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 Source | ID |
|---|---|
| PubMed CID | 8150 |
| CHEMBL ID | 1234162 |
| CHEBI ID | 46784 |
| SCHEMBL ID | 398 |
| MeSH ID | M0050565 |
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
| Excerpt | Reference | Relevance |
|---|---|---|
| " 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
| Excerpt | Relevance | Reference |
|---|---|---|
| "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)
| Role | Description |
|---|---|
| solvent | A liquid that can dissolve other substances (solutes) without any change in their chemical composition. |
| xenobiotic | A 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 contaminant | Any 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)
| Class | Description |
|---|---|
| polyether | Any 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
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 38.6492 | 0.0007 | 14.5928 | 83.7951 | AID1259369 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 61.2549 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Research
Studies (43)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 8 (18.60) | 18.7374 |
| 1990's | 11 (25.58) | 18.2507 |
| 2000's | 8 (18.60) | 29.6817 |
| 2010's | 14 (32.56) | 24.3611 |
| 2020's | 2 (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.
| This Compound (56.00) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 43 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||