2-Phenoxyethanol

Base Information

• Chemical Name: 2-Phenoxyethanol
• CAS No.: 122-99-6
• Deprecated CAS: 37220-49-8,56257-90-0,1020398-73-5,1020398-73-5,56257-90-0
• Molecular Formula: C8H10O2
• Molecular Weight: 138.166
• Hs Code.: 2909.49
• European Community (EC) Number: 204-589-7,500-013-6
• ICSC Number: 0538
• NSC Number: 1864
• UNII: HIE492ZZ3T
• DSSTox Substance ID: DTXSID9021976
• Nikkaji Number: J5.360K
• Wikipedia: Phenoxyethanol
• Wikidata: Q418038
• NCI Thesaurus Code: C77054
• RXCUI: 89552
• Metabolomics Workbench ID: 49444
• ChEMBL ID: CHEMBL1229846
• Mol file: 122-99-6.mol

Synonyms:2-phenoxyethanol;Emuclens;Erisept;ethylene glycol monophenyl ether;phenoxethol;phenoxyethanol

Chemical Property of 2-Phenoxyethanol

Chemical Property:

• Appearance/Colour: colorless or light yellow liquid
• Vapor Pressure: 0.01 mm Hg ( 20 °C)
• Melting Point: 11-13 °C
• Refractive Index: 1.5386
• Boiling Point: 245.199 °C at 760 mmHg
• PKA: 14.36±0.10(Predicted)
• Flash Point: 105.275 °C
• PSA: 29.46000
• Density: 1.102 g/cm³
• LogP: 1.05770
• Storage Temp.: room temp
• Solubility.: soluble, clear, colorless to very faintly yellow
• Water Solubility.: 30 g/L (20 ºC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 138.068079557
• Heavy Atom Count: 10
• Complexity: 77.3

Purity/Quality:

Phenoxyethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36-R36-R22
• Safety Statements: 26-S26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Glycol Ethers (E Series)
• Canonical SMILES: C1=CC=C(C=C1)OCCO
• Recent EU Clinical Trials: An open-label, controlled, randomized, prospective, between groups, multicenter clinical trial on the efficacy and safety of Fitostimoline (vaginal cream, vaginal suppositories and vaginal solution) and of Tantum Rosa (vaginal cream and vaginal solution) in the treatment of the vaginosis (non specific vaginitis)
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system and peripheral nervous system. This may result in impaired functions.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the central nervous system. This may result in impaired functions.
• Description: Phenoxyethanol is an organic chemical compound, a glycol ether often used in dermatological products such as skin creams and sunscreen. It is a colorless oily liquid. It is a bactericide (usually used in conjunction with quaternary ammonium compounds). Phenoxyethanol is used in many applications such as cosmetics, vaccines and pharmaceuticals as a preservative.
• Uses: phenoxyethanol is a broad-range preservative with fungicidal, bactericidal, insecticidal, and germicidal properties. It has a relatively low sensitizing factor in leave-on cosmetics. Phenoxyethanol can be used in concentrations of 0.5 to 2.0 percent, and in combination with other preservatives such as sorbic acid or parabens. In addition, it is used as a solvent for aftershaves, face and hair lotions, shampoos, and skin creams of all types. It can be obtained from phenol. Ethylene glycol phenyl ether at a 1.0% level acts as a preservative in personal care products. Phenoxyethanol is a preservative used in consumer and health care products, including vaccines, pen inks, ear drops, shampoos, skin cleansers, moisturizers, sun care products, and topical medicaments. The preservative Euxyl-K 400 also contains 2-phenoxyethanol, in combination with methyldibromoglutaronitrile. Phenoxyethanol is commonly used in cosmetics for its antibacterial and antifungal properties. It is increasingly being used in vaccines as a substitute for thiomersal and is also a component of pen inks and, more rarely, ear drops.Reactions to phenoxyethanol have rarely been reported. Three cases of CoU induced by phenoxyethanol in cosmetics have been reported.2-Phenoxyethanol is used as a single agent and in combination with other preservatives such as 1,2-dibromo-2,4-dicyanobutane (Euxyl K 400) and parabens, or in conjunction with quaternary ammonium compounds.The possibility of immunological IgE-mediated reaction could not be confirmed because specific IgE against 2-phenoxyethanol was negative. Antimicrobial preservative; also used topically in treatment of bacterial infections.

Technology Process of 2-Phenoxyethanol

There total 70 articles about 2-Phenoxyethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

[1,3]-dioxolan-2-one (96-49-1) + phenol (108-95-2,27073-41-2) → 2-Phenoxyethanol (122-99-6,56257-90-0,9004-78-8)

Guidance literature:

With potassium fluoride;

Reference yield: 98.0%

phenoxyacetic acid ethyl ester (2555-49-9) → 2-Phenoxyethanol (122-99-6,56257-90-0,9004-78-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 3h;

DOI:10.1039/d0cc02009e

Reference yield: 96.0%

tert-Butyl-dimethyl-(2-phenoxy-ethoxy)-silane (143038-69-1) → 2-Phenoxyethanol (122-99-6,56257-90-0,9004-78-8)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; at 20 - 25 ℃; for 0.333333h; Flow reactor;

DOI:10.1016/j.tetlet.2017.05.008

upstream raw materials:

oxirane

sodium phenoxide

phenol

potassium phenolate

Downstream raw materials:

oxydi-acetic acid bis-(2-phenoxy-ethyl ester)

4-[4-(2-hydroxy-ethoxy)-phenyl]-4-oxo-butyric acid

bis(2-phenoxyethyl)carbonate

1-chlorocarbonyloxy-2-phenoxy-ethane

Refernces

• 1、 Patat et al.. "-". . p. 322,330, 331. Retrieved 1952.
• 2、 Bobleter. "-". . p. 483,489. Retrieved 1956.
• 3、 Patat et al.. "-". . . Retrieved 1954.
• 4、 Smith. "-". . p. 994. Retrieved 1940.
• 5、 Di Terlizzi, Lorenzo,Protti, Stefano,Ravelli, Davide,Fagnoni, Maurizio. "Diradicals Photogeneration from Chloroaryl-Substituted Carboxylic Acids". . . Retrieved 2022/04/09.
• 6、 Capriati, Vito,García-álvarez, Joaquín,Marinò, Manuela,Perna, Filippo M.,Quivelli, Andrea Francesca,Vitale, Paola. "Ligand-Free Copper-Catalyzed Ullmann-Type C?O Bond Formation in Non-Innocent Deep Eutectic Solvents under Aerobic Conditions". . . Retrieved 2021/12/09.