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2-((1-Methylethoxy)methyl)oxirane

HCID 19920
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Basic information

CAS
4016-14-2
Standard SMILES
CC(C)OCC1CO1
InChIKey
NWLUZGJDEZBBRH-UHFFFAOYSA-N
Molecular formula
C6H12O2
Average molar mass
116.16 g/mol
Monoisotopic mass
116.08372962

Overview

Isopropyl glycidyl ether is a colorless liquid. (USCG, 1999)

Names & identifiers

Preferred name
2-((1-Methylethoxy)methyl)oxirane
IUPAC
2-(propan-2-yloxymethyl)oxirane
English name
Glycidyl isopropyl ether
Molecular formula
C6H12O2
Molecular weight
116.16

Names & synonyms

Glycidyl isopropyl ether4016-14-2ISOPROPYL GLYCIDYL ETHER(Isopropoxymethyl)oxirane3-Isopropyloxypropylene oxide3-Isopropoxy-1,2-epoxypropaneIsopropyl epoxypropyl ether1,2-Epoxy-3-isopropoxypropaneNCI-C56439((1-Methylethoxy)methyl)oxirane2,3-Epoxypropyl-isopropyl etherOxirane, ((1-methylethoxy)methyl)-
Show more names
2-(Isopropoxymethyl)oxiraneIPGEAKOS NCG-0053ISOPROPOXYMETHYLOXIRANEisopropylepoxypropylether2-Isopropyloxymethyloxirane
DTXSID6025480Oxirane, [(1-methylethoxy)methyl]-NSC-4127NSC-46562DTXCID7054801V3116630G2-((1-METHYLETHOXY)METHYL)OXIRANE2-[(1-methylethoxy)methyl]oxirane

Database identifiers

CAS
4016-14-2
PubChem CID
19920
DTXSID
DTXSID6025480
ChEMBL
CHEMBL1487011
UNII
1V3116630G
EC Number
223-672-9
Nikkaji
J35.468F

Properties

Computed structural properties

XLogP
0.6
Topological polar surface area
21.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
8
Formal charge
0
Complexity
70.9

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
PolymersPlastics & Rubber -> Glycidyl Ethers
LogP · 2 items

0.5

0.8

Density · 5 items

0.92 (USCG, 1999) - Less dense than water; will float

0.9186 @ 20 °C/4 °C

Relative density (water = 1): 0.92

0.92

0.92

Color/Form · 2 items

MOBILE, COLORLESS LIQUID

Colorless liquid.

Solubility · 4 items

greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)

18.8% IN WATER, SOL IN KETONES & ALCOHOLS

Solubility in water, g/100ml: 19

19%

Flash Point · 5 items

92 °F (NTP, 1992)

33 °C

33 °C c.c.

92 °F

92 °F

Boiling Point · 5 items

261 °F at 760 mmHg (NTP, 1992)

137 °C @ 760 MM HG

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H360: May damage fertility or the unborn child [Danger Reproductive toxicity]

Hazard information

Regulatory Information · 5 items

Hazard Traits - Reproductive Toxicity

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

REACH registered substance: 2,3-epoxypropyl isopropyl ether (EC: 223-672-9)

Isopropyl glycidyl ether IGE: 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.)

DOT LabelFlammable Liquid
Fire Hazards · 2 items

Special Hazards of Combustion Products: Toxic vapors and gases, such as carbon monoxide, may be released in a fire.

Flammable. Above 33 °C explosive vapour/air mixtures may be formed.

Health HazardsExposure can cause mental confusion and moderate irritation of the eyes, skin, and respiratory tract. Chronic exposure can cause dermatitis and skin sensitization. (USCG, 1999)

Chemistry & industry

Uses & manufacturing

Uses · 4 items

Glycidyl ethers are used as reactive diluents in epoxy resins. [LaDou, p. 550]

Plastic Composites Manufacturing [Category: Industry]

STABILIZER FOR ORG COMPD & AS INTERMEDIATE FOR SYNTH OF ETHERS & ESTERS

REACTIVE DILUENT FOR EPOXY RESINS

U.S. Exports · 2 items

(1977) No Data

(1979) No Data

U.S. Imports · 2 items

(1977) No Data

(1979) No Data

U.S. Production · 2 items

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Methods of ManufacturingREACTION OF EPICHLOROHYDRIN WITH ISOPROPYL ALCOHOL FOLLOWED BY REACTION WITH SODIUM HYDROXIDE
General Manufacturing InformationOxirane, 2-[(1-methylethoxy)methyl]-: ACTIVE
Applications · 4 items

UsesIsopropyl glycidyl ether (IGE) is used to sta-bilize chlorinated solvents and as a viscosityreducer of epoxy resins.

UsesReactive diluent for epoxy resins; stabilizer for organic compounds; chemical intermediate for synthesis of ethers and esters

UsesGlycidyl isopropyl ether is a stabilizer of chlorinated solvents, and viscosity reducer of epoxy resins.

