Product Name

  • Name

    2-(2-phenoxyethoxy)ethanol

  • EINECS
  • CAS No. 104-68-7
  • Article Data14
  • CAS DataBase
  • Density 1.092g/cm3
  • Solubility 35g/L at 20℃
  • Melting Point -49.9°C
  • Formula C10H14 O3
  • Boiling Point 309.3°Cat760mmHg
  • Molecular Weight 182.219
  • Flash Point 140.9°C
  • Transport Information
  • Appearance
  • Safety 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.
  • Risk Codes
  • Molecular Structure Molecular Structure of 104-68-7 (2-(2-phenoxyethoxy)ethanol)
  • Hazard Symbols
  • Synonyms 2-(2-Phenoxyethoxy)ethanol;Diethylene glycol monophenyl ether; Diethylene glycol phenyl ether; NSC 406593;Phenoxydiglycol; Phenyl Di Glycol; Phenyl carbitol; Sunfine PH 20
  • PSA 38.69000
  • LogP 1.07430

Synthetic route

2-(2-bromoethoxy)ethan-1-ol
57641-66-4

2-(2-bromoethoxy)ethan-1-ol

phenol
108-95-2

phenol

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
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

bromobenzene

aniline
62-53-3

aniline

diethylene glycol
111-46-6

diethylene glycol

A

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

B

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
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

oxirane

sodium phenoxide
139-02-6

sodium phenoxide

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
at 95℃; for 2h;69%
bromobenzene
108-86-1

bromobenzene

4-nitro-aniline
100-01-6

4-nitro-aniline

diethylene glycol
111-46-6

diethylene glycol

A

4-ntrophenyl(phenyl)amine
836-30-6

4-ntrophenyl(phenyl)amine

B

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 20h; Inert atmosphere;A 68%
B 22%
bromobenzene
108-86-1

bromobenzene

diethylene glycol
111-46-6

diethylene glycol

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
With N-Methyldicyclohexylamine; C46H67BN2; nickel dibromide In N,N-dimethyl-formamide at 60℃; for 24h;65%
bromobenzene
108-86-1

bromobenzene

o-toluidine
95-53-4

o-toluidine

diethylene glycol
111-46-6

diethylene glycol

A

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

B

N-phenyl-2-methylaniline
1205-39-6

N-phenyl-2-methylaniline

Conditions
ConditionsYield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 12h; Inert atmosphere;A 33%
B 63%
bromobenzene
108-86-1

bromobenzene

2,6-diisopropylbenzenamine
24544-04-5

2,6-diisopropylbenzenamine

diethylene glycol
111-46-6

diethylene glycol

A

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

B

(2,6-diisopropyl-N-phenyl)phenylamine

(2,6-diisopropyl-N-phenyl)phenylamine

Conditions
ConditionsYield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 20h; Inert atmosphere;A 30%
B 11%
oxirane
75-21-8

oxirane

phenol
108-95-2

phenol

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
With sodium phenoxide at 200℃;
sodium phenoxide
139-02-6

sodium phenoxide

phenol
108-95-2

phenol

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
at 100℃; Einleiten von Aethylenoxyd;
bis(phenoxyethoxyethyl) peroxydicarbonate
31603-33-5

bis(phenoxyethoxyethyl) peroxydicarbonate

A

carbon dioxide
124-38-9

carbon dioxide

B

β,β'-Bis(phenoxyethyl)ether
622-87-7

β,β'-Bis(phenoxyethyl)ether

C

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

D

Glycolaldehyde
141-46-8

Glycolaldehyde

E

Carbonic acid 2-hydroxy-1-(2-phenoxy-ethoxy)-ethyl ester 2-(2-phenoxy-ethoxy)-ethyl ester

Carbonic acid 2-hydroxy-1-(2-phenoxy-ethoxy)-ethyl ester 2-(2-phenoxy-ethoxy)-ethyl ester

Conditions
ConditionsYield
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

2-(2-Chloroethoxy)ethanol

phenol
108-95-2

phenol

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
With potassium carbonate In acetonitrile
Williamson ether synthesis; Inert atmosphere;
diethylene glycol
111-46-6

diethylene glycol

η6-chlorobenzene(cyclopentadienyl)iron(II) hexafluorophosphate

η6-chlorobenzene(cyclopentadienyl)iron(II) hexafluorophosphate

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
With sodium hydride 1.) THF, r.t., 4 h, 2.) hν; Yield given. Multistep reaction;
2-chloro-ethanol
107-07-3

2-chloro-ethanol

sodium-<2-phenoxy ethylate>

sodium-<2-phenoxy ethylate>

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

oxirane
75-21-8

oxirane

phenol
108-95-2

phenol

A

2-Phenoxyethanol
122-99-6

2-Phenoxyethanol

B

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

Conditions
ConditionsYield
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

oxirane

phenol
108-95-2

phenol

A

2-Phenoxyethanol
122-99-6

2-Phenoxyethanol

B

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

C

2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol
7204-16-2

2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol

Conditions
ConditionsYield
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

oxirane

phenol
108-95-2

phenol

A

2-Phenoxyethanol
122-99-6

2-Phenoxyethanol

B

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

C

2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol
7204-16-2

2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol

D

2-<2-<2-(2-phenoxyethoxy)ethoxy>ethoxy>ethanol
36366-93-5

2-<2-<2-(2-phenoxyethoxy)ethoxy>ethoxy>ethanol

Conditions
ConditionsYield
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

iodobenzene

aniline
62-53-3

aniline

diethylene glycol
111-46-6

diethylene glycol

A

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

B

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 20h; Inert atmosphere;
iodobenzene
591-50-4

