Grundinformationen
- Standard-SMILES
C=CCOCC1CO1- InChIKey
LSWYGACWGAICNM-UHFFFAOYSA-N- Summenformel
- C6H10O2
- Durchschnittliche Molmasse
- 114,14 g/mol
- Monoisotopische Masse
- 114,06807956
Überblick
Allyl glycidyl ether appears as a colorless liquid with a pleasant odor. Slightly less dense than water and insoluble in water. Hence floats on water. Poisonous by ingestion and mildly toxic by inhalation and skin contact. Very irritating to skin and eyes. Used to make other chemicals.
Namen und Bezeichner
- Bevorzugter Name
- Allyl glycidyl ether
- IUPAC
- 2-(prop-2-enoxymethyl)oxirane
- Lokaler Name
- 1-Allyloxy-2,3-epoxy-propan
- Englischer Name
- Allyl glycidyl ether
- Summenformel
- C6H10O2
- Molmasse
- 114.14
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
106-92-3- PubChem CID
- 7838
- DTXSID
DTXSID9039232- ChEMBL
CHEMBL1528174- UNII
- HDC0791894
- EC Number
- 203-442-4
- Nikkaji
- J34.520B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,4
- Polarare Oberfläche (TPSA)
- 21,8 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 80,6
Experimentelle und physikochemische Eigenschaften
Odor
CHARACTERISTIC, NOT UNPLEASANT ODOR
... Pleasant odor.
Density
0.969 at 68 °F (NTP, 1992) - Less dense than water; will float
SP GR: 0.9698 AT 20 °C/40 °C
Relative density (water = 1): 0.97
0.97
0.97
Color/Form
COLORLESS LIQUID
Colorless liquid ...
Solubility
greater than or equal to 100 mg/mL at 65.3 °F (NTP, 1992)
14.1% IN WATER; MISCIBLE WITH ACETONE, TOLUENE, & OCTANE
Solubility in water, g/100ml: 14 (freely soluble)
14%
Flash Point
135 °F (NTP, 1992)
57 °C
135 °F (OPEN CUP)
45 °C c.c.
135 °F
135 °F
Boiling Point
309 °F at 760 mmHg (NTP, 1992)
153.9 °C AT 760 MM HG
154 °C
309 °F
309 °F
Melting Point
-148 °F (NTP, 1992)
FREEZING POINT: FORMS GLASS @ -100 °C
-100 °C
-148 °F [forms glass]
-148 °F [forms glass]
Vapor Density
3.94 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
3.32 @ 25 °C (AIR= 1)
Relative vapor density (air = 1): 3.9
3.94
Odor Threshold
Odor Threshold Low: 9.4 [ppm]
44 mg/cu m odor low; 44 mg/cu m odor high.
Physikochemische Eigenschaften
- Schmelzpunkt
- -100 °C · -100 °C
- Siedepunkt
- 154 °C · 154 °C(lit.)
- Dichte
- 0.962 g/mL · 0.962 g/mL at 25 °C(lit.)
- Dampfdichte
- 3.9 · 3.9 (vs air)
- Dampfdruck
- 4.7 mm · 4.7 mm Hg ( 25 °C)
- Brechungsindex
- 20 · n20/D 1.433(lit.)
- Flammpunkt
- 135 °F · 135 °F
- storage temp.
- 20 °C · Store at <= 20°C.
- Löslichkeit
- 50 g/L · 50 g/L (20°C)
- Aggregatzustand
- Liquid
- Wichte
- 0.962 · 0.962
- Farbe
- Clear colorless
- Wasserlöslichkeit
- 50 g/L · 50 g/L (20 ºC)
- BRN
- 105871 · 105871
- Henry's Law Constant
- (x 10-6 atmm3/mol): 3.83 at 20 °C (approximate - calculated from water solubility and vapor pressure)
- Stabilität
- Stable. Combustible. Incompatible with strong oxidizing agents, acids, bases. May form peroxides in storage if in contact with air.
- InChI
- 1S/C6H10O2/c1-2-3-7-4-6-5-8-6/h2,6H,1,3-5H2
- InChIKey
- LSWYGACWGAICNM-UHFFFAOYSA-N
- SMILES
- C=CCOCC1OC1
- LogP
- 0.45 at · 0.45 at 25℃
- CAS Datenbank
- 106 · 106-92-3(CAS DataBase Reference)
- NIST chemische Informationen
- Oxirane, [(2-propenyloxy)methyl]-(106-92-3)
- EPA chemische Informationen
- Allyl glycidyl ether (106-92-3)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H226: Flammable liquid and vapor [Warning Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Danger
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P333+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Chemical: Oxirane, [(2-propenyloxy)methyl]-
Oxirane, 2-[(2-propen-1-yloxy)methyl]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Oxirane, 2-[(2-propen-1-yloxy)methyl]- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.
