Page last updated: 2024-12-05

diglyme

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Diglyme, also known as bis(2-methoxyethyl) ether, is a colorless, flammable liquid that is commonly used as a solvent in organic chemistry. It is synthesized by the reaction of ethylene glycol with two equivalents of methanol in the presence of a strong acid catalyst. Diglyme is a polar aprotic solvent, meaning it has a high dielectric constant but does not donate protons. This makes it a suitable solvent for reactions involving organometallic reagents, such as Grignard reagents and lithium aluminum hydride. Diglyme is also used as a solvent for lithium-ion batteries. It is studied for its potential use in various applications, including the synthesis of organic compounds, the development of new battery technologies, and the study of chemical reactions. Its high boiling point and stability make it a useful solvent for a variety of applications.'

diglyme : A polyether that is the dimethyl ether derivative of diethylene glycol. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID8150
CHEMBL ID1234162
CHEBI ID46784
SCHEMBL ID398
MeSH IDM0050565

Synonyms (113)

Synonym
2-methoxyethyl ether
CHEMBL1234162
1,1'-oxybis(2-methoxyethane)
2-(2-methoxyethoxy)-1-methoxyethane
dimethyl carbitol
ethanol,2'-oxybis-, dimethyl ether
diethylene glycol dimethyl ether
di(2-methoxyethyl) ether
glyme-2
ether, bis(2-methoxyethyl)
nsc59726
diglyme
nsc-59726
(2-methoxyethyl) ether
bis(2-methoxyethyl) ether
2,8-trioxanonane
ethane,1'-oxybis[2-methoxy-
ethane, 1,1'-oxybis[2-methoxy-
1-methoxy-2-(2-methoxyethoxy)ethane
111-96-6
inchi=1/c6h14o3/c1-7-3-5-9-6-4-8-2/h3-6h2,1-2h
m2m ,
ai3-28583
bis(2-methoxyethyl)ether
diethyl glycol dimethyl ether
hsdb 72
nsc 59726
ccris 6212
glyme 2
ethanol, 2,2'-oxybis-, dimethyl ether
ethane, 1,1'-oxybis(2-methoxy-
dimethoxydiglycol
einecs 203-924-4
brn 1736101
methyldiglyme
diglycol methyl ether
DB02935
ch3-o-ch2-ch2-o-ch2-ch2-o-ch3
2,2'-oxybis(1-methoxyethane)
2,5,8-trioxanonane
CHEBI:46784 ,
2,2'-oxybis[1-(methyloxy)ethane]
diethylene glycol dimethyl ether, anhydrous, 99.5%
diethylene glycol dimethyl ether, puriss., absolute, over molecular sieve (h2o <=0.005%), >=99.5% (gc)
dimethylcarbitol
B0498
AKOS000120199
diethylene glycol dimethyl ether stabilized with 100ppm bht
NCGC00247897-02
NCGC00247897-01
methyl diglyme
tox21_202340
NCGC00253963-01
tox21_300077
dtxcid604621
cas-111-96-6
NCGC00259889-01
dtxsid1024621 ,
STL280534
dimethyldiglycol
unii-m4bh3x0mvz
m4bh3x0mvz ,
ec 203-924-4
FT-0624894
SCHEMBL398
diglyme [mi]
diethylene glycol dimethylether
dimethoxydiglycol [inci]
hisolve mdm
diethylene glycol dimethyl ether [hsdb]
ch3och2ch2och2ch2och3
dimethyldigol
1,1'-oxybis(2-methoxy)ethane
1-methoxy-2-(2-methoxyethoxy)ethane #
2,2'-oxybisethanol dimethyl ether
dimethoxydiethylene glycol
diethylene-glycol dimethyl ether
2-methoxylethyl ether
(2-methoxyethyl)ether
di-(2-methoxyethyl)ether
bis(2methoxyethyl)ether
1-(2-methoxyethoxy)-2-methoxyethane
dimethyl digol
2-methoxyethylether
1-methoxy-2-(2-methoxyethoxyl)ethane
bis-(2-methoxyethyl) ether
diethyleneglycol dimethyl ether
1,1'-oxybis[2-methoxyethane]
2-methyoxyethyl ether
bis-(2-methoxy ethyl) ether
bis-(2-methoxy ethyl)ether
methoxyethyl ether
Q-200977
J-509864
F1908-0129
mfcd00008503
diethylene glycol dimethyl ether, analytical standard
diethylene glycol dimethyl ether, spectrophotometric grade, >=99%
diethylene glycol dimethyl ether, puriss. p.a., >=99.5% (gc)
bis(2-methoxyethyl) ether, reagent
diethylene glycol dimethyl ether, vetec(tm) reagent grade, 98%
diethylene glycol dimethyl ether, reagentplus(r), 99%
bis(2-methoxyethyl) ether-d14
diglyme; 1-methoxy-2-(2-methoxyethoxy)ethane; bis(2-methoxyethyl)ether; diethylene glycol dimethyl ether
CS-0017205
Q865952
1-methoxy-2-(2-methoxyethoxy)ethane(stabilized with 0.01%bht)
D72523
diethyleneglycoldimethylether
(diglyme)
diethylene glycol dimethyl ether(diglyme)
EN300-19205
Z104473160

