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
Show more names
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
- Formal charge
- 0
- Complexity
- 67.5
Experimental & physicochemical properties
Density
0.99 at 68 °F (NTP, 1992) - Less dense than water; will float
Relative density (water = 1): 0.99
0.986 @25 °C
Solubility
greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)
Solubility in water: miscible
Flash Point
232 °F (NTP, 1992)
111 °C o.c.
Boiling Point
421 °F at 760 mmHg (NTP, 1992)
216 °C
216 °C @760 [mm Hg]
Melting Point
-49 °F (NTP, 1992)
-45 °C
Vapor Density
4.7 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Relative vapor density (air = 1): 6.14
Vapor Pressure
0.9 mmHg at 68 °F (NTP, 1992)
0.04 [mmHg]
Vapor pressure, kPa at 20 °C: 0.12
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.)
- Flash point
- 231 °F · 231 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 1000 g/l · >1000g/l soluble
- form
- Liquid
- color
- 20 · APHA: ≤20
- PH
- 7 · 7
- explosive limit
- 0.7 % · 0.7%(V)
- Water Solubility
- Soluble
- Thermal Conductivity
- 0.13 W/ · 0.13 W/(m·K) at 25 ℃
- Sensitive
- Hygroscopic
- Merck
- 14 · 14,9692
- BRN
- 1700630 · 1700630
- Dielectric constant
- 7.5 · 7.5
- Major Application
- environmental
- InChI
- 1S/C8H18O4/c1-9-3-5-11-7-8-12-6-4-10-2/h3-8H2,1-2H3
- InChIKey
- YFNKIDBQEZZDLK-UHFFFAOYSA-N
- SMILES
- COCCOCCOCCOC
- LogP
- -0.52 at · -0.52 at 20℃
- Surface tension
- 27.56 mN/m · 27.56mN/m at 298.15K
- Substances of Very High Concern (SVHC) Candidate List
- 1 · 1,2-bis(2-methoxyethoxy)ethane (TEGDME; triglyme) (112-49-2)
- CAS DataBase Reference
- 112 · 112-49-2(CAS DataBase Reference)
- EWG's Food Scores
- 2 · 2
- FDA UNII
- 32 YXG88KK0 · 32YXG88KK0
- NIST Chemistry Reference
- 2 · 2,5,8,11-Tetraoxadodecane(112-49-2)
- EPA Substance Registry System
- Triethylene glycol dimethyl ether (112-49-2)
- UNSPSC Code
- 12352112 · 12352112
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 319 · H319-H360Df
- Precautionary statements
- 202 · P202-P264-P280-P305+P351+P338-P308+P313-P337+P313
- Hazard Codes
- T
- Risk Statements
- 61 · 61-19-62
- Safety Statements
- 53 · 53-45
- WGK Germany
- 1 · 1
- RTECS
- 665000 · XF0665000
- F
- 3 · 3
- Autoignition Temperature
- 375 °F · 375 °F
- TSCA
- TSCA listed
- HS Code
- 29094990 · 29094990
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 2 Repr · Eye Irrit. 2Repr. 1B
- Toxicity
- 50 orally · LD50 orally in Rabbit: 5390 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
Fire Hazards
This chemical is combustible. (NTP, 1992)
Combustible.
Hazards Summary
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.
Reactivity Profile
TRIETHYLENE GLYCOL DIMETHYL ETHER forms explosive peroxides on prolonged exposure to air. Its decomposition products may be sensitive to shock. The bulk chemical is stable for 2 weeks at temperatures up to 140 °F when protected from light. This chemical is incompatible with strong oxidizers. It is also incompatible with strong acids. It may react with peroxides, oxygen, nitric acid and sulfuric acid. (NTP, 1992).
Hazard Classes and Categories
Eye Irrit. 2 (22.6%)
Reproductive toxicity - category 1B
Reproductive toxicity - Category 2
Repr. 1B
Safety & protection
Fire Fighting
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
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
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.
Nonfire Spill Response
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.
Toxicology
Safety data
- F
- 3
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- XF0665000
- hs_code
- 29094990
- Toxicity
- LD50 orally in Rabbit: 5390 mg/kg
- risk_code
- 61-19-62
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H319-H360Df
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Repr. 1B
- Autoignition Temperature
- 375 °F
- Precautionary statements
- P202-P264-P280-P305+P351+P338-P308+P313-P337+P313
Chemistry & industry
Uses & manufacturing
Applications
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
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
Downstream products
Suppliers100 total
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
Compound notes
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