Product Name

  • Name

    Allyl glycidyl ether

  • EINECS 203-442-4
  • CAS No. 106-92-3
  • Article Data27
  • CAS DataBase
  • Density 0.962 g/cm3
  • Solubility 50 g/L (20 °C) in water
  • Melting Point -100 °C
  • Formula C6H10O2
  • Boiling Point 153.2 °C at 760 mmHg
  • Molecular Weight 114.144
  • Flash Point 57.2 °C
  • Transport Information UN 2219 3/PG 3
  • Appearance colourless liquid
  • Safety 24/25-26-36/37/39-61
  • Risk Codes 10-20/22-37/38-40-41-43-52/53-62-68
  • Molecular Structure Molecular Structure of 106-92-3 (Allyl glycidyl ether)
  • Hazard Symbols HarmfulXn
  • Synonyms Oxirane,[(2-propenyloxy)methyl]- (9CI);Propane, 1-(allyloxy)-2,3-epoxy- (6CI,8CI);1,2-Epoxy-3-allyloxypropane;1-(2-Propenyloxy)-2,3-epoxypropane;1-Allyloxy-2,3-epoxypropane;2-(Allyloxymethyl)oxirane;2-[[(2-Propenyl)oxy]methyl]oxirane;AGE;Allyl 2,3-epoxypropyl ether;Allyl oxiranemethyl ether;Denacol EX 111;Glycidyl2-propenyl ether;Glycidyl allyl ether;NSC 18596;NSC 631;[(2-Propenyloxy)methyl]oxirane;[(Allyloxy)methyl]oxirane;
  • PSA 21.76000
  • LogP 0.58780

Synthetic route

Allyl ether
557-40-4

Allyl ether

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

Conditions
ConditionsYield
With oxygen In acetonitrile at 60℃; under 760.051 Torr; for 3h; Catalytic behavior; chemoselective reaction;83%
With dihydrogen peroxide; MFI-type titanosilicate catalyst, Ti/Si molar ratio of 0.0233 In methanol; water at 57 - 60℃; for 0.5h; Conversion of starting material; Heating / reflux;33.2%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 45℃; for 48h;
allyl alcohol
107-18-6

allyl alcohol

epichlorohydrin
106-89-8

epichlorohydrin

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

Conditions
ConditionsYield
Stage #1: allyl alcohol; epichlorohydrin With trifluorormethanesulfonic acid; sulfuric acid at 45 - 55℃; for 5h; Molecular sieve;
Stage #2: With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide at 40 - 45℃; for 3h; Reagent/catalyst; Temperature;
97.17%
With tin(IV) chloride Behandeln des Reaktionsprodukts mit wss. Natronlauge;
With perchloric acid Behandeln des Reaktionsprodukts mit wss. Natronlauge;
With sodium hydride In tetrahydrofuran 1.) 2h, 2.) RT, 16h; 4h, reflux;
Stage #1: allyl alcohol; epichlorohydrin With boron trifluoride diethyl etherate at 20 - 22℃; for 3h;
Stage #2: With sodium hydroxide In diethyl ether at 35 - 40℃;
Ce(IV)

Ce(IV)

Allyl ether
557-40-4

Allyl ether

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

Conditions
ConditionsYield
With dihydrogen peroxide; MWW-type titanosilicate In acetonitrile
With dihydrogen peroxide; MWW-type titanosilicate In acetonitrile
3-allyloxy-1-chloro-2-propanol
4638-03-3

3-allyloxy-1-chloro-2-propanol

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

Conditions
ConditionsYield
With potassium hydroxide In diethyl ether at 30℃; for 2h;79%
With Ph4SbOMe In dichloromethane at 40℃; for 4h;61 % Chromat.
1,1,1-trifluoro-2-(trifluoromethyl)but-3-en-2-ol
19701-19-0