Status: Active Update: 26-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14565
Allyl 2,3-epoxypropyl ether: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Flammable. Above 48 °C explosive vapour/air mixtures may be formed.
Health Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· May cause toxic effects if inhaled or absorbed through skin.
DOT ID and Guide
2219 129
2219 129
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, ((2-propenyloxy)methyl)- is included on this list.
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Use powder, foam, carbon dioxide, water. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Give one or two glasses of water to drink. Refer immediately for medical attention.
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
General First Aid:
(General first aid procedures)
Spillage Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in inert absorbent. Wash away remainder with plenty of water. Store and dispose of according to local regulations. Do NOT let this chemical enter the environment.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Clothing which becomes contaminated with allyl glycidyl ether should removed immediately and placed in closed containers for storage until it can be discarded or until provision is made for removal of alllyl glycidyl ether from clothing. If the clothing is to be laundered or cleaned, the person performing the operation should be informed of allyl glycidyl ether's hazardous properties.
Where there is any possibility of a worker's eyes being exposed to AGE, an eye-wash fountain should be provided within the immediate work area for emergency use. ...
Where there is any possibility of a worker's body being exposed to AGE, facilities for quick drenching of the body should be provided within the immediate work area for emergency use. ...
For more Preventive Measures (Complete) data for ALLYL GLYCIDYL ETHER (6 total), please visit the HSDB record page.
Isolation and Evacuation
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Immediate precautionary measure
Toxikologische Informationen
Ecotoxicity Values
LD50 Goldfish 78 mg/l/24 hr /Conditions of bioassay not specified/
LD50 Goldfish 30 mg/l/96 hr /Conditions of bioassay not specified/
Exposure Routes
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
inhalation, skin absorption, ingestion, skin and/or eye contact
Signs and Symptoms
Cough. Sore throat. Burning sensation. Drowsiness. Lethargy.
MAY BE ABSORBED! Dry skin. Redness. Pain. Blisters.
Redness. Pain. Blurred vision. Severe deep burns.
Burning sensation. Headache. Dullness. Drowsiness. Nausea. Vomiting.
irritation eyes, skin, nose, respiratory system; dermatitis; pulmonary edema; narcosis; possible hematopoietic, reproductive effects
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=106-92-3]
TSCA Test Submissions
The mutagenicity of allyl glycidyl ether (AGE) was evaluated in Salmonella tester strains TA98 and TA1535, both in the presence and absence of added metabolic activation by either Aroclor-induced or phenobarbitol-induced rat liver S9 fraction. AGE was tested for mutagenicity at concentrations of 0.5, 1.0 and 2.0 micromoles/plate using the plate incorporation method. AGE caused a positive response in tester strain 1535 at 2.0 micromoles/plate in the presence of metabolic activation by Aroclor-induced rat liver S9 fraction.
The effect of allyl glycidyl ether was examined in the DNA repair assay. Human mononucleated white cells in G-0 phase were exposed to 1, 10, 100 or 500 ppm test article (dissolved in DMSO) for 5 hours. Exposure at any concentration did not statistically significantly (Duncan's LSD test, p > 0.05) increase the number of grains per nucleus counted on autoradiographs, or increase the intracellular incorporation of tritiated thymidine measured by liquid scintillation counting. In a preliminary range finding test, toxicity was reported at the upper dose levels used in the definitive test.
The mutagenicity of allyl glycidyl ether (AGE) was evaluated in male B6D2F1 mice (at least 10) dermally exposed to GBE at a dose level of 1.5 g/kg three times/week for a minimum of 8 weeks. Following the treatment period, the male mice were mated with 3 untreated, virgin female B6D2F1f mice for one week and mated with 3 fresh females for a second week. Significant differences were observed between treated and control mice in the following: proportion of deaths/pregnancy (decreased throughout the study). Significant differences were observed between treated mice over time in the following: number of implants/pregnancy (decreased versus controls in 1st week post-treatment, decreased versus controls in 2nd week post-treatment). There were no differences between treated and control mice or in treated mice over time with respect to percent pregnancy.
Human Toxicity Excerpts
SEVERAL CASES OF DERMATITIS AND 1 CASE OF EYE IRRITATION CONSTITUTE THE HUMAN DATA.
Allyl glycidyl ether is a CNS depressant and also causes acute pulmonary edema. It is classified as slightly toxic after oral administration and percutaneous application, appreciably irritating and injurious to the eyes and skin, capable of causing skin sensitization in human subjects ... .
