3-Ethylphenol

3-Ethyl phenol
Names
	Preferred IUPAC name 3-Ethylphenol
Identifiers
CAS Number	620-17-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34332;
ChemSpider	11604;
ECHA InfoCard	100.009.663
KEGG	C14386;
PubChem CID	12101;
UNII	0G9ZK222JX ;
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

^ ^a ^b 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.
^ 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.
^ Horikawa Y (1998). "Industrialization of the process for cyancoupler intermediate production". Res Dev Rep Sumitomo Chem. 2: 44–48.
^ 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.

[Ull-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.

[HitschlerGrininger2020-4] 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.

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