1,1,1-trifluoro-2-(trifluoromethyl)but-3-en-2-ol

tetra(n-butyl)ammonium hydrogensulfate
32503-27-8

tetra(n-butyl)ammonium hydrogensulfate

epichlorohydrin
106-89-8

epichlorohydrin

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

Conditions
ConditionsYield
With sodium hydroxide; sodium sulfate65%
oxiranyl-methanol
556-52-5

oxiranyl-methanol

allyl bromide
106-95-6

allyl bromide

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

Conditions
ConditionsYield
Stage #1: oxiranyl-methanol With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: allyl bromide In tetrahydrofuran for 7h;
43%
peracetic acid
79-21-0

peracetic acid

Allyl ether
557-40-4

Allyl ether

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

Conditions
ConditionsYield
With ethyl acetate
With acetone
allyl alcohol
107-18-6

allyl alcohol

epichlorohydrin
106-89-8

epichlorohydrin

A

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

B

1,2-epoxy-3-(1-chloromethyl-2-allyloxy)ethoxypropane
74944-70-0

1,2-epoxy-3-(1-chloromethyl-2-allyloxy)ethoxypropane

C

1-chloro-3-allyloxy-2-(2'-chloromethyl-2'-glycidyl)ethoxypropane
123046-07-1

1-chloro-3-allyloxy-2-(2'-chloromethyl-2'-glycidyl)ethoxypropane

Conditions
ConditionsYield
Stage #1: allyl alcohol; epichlorohydrin With boron trifluoride diethyl etherate at 30 - 35℃; for 2h;
Stage #2: With sodium hydroxide In diethyl ether at 30 - 45℃;
A 34.5 g
B 17.5 g
C 11 g
Allyl ether
557-40-4

Allyl ether

A

Diglycidyl ether
2238-07-5

Diglycidyl ether

B

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

Conditions
ConditionsYield
With Ti-MWW; dihydrogen peroxide In acetonitrile at 59.85℃; for 0.5h; Product distribution; Further Variations:; Solvents; Temperatures; Catalysts;
morpholine
110-91-8

morpholine

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

N-(3-allyloxy-2-hydroxypropyl)morpholine

N-(3-allyloxy-2-hydroxypropyl)morpholine

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 6h; regioselective reaction;100%
With copper(II) ferrite In dichloromethane at 20℃; regioselective reaction;95%
With Montmorillonite K10 clay for 0.0166667h; aminolysis, ring cleavage; Irradiation;74%
at 130 - 140℃; for 3h;60%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

carbon dioxide
124-38-9

carbon dioxide

4-allyloxymethyl-1,3-dioxolan-2-one
826-29-9

4-allyloxymethyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
With lithium bromide In N,N-dimethyl-formamide at 80℃; under 1500.15 Torr; for 12h;100%
With tetrabutylammomium bromide at 85℃; under 760.051 Torr; for 20h; Schlenk technique;100%
With potassium iodide In neat (no solvent) at 80℃; under 5250.53 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure; Autoclave;100%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

1-(allyloxy)-3-azidopropan-2-ol

1-(allyloxy)-3-azidopropan-2-ol

Conditions
ConditionsYield
With sodium azide; zirconium tetrakis(dodecyl sulfate) In water at 20℃; for 2.5h;100%
With sodium azide In ethanol; water96%
With sodium azide In water at 20℃; for 0.416667h; Sonication; Green chemistry;96%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

prop-2-ene-1-thiol
870-23-5

prop-2-ene-1-thiol

1-allyloxy-3-(allylthio)propan-2-ol
401479-52-5

1-allyloxy-3-(allylthio)propan-2-ol

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 1h;100%
With 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene.HL at 30℃; for 0.5h;90%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

aniline
62-53-3

aniline

1-(allyloxy)-3-(phenylamino)propan-2-ol

1-(allyloxy)-3-(phenylamino)propan-2-ol

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 6h; regioselective reaction;100%
With mesoporous titania-iron(III) oxide In neat (no solvent) at 20℃; for 2.5h; Green chemistry; regioselective reaction;98%
With lithium perchlorate In diethyl ether at 20℃; for 0.5h;95%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

diethylene glycol divinyl ether
764-99-8

diethylene glycol divinyl ether

3,6-dioxa-1,8-octandithiol
14970-87-7

3,6-dioxa-1,8-octandithiol

poly(allyl glycidyl ether-co-diethylene glycol divinyl ether-co-dimercaptodioxaoctane)

poly(allyl glycidyl ether-co-diethylene glycol divinyl ether-co-dimercaptodioxaoctane)

