1-Chloro-2-(chloromethyl)-3,5-dioxahexane, systematically named 1,3-dichloro-2-(methoxymethoxy)propane, is an acyclic, halogenated diether characterized by a central methine carbon flanked by two chloromethyl groups (–CH₂Cl) and a methoxymethyl (–OCH₂OCH₃) substituent. The combination of an electrophilic, α-haloalkyl ether structure with two labile chloromethyl moieties provides three distinct points for nucleophilic attack, positioning it as a uniquely versatile, three-pronged alkylating agent for constructing elaborate synthetic intermediates. This reactivity pattern makes it a valuable synthetic intermediate for the preparation of more complex molecules, particularly in pharmaceutical manufacturing and advanced organic synthesis.
1-Chloro-2-(chloromethyl)-3,5-dioxahexane (CAS 70905-45-2) is a multi‑functional, chlorine‑containing organic compound valued as a synthetic building block. At room temperature, it presents as a clear, colorless to almost colorless liquid with a characteristic ether‑like odor. The molecular formula is C₅H₁₀Cl₂O₂, with a molecular weight of 173.03 g/mol. [7†L12-L13][9†L23-L24] The compound is commercially available at purities exceeding 95.0% (GC), with higher grade material available for specialized applications.
1-Chloro-2-(chloromethyl)-3,5-dioxahexane is distinguished by its unique combination of functional groups: two acid-sensitive methoxy groups protect the central carbon as an acetal, and three halogens act as leaving groups. The central –OCH₂O– linkage is an acetal, which can be selectively cleaved under mild acidic conditions to reveal a reactive α‑chloro alcohol. The primary chloromethyl groups readily participate in nucleophilic substitution reactions (SN2) with a wide range of nucleophiles, including amines, thiols, and alkoxides. In the pharmaceutical industry, 1-chloro-2-(chloromethyl)-3,5-dioxahexane is employed as a key synthetic building block and intermediate for the manufacture of active pharmaceutical ingredients (APIs) such as ganciclovir and octreotide acetate, as its multi‑halogenated structure is crucial for constructing the side chains of complex antiviral and peptide drugs. Its excellent solubility profile allows it to serve as a specialized solvent for various organic and inorganic compounds, dissolving a broad spectrum of substances for use as a reaction medium in organic synthesis. Additionally, its rigid backbone and terminal leaving groups make it a suitable monomer for synthesizing specialty polymers, where it introduces specific chlorinated side chains to modify material properties. The compound also serves as a precursor for generating unstable reactive intermediates, such as 2-(chloromethyl)-3,5-dioxa-1-hexene, which are used in further synthetic transformations.
Product Parameters
Parameter
Specification
CAS Number
70905-45-2
Molecular Formula
C₅H₁₀Cl₂O₂
Molecular Weight
173.03 g/mol
Purity
≥95.0% (GC) as standard; ≥98% and ≥99% available upon request
Appearance
Colorless to almost colorless clear liquid
Density
1.23 g/cm³ at 20 °C (reference value)
Refractive Index
n20/D 1.45 (reference value)
Boiling Point
95 °C / 30 mmHg
Flash Point
71.3 °C (closed cup)
XLogP3
1.3
Solubility
Soluble in chloroform and dichloromethane; soluble in many polar aprotic organic solvents; compatible with a wide range of organic compounds
Storage Condition
Room temperature (store in a cool, dry place, at or below 15 °C); store away from moisture
Stability
Stable under recommended storage conditions; avoid moisture and strong bases
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Each batch undergoes:
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● Appearance – colorless to light yellow to light orange clear liquid
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