobenzocyclobutene: a convenient entry into the benzocyclobutene ring system.
DeCamp MR and Viscogliosi LA.
The Journal of Organic Chemistry, 46(19), 3918-3920 (1981)
T V V Ramakrishna et al.
Organic letters, 5(6), 877-879 (2003-03-14)
[reaction: see text] Commercially available 1-bromobenzocyclobutene is a potentially useful synthon particularly with the application of organometallic methodology. Here we show that it is readily converted into Cp(2)Zr(benzocyclobutadiene), which couples with alkynes or nitriles giving five-membered zirconacycles. Treatment of these
Studies on the syntheses of heterocyclic compounds-DXLV: An alternative synthesis of the protoberberine ring system.
Kametani T, et al.
Tetrahedron, 30(9), 1043-1046 (1974)
Condensed Cyclobutane Aromatic Compounds. IX. Benzocyclobutenol and Benzocyclobutenone.
Cava MP and Muth K.
Journal of the American Chemical Society, 82(3), 652-654 (1960)

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