2-Methoxyethanol

Base Information

• Chemical Name: 2-Methoxyethanol
• CAS No.: 109-86-4
• Molecular Formula: C3H8O2
• Molecular Weight: 76.0953
• Hs Code.: 29332990
• European Community (EC) Number: 203-713-7,251-174-1
• ICSC Number: 0061
• NSC Number: 1258
• UN Number: 1188
• UNII: EK1L6XWI56
• DSSTox Substance ID: DTXSID5024182
• Nikkaji Number: J2.442B
• Wikipedia: 2-Methoxyethanol
• Wikidata: Q903362
• RXCUI: 1314193
• Metabolomics Workbench ID: 52445
• ChEMBL ID: CHEMBL444144
• Mol file: 109-86-4.mol

Synonyms:1-Hydroxy-2-methoxyethane;2-Methoxy-1-ethanol;2-Methoxyethyl alcohol;2-Methyloxyethanol;3-Oxa-1-butanol;Amsco-Solv EE;Dowanol EM;Ektasolve EM;Ethylene glycol methyl ether;Ethylene glycol monomethyl ether;Methyl Cellosolve;Methyl glycol;Methyl oxitol;Monoethylene glycol methyl ether;Monomethylglycol;NSC 1258;Poly-Solv EM;b-Methoxyethanol;

Chemical Property of 2-Methoxyethanol

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 6.17 mm Hg ( 20 °C)
• Melting Point: -85 °C
• Refractive Index: n20/D 1.402(lit.)
• Boiling Point: 124.4 °C at 760 mmHg
• PKA: 15.7(at 25℃)
• Flash Point: 46.1 °C
• PSA: 29.46000
• Density: 0.958 g/cm³
• LogP: -0.37490
• Storage Temp.: 5°C
• Solubility.: Very soluble in acetone, dimethylsulfoxide, and 95% ethanol (quoted, Keith and Walters, 1992). Miscible with N,N-dimethylformamide, ether, and glycerol (Windholz et al., 1983).
• Water Solubility.: SOLUBLE
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 76.052429494
• Heavy Atom Count: 5
• Complexity: 14.4
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Methyl glycol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,F,C
• Hazard Codes: T,F,C
• Statements: 60-61-10-20/21/22-39/23/24/25-23/24/25-11-35-34-36/38
• Safety Statements: 53-45-36/37-16-26-23-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Glycol Ethers (E Series)
• Canonical SMILES: COCCO
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and respiratory tract. The substance may cause effects on the central nervous system, blood, bone marrow, kidneys and liver. Exposure at high levels could cause unconsciousness. Medical observation is indicated.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the blood and bone marrow. This may result in anaemia and lesions of blood cells. May cause toxicity to human reproduction or development.
• Description: Methoxyethanol is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. Cellosolve was a solvent product containing glycol ethers and registered in the 1920s by Carbide and Carbon Chemicals Corp. Glycol ethers are derived from either ethylene oxide (E-series) or propylene oxide (p-series) combined with an alcohol. Methoxyethanol is an E-series glycol ether derived from methanol and ethylene oxide. Other commonly used glycol ethers include ethoxyethanol, butoxyethanol, and methoxypropanol. Use of methoxyethanol has declined in recent years due to risk management procedures and replacement by other substances.
• Physical properties: Colorless liquid with a mild, ether-like odor. Experimentally determined detection and recognition odor threshold concentrations were <300 μg/m3 (<96 ppbv) and 700 μg/m3 (220 ppbv), respectively (Hellman and Small, 1974).
• Uses: 2-Methoxyethanol is considered a non-comedogenic raw material. It is used as a solvent in nail products and as a stabilizer in cosmetic emulsions. It is able to penetrate the skin and may cause skin irritation. The primary use of 2-methoxyethanol is as asolvent for cellulose acetate, certain syntheticand natural resins, and dyes. Other applications are in jet fuel deicing, sealing moisture-proof cellophane, dyeing leather, and use innail polishes, varnishes, and enamels. Solvent for low-viscosity cellulose acetate, natural resins, some synthetic resins and some alcohol-soluble dyes; in dyeing leather, sealing moistureproof cellophane; in nail polishes, quick-drying varnishes and enamels, wood stains. In modified Karl Fischer reagent: Peters, Jungnickel, Anal. Chem. 27, 450 (1955).