iodobenzene

4-methoxy-aniline
104-94-9

4-methoxy-aniline

diethylene glycol
111-46-6

diethylene glycol

A

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

B

N-(4-methoxyphenyl)phenylamine
1208-86-2

N-(4-methoxyphenyl)phenylamine

Conditions
ConditionsYield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 8h; Inert atmosphere;
phosgene
75-44-5

phosgene

2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

phenoxyethoxyethyl chloroformate
81731-00-2

phenoxyethoxyethyl chloroformate

Conditions
ConditionsYield
at 3 - 5℃; for 3h;99%
2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

acetic anhydride
108-24-7

acetic anhydride

C12H16O4

C12H16O4

Conditions
ConditionsYield
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-(2-phenoxyethoxy)ethanol

2',3'-di-O-acetylnicotinamide mononucleotide
154591-45-4

2',3'-di-O-acetylnicotinamide mononucleotide

C25H31N2O12P
1193377-76-2

C25H31N2O12P

Conditions
ConditionsYield
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-phenoxyethoxy)ethanol

(2-(2-bromoethoxy)ethoxy)benzene
123824-56-6

(2-(2-bromoethoxy)ethoxy)benzene

Conditions
ConditionsYield
With phosphorus tribromide In pyridine at 0 - 50℃;62%
2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

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-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

2-chloro-N-(4-(5-(3,4-dichlorophenyl)-3-(2-(2-phenoxyethoxy)ethoxy)-1H-1,2,4-triazol-1-yl)phenyl)acetamide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 5h;28%
2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

1-acryloyloxy-2-(2-phenoxy-ethoxy)-ethane
61630-25-9

1-acryloyloxy-2-(2-phenoxy-ethoxy)-ethane

Conditions
ConditionsYield
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

2-(2-phenoxyethoxy)ethanol

ethyl acrylate
140-88-5

ethyl acrylate

1-acryloyloxy-2-(2-phenoxy-ethoxy)-ethane
61630-25-9

1-acryloyloxy-2-(2-phenoxy-ethoxy)-ethane

Conditions
ConditionsYield
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-phenoxyethoxy)ethanol

A

2-(2-(4-bromophenoxy)ethoxy)ethanol
333382-85-7

2-(2-(4-bromophenoxy)ethoxy)ethanol

B

2-[2-(2-Bromo-phenoxy)-ethoxy]-ethanol

2-[2-(2-Bromo-phenoxy)-ethoxy]-ethanol

Conditions
ConditionsYield
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

2-(2-phenoxyethoxy)ethanol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

Toluene-4-sulfonic acid 2-(2-phenoxy-ethoxy)-ethyl ester
50964-17-5

Toluene-4-sulfonic acid 2-(2-phenoxy-ethoxy)-ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane
2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

bis(phenoxyethoxyethyl) peroxydicarbonate
31603-33-5

bis(phenoxyethoxyethyl) peroxydicarbonate

Conditions
ConditionsYield
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

2-(2-phenoxyethoxy)ethanol

{4-[2-(2-Phenoxy-ethoxy)-ethoxy]-phenyl}-methanol
220128-92-7

{4-[2-(2-Phenoxy-ethoxy)-ethoxy]-phenyl}-methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NEt3 / CH2Cl2
2: K2CO3 / acetonitrile
View Scheme
2-(2-phenoxyethoxy)ethanol
104-68-7

2-(2-phenoxyethoxy)ethanol

1-Chloromethyl-4-[2-(2-phenoxy-ethoxy)-ethoxy]-benzene
220128-94-9

1-Chloromethyl-4-[2-(2-phenoxy-ethoxy)-ethoxy]-benzene

Conditions
ConditionsYield
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

2-(2-phenoxyethoxy)ethanol

C27H27N2O3(1+)*F6P(1-)

C27H27N2O3(1+)*F6P(1-)

Conditions
ConditionsYield
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

2-(2-phenoxyethoxy)ethanol

C38H36N4O3(2+)*2F6P(1-)

C38H36N4O3(2+)*2F6P(1-)

Conditions
ConditionsYield
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-phenoxyethoxy)ethanol

2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol
7204-16-2

2-(2-(2-phenoxyethoxy)ethoxy)ethan-1-ol

Conditions
ConditionsYield
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-phenoxyethoxy)ethanol

2-<2-<2-(2-phenoxyethoxy)ethoxy>ethoxy>ethanol
36366-93-5

2-<2-<2-(2-phenoxyethoxy)ethoxy>ethoxy>ethanol

Conditions
ConditionsYield
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

PHENYL CARBITOL Chemical Properties

MF: C10H14O3
MW: 182.21636
EINECS: 203-227-5

PHENYL CARBITOL Toxicity Data With Reference

1.   

skn-rbt 505 mg open MLD

   UCDS**    Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 8/16 ,1961.
2.   

eye-rbt 2 mg open SEV

   AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.
3.   

orl-rat LD50:2140 mg/kg

   AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.
4.   

skn-rbt LD50:2120 mg/kg

   UCDS**    Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 8/16 ,1961.

RTECS: KM0875000

PHENYL CARBITOL Consensus Reports

Glycol ether compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

PHENYL CARBITOL 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.
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