104-68-7

Basic information

• Product Name: 2-(2-phenoxyethoxy)ethanol
• Synonyms: 2-(2-phenoxyethoxy)ethanol;Diethylene glycol phenyl ether;Ethanol, 2-(2-phenoxyethoxy)-;2-(2-phenoxyethoxy)-ethano;fenylkarbitol;phenyl carbitol;[2-(2-Hydroxyethoxy)ethoxy]benzene;phenyldigol
• CAS NO: 104-68-7
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.21636
• EINECS: 203-227-5
• Mol File: 104-68-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: -49.9°C
• Boiling Point: 298°C(lit.)
• Flash Point: 140.9°C
• Appearance: /
• Density: 1.1160
• Vapor Pressure: 0.000277mmHg at 25°C
• Refractive Index: 1.5230 to 1.5270
• PKA: 14.36±0.10(Predicted)
• Water Solubility: 35g/L at 20℃
• CAS DataBase Reference: 2-(2-phenoxyethoxy)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-phenoxyethoxy)ethanol(104-68-7)
• EPA Substance Registry System: 2-(2-phenoxyethoxy)ethanol(104-68-7)

Safety Data

• RTECS: KM0875000
• Hazardous Substances Data: 104-68-7(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion and skin contact. A skin and severe eye irritant. Some glycol ethers have dangerous human reproductive effects, When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

InChI:InChI=1/C10H14O3/c11-6-7-12-8-9-13-10-4-2-1-3-5-10/h1-5,11H,6-9H2

Synthetic route

2-(2-bromoethoxy)ethan-1-ol (57641-66-4) + phenol (108-95-2) → 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
Stage #1: phenol With potassium hydroxide In acetonitrile at 60℃; for 2h; Inert atmosphere; Stage #2: 2-(2-bromoethoxy)ethan-1-ol With potassium iodide In acetonitrile at 60℃; for 10h; Inert atmosphere;	72%

bromobenzene (108-86-1) + aniline (62-53-3) + diethylene glycol (111-46-6) → 2-(2-phenoxyethoxy)ethanol (104-68-7) + diphenylamine (122-39-4)

Conditions	Yield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 8h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;	A 28% B 70%

oxirane (75-21-8) + sodium phenoxide (139-02-6) → 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
at 95℃; for 2h;	69%

bromobenzene (108-86-1) + 4-nitro-aniline (100-01-6) + diethylene glycol (111-46-6) → 4-ntrophenyl(phenyl)amine (836-30-6) + 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 20h; Inert atmosphere;	A 68% B 22%

bromobenzene (108-86-1) + diethylene glycol (111-46-6) → 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
With N-Methyldicyclohexylamine; C46H67BN2; nickel dibromide In N,N-dimethyl-formamide at 60℃; for 24h;	65%

bromobenzene (108-86-1) + o-toluidine (95-53-4) + diethylene glycol (111-46-6) → 2-(2-phenoxyethoxy)ethanol (104-68-7) + N-phenyl-2-methylaniline (1205-39-6)

Conditions	Yield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 12h; Inert atmosphere;	A 33% B 63%

bromobenzene (108-86-1) + 2,6-diisopropylbenzenamine (24544-04-5) + diethylene glycol (111-46-6) → 2-(2-phenoxyethoxy)ethanol (104-68-7) + (2,6-diisopropyl-N-phenyl)phenylamine

Conditions	Yield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 20h; Inert atmosphere;	A 30% B 11%

oxirane (75-21-8) + phenol (108-95-2) → 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
With sodium phenoxide at 200℃;

sodium phenoxide (139-02-6) + phenol (108-95-2) → 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
at 100℃; Einleiten von Aethylenoxyd;

bis(phenoxyethoxyethyl) peroxydicarbonate (31603-33-5) → carbon dioxide (124-38-9) + β,β'-Bis(phenoxyethyl)ether (622-87-7) + 2-(2-phenoxyethoxy)ethanol (104-68-7) + Glycolaldehyde (141-46-8) + Carbonic acid 2-hydroxy-1-(2-phenoxy-ethoxy)-ethyl ester 2-(2-phenoxy-ethoxy)-ethyl ester

