ethane-1,2-diol

• ChemBase ID: 103244
• Molecular Formular: C2H6O2
• Molecular Mass: 62.06784
• Monoisotopic Mass: 62.03677943
• SMILES: OCCO
• Canonical SMILES: OCCO
• InChI: InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2
• InChIKey: LYCAIKOWRPUZTN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethane-1,2-diol
• IUPAC Traditional name: ethylene glycol
• Synonyms: Additive Screening Solution 01/Fluka kit no 78374; Ethylene glycol solution; Ethylene glycol 5 M solution; Ethylene glycol solution; Hypodicarbonous acid; Ethylene glycol; PEG 6000; Polyethylene glycol 6,000; PEG 4000; Polyethylene glycol 4,000; PEG 1500; Polyethylene glycol 1,500; 1,2-Dihydroxyethane; PEG 20000; Polyethylene glycol 20,000; PEG 200; Polyethylene glycol 200; PEG 10000; Polyethylene glycol 10,000; PEG 2000; Polyethylene glycol 2,000; PEG 8000; Polyethylene glycol 8,000; Polyethylene oxide, M.W. 1,000,000; Ethylene glycol, Spectrophotometric grade; Glycol; Ethylene alcohol; Monoethylene glycol; Glycol alcohol; 1,2-Ethanediol; ETHYLENE GLYCOL; ETHYLENE GLYCOL, SPECTRO GRADE; ETHYLENE GLYCOL, CERTIFIED GRADE; PEG 600; Polyethylene glycol 600; PEG 1000; Polyethylene glycol 1,000; PEG 400; Polyethylene glycol 400; PEG 12000; Carbowax?; Polyethylene glycol 12,000; Polyethylene oxide, M.W. 300,000; Polyethylene glycol monomethylether, 350; Polyethylene oxide, M.W. 100,000; Ethane-1,2-diol; 乙二醇 溶液; 1,2-乙二醇; 乙二醇; 聚乙二醇 6,000; 聚乙二醇 4,000; 聚乙二醇 1,500; 聚乙二醇 20,000; 聚乙二醇 200; 聚乙二醇, 10,000; 聚乙二醇 2,000; 聚乙二醇 8,000; 聚环氧乙烷, M.W. 1,000,000; 乙二醇, 光谱级; 聚乙二醇 600; 聚乙二醇 1,000; 聚乙二醇 400; 聚乙二醇 12,000; 聚环氧乙烷, M.W. 300,000; 聚乙二醇单甲醚, 350; 聚环氧乙烷, M.W. 100,000

Database IDs

• CAS Number: 25322-68-3; 9004-74-4; 107-21-1
• EC Number: 500-038-2; 203-473-3
• MDL Number: MFCD00081839; MFCD00147979; MFCD00002885; MFCD00147970; MFCD00147971; MFCD00084416; MFCD01779596; MFCD01779614; MFCD01779601; MFCD01779605; MFCD01779615; MFCD01779611; MFCD01779609; MFCD01779612
• Beilstein Number: 505945
• Merck Index: 147568; 143798
• PubChem SID: 24859881; 24859450; 162090554; 24857645; 24888490; 24845589; 24846577
• PubChem CID: 174
• CHEBI ID: 30742
• CHEMBL: 457299
• Chemspider ID: 13835235
• DrugBank ID: DB01867
• Gmelin ID: 943
• KEGG ID: D06424
• MeSH Name: Ethylene+glycol
• Unique Ingredient Identifier: FC72KVT52F
• Wikipedia Title: Ethylene_glycol

CALCULATED PROPERTIES

• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 14.830189
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.2086791
• LogD (pH = 7.4): -1.2086791
• Log P: -1.2086791
• Molar Refractivity: 14.5536 cm^3
• Polarizability: 5.7186804 Å^3