General DescriptionColorless liquid.

Upstream & downstream products

Upstream raw materials

Sodium

Related reactions

10 records
New reaction record
HRID 116168 reaction equation
HRID 116168As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 259267 reaction equation
HRID 259267As reactantuspto-grants-1977_07
HRID 291527 reaction equation
HRID 291527As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 376917 reaction equation
HRID 376917As reactantuspto-grants-2000_02
HRID 1050889 reaction equation
HRID 1050889As reactantuspto-grants-2016_07
HRID 1060352 reaction equation
HRID 1060352As reactantuspto-grants-2003_02
HRID 1665366 reaction equation
HRID 1665366As reactantuspto-grants-2011_10
HRID 2302152 reaction equation
HRID 2302152As reactantuspto-grants-2002_08
Page 1 of 2

Compound notes

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137 °C

261 °F

279 °F

Vapor Density · 2 items

4.15 (AIR= 1)

Relative vapor density (air = 1): 4.15

Odor ThresholdOdor Threshold Low: 300.0 [ppm]
Vapor Pressure · 6 items

9.4 mmHg at 77 °F (NTP, 1992)

9.4 [mmHg]

9.4 MM HG @ 25 °C

Vapor pressure, kPa at 25 °C: 1.25

9 mmHg at 77 °F

(77 °F): 9 mmHg

Physical Description · 5 items

Isopropyl glycidyl ether is a colorless liquid. (USCG, 1999)

Colorless liquid; [NIOSH]

COLOURLESS LIQUID.

Colorless liquid.

Colorless liquid.

Physicochemical properties

Boiling point
131 · 131-132 °C (lit.)
Density
0.924 g/mL · 0.924 g/mL at 25 °C (lit.)
vapor pressure
13 hPa · 13 hPa (25 °C)
refractive index
20 · n20/D 1.410(lit.)
Flash point
92 °F · 92 °F
storage temp.
30 °C · Store below +30°C.
solubility
188 g/l · 188g/l
form
Colorless liquid
color
Colorless to Almost colorless
PH
7 · 7 (188g/l, H2O, 20℃)
Water Solubility
19 g/L · 19g/L at 25℃
BRN
103028 · 103028
Exposure limits
50 ppm · ACGIH:TLV-TWA 50 ppm (238 mg/m3); TLV-STEL 75 ppm (356 mg/m3)OSHA:PEL-TWA 50 ppm (240 mg/m3)NIOSH:REL-Ceiling 50 ppm [15-min]
Stability
Stable. Flammable. Incompatible with strong oxidizing agents.
InChI
1S/C6H12O2/c1-5(2)7-3-6-4-8-6/h5-6H,3-4H2,1-2H3
InChIKey
NWLUZGJDEZBBRH-UHFFFAOYSA-N
SMILES
CC(C)OCC1CO1
LogP
0.8 at · 0.8 at 25℃
CAS DataBase Reference
4016 · 4016-14-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
1 V3116630G · 1V3116630G
EPA Substance Registry System
Isopropyl glycidyl ether (4016-14-2)
UNSPSC Code
12352112 · 12352112
NACRES
23 · NA.23
Symbol(GHS)
2 · GHS02,GHS06,GHS08
Signal word
Danger
Hazard statements
226 · H226-H317-H331-H334-H341
Precautionary statements
201 · P201-P210-P280-P302+P352-P304+P340+P311-P308+P313
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xi
Risk Statements
10 · 10-19-36/37/38-43
Safety Statements
16 · 16-26-36/37
RIDADR
3271 · UN 3271 3/PG 3
OEL
50 ppm · Ceiling: 50 ppm (240 mg/m3) [15-minute]
WGK Germany
2 · 2
RTECS
3500000 · TZ3500000
Autoignition Temperature
290 °C · 290 °C
TSCA
TSCA listed
HS Code
2910 · 2910 90 00
HazardClass
3 · 3
PackingGroup
III
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 InhalationFlam · Acute Tox. 3 InhalationFlam. Liq. 3Muta. 2Resp. Sens. 1Skin Sens. 1
Hazardous Substances Data
4016 · 4016-14-2(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 4200 mg/kg LD50 dermal Rabbit 9650 mg/kg
IDLA
400 ppm · 400 ppm
REACH Registrations
Inactive
Hazards Summary
Repeated or prolonged contact may cause skin sensitization. [ICSC}
Reactive GroupEthers
UN ClassificationUN Hazard Class: 3; UN Pack Group: III
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 item

Ethers can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Chemical DangersThe substance can presumably form explosive peroxides upon exposure to air or light. Reacts violently with strong oxidants, amines and acids.
Flammable LimitsClass IC Flammable Liquid: Fl.P. at or above 73 °F and below 100 °F.
Air and Water ReactionsHighly flammable. Water soluble.

