2-Methoxyethoxymethyl chloride

Base Information

• Chemical Name: 2-Methoxyethoxymethyl chloride
• CAS No.: 3970-21-6
• Deprecated CAS: 847026-63-5,847026-64-6,847026-64-6
• Molecular Formula: C4H9ClO2
• Molecular Weight: 124.567
• Hs Code.: 29091990
• European Community (EC) Number: 223-589-8
• UNII: A5RRM67QUG
• DSSTox Substance ID: DTXSID8063250
• Nikkaji Number: J149.671I
• Wikipedia: 2-Methoxyethoxymethyl_chloride
• Wikidata: Q63392107
• Mol file: 3970-21-6.mol

Synonyms:1-(Chloromethoxy)-2-methoxyethane;2,5-Dioxahexyl chloride;2-(Chloromethoxy)ethoxymethane;Chloromethyl 2-methoxyethyl ether;Methoxyethoxymethyl chloride;b-Methoxyethoxymethyl chloride;MEM chloride;

Chemical Property of 2-Methoxyethoxymethyl chloride

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Vapor Pressure: 4.68E-10mmHg at 25°C
• Melting Point: 200-202 °C
• Refractive Index: n20/D 1.427(lit.)
• Boiling Point: 161.3 °C at 760 mmHg
• Flash Point: 32.4 °C
• PSA: 18.46000
• Density: 1.049 g/cm³
• LogP: 0.84570
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform, Methanol
• Water Solubility.: It hydrolyzes with water.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 124.0291072
• Heavy Atom Count: 7
• Complexity: 32.9

Purity/Quality:

99% ^*data from raw suppliers

2-Methoxyethoxymethyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-10-36/37/38-20/21/22-46-40-23/24/25-20/22
• Safety Statements: 53-26-36/37/39-45-16-23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCOCCl
• Uses: 2-Methoxyethoxymethyl Chloride is an OH-protecting reagent. 2-Methoxyethoxymethyl Chloride is used in the modification of antibiotics. 2-Methoxyethoxymethyl chloride, is used as selectively cleaved under aprotic conditions in the presence of a wide range of OH-protected reagents. It is used as an OH-protecting reagent. An examples of the target molecule MEM Chloride is the side chain of roxithromycin. It is also used in the protection of the OH groups in serine and threonine during peptide synthesis. Some of the other applications include have the ability to coordinate to metals, which is thought to accelerate the cleavage by Lewis acids. The chelating ability of the MEM ether also makes it useful as a stereodirecting group in organometallic reactions, first noted in the stereo controlled addition of ?-methoxyvinyllithium to a carbonyl in the synthesis of taxusin. OH-protecting reagent. MEM ethers are stable to a variety of reaction conditions and are selectively cleaved under aprotic conditions in the presence of a wide rangeof OH-protected moieties.

Technology Process of 2-Methoxyethoxymethyl chloride

There total 5 articles about 2-Methoxyethoxymethyl chloride 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: 87.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-methoxy-ethanol (109-86-4,95507-80-5) → 2-Methoxyethoxymethyl chloride (3970-21-6)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/0040-4020(80)80089-5

Reference yield: 70.0%

thionyl chloride (7719-09-7) + bis(dimethoxyethyoxyl)methane (4431-83-8) → 2-Methoxyethoxymethyl chloride (3970-21-6)

Guidance literature:

With sulfur dioxide;

Reference yield:

1,3,5-Trioxan (110-88-3) + 2-methoxy-ethanol (109-86-4,95507-80-5) → 2-Methoxyethoxymethyl chloride (3970-21-6)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/S0040-4039(00)92890-9

upstream raw materials:

1,3,5-Trioxan

2-methoxy-ethanol

formaldehyd

thionyl chloride

Downstream raw materials:

<(2-methoxyethoxy)methyl>triethylammonium chloride

3,4-diphenyl-2-(1,3,6-trioxaheptyl)-2-cyclobutenone

3-(β-methoxyethoxymethyloxy)-4-methoxybenzaldehyde

2-(1-Methyl-1H-imidazol-2-yl)-1-(4-nitro-phenyl)-ethanol

Refernces

Highly stereocontrolled synthesis of gem-difluoromethylenated azasugars: D- and L-1,4,6-trideoxy-4,4-difluoronojirimycin

10.1021/ol050558h

The research focuses on the synthesis of D- and L-1,4,6-trideoxy-4,4-difluoronojirimycin, a novel series of gem-difluoromethylenated azasugars. The synthesis involves 10 steps starting from trifluoroethanol, with key chemicals including trifluoroethanol, LDA (lithium diisopropylamide), formaldehyde, MEMCl (2-methoxyethoxymethyl chloride), mesyl chloride, NaN3 (sodium azide), Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium(0)), PPh3 (triphenylphosphine), CbzCl (benzyl chloroformate), SOCl2 (thionyl chloride), and (DHQ)2PHAL or (DHQD)2PHAL (chiral ligands for Sharpless asymmetric dihydroxylation). The synthesis process includes multiple steps such as protection, elimination, vinyl anion formation, sigmatropic rearrangement, allylic substitution, imine formation, Sharpless asymmetric dihydroxylation, and hydrogenation. The final products are obtained with good diastereoselectivity and enantiomeric excess, demonstrating the effectiveness of the synthetic route.

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