Triglyme

HCID 8189

Basic information

CAS
112-49-2
Standard SMILES
COCCOCCOCCOC
InChIKey
YFNKIDBQEZZDLK-UHFFFAOYSA-N
Molecular formula
C8H18O4
Average molar mass
178.23 g/mol
Monoisotopic mass
178.12050906

Overview

Triethylene glycol dimethyl ether is a clear colorless liquid with a mild ethereal odor. (NTP, 1992)

Names & identifiers

Preferred name
Triglyme
IUPAC
1-methoxy-2-[2-(2-methoxyethoxy)ethoxy]ethane
English name
Triethylene glycol dimethyl ether
Molecular formula
C8H18O4
Molecular weight
178.23

Names & synonyms

Triglyme112-49-22,5,8,11-TETRAOXADODECANETriethylene glycol dimethyl ether1,2-Bis(2-methoxyethoxy)ethaneGlyme 4Ansul ether 161Glyme-31-methoxy-2-[2-(2-methoxyethoxy)ethoxy]ethaneTEGDIMETEGDMEDTXSID8026224
Show more names
DIMETHYLTRIGLYCOLglyme4riglymeansulether161dimethyltrigol
Dimethyl ether of triethylene glycolEthane, 1,2-bis(2-methoxyethoxy)-32YXG88KK0NSC-66400DTXCID206224CHEBI:448421-methoxy-2-(2-(2-methoxyethoxy)ethoxy)ethaneMETHYLTRIGLYME

Database identifiers

CAS
112-49-2
PubChem CID
8189
DTXSID
DTXSID8026224
ChEMBL
CHEMBL1235255
ChEBI
CHEBI:44842
UNII
32YXG88KK0
EC Number
203-977-3
Nikkaji
J5.127F

Properties

Computed structural properties

XLogP
-0.5
Topological polar surface area
36.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
9
Heavy atoms
12

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
SolventsSolvents -> Glycol Ethers (Glymes)
SpringerMaterials PropertiesDielectric constant
SurfactantsSurfactant
LogP-0.48
Density · 3 items

0.99 at 68 °F (NTP, 1992) - Less dense than water; will float

Relative density (water = 1): 0.99

0.986 @25 °C

Physicochemical properties

Melting point
45 °C · −45 °C(lit.)
Boiling point
216 °C · 216 °C(lit.)
Density
0.986 g/mL · 0.986 g/mL at 25 °C(lit.)
vapor density
4.7 · >4.7 (vs air)
vapor pressure
1.2 hPa · 1.2 hPa (20 °C)
refractive index
20 · n20/D 1.423(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H360Df: May damage the unborn child; Suspected of damaging fertility [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Danger

H319 (22.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P203, P264+P265, P280, P305+P351+P338, P318, P337+P317, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Chemical: 2,5,8,11-Tetraoxadodecane

Hazard Traits - Reproductive Toxicity

S - indicates a substance that is identified in a final Significant New Use Rule.

Status: Active Update: 04-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10247

Substance: 1,2-bis(2-methoxyethoxy)ethane (TEGDME; triglyme)

Triethylene glycol dimethyl ether: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2,5,8,11-Tetraoxadodecane: Environment tier I assessment
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound include irritation of the skin and eyes, abdominal pain, coughing, extrasystoles, nausea and vomiting.
Hazards Summary · 1 item

May have adverse effects on human reproduction, based on animal studies; [ICSC] Labeled as May impair fertility and May cause harm to the unborn child by EU regulations; [Glycol Ethers Online] Prolonged contact with air can form explosive peroxides; [CAMEO] A skin and eye irritant; [NTP] May form explosive peroxides; An irritant; May cause impaired fertility and fetal toxicity; [Alfa Aesar MSDS] See Monoglyme.

Reactive GroupEthers

Safety & protection

Fire Fighting · 2 items

Fires involving this material can be controlled with a carbon dioxide, dry chemical or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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 · 1 item

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.

Safe StorageSeparated from strong oxidants.
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 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 DisposalPersonal 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.

Toxicology

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Safety data

F
3
wgk
1
tsca
TSCA listed
rtecs
XF0665000
hs_code
29094990
Toxicity
LD50 orally in Rabbit: 5390 mg/kg

Chemistry & industry

Uses & manufacturing

UsesUsed as a solvent; [Merck Index] Used as a solvent for gases and coupling immiscible liquid; [NTP] Not produced commercially in the EU; [Glycol Ethers Online]
Household ProductsCosmetics product ingredient: 1,2-Bis(2-methoxyethoxy)ethane
General Manufacturing Information2,5,8,11-Tetraoxadodecane: ACTIVE
Applications · 3 items

UsesTriethylene glycol dimethyl ether is used as a solvent for gases and coupling immiscible liquid. It is also used to prepare perfluoro-triethyleneglycoldimethylether.

UsesTriethylene glycol dimethyl ether may be used as an analytical standard for the quantification of the analyte in water samples using in vitro bioassays and chemical screening technique.

UsesLabelled Triglyme. It is used as a solvent.

Preparation methods · 1 item

PreparationAt 0°C, 33 mL of triethylene glycol (0.25 mol) in 200 mL of tetrahydrofuran was added dropwise to a suspension of NaH (80% in mineral oil) (9.75 g, 0.325 mol) in 500 mL of tetrahydrofuran. The resulting mixture was stirred at 0°C for another 60 minutes. A solution of iodomethane in 200 mL of tetrahydrofuran was slowly added dropwise to the mixture, and the mixture was stirred overnight. The mixture was then allowed to warm to room temperature. The reaction progress was monitored by TLC. After the reaction was complete, the reaction system was filtered to remove the solid precipitate from the reaction mixture, and all volatile substances were removed by rotary evaporation of the filtrate. Dissolve the yellow oily liquid in toluene (100 mL), wash the organic layer with 3 x 150 mL of water, combine the aqueous layers, and then extract the aqueous layer with 3 x 150 mL of chloroform to obtain a mixed chloroform organic phase. Dry the combined organic layer with anhydrous magnesium sulfate, filter to remove the anhydrous magnesium sulfate solid, and remove the solvent from the filtrate by rotary evaporation to obtain the target product triethylene glycol dimethyl ether.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
聊城作之杭化工有限公司19163518031; 19163518031
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Additional notes

DefinitionChEBI: A polyether that consists of dodecane in which the carbon atoms at positions 2, 5, 8 and 11 are replaced by oxygen atoms.

Related reactions

51 records

Compound notes

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