Conditions	Yield
In benzene at 60℃; Rate constant; Kinetics; var. temp., also with inhibiting addition of styrene or α-naphthol, Eact;

2-(2-Chloroethoxy)ethanol (628-89-7) + phenol (108-95-2) → 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
With potassium carbonate In acetonitrile
Williamson ether synthesis; Inert atmosphere;

diethylene glycol (111-46-6) + η6-chlorobenzene(cyclopentadienyl)iron(II) hexafluorophosphate → 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
With sodium hydride 1.) THF, r.t., 4 h, 2.) hν; Yield given. Multistep reaction;

2-chloro-ethanol (107-07-3) + sodium-<2-phenoxy ethylate> → 2-(2-phenoxyethoxy)ethanol (104-68-7)

oxirane (75-21-8) + phenol (108-95-2) → 2-Phenoxyethanol (122-99-6) + 2-(2-phenoxyethoxy)ethanol (104-68-7)

Conditions	Yield
pyridine at 165℃; under 2311.54 - 3345.86 Torr; for 0.333333h; Product distribution / selectivity; Inert atmosphere;
anion exchange resin A (Cl-type) In 2-methoxy-ethanol at 90 - 100℃; for 7h; Autoclave;	A 98.6 %Chromat. B 1.4 %Chromat.
anion exchange resin A (Cl-type) at 100℃; for 9h; Autoclave;	A 95 %Chromat. B 4.9 %Chromat.

oxirane (75-21-8) + phenol (108-95-2) → 2-Phenoxyethanol (122-99-6) + 2-(2-phenoxyethoxy)ethanol (104-68-7) + 2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol (7204-16-2)

Conditions	Yield
sodium hydroxide at 160℃; for 5.00333 - 5.01167h; Product distribution / selectivity;
sodium hydroxide In water at 140℃; for 5.00333 - 5.01167h; Product distribution / selectivity;

oxirane (75-21-8) + phenol (108-95-2) → 2-Phenoxyethanol (122-99-6) + 2-(2-phenoxyethoxy)ethanol (104-68-7) + 2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol (7204-16-2) + 2-<2-<2-(2-phenoxyethoxy)ethoxy>ethoxy>ethanol (36366-93-5)

Conditions	Yield
trifluoroacetic acid at 160℃; for 5.00333 - 5.01167h; Product distribution / selectivity;
at 140℃; for 5.00333 - 5.01167h; Product distribution / selectivity;

iodobenzene (591-50-4) + aniline (62-53-3) + diethylene glycol (111-46-6) → 2-(2-phenoxyethoxy)ethanol (104-68-7) + diphenylamine (122-39-4)

Conditions	Yield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 20h; Inert atmosphere;

iodobenzene (591-50-4) + 4-methoxy-aniline (104-94-9) + diethylene glycol (111-46-6) → 2-(2-phenoxyethoxy)ethanol (104-68-7) + N-(4-methoxyphenyl)phenylamine (1208-86-2)

Conditions	Yield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 8h; Inert atmosphere;

phosgene (75-44-5) + 2-(2-phenoxyethoxy)ethanol (104-68-7) → phenoxyethoxyethyl chloroformate (81731-00-2)

Conditions	Yield
at 3 - 5℃; for 3h;	99%

2-(2-phenoxyethoxy)ethanol (104-68-7) + acetic anhydride (108-24-7) → C12H16O4

Conditions	Yield
at 120℃; for 6h;	98%
at 90 - 120℃; for 6h;	98%
at 90 - 120℃; for 6h;	98%
at 90 - 120℃; for 6h;	98%

2-(2-phenoxyethoxy)ethanol (104-68-7) + 2',3'-di-O-acetylnicotinamide mononucleotide (154591-45-4) → C25H31N2O12P (1193377-76-2)

Conditions	Yield
With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride In N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere;	89%

2-(2-phenoxyethoxy)ethanol (104-68-7) → (2-(2-bromoethoxy)ethoxy)benzene (123824-56-6)

Conditions	Yield
With phosphorus tribromide In pyridine at 0 - 50℃;	62%

2-(2-phenoxyethoxy)ethanol (104-68-7) + 2-chloro-N-(4-(5-(3,4-dichlorophenyl)-3-hydroxy-1H-1,2,4-triazol-1-yl)phenyl)acetamide → 2-chloro-N-(4-(5-(3,4-dichlorophenyl)-3-(2-(2-phenoxyethoxy)ethoxy)-1H-1,2,4-triazol-1-yl)phenyl)acetamide

