Benzene

July 03, 2023
I鈥檓 a notorious chemical that has been much in the news lately.
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Benzene is the cornerstone of aromatic organic molecules. It has a long and checkered history鈥攎uch too long to cover here鈥攕o the focus will be on the very old and very new.

Legendary British scientist Michael Faraday is primarily known for his discoveries in electricity and electromagnetism; but it was he who first isolated benzene in 1825 from coal-derived 鈥渋lluminating gas鈥�, which was used for lighting in the early 19th century.

Chemists soon determined that the benzene molecule contains six carbon and six hydrogen atoms; but for decades, they struggled to determine its precise structure. In 1865, German chemist Friedrich August Kekul茅 published a paper in which he described benzene as consisting of a ring of six carbon atoms, each bonded to a hydrogen atom. The story goes that Kekul茅 dreamt of a snake biting its tail, which inspired him to conceive of the structure.

Kekul茅鈥檚 original concept was that the carbon atoms are attached to each other by alternating single and double bonds. But in the years following his original paper, his experiments showed that all six bonds are equivalent, which meant that each one oscillates between single and double bonding. Eventually, researchers, including Linus Pauling, concluded that this phenomenon is the basis of aromaticity, in which the carbon atoms are connected to each other via 蟽- and 蟺-bonding rather than discrete double bonds.

In the 20th century, benzene, derived mostly from petroleum, came into widespread production for use as a solvent and as a starting material for manufacturing other organic compounds, especially ethylbenzene, which is converted to styrene. The use of benzene for making a large array of products continues today; but its use as a solvent declined abruptly in the 1980s, when it was established as a human carcinogen.

People nonetheless continue to be exposed to benzene. Gasoline contains 0.5鈥�2.0 vol% benzene, which is one reason that gasoline dispensers now connect tightly to automobiles鈥� fuel tanks. In the past year, studies have shown that household stoves that use natural gas or propane can expose residents to harmful concentrations of benzene.

Last month, Robert B. Jackson at Stanford University (CA) and colleagues there and at other institutions in the San Francisco Bay area reported that . They reported that the mean benzene emissions from gas and propane burners set on high and ovens set to 350 掳F [177 掳C] ranged from 2.8 to 6.5 渭g/min, 10鈥�25 times higher than emissions from electric coil and radiant alternatives.

Jackson et al.鈥檚 findings verify others鈥� reports that gas stovetops and ovens could be health hazards. The issue has become political: Some jurisdictions have already banned new installations of gas-fueled cooking equipment; in other areas, protesters are loudly crying, 鈥淪ave our gas stoves!鈥�

Benzene hazard information

Hazard class*GHS code and hazard statement
Flammable liquids, category 2H225鈥擧ighly flammable liquid and vaporChemical Safety Warning
Aspiration hazard, category 1H304鈥擬ay be fatal if swallowed and enters airwaysChemical Safety Warning
Skin corrosion/irritation, category 2H315鈥擟auses skin irritationChemical Safety Warning
Serious eye damage/eye irritation, category 2AH319鈥擟auses serious eye irritationChemical Safety Warning
Germ cell mutagenicity, category 1BH340鈥擬ay cause genetic defectsChemical Safety Warning
Carcinogenicity, category 1AH350鈥擬ay cause cancerChemical Safety Warning
Specific target organ toxicity, repeated exposure, category 1H372鈥擟auses damage to blood through prolonged or repeated exposureChemical Safety Warning
Short-term (acute) aquatic hazard, category 2H401鈥擳oxic to aquatic lifeChemical Safety Warning
Long-term (chronic) aquatic hazard, category 3H412鈥擧armful to aquatic life with long-lasting effectsChemical Safety Warning

*Globally Harmonized System (GHS) of Classification and Labeling of Chemicals. .

Molecules from the journals

L-Methionine1 is a sulfur-containing essential amino acid. In 1921, pathologist John Howard Mueller at Columbia University (New York City) and found that it contributed to bacterial growth. Seven years later, George Barger* and Frederick Philip Coyne at the University of Edinburgh .

Ever since this early work, the biosynthesis, biochemistry, and nutritional aspects of proteinogenic methionine have been thoroughly investigated. Although methionine is generally considered to be beneficial in the diet, this past March, Guowei Le and colleagues at Jiangnan University (Wuxi, China) and other Chinese universities reported that restricting methionine in the diet of middle-aged mice by alleviating pancreatic apoptosis, thus promoting insulin secretion.

Cannabichromene2 (CBC) is a minor nonpsychoactive component of marijuana (Cannabis sativa). It may contribute to the analgesic effect of cannabis and has been suspected of enhancing the psychoactivity of 9-tetrahydrocannabinol3 (螖9-THC).

Both enantiomers of CBC are found in C. sativa; the abundance of CBC and the relative amounts of each enantiomer depend on the specific strain of the plant. This April, Giulia Mazzoccanti, Giovanni Appendino, and colleagues at the Sapienza University of Rome and other Italian institutions described their study of the . CBC concentrations are greater in the leaves of young plants; because of the potent synergistic activity of CBC with 螖9-THC, the authors emphasized the desirability of cultivating strains that retain this juvenile metabolic trait.

1. CAS Reg. No. 63-68-3.
2. CAS Reg. No. 20675-51-8.
3. CAS Reg. No. 1972-08-3.

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Benzene fast facts

CAS Reg. No.71-43-2
SciFinder nomenclatureBenzene
Empirical formulaC6H6
Molar mass78.11 g/mol
AppearanceColorless liquid
Boiling point80 掳C
Water solubility1.8 g/L (20 掳C)

Molecule in the News: April 28, 2025

Benzene1聽is a useful solvent; but its use has declined since it was established as a human carcinogen in the 1980s. Recently, however, the molecule appeared in a new setting: outer space. In March, G. Stephen Kocheril*, C. Zagorec-Marks, and H. J. Lewandowski at the University of Colorado (Boulder) tested the theoretical formation of benzene in interstellar space, starting with acetylene. The reaction sequence proceeded smoothly until the phenylium cation2, C6H5+, was produced. But the final purported step, , putting the theory to bed.

1. CAS Reg. No. 71-43-2.
2. CAS Reg. No. 17333-73-2.

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