5412-14-6

Usage

Physical state

Colorless liquid

Odor

Mild, ether-like

Uses

Chemical intermediate in the production of resins, plastics, and adhesives; stabilizer in the production of PVC and chlorinated rubber; solvent for various applications in chemical synthesis

Hazard class

Moderately hazardous

Safety precautions

Appropriate safety precautions should be taken when handling and storing.

Upstream product

• 27905-76-6 2-(2-chloroethoxy)-3-chloropropan-2-ol 
• 35982-12-8 3-(2-chloroethoxy)-1,2-propanediol 
• 106-89-8 epichlorohydrin 
• 107-07-3 2-chloro-ethanol 

Downstream Products

• 29908-11-0 (+/-)-2-(hydroxymethyl)-1,4-dioxane 
• 250340-69-3 1-(2-chloroethoxy)-2-tosyl-3-methoxypropane 
• 250340-68-2 1-(2-chloroethoxy)-2-tosyl-3-azidopropane 
• 56217-56-2 1,4-dioxane-2-carbaldehyde 
• 21048-16-8 2-(chloromethyl)-1,4-dioxane 

Relevant academic research and scientific papers

Synthesis and thermal properties of poly(2-chloroethyl glycidyl ether)-based side-chain liquid-crystalline polymers

A novel series of poly(2-chloroethyl glycidyl ether)-based side-chain liquid-crystalline copolymers has been synthesized in which the mesogenic units are biphenyl 4-methoxybiphenyl, 4-methoxyazobenzene, and N-benzylidene-4- methoxyaniline, respectively (corresponding polymers are referred to as PCBH, PCMB, PCMA, and PCBM). The structures of the compounds obtained are characterized by infrared (IR) and 1H nuclear magnetic resonance (NMR). The thermal properties were investigated using polarized optical microscopy, differential scanning calorimetry, and X-ray diffraction analysis. The results indicate that PCMA, PCMB, and PCBM exhibit thermotropic liquid-crystalline behavior and present nematic phases with Schlieren textures. However, PCBH does not display a mesogenic phase. The decomposition temperatures of copolymers begin at 290°C. Copyright Taylor & Francis Group, LLC.

Meso-Tetra(dioxanyl)porphyrins: Neutral, low molecular weight, and chiral porphyrins with solubility in aqueous solutions

The synthesis of the low-molecular weight, meso-Tetra(dioxan-2-yl)porphyrin with considerable solubility in aqueous solution is described. The key intermediate dioxan-2-carbaldehyde is accessible in either racemic or in stereo-pure forms from commercially available starting materials in three steps. Using 4 × 1 or 2 + 2-Type syntheses provide the porphyrin in modest yields. While the racemic aldehyde created an intractable mixture of diastereomers, the enantiopure aldehyde created a single enantiomer of the target porphyrin. The porphyrin was spectroscopically characterized. As its free base or zinc complex, it showed excellent solubility properties in organic and aqueous solvents, though free water-solubility was not achieved. The work expands on the availability of chiral porphyrins and neutral porphyrins with considerable solubility in aqueous solution.

Self-neutralizing oligonucleotides with enhanced cellular uptake

There is tremendous potential for oligonucleotide (ON) therapeutics, but low cellular penetration due to their polyanionic nature is a major obstacle. We addressed this problem by developing a new approach for ON charge neutralization in which multiple branched charge-neutralizing sleeves (BCNSs) are attached to the internucleoside phosphates of ON by phosphotriester bonds. The BCNSs are terminated with positively charged amino groups, and are optimized to form ion pairs with the neighboring phosphate groups. The new modified ONs can be prepared by standard automated phosphoramidite chemistry in good yield and purity. They possess good solubility and hybridization properties, are not involved in non-standard intramolecular aggregation, have low cytotoxicity, adequate chemical stability, improved serum stability, and above all, display significantly enhanced cellular uptake. Thus, the new ON derivatives exhibit properties that make them promising candidates for the development of novel therapeutics or research tools for modulation of the expression of target genes.

Synthesis of Substituted Dithia-9-crown-3-ethers

Diethylene glycol monochlorides were prepared from epoxides by action of the chloroethanol. Their conversion into substituted dithia-9-crown-3-ethers has been realized by treatment with p-toluenesulfonyl chloride, followed by the action of 1,2-dimercaptoe

Synthesis of N-3-chloroalkoxy-2-nitroxypropyl-N-alkylnitramines and their subsequent azidation

Nitration of N-3-chloroalkoxy-2-hydroxypropyl-N-alkylsulfamates gave the corresponding N-3-chloroalkoxy-2-nitroxypropyl-N-alkylnitramines. Azidation of the latter resulted in N-azido-3-azidoalkoxypropyl-N-alkylnitramines.

SYNTHESIS OF OLIGO(ETHYLENE GLYCOL) DERIVATIVES

Oligo(ethylene glycol) derivatives were obtained by the reaction of oligo(ethylene glycol) chlorohydrins with epichlorohydrin using H2SO4 catalyst and sunsequent treatment with NaOH in ether solution.The structure of the obtained products was characterized by 13C NMR and IR spectra.

RADICAL THIYLATION OF SOME UNSATURATED 1,3-DIOXOLANES

The radical addition of thiols to unsaturated 1,3-dioxolanes leads to the formation of the products from addition against the Markovnikov rule.Identical thioethers are produced as a result of nucleophilic substitution of the corresponding chloromethyl derivatives of 1,3-dioxolanes by sodium butanethiolate or phenylmethanethiolate.