Bis(2-chloroethyl) ether

Base Information

• Chemical Name: Bis(2-chloroethyl) ether
• CAS No.: 111-44-4
• Deprecated CAS: 92091-28-6
• Molecular Formula: C4H8Cl2O
• Molecular Weight: 143.013
• Hs Code.: 29091900
• European Community (EC) Number: 203-870-1
• ICSC Number: 0417
• NSC Number: 406647
• UN Number: 1916
• UNII: 6K7D1G5M5N
• DSSTox Substance ID: DTXSID9020168
• Nikkaji Number: J2.455D
• Wikipedia: Bis(chloroethyl)_ether
• Wikidata: Q2509768
• ChEMBL ID: CHEMBL1613350
• Mol file: 111-44-4.mol

Synonyms:2,2'-dichlorodiethyl ether;bis(2-chloroethyl)ether;Chlorex

Chemical Property of Bis(2-chloroethyl) ether

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.4 mm Hg ( 20 °C)
• Melting Point: -47 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• Boiling Point: 178.7 °C at 760 mmHg
• Flash Point: 55 °C
• PSA: 9.23000
• Density: 1.156 g/cm³
• LogP: 1.48060
• Storage Temp.: 2-8°C
• Solubility.: 0.01g/l
• Water Solubility.: Slightly soluble. 1.72 g/100 mL
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 141.9952203
• Heavy Atom Count: 7
• Complexity: 28.9
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Bis(2-?chloroethyl)Ether(1,1''-Oxybis[2-chloro-ethane]) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,T+,F
• Hazard Codes: T+,T,F
• Statements: 10-26/27/28-40-39/23/24/25-23/24/25-11
• Safety Statements: 27-28-36/37-45-7/9-28A-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Ethers
• Canonical SMILES: C(CCl)OCCCl
• 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 irritating to the eyes and respiratory tract. Inhalation of the vapour may cause lung oedema. Exposure far above the OEL could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.
• Physical properties: Colorless to pale yellow volatile liquid with a pungent, fruity, chlorinated-like odor. The low odor and high odor threshold concentrations were 90.0 and 2,160 mg/m3, respectively (Ruth, 1986).
• Uses: Reagent for organic synthesis; solvent. Has been used as a scouring agent for textiles; as soil fumigant. Soil fumigant; acaricide. Bis(2-chloroethyl)ether (BCEE) is used as ascouring agent for textiles; as a dewaxingagent for lubricating oils; as a soil fumigant;as a solvent for resins, oils, and lacquers; andin organic synthesis.

Technology Process of Bis(2-chloroethyl) ether

There total 29 articles about Bis(2-chloroethyl) 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: 92.0%

2-(2-Chloroethoxy)ethanol (628-89-7) → 3-oxa-1,5-dichloropentane (111-44-4)

Guidance literature:

With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1021/jo990211q

Reference yield: 91.0%

diethylene glycol bischloroformate (106-75-2) → 3-oxa-1,5-dichloropentane (111-44-4)

Guidance literature:

With hexabutylguanidinium chloride; at 120 ℃; for 4h;

DOI:10.1081/SCC-100000525

Reference yield: 86.0%

diethylene glycol (111-46-6) → 3-oxa-1,5-dichloropentane (111-44-4)

Guidance literature:

With thionyl chloride; Reflux;

upstream raw materials:

tert-butylhypochlorite

ethene

2-chloroethyl nitrite

2-chloro-ethanol

Downstream raw materials:

N-(2-vinyloxyethyl)morpholine

1,1'-(3-oxa-pentanediyl)-bis-pyridinium; dichloride

4-(4-morpholinyl)phenol

4-(4-methylphenyl)morpholine

Refernces

• 1、 Liu, Shu-Di,Zhang, Liang-Wei,Liu, Xiang. "A highly sensitive and selective fluorescent probe for Fe3+ based on 2-(2-hydroxyphenyl)benzothiazole". . p. 821 - 826. Retrieved 2013.
• 2、 -. "Preparation method of 4-dodecylphenol polyoxyethylene diether". Page/Page column 6; 7. . Retrieved 2018/09/13.