Conditions
ConditionsYield
Stage #1: diethylene glycol divinyl ether; 3,6-dioxa-1,8-octandithiol With azobis(2-cyanobutane) at 50 - 70℃; for 2h;
Stage #2: Allyl glycidyl ether With azobis(2-cyanobutane) at 70℃; for 37h;
100%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

benzoic acid
65-85-0

benzoic acid

2-hydroxy-3-(prop-2-en-1-yloxy)propyl benzoate
73097-87-7

2-hydroxy-3-(prop-2-en-1-yloxy)propyl benzoate

Conditions
ConditionsYield
With tetrabutyl phosphonium bromide In toluene at 110℃; for 5h;99%
With chitosan-silica sulfate nano hybrid In acetonitrile for 4h; Reflux; regioselective reaction;95%
With tetrabutylammomium bromide In acetonitrile for 6h; Heating;94%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

1-allyloxy-3-{[2-(3-allyloxy-2-hydroxypropyl)sulfanylethyl]sulfanyl}-2-propanol

1-allyloxy-3-{[2-(3-allyloxy-2-hydroxypropyl)sulfanylethyl]sulfanyl}-2-propanol

Conditions
ConditionsYield
With potassium carbonate for 3h; Heating;99%
N-benzyl-trimethylammonium hydroxide
With potassium carbonate In water Reflux;
oxirane
75-21-8

oxirane

Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

2,2-dimethylpropyl-(2-chloro-3-(2,3-dibromopropoxy)propyl)(2-chloroethyl)phosphorate

2,2-dimethylpropyl-(2-chloro-3-(2,3-dibromopropoxy)propyl)(2-chloroethyl)phosphorate

Conditions
ConditionsYield
With bromine; chlorine; AlCl3 In dichloromethane99%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

poly(allyl glycidyl ether)

poly(allyl glycidyl ether)

Conditions
ConditionsYield
C64H74Cl2Co2N4O4; bis(triphenylphosphoranylidene)-ammonium acetate In toluene at 0℃; for 3.5h;99%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

3-(2,2,3,3,4,4,5,5-octafluoropentyloxy)-1-propene
3108-07-4

3-(2,2,3,3,4,4,5,5-octafluoropentyloxy)-1-propene

octakis(dimethylsiloxy)octasilsesquioxane

octakis(dimethylsiloxy)octasilsesquioxane

heptakis({1,1,2,2,3,3,4,4-octafluoropentyloxypropyl}dimethylsiloxy)-({3-glicydoxypropyl} dimethylsiloxy)octasilsesquioxane

heptakis({1,1,2,2,3,3,4,4-octafluoropentyloxypropyl}dimethylsiloxy)-({3-glicydoxypropyl} dimethylsiloxy)octasilsesquioxane

Conditions
ConditionsYield
Stage #1: 3-(2,2,3,3,4,4,5,5-octafluoropentyloxy)-1-propene; octakis(dimethylsiloxy)octasilsesquioxane; bis(1,5-cyclooctadiene)-di-μ-trimethylsiloxy-dirhodium(I) In toluene at 110℃; for 4h;
Stage #2: Allyl glycidyl ether In toluene for 4h;
99%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

octakis(dimethylsiloxy)octasilsesquioxane

octakis(dimethylsiloxy)octasilsesquioxane

octakis(3-glycidyloxypropyldimethylsiloxy)octasilsesquioxane

octakis(3-glycidyloxypropyldimethylsiloxy)octasilsesquioxane

Conditions
ConditionsYield
With rhodium siloxide complexes immobilized on silica(Aerosil 200) In toluene at 100℃; for 1h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;99%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