Safety & protection

Fire Fighting · 2 items

Fire Extinguishing Agents Not to Be Used: Water.

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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.

First Aid · 2 items

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 procedures)

Safe StorageFireproof. Separated from strong oxidants and acids. Cool. Dry. Keep in the dark. Well closed.
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Spillage Disposal · 1 item

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 3 items

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.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet should be immediately removed due to its flammability hazard.

Isolation and EvacuationExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Eye PreventionWear safety spectacles or eye protection in combination with breathing protection.
Fire PreventionNO open flames, NO sparks and NO smoking. Above 33 °C use a closed system, ventilation and explosion-proof electrical equipment.
Inhalation RiskA harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
Skin PreventionProtective gloves.

Toxicology

Target OrgansEyes, skin, respiratory system, blood, reproductive system
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation of its vapour.

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 4 items

Burning sensation. Cough. Dizziness. Headache. Laboured breathing. Shortness of breath. Sore throat. Symptoms may be delayed.

Redness. Pain.

Redness. Pain.

irritation eyes, skin, upper respiratory system; skin sensitization; possible hematopoietic, reproductive effects

Human Toxicity Excerpts · 2 items

NO UNTOWARD EFFECTS REPORTED OTHER THAN SLIGHT SKIN IRRITATION ON REPEATED CONTACT.

SLIGHTLY TOXIC FOLLOWING INGESTION OR RESP EXPOSURE. PRACTICALLY NONTOXIC FOLLOWING ABSORPTION THROUGH SKIN. MODERATELY IRRITATING TO EYES & SKIN & CAPABLE OF CAUSING SKIN SENSITIZATION. NO RADIOMIMETIC EFFECTS DEMONSTRATED.

Non-Human Toxicity Excerpts · 5 items

...TESTED BY APPLICATION OF DROP TO RABBIT EYES HAS BEEN FOUND TO CAUSE MODERATE REVERSIBLE CORNEAL INJURY. VAPOR IS MODERATE EYE IRRITANT.

SKIN IRRITATION. SCORE OF 4.3...BY DRAIZE TECHNIQUE. ...CLASSIFIED AS MODERATELY IRRITATING. REPEATED 1-HR EXPOSURES RESULT IN SOME TOLERANCE & SCORING OF 2.2...AFTER 20 APPLICATIONS.

INCOORDINATION & DEPRESSED MOTOR ACTIVITY PRECEDING RESP DEPRESSION OCCUR ON ABSORPTION. ... RABBITS ADMIN COMPD PERCUTANEOUSLY SHOWED ALTERED PHYSIOLOGY ONLY @ HIGH DOSES... RESP EXPOSURE PRODUCED TYPICAL CHEMICAL PNEUMONIA IN LEVELS EXCEEDING 500 PPM.

RATS EXPOSED @ 400 PPM...7 HR DAILY FOR 50 DAYS, SHOWED SIGNIFICANTLY GREATER DECR IN MEAN WEEKLY WT GAIN THAN CONTROLS. @ NECROPSY, SOME DECR IN PERITONEAL FAT...& LUNGS OF 4 OF 10 RATS APPEARED...EMPHYSEMATOUS; 2 SHOWED MOTTLING OF LIVER. 1 OF LATTER SHOWED CONFLUENT PNEUMONIA. ...OCULAR IRRITATION & RESP DISTRESS...

...ONLY OBSERVED PHARMACOLOGICAL PROPERTY IS THAT OF CENTRAL NERVOUS SYSTEM DEPRESSION. CAUSE OF DEATH: CENTRAL DEPRESSION OF RESPIRATION.

Toxicity DataLC50 (rat) = 1,100 ppm/8H

Safety data

OEL
Ceiling: 50 ppm (240 mg/m3) [15-minute]
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
IDLA
400 ppm
tsca
TSCA listed
rtecs
TZ3500000
ridadr
UN 3271 3/PG 3
hs_code
2910 90 00
Toxicity
LD50 orally in Rabbit: 4200 mg/kg LD50 dermal Rabbit 9650 mg/kg
risk_code
10-19-36/37/38-43
Signal word
Danger
Symbol(GHS)
GHS02,GHS06,GHS08
hazard_code
Xi
safety_code
16-26-36/37
hazard_class
3
Storage Class
3 - Flammable liquids
packing_group
III
Hazard statements
H226-H317-H331-H334-H341
REACH Registrations
Inactive
Hazard Classifications
Acute Tox. 3 InhalationFlam. Liq. 3Muta. 2Resp. Sens. 1Skin Sens. 1
Autoignition Temperature
290 °C
Precautionary statements
P201-P210-P280-P302+P352-P304+P340+P311-P308+P313
Hazardous Substances Data
4016-14-2(Hazardous Substances Data)
Epichlorohydrin
Isopropyl alcohol

Downstream products

1-Amino-3-isopropoxy-propan-2-ol