Description
1,8-Dibromonaphthalene (CAS No. 17135-74-9) is a high-purity aromatic compound with the molecular formula C10H6Br2. This halogenated naphthalene derivative is widely utilized in organic synthesis, materials science, and pharmaceutical research due to its versatile reactivity. The compound features two bromine atoms positioned at the 1 and 8 locations of the naphthalene ring, making it a valuable precursor for cross-coupling reactions, such as Suzuki and Negishi couplings. Our product is rigorously tested for purity (typically ≥97% by GC) and is supplied as a crystalline solid with excellent stability under recommended storage conditions. Ideal for researchers developing advanced organic materials, liquid crystals, or ligands for catalytic systems.
Properties
- CAS Number: 17135-74-9
- Complexity: 142
- IUPAC Name: 1,8-dibromonaphthalene
- InChI: InChI=1S/C10H6Br2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H
- InChI Key: DLXBGTIGAIESIG-UHFFFAOYSA-N
- Exact Mass: 285.88158
- Molecular Formula: C10H6Br2
- Molecular Weight: 285.96
- SMILES: C1=CC2=C(C(=C1)Br)C(=CC=C2)Br
- Monoisotopic Mass: 283.88363
- Synonyms: 1,8-Dibromonaphthalene, 17135-74-9, DTXSID80347743, DTXCID10298815, 803-137-1, 1,8-dibromonaphtalene, 1,8-DIBROMO-NAPHTHALENE, Naphthalene, 1,8-dibromo-, MFCD00183574, 1,8-Dibromonaphthalene #, SCHEMBL1187339, SCHEMBL7794437, SCHEMBL8373000, BBL103576, STL557386, AKOS015903753, CS-W002485, SB67004, AS-19094, SY019521, DB-081020, D4656, EN300-6473453
Application
1,8-Dibromonaphthalene serves as a key intermediate in the synthesis of polycyclic aromatic hydrocarbons (PAHs) and functionalized naphthalene derivatives. Researchers employ this compound in the development of organic semiconductors and luminescent materials due to its planar structure and electron-accepting properties. The bromine substituents allow for further functionalization through metal-catalyzed coupling reactions, making it valuable in medicinal chemistry for scaffold diversification.
Safety and Hazards
GHS Hazard Statements
- H302 (97.7%): Harmful if swallowed [Warning Acute toxicity, oral]
- H411 (97.7%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
Precautionary Statements
- P264, P270, P273, P301+P317, P330, P391, and P501
Hazard Classes and Categories
- Acute Tox. 4 (97.7%)
- Aquatic Chronic 2 (97.7%)
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