PROPERTIES

Physical Property

• Solubility: Miscible with water; in all proportions.; Soluble in toluene, THF, hot water, DMF, CHCl3
• Apperance: blue; Liquid; Powder
• Melting Point: -11 - -12 °C; -12.9°C; -13 °C(lit.); -13°C; -13--11 °C; 17-23°C; 35-40°C; 44-48°C; 4-8°C; 53-55°C; -55 to -40°C; 58-62°C; 58-63°C; 60-63°C; 63-66°C; 64-65°C; 65°C; -8°C
• Boiling Point: 195-198 °C; 196 - 199 °C at 1013 hPa; 196-198°C; 197.3°C
• Flash Point: >240°C(464°F); 111 °C; 111 °C (231.8 °F) (closed cup); 111.1 °C (closed cup); 119°C(246°F); 171°C(339°F); 231.8 °F; 252°C(485°F); 260°C(500°F); 265°C(509°F)
• Auto Ignition Point: 410 °C; 410 °C (770 °F); 752 °F
• Density: 1.04 g/mL at 20 °C; 1.094; 1.101; 1.113; 1.113 g/cm^3 at 20 °C; 1.113 g/mL at 25 °C(lit.); 1.1132 g/cm3; 1.120; 1.127; 1.2; 1.20; 1.21; 1.4539
• Refractive Index: 1.4310; 1.4539; 1.4590; 1.4660; 1.4680; n20/D 1.4300-1.4330; n20/D 1.431; n20/D 1.431(lit.)
• Vapor Pressure: .1 hPa at 20 °C; 0.08 mmHg ( 20 °C)
• Vapor Density: 2.1 (vs air); 2.14 (air = 1)
• Absorption Wavelength: λ: 210 nm Amax: 1.00; λ: 220 nm Amax: 0.40; λ: 250 nm Amax: 0.10; λ: 300 nm Amax: 0.01
• Viscosity: 1.61×10^-2 N*s / m^2
• Transmittance: 210 nm, ≥10%; 220 nm, ≥40%; 250 nm, ≥80%; 300 nm, ≥95%

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic
• RTECS: KW2975000; TQ3600000; TQ3630000; TQ3800000; TQ4025000; TQ4030000; TQ4041000; TQ4050000; TQ4100000; TQ4110000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 3082
• German water hazard class: 1
• Hazard Class: 9
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 22; R:22; R22 R36
• Safety Statements: 2; S26 S36 S37 S39 S45 S53
• EU Classification: M6
• EU Hazard Identification Number: 13
• Emergency Response Guidebook(ERG) Number: 171
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• Main Hazard: It is extremely harmful to pets and children. If ingested, get medical help immediately.
• NFPA704:
  

  1

  2

  1
• Explode Limits: 15.3 %
• GHS Hazard statements: H302; H303
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A; P312
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); ≥99%; ≥99.0%; ≥99.5%; ≥99.5% (GC); ≥99.8% (GC); ≥99.9% (GC); 95+%; 99%; 99.8%; 99+%
• Concentration: 80% in DMSO-d6 (99.9 atom % D)
• Grade: analytical standard; anhydrous; JIS special grade; NMR reference standard; puriss.; puriss. p.a.; purum; ReagentPlus®; SAJ first grade; SPECTRANAL™; spectrophotometric grade; technical
• Suitability: passes test for IR spectroscopy; passes test for reaction against H2SO4; passes test for suitability for UV spectroscopy
• Ignition Residue: ≤0.005% (as SO4)
• Impurities: ~5% water; <0.003% water; <0.005% water(100 mL pkg); <0.050% water; ≤0.0003% KMnO4 red. matter (as O); ≤0.001% free acid (as CH3COOH); ≤0.005% formaldehyde; ≤0.1% water; ≤0.1% water (Karl Fischer); ≤0.2% water (Karl Fischer); ≤2% water; ≤50 mg/kg formaldehyde (HCHO)
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.2 mg/kg; Fe: ≤2 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.05 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤1 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.2 mg/kg
• Antion Traces: chloride (Cl-): ≤0.2 mg/kg; chloride (Cl-): ≤2 mg/kg; sulfate (SO42-): ≤10 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• NMR tube O.D. × L: 3 mm × 8 in.; 5 mm × 8 in.
• λ: H2O reference
• Pharmacopeia Traceability: traceable to USP 1265515
• Linear Formula: HOCH2CH2OH
• Empirical Formula (Hill Notation): C2H6O2