Short-term (acute): Exposure to AGE can cause moderate irritation of the skin and severe irritation of the eyes and respiratory tract. Long-term (chronic): Exposure to AGE can cause dermatitis with itching, swelling, and blisters. Skin sensitization to AGE and cross sensitization with other epoxy agents can also occur.
Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl & diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl & diglycidyl ethers/
Carcinogen Classification
Allyl Glycidyl Ether
TR-376: Toxicology and Carcinogenesis Studies of Allyl Glycidyl Ether (CASRN 106-92-3) in Osborne-Mendel Rats and B6C3F1 Mice (Inhalation Studies) (1990 )
06/27/89
Equivocal Evidence
No Evidence
Some Evidence
Non-Human Toxicity Excerpts
... CLASSIFIED AS A MODERATE PRIMARY SKIN IRRITANT AND SEVERE EYE IRRITANT. ... SYSTEMIC TOXICITY TO RATS WAS OBSERVED AFTER 50 DAILY, 7 HOUR EXPOSURES AT 260, 400 AND 900 PPM, MANIFESTED BY INCREASED WEIGHT GAIN AT 260 PPM, AND HIGH MORTALITY AT 600 AND 900 PPM.
KIDNEYS OF ... /RATS/ EXPOSED TO 400 PPM /50 DAYS/ ... EXCESSIVE KIDNEY-BODY WT RATIOS. 260 PPM ... VERY SLIGHT IRRITATION OF EYES & SLIGHT RESPIRATORY DISTRESS. AT HIGHER LEVELS CORNEAL OPACITIES ... & SEVERE RESPIRATORY DIFFICULTIES. ... AUTOPSY SHOWED BRONCHOPNEUMONIA, EMPHYSEMA, BRONCHIECTASIS, PNEUMONITIS & HEMORRHAGE.
/AT LEVELS HIGHER THAN 260 PPM AUTOPSY OF RATS EXPOSED 50 DAYS REVEALED/ ... MOTTLED DISCOLORATION OF THE LIVER & ENLARGED ADRENAL GLANDS. 2 ANIMALS EXPOSED TO 900 PPM HAD NECROTIC SPLEENS. ... PREDOMINANT TOXICOLOGIC ACTIVITY WAS DEPRESSION OF CNS AFTER INTRAGASTRIC ADMINISTRATION.
ADMIN TO MICE & RATS ORALLY PRODUCED MODERATE DEPRESSION & DYSPNEA WITHIN 15-19 MIN. DEATH OCCURRED IN 4 HR TO 5 DAYS. ... @ AUTOPSY HYPOTONICITY OF ENTERIC TRACT & EXTENSIVE ADHESIONS OF STOMACH WALLS TO ADJACENT TISSUES WERE NOTED. NO CHARACTERISTIC MICROSCOPIC PATHOLOGY OCCURRED ... .
For more Non-Human Toxicity Excerpts (Complete) data for ALLYL GLYCIDYL ETHER (12 total), please visit the HSDB record page.
Regulatorische Informationen
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, ((2-propenyloxy)methyl)- is included on this list.
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.
Sicherheitsdaten
- OEB
- A
- OEL
- TWA: 5 ppm (22 mg/m3), STEL: 10 ppm (44 mg/m3) [skin]
- wgk
- 3
- IDLA
- 50 ppm
- tsca
- TSCA listed
- ridadr
- UN 2219
- hs_code
- 29109000
- RTECS-Nr.
- RR0875000
- risk_code
- 10-20/22-37/38-40-41-43-52/53-62-68
- Toxizität
- LD50 orally in Rabbit: 922 mg/kg LD50 dermal Rabbit 2550 mg/kg
- hazard_code
- Xn
- safety_code
- 24/25-26-36/37/39-61
- hazard_class
- 3
- packing_group
- III
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 106-92-3(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Carc. 2Eye Dam. 1Flam. Liq. 3Muta. 2Repr. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
- Selbstentzündungstemperatur
- 264 °C
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as a reactive diluent and intermediate in the production of resins; [ACGIH]
Plastic Composites Manufacturing [Category: Industry]
STABILIZER OF CHLORINATED COMPOUNDS, VINYL RESINS, RUBBER; RESIN INTERMEDIATE
General Manufacturing Information
Utilities
Oxirane, 2-[(2-propen-1-yloxy)methyl]-: ACTIVE
IT IS NOT CLASSIFIED AS DANGEROUS ARTICLE AND IS NOT REGULATED BY THE BUREAU OF EXPLOSIVES.
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