Bis(chloromethyl) ether

Base Information

• Chemical Name: Bis(chloromethyl) ether
• CAS No.: 542-88-1
• Molecular Formula: C2H4 Cl2 O
• Molecular Weight: 114.959
• Hs Code.: 29309070
• European Community (EC) Number: 208-832-8
• ICSC Number: 0237
• UN Number: 2249
• UNII: 77382IHE37
• DSSTox Substance ID: DTXSID8020173
• Nikkaji Number: J3.293J
• Wikipedia: Bis(chloromethyl)_ether
• Wikidata: Q2283186
• NCI Thesaurus Code: C44343
• ChEMBL ID: CHEMBL3185875
• Mol file: 542-88-1.mol

Synonyms:Bis(Chloromethyl) Ether;Bis(Chloromethyl)Ether;Chloromethyl Ether;Dichloromethyl Ether;Ether, Chloromethyl;Ether, Dichloromethyl

Chemical Property of Bis(chloromethyl) ether

Chemical Property:

• Vapor Pressure: 1.1mmHg at 25°C
• Melting Point: 171℃
• Refractive Index: 1.44433
• Boiling Point: 106°Cat760mmHg
• Flash Point: 74.9°C
• PSA: 9.23000
• Density: 1.267g/cm³
• LogP: 1.39560
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in alcohol, ether (Weast, 1986), benzene (Hawley, 1981), and other solvents including acetone and chloroform.
• Water Solubility.: decomposes. 2.2 g/100 mL
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 113.9639201
• Heavy Atom Count: 5
• Complexity: 15.1
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s): A carcinogen. Toxic by ingestion. TLV: 0.001 ppm.
• Hazard Codes: T+
• Statements: 10-36/37/38-40-26-24-22-45
• Safety Statements: 26-36/37/39-45-53

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Ethers
• Canonical SMILES: C(OCCl)Cl
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema. The effects may be delayed. Exposure at high concentrations could cause death.
• Effects of Long Term Exposure: This substance is carcinogenic to humans.
• Uses: Bis(chloromethyl)ether (BCME) is used asan intermediate in anion-exchange quater nary resins. Its use as a chloromethylationreagent in industry is being discontinuedbecause of its high carcinogenic properties.Exposure risks associated with this com pound can arise during the use or productionof chloromethyl methyl ether when the lat ter compound comes in contact with tracesof water in the presence of hydrogen orhydroxyl ions. It may occur in trace amountsin chloromethyl methyl ether. Bis(chloromethyl) ether is a clear liquid with a strong unpleasant odour. It does not occur naturally. It dissolves easily in water but degrades rapidly and readily evaporates into air. During earlier years, bis(chloromethyl) was used to make several types of polymers, resins, and textiles, but its use is now highly restricted. Only small quantities of bis(chloromethyl) ether are produced in the United States. The small quantities that are produced are only used in enclosed systems to make other chemicals. Reagent used in the formation of ether linked dimers

Technology Process of Bis(chloromethyl) ether

There total 33 articles about Bis(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: 90.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) → bis(2-chloromethyl)ether (542-88-1)

Guidance literature:

With hydrogenchloride; chlorosulfonic acid; at 0 - 20 ℃;

DOI:10.1016/j.cbi.2019.05.048

Reference yield: 85.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + acetyl chloride (75-36-5) → bis(2-chloromethyl)ether (542-88-1) + Chloromethyl acetate (625-56-9)

Guidance literature:

With zinc(II) chloride; for 3h; Yield given; Heating;

Reference yield: 71.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) → bis {[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]methyl} ether (194039-83-3) + bis(2-chloromethyl)ether (542-88-1) + C5H5ClF6O2 + 1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether (26103-07-1) + formaldehyde di[2,2,2-trifluoro-1-(trifluoromethyl)ethyl] acetal

Guidance literature:

With thionyl chloride; sulfuric acid; at 15 - 35 ℃; for 6h; Product distribution / selectivity;

upstream raw materials:

methanol

formaldehyd

Dimethyl ether

hexamethylenetetramine

Downstream raw materials:

phosgene

bis(4-bromophenyl)methane

p-bromobenzyl chloride

nitro-6 benzo (4H) dioxinne-1,3

Refernces

• 1、 Cavalcante, Samir F. de A.,Kitagawa, Daniel A.S.,Rodrigues, Rafael B.,Bernardo, Leandro B.,da Silva, Thiago N.,dos Santos, Wellington V.,Correa, Ana Beatriz de A.,de Almeida, Joyce S.F.D.,Fran?a, Tanos C.C.,Ku?a, Kamil,Simas, Alessandro B.C.. "Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate". . . Retrieved 2019/06/24.
• 2、 Bortoluzzi, Marco,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano. "Reactivity of [WCl6] with Ethers: A Joint Computational, Spectroscopic and Crystallographic Study". . p. 3169 - 3177. Retrieved 2016/07/14.