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 5h;	28%

2-(2-phenoxyethoxy)ethanol (104-68-7) + acrylic acid methyl ester (292638-85-8) → 1-acryloyloxy-2-(2-phenoxy-ethoxy)-ethane (61630-25-9)

Conditions	Yield
With sulfuric acid; hydroquinone Entfernung des entstehenden Methanols;
With toluene-4-sulfonic acid; hydroquinone Entfernung des entstehenden Methanols;

2-(2-phenoxyethoxy)ethanol (104-68-7) + ethyl acrylate (140-88-5) → 1-acryloyloxy-2-(2-phenoxy-ethoxy)-ethane (61630-25-9)

Conditions	Yield
With sulfuric acid; hydroquinone Entfernung des entstehenden Aethanols;
With toluene-4-sulfonic acid; hydroquinone Entfernung des entstehenden Aethanols;

2-(2-phenoxyethoxy)ethanol (104-68-7) → 2-(2-(4-bromophenoxy)ethoxy)ethanol (333382-85-7) + 2-[2-(2-Bromo-phenoxy)-ethoxy]-ethanol

Conditions	Yield
With n-dodecyl sulfate; bromine In water for 48h; Yields of byproduct given;
With bromine; cetyltrimethylammonim bromide In water for 48h; Yields of byproduct given;

2-(2-phenoxyethoxy)ethanol (104-68-7) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid 2-(2-phenoxy-ethoxy)-ethyl ester (50964-17-5)

Conditions	Yield
With triethylamine In dichloromethane

2-(2-phenoxyethoxy)ethanol (104-68-7) → bis(phenoxyethoxyethyl) peroxydicarbonate (31603-33-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / 3 h / 3 - 5 °C 2: 62 percent / aq. Na2O2 / diethyl ether / 0.5 h / 0 - 5 °C View Scheme

2-(2-phenoxyethoxy)ethanol (104-68-7) → {4-[2-(2-Phenoxy-ethoxy)-ethoxy]-phenyl}-methanol (220128-92-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: NEt3 / CH2Cl2 2: K2CO3 / acetonitrile View Scheme

2-(2-phenoxyethoxy)ethanol (104-68-7) → 1-Chloromethyl-4-[2-(2-phenoxy-ethoxy)-ethoxy]-benzene (220128-94-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: NEt3 / CH2Cl2 2: K2CO3 / acetonitrile 3: SOCl2, pyridine / CH2Cl2 View Scheme

2-(2-phenoxyethoxy)ethanol (104-68-7) → C27H27N2O3(1+)*F6P(1-)

Conditions	Yield
Multi-step reaction with 4 steps 1: NEt3 / CH2Cl2 2: K2CO3 / acetonitrile 3: SOCl2, pyridine / CH2Cl2 4: 2.) NH4PF6 / 1.) MeCN, 2.) Me2CO, H2O View Scheme

2-(2-phenoxyethoxy)ethanol (104-68-7) → C38H36N4O3(2+)*2F6P(1-)

Conditions	Yield
Multi-step reaction with 5 steps 1: NEt3 / CH2Cl2 2: K2CO3 / acetonitrile 3: SOCl2, pyridine / CH2Cl2 4: 2.) NH4PF6 / 1.) MeCN, 2.) Me2CO, H2O 5: 2.) NH4PF6 / 2.) Me2CO, H2O View Scheme

2-(2-phenoxyethoxy)ethanol (104-68-7) → 2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol (7204-16-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / phosphorous tribromide / pyridine / 0 - 50 °C 2: 67 percent / 1.) potassium hydroxide / H2O / 1.) 115 deg C, 1h; 2.) 120 deg C, 1h View Scheme

