3-Ethylphenol

3-Ethyl phenol

Chemical structure of 3-ethyl phenol
Names
Preferred IUPAC name 3-Ethylphenol
Identifiers
CAS Number	620-17-7  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34332
ChemSpider	11604
ECHA InfoCard	100.009.663
KEGG	C14386
PubChem CID	12101
UNII	0G9ZK222JX  Y
CompTox Dashboard (EPA)	DTXSID0022480
InChI InChI=1S/C8H10O/c1-2-7-4-3-5-8(9)6-7/h3-6,9H,2H2,1H3 Key: HMNKTRSOROOSPP-UHFFFAOYSA-N
SMILES Oc1cc(ccc1)CC
Properties
Chemical formula	C8H10O
Molar mass	122.167 g·mol−1
Appearance	colorless liquid
Density	1.0076 g/cm3
Melting point	−4.5 °C (23.9 °F; 268.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Ethylphenol is an organic compound with the formula C₂H₅C₆H₄OH. It is one of three isomeric ethylphenols. A colorless liquid, it occurs as an impurity in xylenols and as such is used in the production of commercial phenolic resins. ^[1]

Production

3-Ethylphenol is produced by vigorous sulfonation of ethylbenzene, whereby initially produced 4-ethylphenylsulfonic acid converts to 3-ethylphenylsulfonic acid. ^[1] The sulfonic acid is subsequently subjected to alkaline fusion, the dissolution of the sulfonic acid in molten alkali metal base (at 350 °C). The main steps in the synthesis are shown:

EtC₆H₅ + SO₃ → EtC₆H₄SO₃H (Et = ethyl)

EtC₆H₄SO₃H + NaOH → EtC₆H₄ONa + NaHSO₃

EtC₆H₄ONa + H⁺ → ArOH + Na⁺

Niche use and occurrence

3-Ethylphenol is found in urine samples of female elephants. ^[2]

It is used as a photographic chemical intermediate and an intermediate for the cyan coupler of photographic paper. ^[3] It's a tsetse fly attractant. Therefore, it's a kairomone. ^[4]

References

1. Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN   3527306730.
2. L.E.L. Rasmussen and V. Krishnamurthy (January 2001). "Urinary, temporal gland, and breath odors from Asian elephants of Mudumalai National Park" (PDF). GAJAH, the Journal of the Asian Elephant Specialist Group (20): 1–8.
3. Horikawa Y (1998). "Industrialization of the process for cyancoupler intermediate production". Res Dev Rep Sumitomo Chem. 2: 44–48.
4. Hitschler, Julia; Grininger, Martin; Boles, Eckhard (2020). "Substrate promiscuity of polyketide synthase enables production of tsetse fly attractants 3-ethylphenol and 3-propylphenol by engineering precursor supply in yeast". Scientific Reports. 10 (1): 9962. Bibcode:2020NatSR..10.9962H. doi: 10.1038/s41598-020-66997-5 . ISSN   2045-2322. PMC   7305150 . PMID   32561880.