1,1,3,3-Tetramethyldisiloxane
3277-26-7

1,1,3,3-Tetramethyldisiloxane

1,1,3,3-tetramethyl-1-(3-(oxiran-2-ylmethoxy)propyl)disiloxane
17980-29-9

1,1,3,3-tetramethyl-1-(3-(oxiran-2-ylmethoxy)propyl)disiloxane

Conditions
ConditionsYield
With Halloysite supported platinum catalyst at 60℃; for 10h;98.95%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In neat (no solvent) at 50℃; for 2h;98%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene at 60℃; for 18h;91%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

1,2-epoxytetradecane
3234-28-4

1,2-epoxytetradecane

2,4,6-tri-(α-methylbenzyl)phenol
18254-13-2

2,4,6-tri-(α-methylbenzyl)phenol

C49H66O4

C49H66O4

Conditions
ConditionsYield
Stage #1: 1,2-epoxytetradecane; 2,4,6-tri-(α-methylbenzyl)phenol With potassium methanolate at 120 - 145℃; for 20.1167h; Inert atmosphere;
Stage #2: Allyl glycidyl ether for 5h; Inert atmosphere;
98.1%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

tridecane-1-thiol
19484-26-5

tridecane-1-thiol

resorcinol diglycidyl ether
101-90-6

resorcinol diglycidyl ether

C50H90O8S2

C50H90O8S2

Conditions
ConditionsYield
Stage #1: tridecane-1-thiol; resorcinol diglycidyl ether With potassium methanolate at 100℃; for 0.983333h; Inert atmosphere;
Stage #2: Allyl glycidyl ether at 110℃; for 5.45h; Inert atmosphere;
98.1%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

isopropyl alcohol
67-63-0

isopropyl alcohol

1-Allyloxy-3-isopropoxy-propan-2-ol
61940-59-8

1-Allyloxy-3-isopropoxy-propan-2-ol

Conditions
ConditionsYield
With tin(IV)tetraphenylporphyrinato trifluoromethanesulfonate for 0.5h; Heating;98%
With sulfuric acid; silica gel at 20℃; for 1.5h;96%
With iron(III) chloride at 85℃; for 1h;95%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

acetone
67-64-1

acetone

4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane
4421-23-2, 18657-14-2, 56083-15-9

4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With 12-molybdo phosphoric acid n-hydrate at 20℃; for 0.0166667h; neat (no solvent);98%
With bismuth(lll) trifluoromethanesulfonate for 0.5h; Heating;97%
With trichloro(trifluoromethanesulfonato)titanium(IV); n-tetrabutylammonium hydroxide In water for 0.166667h; Ambient temperature;96%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

O-Trimethylsilylhydroxylamine
22737-36-6

O-Trimethylsilylhydroxylamine

C9H21NO3Si

C9H21NO3Si

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether at 20℃; for 0.5h;98%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

poly(methylhydrosiloxane)

poly(methylhydrosiloxane)

poly[methyl(propylglycidylether)]siloxane

poly[methyl(propylglycidylether)]siloxane

Conditions
ConditionsYield
With platinum In benzene at 20℃; for 32h;98%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

1-allyloxy-3-(2-aminophenylthio)propan-2-ol

1-allyloxy-3-(2-aminophenylthio)propan-2-ol

Conditions
ConditionsYield
With 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene.HL at 30℃; for 1.5h;98%
Allyl glycidyl ether
106-92-3

Allyl glycidyl ether

2-Naphthalenethiol
91-60-1

2-Naphthalenethiol

1-allyloxy-3-(naphthalen-2-ylsulfanyl)-propan-2-ol

1-allyloxy-3-(naphthalen-2-ylsulfanyl)-propan-2-ol

Conditions
ConditionsYield
With magnesium bromide at 20℃; for 0.0833333h;98%

ALLYL GLYCIDYL ETHER Consensus Reports

Reported in EPA TSCA Inventory.