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In summary, oral administration of diEGdiME during major organogenesis did not produce any distinctive signs of maternal toxicity, but did produce selective and profound adverse effects upon fetal growth, viability, and morphological development at greater than or equal to 125 mg/kg/day."( The developmental toxicity of diethylene glycol dimethyl ether in mice.
George, JD; Kimmel, CA; Marr, MC; Price, CJ, 1987
)
0.27
" Not only does the approach provide a useful way to investigate the relationship between adverse fetal outcomes, it also yields a natural framework for conducting quantitative risk assessment."( Statistical model for fetal death, fetal weight, and malformation in developmental toxicity studies.
Catalano, PJ; Kimmel, CA; Kimmel, GL; Ryan, LM; Scharfstein, DO, 1993
)
0.29
" In this study, diglyme was embryolethal at 400 ppm; a level that otherwise was only marginally toxic to the dam."( Developmental toxicity of diglyme by inhalation in the rat.
Chromey, NC; Driscoll, CD; Kennedy, GL; Staples, RE; Valentine, R, 1998
)
0.95

Dosage Studied

ExcerptRelevanceReference
"The Rai and Van Ryzin dose-response model proposed for teratology experiments has been characterized for its appropriateness and applicability in modeling the dichotomous response data from developmental toxicity studies."( Characterization of a developmental toxicity dose-response model.
Faustman, EM; Kimmel, CA; Smith, WP; Wellington, DG, 1989
)
0.28
"Time-mated CD-1 mice were orally dosed on gestation day 11 (plug = 0) with distilled water (control) or one of four glycol ethers at a dose of 4 mmol/kg: ethylene glycol monomethyl ether (EGME, 304 mg/kg), ethylene glycol dimethyl ether (EGdiME, 361 mg/kg), diethylene glycol dimethyl ether (diEGdiME, 537 mg/kg), triethylene glycol dimethyl ether (triEGdiME, 713 mg/kg)."( Relative potency of four ethylene glycol ethers for induction of paw malformations in the CD-1 mouse.
Eisenmann, CJ; Hardin, BD, 1987
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
solventA liquid that can dissolve other substances (solutes) without any change in their chemical composition.
xenobioticA xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
polyetherAny ether that contains more than one ether linkage.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLI family zinc finger 3Homo sapiens (human)Potency38.64920.000714.592883.7951AID1259369
pregnane X nuclear receptorHomo sapiens (human)Potency61.25490.005428.02631,258.9301AID1346982
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (18.60)18.7374
1990's11 (25.58)18.2507
2000's8 (18.60)29.6817
2010's14 (32.56)24.3611
2020's2 (4.65)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 56.00

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index56.00 (24.57)
Research Supply Index3.78 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index88.86 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (56.00)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other43 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]