Technology Process of 2-Methoxyethanol

There total 133 articles about 2-Methoxyethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-benzyloxycarbonylaminobutyric acid 2-methoxyethyl ester (1245613-17-5) → 2-methoxy-ethanol (109-86-4,95507-80-5) + 4-(benzyloxycarbonylamino)butyric acid (5105-78-2)

Guidance literature:

With methanol; Bacillus subtilis esterase; In hexane; at 37 ℃; for 0.5h; pH=7.4; Reagent/catalyst; Time; Kinetics; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/adsc.200900325

Reference yield: 72.0%

[1,3]-dioxolan-2-one (96-49-1) + methanol (67-56-1) → 2-methoxy-ethanol (109-86-4,95507-80-5) + ethylene glycol (107-21-1) + carbonic acid dimethyl ester (616-38-6) + diethylene glycol (111-46-6)

Guidance literature:

at 76.7 - 79.6 ℃; under 757.576 Torr; Product distribution / selectivity; Industry scale;

Reference yield: 40.2%

oxirane (75-21-8,99932-75-9) + methanol (67-56-1) + carbon monoxide (201230-82-2) → 1,1-dimethoxyethane (534-15-6) + 2-methoxy-ethanol (109-86-4,95507-80-5) + methyl ester (3-hydroxy) propionic acid (6149-41-3) + methyl β-(β-hydroxypropionyloxy)propionate (27313-49-1) + acetaldehyde (75-07-0,9002-91-9)

Guidance literature:

1H-imidazole; dicobalt octacarbonyl; at 60 - 80 ℃; for 3 - 4h; under 25502.6 - 60006 Torr; Heating / reflux;

upstream raw materials:

oxirane

methanol

naphthalene-2-sulfonate

trifluoroborane diethyl ether

Downstream raw materials:

methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside

bis(2-methoxyethyl)carbonate

(4-hydroxy-phenyl)-carbamic acid-(2-methoxy-ethyl ester)

adipic acid bis-(2-methoxy-ethyl ester)

Refernces

• 1、 Moriya, Makoto,Kato, Daiki,Sakamoto, Wataru,Yogo, Toshinobu. "Plastic crystalline lithium salt with solid-state ionic conductivity and high lithium transport number". . p. 6311 - 6313. Retrieved 2011.
• 2、 Herati-Sedaghat, M. R.,McManus, Samuel P.,Harris, J. Milton. "SN2 Displacement on 2-(Alkylthio)ethyl Derivatives". . p. 2539 - 2543. Retrieved 1988.
• 3、 Moloy, Kenneth G.. "A Simple, effective boron-halide ethoxylation catalyst". . p. 821 - 826. Retrieved 2010.
• 4、 Yu, Weiqiang,Lu, Fang,Huang, Qianqian,Lu, Rui,Chen, Shuai,Xu, Jie. "Selective synthesis of dimethoxyethane via directly catalytic etherification of crude ethylene glycol". . p. 3327 - 3333. Retrieved 2017.
• 5、 Das, Uttam Kumar,Kumar, Amit,Ben-David, Yehoshoa,Iron, Mark A.,Milstein, David. "Manganese catalyzed hydrogenation of carbamates and urea derivatives". supporting information. p. 12962 - 12966. Retrieved 2019/08/26.
• 6、 Vlasov,Kholodkova,Ponomarev. "Influence of Boiling on the Radiolysis of Diglyme". . p. 312 - 318. Retrieved 2018/08/01.