ALLYL GLYCIDYL ETHER Standards and Recommendations

OSHA PEL: TWA 5 ppm; STEL 10 ppm
ACGIH TLV: 1 ppm; Not Classifiable as a Human Carcinogen
DFG MAK: Confirmed Animal Carcinogen, Suspected Human Carcinogen
NIOSH REL: (Glycidyl Ethers) CL 45 mg/m3/15M
DOT Classification:  3; Label: Flammable Liquid, Poison

ALLYL GLYCIDYL ETHER Analytical Methods

For occupational chemical analysis use NIOSH: Allyl Glycidyl Ether S346.

ALLYL GLYCIDYL ETHER Specification

The Allyl glycidyl ether, with the cas register number 106-92-3, has the systematic name of 2-[(prop-2-en-1-yloxy)methyl]oxirane. And its product categories of Industrial/Fine Chemicals; Simple 3-Membered Ring Compounds; Oxiranes.

The basic information of this chemical is below: This is a kind of colourless liquid, and it is insoluble in water and is flammable. And this is stable but incompatible with strong oxidizing agents, acids, bases. May form peroxides in storage if in contact with air. When store it, this chemical should be stored in the temp. Refrigerator (+4°C), and away from the oxidizing agent.

The characteristics of this chemical are as following: (1)ACD/LogP: 0.78; (2)ACD/LogD (pH 5.5): 0.78; (3)ACD/LogD (pH 7.4): 0.78; (4)ACD/BCF (pH 5.5): 2.3; (5)ACD/BCF (pH 7.4): 2.3; (6)ACD/KOC (pH 5.5): 63.18; (7)ACD/KOC (pH 7.4): 63.18; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 21.76; (11)Index of Refraction: 1.443; (12)Molar Refractivity: 30.89 cm3; (13)Molar Volume: 116.3 cm3; (14)Polarizability: 12.24 ×10-24 cm3; (15)Surface Tension: 32.1 dyne/cm; (16)Density: 0.981 g/cm3; (17)Flash Point: 57.2 °C; (18)Enthalpy of Vaporization: 37.39 kJ/mol; (19)Boiling Point: 153.2 °C at 760 mmHg; (20)Vapour Pressure: 4.32 mmHg at 25°C.

Use of Allyl glycidyl ether: Allyl glycidyl ether could react with 7(9)H-purin-6-ylamine to produce 1-allyloxy-3-(6-amino-purin-9-yl)-propan-2-ol, in the following condtion: reagent: K2CO3; solvent: dimethylsulfoxide; reaction time: 5 days; field: 40%; other condition: Ambient temperature.

When you deal with this chemical, you should be very cautious. Being a kind of harmful chemical, it may cause damage to health, and if by inhalation or if swallowed, it will be very harmful. Then it may even have limited evidence of a carcinogenic effect and has possible risk of impaired fertility. Besides, it is irritating to respiratory system and skin and it may cause sensitisation by skin contact. What's more, it is harmful to aquatic organisms, and it may cause long-term adverse effects in the aquatic environment. Then it has possible risk of irreversible effects. So you should take the following instructions while using. Wear suitable protective clothing, gloves and eye/face protection, and avoid contacting with skin and eyes. If in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. Besides, avoid releasing to the environment and then refer to special instructions/safety data sheet.

In addition, you could convert the following datas into the molecular structure:
SMILES: C=CCOCC1CO1Copy

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 270ppm/4H (270ppm) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.
mouse LD50 oral 390mg/kg (390mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.
rabbit LD50 skin 2550mg/kg (2550mg/kg)   AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.
rat LC50 inhalation 670ppm/8H (670ppm) SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.
rat LD50 oral 1600mg/kg (1600mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA
AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.

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