DETAILS

MP Biomedicals - 02151089

Purity: 99% min.
1 ml = approx. 1.11 g

Sigma Aldrich - 03770

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Sigma Aldrich - 03750

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Sigma Aldrich - 85978

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Sigma Aldrich - 293237

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Packaging
1, 6×1, 2, 4×2 L in glass bottle

Sigma Aldrich - 324558

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Packaging
1, 6×1, 2 L in Sure/Seal™
100, 12×100 mL in Sure/Seal™
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 324558.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 102466

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Application
Reagent typically used in cyclocondensation reactions with aldehydes1 and ketones1,2 to form 1,3-dioxolanes.
Packaging
1, 4 L in poly bottle
20 L in steel drum
500, 6×500 mL in poly bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 34907

Legal Information
SPECTRANAL is a trademark of Sigma-Aldrich Laborchemikalien GmbH

REFERENCES

• For examples of use in acetal (1,3-dioxolane) formation, catalyzed by tosic acid with azeotropic water removal, see: Org. Synth. Coll., 6, 567 (1988); 7, 241, 271 (1990). A mild dehydrating agent, e.g. triethyl orthoformate may be used as an alternative: J. Org. Chem., 48, 2122 (1983). PPTS (Pyridinium p-toluenesulfonate, A15708) has been recommended as a catalyst for the formation and cleavage of ethylene acetals, being less likely to cause acid-catalyzed rearrangements than tosic acid itself: Synthesis, 724 (1979). For acetalization of ɑ?-enals, tartaric acid in the presence of anhydrous MgSO₄ gives good results: J. Org. Chem., 60, 2931 (1995). Review of the preparation of acetals: Synthesis, 501 (1981). See also 2,2-Dimethyl-1,3-dioxolane, L00482.
• In combination with TMS chloride, ɑ?-enones are converted to ?-chloro acetals in one step: Tetrahedron Lett., 25, 3805 (1984).
• Catalyzes the reaction of potassium aryloxides with dichloromethane at room temperature to give good yields of diaryloxymethanes: J. Chem. Res. (Synop.), 503 (1995).
• Polyethylene glycols can act as effective solvents and low-cost phase-transfer catalysts by complexing with cations (see Appendix 2). Examples of reactions promoted by these species:
• Nucleophilic displacements of benzyl halides: Synthesis, 184 (1977). Permanganate oxidations: J. Org. Chem., 43, 1532 (1978); Tetrahedron Lett., 3543 (1979). Dichromate oxidations; similar results to carcinogenic HMPA, and to crown ethers.
• Good solvent for borohydride reductions: Tetrahedron Lett., 4581 (1979). Stereoselective reduction of alkynes to cis-alkenes using NaBH₄ and a catalytic amount of PdCl₂ in dichloromethane-PEG: J. Chem. Soc., Chem. Commun., 515 (1982).
• Wacker oxidation of olefins to methyl ketones: Tetrahedron Lett., 26, 2263 (1985). Conversion of acids to peracids; see Potassium peroxydisulfate, A15310. Recyclable medium for rapid Baylis-Hillman reactions (see Ammonium bismuth citrate, A17003): Tetrahedron Lett., 45, 5865 (2004).
• A mixture of PEG200 with dichloromethane has been recommended as a solvent system for the Sandmeyer conversion of aromatic amines to halides, giving particularly good results for aryl chlorides: J. Chem. Soc., Chem. Commun., 1523 (1984).
• For use of polyethylene glycols as phase-transfer catalysts, see Polyethylene glycol 400, B21992.