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106-92-3

Basic Information
CAS No.: 106-92-3
Name: Allyl glycidyl ether
Article Data: 27
Molecular Structure:
Molecular Structure of 106-92-3 (Allyl glycidyl ether)
Formula: C6H10O2
Molecular Weight: 114.144
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;
EINECS: 203-442-4
Density: 0.962 g/cm3
Melting Point: -100 °C
Boiling Point: 153.2 °C at 760 mmHg
Flash Point: 57.2 °C
Solubility: 50 g/L (20 °C) in water
Appearance: colourless liquid
Hazard Symbols: HarmfulXn
Risk Codes: 10-20/22-37/38-40-41-43-52/53-62-68
Safety: 24/25-26-36/37/39-61
Transport Information: UN 2219 3/PG 3
PSA: 21.76000
LogP: 0.58780
Synthetic route
557-40-4

Allyl 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;
107-18-6

allyl alcohol

106-89-8

epichlorohydrin

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)

557-40-4

Allyl 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
4638-03-3

3-allyloxy-1-chloro-2-propanol

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.
19701-19-0

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

32503-27-8

tetra(n-butyl)ammonium hydrogensulfate

106-89-8

epichlorohydrin

106-92-3

Allyl glycidyl ether

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

oxiranyl-methanol

106-95-6

allyl bromide

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%
79-21-0

peracetic acid

557-40-4

Allyl ether

106-92-3

Allyl glycidyl ether

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

allyl alcohol

106-89-8

epichlorohydrin

A

106-92-3

Allyl glycidyl ether

B

74944-70-0

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

C

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
557-40-4

Allyl ether

A

2238-07-5

Diglycidyl ether

B

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;
110-91-8

morpholine

106-92-3

Allyl glycidyl ether

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%
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    Allyl glycidyl ether

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    Molecular Formula:C6H10O2 Molecular Weight:114.16 Density:0.962 Melting Point:-100 oC Boiling Point:154 oC Flash Point:48 oC Solubility:50 g/L (…Appearance:Colorless transparent liquid

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  • Casno:

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Consensus Reports

Reported in EPA TSCA Inventory.

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

Analytical Methods

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

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.