2-(2-phenoxyethoxy)ethanol (104-68-7) → 2-<2-<2-(2-phenoxyethoxy)ethoxy>ethoxy>ethanol (36366-93-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / phosphorous tribromide / pyridine / 0 - 50 °C 2: 67 percent / 1.) potassium hydroxide / H2O / 1.) 115 deg C, 1h; 2.) 120 deg C, 1h 3: 48 percent / phosphorous tribromide / pyridine / 0 - 50 °C 4: 72 percent / 1.) potassium hydroxide / H2O / 1.) 115 deg C, 1h; 2.) 120 deg C, 1h View Scheme

Upstream product

• 75-21-8 oxirane 
• 139-02-6 sodium phenoxide 
• 591-50-4 iodobenzene 
• 62-53-3 aniline 
• 111-46-6 diethylene glycol 
• 108-86-1 bromobenzene 
• 95-53-4 o-toluidine 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 104-94-9 4-methoxy-aniline 
• 100-01-6 4-nitro-aniline 
• 57641-66-4 2-(2-bromoethoxy)ethan-1-ol 
• 108-95-2 phenol 
• 107-07-3 2-chloro-ethanol 
• 628-89-7 2-(2-Chloroethoxy)ethanol 

Downstream Products

• 1392287-83-0 (3-(3-carbamoyl-1H-pyrrol-1-yl)phenoxycarbonyl)(2-(2-phenoxyethoxy)ethyl)amine 
• 1392288-10-6 2-(2-phenoxyethoxy)ethanisocyanate 
• 6338-54-1 2-(2-phenoxyethoxy)ethanamine 
• 80392-30-9 diethylene glycol methyl phenyl ether 
• 6594-70-3 N-[2-(2-phenoxy-ethoxy)-ethyl]-phthalimide 
• 1193377-76-2 C₂₅H₃₁N₂O₁₂P 
• 333382-87-9 2-(2-(2-(2-(4-bromophenoxy)ethoxy)ethoxy)ethoxy)ethan-1-ol 
• 125808-05-1 1-bromo-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzene 
• 333382-86-8 2-(2-(2-(4-bromophenoxy)ethoxy)ethoxy)ethan-1-ol 
• 123824-57-7 1-bromo-9-phenyl-3,6,9-trioxanonane 

Relevant articles and documents

Selective Arylation of Diols Using Arene-Iron Chemistry

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Photo/nickel synergistic catalysis method for monoarylation of diol

The invention discloses a photo/nickel synergistic catalysis method for monoarylation of a diol. The method directly uses a brominated aromatic hydrocarbon and a diol as raw materials, wherein the brominated aromatic hydrocarbon and the diol are simple and easy to obtain, and adopts a BODIPY organic photosensitizer and an inexpensive nickel source to synergistically catalyze cross-coupling of thediol and the brominated aromatic hydrocarbon without an additionally-added ligand to realize selective monoarylation of a diol compound, and a mono/dual arylation ratio is up to 18:1. The method disclosed by the invention has good tolerance of functional groups and is suitable for a plurality of diol compounds with different structures, such as o-diol, 1,3-diol, 1,4-diol and monodisperse polyethylene glycol; more importantly, the photosensitizer used in the method has a low using amount, the reaction temperature is close to room temperature, and the method is green, economical and highly-efficient; and the advantages make the method have higher scale synthetic value and can serve social and economic development.

PROCESS FOR THE CONTINUOUS PRODUCTION OF HIGH PURITY PHENOLIC GLYCOL ETHER

Phenolic glycol ethers, e.g., ethylene glycol phenyl ether, are prepared by a continuous, nonaqueous process comprising the steps of (A) contacting under isothermal reactive conditions in a first reactor or reaction zone an alkylene oxide, e.g., ethylene oxide, with (i) a stoichiometric molar excess of a phenolic compound, e.g., phenol, and (ii) a catalytic amount of a base, e.g., sodium hydroxide, homogeneously dispersed throughout the phenolic compound, to form a first intermediate phenolic glycol ether product, (Bj transferring the first intermediate phenolic glycol ether product to a second reactor or reaction zone, and ( C) subjecting the first intermediate phenolic glycol ether product to adiabatic reactive conditions in the second reactor or reaction zone to form a second intermediate phenolic glycol ether product comprising phenolic glycol ether, unreacted phenolic compound, catalyst, water and byproduct glycols. In addition, the mono-/di-product weight ratio can be adjusted by increasing or decreasing the amount of base catalyst employed.