Bis(2-chloroethoxy)methane
[CAS# 111-91-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: Bis(2-chloroethoxy)methane
• Molecular Formula: C₅H₁₀Cl₂O₂
• Molecular Weight: 173.04
• CAS Registry Number: 111-91-1
• EC Number: 203-920-2
• SMILES: C(CCl)OCOCCCl

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.437, Calc.^*
• Boiling Point: 205.9±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 76.9±21.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Hazard Statements: H301-H312-H330-H370-H373
• Precautionary Statements: P260-P264-P270-P271-P280-P284-P301+P316-P302+P352-P304+P340-P308+P316-P316-P317-P319-P320-P321-P330-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Specific target organ toxicity - single exposure	STOT SE	1	H370
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	2	H330

Discovory and Applicatios

Bis(2-chloroethoxy)methane is an organic compound with the molecular formula C₅H₁₀Cl₂O₂. It belongs to the class of dialkyl ethers, where a central methylene group is bonded to two 2-chloroethoxy units. The compound appears as a colorless to light yellow liquid under standard conditions and is characterized by its ether linkage and reactive chloroethyl substituents. Its structure features functional groups that render it both a useful synthetic intermediate and a potential alkylating agent under controlled conditions.

The synthesis of bis(2-chloroethoxy)methane has been documented in the context of etherification reactions. It is typically prepared by reacting formaldehyde or paraformaldehyde with 2-chloroethanol under acidic or catalytic conditions, facilitating the formation of the methylene bridge linking two ethereal arms. This method has been described in patents and literature related to chemical process development, particularly where alkylating agents or bifunctional reagents are required.

Bis(2-chloroethoxy)methane has found specific application in the field of organic synthesis, especially as a protected form of formaldehyde or as a crosslinking reagent. The chloroethoxy groups can undergo substitution reactions with nucleophiles such as amines or thiols, enabling its use in stepwise synthesis of more complex molecules. It can act as a linker in the preparation of polymer precursors or functional materials requiring difunctional alkylating moieties. In particular, the compound has been used in the modification of cellulose and other polysaccharides, where its bifunctionality contributes to crosslinking and derivatization.

In the pharmaceutical and agrochemical sectors, bis(2-chloroethoxy)methane has been employed in the synthesis of intermediates for active compounds. Its electrophilic character and bifunctional nature allow it to be used in reactions where two sites of functionalization are required. The compound's use has been reported in processes involving the generation of heterocyclic rings or the attachment of ether-based side chains to core molecules.

Industrial applications include its role as a building block in the production of specialty chemicals, particularly where halogenated ether structures are desired. In polymer chemistry, bis(2-chloroethoxy)methane has been evaluated as a component in epoxy resins or other systems requiring latent curing agents. Its chemical properties permit its incorporation into polymer chains or networks via substitution or elimination reactions.

The handling and storage of bis(2-chloroethoxy)methane require standard precautions used for reactive halogenated ethers. It is classified as a hazardous material due to its potential to cause irritation and its reactivity with strong bases and nucleophiles. Proper ventilation, personal protective equipment, and adherence to material safety data guidelines are necessary to ensure safe usage. It should be stored away from moisture and incompatible chemicals, such as strong acids or oxidizing agents.

Toxicological data on bis(2-chloroethoxy)methane are limited but indicate that exposure may cause irritation to the skin, eyes, and respiratory tract. The compound should be treated as potentially harmful, and laboratory or industrial users are advised to minimize exposure and use appropriate containment and disposal methods. Environmental precautions are also advised, as halogenated organics can pose risks to aquatic organisms and soil systems if improperly released.

Overall, bis(2-chloroethoxy)methane is a well-documented chemical intermediate whose utility in organic synthesis, polymer science, and materials development is supported by verified procedures and applications in the chemical literature. Its bifunctional structure makes it particularly suitable for use in crosslinking, alkylation, and etherification processes across various chemical sectors.

References

2017. Methodology for non-target screening of sewage sludge using comprehensive two-dimensional gas chromatography coupled to high-resolution mass spectrometry. Analytical and Bioanalytical Chemistry, 409(20), 4867�4883.
DOI: 10.1007/s00216-017-0429-0

2011. Toxicokinetics of bis(2-chloroethoxy)methane following intravenous administration and dermal application in male and female F344/N rats and B6C3F1 mice. Toxicology Letters, 205(2), 215�226.
DOI: 10.1016/j.toxlet.2011.06.012

2009. Bis(2-chloroethoxy)methane degradation by TiO2 photocatalysis: Parameter and reaction pathway investigations. Journal of Hazardous Materials, 171(1-3), 1026�1032.
DOI: 10.1016/j.jhazmat.2009.07.093