1-Bromopyrene
[CAS 1714-29-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1-Bromopyrene
• Molecular Formula: C₁₆H₉Br
• Molecular Weight: 281.15
• CAS Registry Number: 1714-29-0
• EC Number: 626-844-5
• SMILES: C1=CC2=C3C(=C1)C=CC4=C(C=CC(=C43)C=C2)Br

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Melting point: 102 - 105 °C (Expl.)
• Boiling point: 422.5±14.0 °C 760 mmHg (Calc.)^*
• Flash point: 209.4±14.5 °C (Calc.)^*
• Index of refraction: 1.858 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

chemBlink Chemical Story

1-Bromopyrene, CAS 1714-29-0, is a brominated derivative of pyrene, one of the classic polycyclic aromatic hydrocarbons. Its value in synthesis comes from combining the large, rigid, conjugated pyrene pi-system with a carbon-bromine bond that can be transformed selectively. In effect, bromination converts pyrene from an interesting aromatic hydrocarbon into a practical coupling building block.

Pyrene has four fused benzene rings and a delocalized electronic system that gives the molecule characteristic ultraviolet absorption and fluorescence. Pyrene derivatives are therefore widely investigated in photophysics, fluorescent probes and organic electronic materials. Unsubstituted pyrene, however, offers relatively few convenient points for attaching it to more complex architectures. Installing bromine at the 1-position solves that synthetic problem.

Aryl bromides are among the standard partners in palladium-catalyzed cross-coupling chemistry. The C-Br bond of 1-bromopyrene can be replaced through Suzuki-Miyaura, Sonogashira, Buchwald-Hartwig and related transformations, allowing pyrene to be connected to aryl, alkynyl or amino-containing partners. The pyrene core can thereby be incorporated into conjugated molecules, polymers, ligands and fluorescent constructs without rebuilding the four-ring system from scratch.

The location of substitution matters because attachment at the 1-position changes conjugation and steric relationships in the final molecule. Synthetic chemists therefore use defined bromopyrene isomers rather than treating all brominated pyrenes as interchangeable. The bromine atom is not usually the desired final feature; it is a deliberately installed leaving group that provides access to a family of products.

1-Bromopyrene is thus a good example of "functionalizing a platform." Pyrene supplies the optical and electronic platform, while bromine supplies synthetic access. A single C-Br bond turns a stable polycyclic aromatic molecule into a versatile entry point for modern carbon-carbon and carbon-heteroatom bond formation.

References:
1. PubChem / CAS Common Chemistry, 1-Bromopyrene, CAS 1714-29-0.
2. Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev. 1995;95:2457-2483.
3. Valeur B, Berberan-Santos MN. Molecular Fluorescence. 2nd ed. Wiley-VCH, 2012.

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