Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

Safety Information

469068

Sigma-Aldrich

1-Bromobenzocyclobutene

95%

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

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.)

functional group

bromo

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

Related Categories

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

204.8 °F - closed cup

Flash Point(C)

96.00 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

469068-250MG:
469068-VAR:
469068-1G:
469068-BULK:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCF6808
26599MJ
09910JH
21429TD
10616ED

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
Condensed Cyclobutane Aromatic Compounds. IX. Benzocyclobutenol and Benzocyclobutenone.
Cava MP and Muth K.
Journal of the American Chemical Society, 82(3), 652-654 (1960)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service