What molecule am I?
2-Phenoxyethanol, known early on as ethylene glycol monophenyl ether, is a high-boiling, oily liquid that is moderately water-soluble. It has a long history and several uses in chemical manufacturing and consumer products.
The earliest mention of 2-phenoxyethanol in the chemical literature appeared in 1894, when Ernst Roithner at the University of Vienna published a treatise on ethylene oxide. In the article, Roithner described the via the reaction of ethylene oxide with phenol in a basic medium.
Two years later, in a paper about 纬-phenoxy derivatives of malonic and acetic acids and the compounds used to synthesize them, William Henry Bentley, Edward Haworth, and William Henry Perkin, Jr.,* at Owens College (Manchester, UK) reported the from sodium phenolate and ethylene chlorohydrin (2-chloroethanol). In 1919, R. E. Rindfusz at the University of Illinois (Urbana鈥揅hampaign) used this method to make 2-phenoxyethanol in the course of . A refined version of Perkin et al.鈥檚 synthesis is used to manufacture 2-hydroxyethanol today.
2-Phenoxyethanol has many industrial uses鈥攑rimarily as a solvent for dyes, inks, and resins; a lubricant preservative; and a reagent in organic chemical synthesis. In consumer products, its uses range from a preservative for cosmetics and drugs to a fixative for perfumes to an attractant in insecticides. In one ironic instance, it is a component of a hair formulation that claims to be 鈥減reservative-free鈥�.
References to 2-phenoxyethanol often omit the numerical prefix, but this is ambiguous because of the existence of an isomer, 1-phenoxyethanol1. The isomer appears much less frequently in the chemical literature and has far fewer commercial uses.
1. CAS Reg. No. 56101-99-6.
2-Phenoxyethanol hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Acute toxicity, oral, category 4 | H302鈥擧armful if swallowed |  |
| Serious eye damage/eye irritation, category 1 | H318鈥擟auses serious eye damage |  |
| Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 | H335鈥擬ay cause respiratory irritation | |
| Specific target organ toxicity, single exposure, narcotic effects, category 3 | H336鈥擬ay cause drowsiness or dizziness | |
*Compilation of multiple safety data sheets.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.聽.
Molecules from the journals
Phainanoids are triterpenoids found in the tropical shrub Paranephelium hainanensis that grows only on Hainan Island (China). These compounds, including (+)-phainanoid A1, are cytotoxic against some cancer cell lines and show immunosuppressive activity similar to that of the established drug cyclosporin A2. In February, Guangbin Dong and co-workers at the University of Chicago reported the of (+)-phainanoid A and some non鈥搉aturally occurring analogues. The authors validated these molecules鈥� immunosuppressive activities and discussed their structure鈥揳ctivity relationships.
Sodium selenogallate3 (NaGaSe2) is an inorganic compound that was first described in a 1998 European patent application by Matsushita (Osaka, Japan) for anodes in nonaqueous-electrolyte batteries. Additional uses for the substance have been reported since then, the latest by Amitava Choudhury and colleagues at Missouri University of Science and Technology (Rolla), Missouri State University (Springfield), and the Indian Institute of Science Education and Research (Bhopal). The structure of NaGaSe2 consists of adamantane-like Ga4Se10 building units connected to each other to form 2-D (GaSe2)n鈥� layers. The authors report that NaGaSe2 鈥渉as an unusual ability to from the atmosphere or a nonanhydrous solvent.鈥� The resulting NaGaSe2鈭�xH2O (x = 1鈥�2) is easily dehydrated to its original form.
1. CAS Reg. No. 1643933-50-9.
2. CAS Reg. No. 59865-13-3.
3. CAS Reg. No. 216600-22-5.
Molecules from the Journals
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2-笔丑别苍辞虫测别迟丑补苍辞濒听
fast facts
| CAS Reg. No. | 122-99-6 |
| SciFinder nomenclature | Ethanol, 2-phenoxy- |
| Empirical formula | C8H10O2 |
| Molar mass | 138.16 g/mol |
| Appearance | Colorless, oily liquid |
| Boiling point | 245鈥�247 掳C |
| Water solubility | 27 g/L (20 掳C) |
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