Benzyl chloromethyl ether

Base Information

• Chemical Name: Benzyl chloromethyl ether
• CAS No.: 3587-60-8
• Molecular Formula: C8H9ClO
• Molecular Weight: 156.612
• Hs Code.: 29093090
• European Community (EC) Number: 252-527-2,628-927-1
• DSSTox Substance ID: DTXSID10956786
• Nikkaji Number: J32.108G
• Wikidata: Q72453166
• Mol file: 3587-60-8.mol

Synonyms:Benzyl chloromethyl ether;3587-60-8;(Chloromethoxymethyl)benzene;[(chloromethoxy)methyl]benzene;chloromethoxymethylbenzene;Chloromethoxymethyl-benzene;Benzyloxymethyl chloride;((Chloromethoxy)methyl)benzene;35364-99-9;Benzene, [(chloromethoxy)methyl]-;chloromethyl benzyl ether;MFCD00000886;benzyl (chloromethyl) ether;EINECS 252-527-2;Benzyl Chloromethyl Ether (90per cent);{(chloromethoxy)methyl}benzene;BOMCl;benzyloxymethylchloride;chloromethylbenzylether;BOM-Cl;choromethylbenzyl ether;chloromethyl benzylether;chloromethylbenzyl ether;benzyl chlormethyl ether;SCHEMBL19520;DTXSID10956786;BCP31684;AKOS006221189;1-[(CHLOROMETHOXY)METHYL]BENZENE;AM100720;SY003069;B1207;CS-0015122;FT-0600021;EN300-91755;Benzyl chloromethyl ether, technical, ~60% (NMR);J-650079;F8881-5092

Chemical Property of Benzyl chloromethyl ether

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: -15oC
• Refractive Index: n20/D 1.527
• Boiling Point: 207.1 °C at 760 mmHg
• Flash Point: 91.1 °C
• PSA: 9.23000
• Density: 1.118 g/cm³
• LogP: 2.39950
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water [2.7 g/L (25 C)]
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 156.0341926
• Heavy Atom Count: 10
• Complexity: 79.3

Purity/Quality:

99%· ^*data from raw suppliers

BenzylChloromethylEther(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xn
• Hazard Codes: T,Xn,N
• Statements: 45-22-23-37/38-41-48/22-36/37/38-20/21/22-50-43
• Safety Statements: 53-26-39-45-36/37/39-36-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCCl
• Uses: Benzyl chloromethyl ether is employed in the introduction of benzoyloxy- and hydroxymethyl groups.

Technology Process of Benzyl chloromethyl ether

There total 14 articles about Benzyl chloromethyl ether 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: 95.8%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + benzyl alcohol (100-51-6,185532-71-2) → Benzyloxymethyl chloride (3587-60-8)

Guidance literature:

With hydrogenchloride; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1007/BF01169253

Reference yield: 87.0%

1,3,5-Trioxan (110-88-3) + benzyl alcohol (100-51-6,185532-71-2) → Benzyloxymethyl chloride (3587-60-8)

Guidance literature:

With hydrogenchloride; at 0 - 20 ℃;

DOI:10.1021/ja991175f

Reference yield: 83.0%

Benzyl-methylthiomethylether (52132-66-8) → Benzyloxymethyl chloride (3587-60-8)

Guidance literature:

With sulfuryl dichloride; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1055/s-1983-30506

upstream raw materials:

benzyl methyl ether

formaldehyd

benzyl alcohol

1,3,5-Trioxan

Downstream raw materials:

(phenylmethoxy)methylphosphonic acid diethyl ester

benzyl methoxymethyl ether

formaldehyde-(benzyl-phenyl-acetal)

(α-chloro-benzyl)-chloromethyl ether

Refernces

Development of a novel nucleoside analogue with S-type sugar conformation: 2′-deoxy-trans-3′,4′-bridged nucleic acids

10.1016/j.tet.2007.06.040

The research focuses on the development of a novel nucleoside analogue, specifically 20-deoxy-trans-3',4'-bridged nucleic acids (trans-3',4'-BNA), which feature an S-type sugar conformation. The purpose of this study was to synthesize two new trans-3',4'-BNA monomers from thymidine, with the aim of creating stable duplexes or triplesxes with single- or double-stranded nucleic acids. The research concluded that these novel nucleosides, with their typical S-type sugar conformation, meet the conformational requirements of the B-type DNA duplex, making them strong candidates for ideal DNA structure mimics. The chemicals used in the synthesis process included thymidine, osmium tetroxide, benzyl chloromethyl ether (BOMCl), dibutyltindimethoxide, chloromethyl methyl ether (MOMCl), and various other reagents employed in the protection and deprotection steps, oxidation, reduction, and construction of the trans-fused ring structures. The synthesized nucleosides were confirmed by X-ray crystallography, which indicated their furanose rings had a typical S-type conformation, similar to that observed in the B-type helical structure of the DNA duplex.

Letter: A simple total synthesis of prostaglandins from 4-cumyloxy-2-cyclopentenone.

10.1021/ja00854a061

The research focuses on a simple total synthesis of prostaglandins, specifically PGF2α, from 4-cumyloxy-2-cyclopentenone, utilizing a synthetic route that involves the key intermediate 2-methylene cyclopentanone. The purpose of this study was to demonstrate the effectiveness of monomeric formaldehyde in trapping kinetic enolates, which are known to be challenging to alkylate. The researchers successfully completed the synthesis in eight steps, yielding (+)-PGF2α and its 15-epimer in an overall 17% yield. The chemicals used in the process include 4-cumyloxy-2-cyclopentenone, (+)-1-iodo-1-octen-3-ol, benzyl chloromethyl ether, tert-butyllithium, tributylphosphine-copper iodide, and formaldehyde, among others. The study concluded that formaldehyde is a valuable trapping agent for certain enolates, and the synthesis described is a relatively simple and convergent method for producing prostaglandins.