Overview
Benz[a]anthracene is a four-ring polycyclic aromatic hydrocarbon (PAH) and a structural isomer of other PAHs like chrysene. It occurs naturally in fossil fuels and is formed during incomplete combustion of organic materials. While it has limited industrial use, it serves as a critical reference compound in environmental and toxicological studies due to its classification as a probable human carcinogen. First identified in coal tar, Benz[a]anthracene is now primarily encountered in research laboratories. Its fluorescence properties make it useful in spectroscopic analysis, and it is often studied as a model compound for understanding PAH metabolism and DNA adduct formation.
Physical and Chemical Properties
Benz[a]anthracene is a stable, crystalline solid at room temperature with a pale yellow to white appearance. Its high melting point (158-160°C) and sublimation tendency at 435°C reflect its aromatic stability. The compound is insoluble in water but dissolves readily in nonpolar organic solvents like benzene, toluene, and dichloromethane. Key chemical properties include its resistance to oxidation under ambient conditions and its ability to undergo electrophilic substitution reactions typical of aromatic hydrocarbons. UV-visible spectroscopy reveals strong absorption in the 250-400 nm range, and it exhibits blue fluorescence under UV light, a trait utilized in analytical detection methods.
Main Applications
The primary use of Benz[a]anthracene is as a reference standard in analytical chemistry, particularly in environmental testing for PAH contamination in soil, water, and air. Regulatory agencies worldwide include it in priority pollutant lists, driving demand for high-purity standards in laboratories. In research, it serves as a model carcinogen to study PAH-DNA interactions and metabolic activation pathways. Industrial applications are minimal due to its toxicity, but it may appear as an unintended byproduct in coke production, coal gasification, and certain combustion processes where its monitoring is legally mandated.
Safety and Storage
Classified by IARC as Group 2B (possibly carcinogenic to humans), Benz[a]anthracene requires strict handling protocols. Laboratory work should employ fume hoods, nitrile gloves, and protective eyewear. Avoid skin contact and inhalation of dust or vapors from heated samples. Storage recommendations include airtight containers in cool (<25°C), dark conditions separate from oxidizers. Spills should be contained with inert absorbents (e.g., vermiculite) and disposed as hazardous waste. SDS documentation must accompany commercial shipments, and facilities handling bulk quantities may need special permits due to environmental persistence.
B2B Procurement Guide
When sourcing Benz[a]anthracene, prioritize suppliers with ISO 17025 accreditation for reference materials. Key specifications to verify include HPLC purity (typically ≥98%), absence of interfering isomers (e.g., chrysene), and proper isotopic labeling if used for mass spectrometry. Bulk purchases (100g+) may attract discounts but require hazardous material transportation compliance. Consider regional regulations—EU REACH and US EPA have strict reporting thresholds. Alternatives like deuterated BA (for internal standards) may warrant evaluation for certain analytical methods. Always request batch-specific certificates of analysis.
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