13879-32-8

Usage

Uses

Used in Chemical Synthesis:
1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene is used as a precursor in the synthesis of a variety of chemical compounds, including surfactants, detergents, and pharmaceuticals, due to its ability to facilitate the formation of complex molecular structures.
Used in Epoxy Resin Production:
In the manufacturing industry, 1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene is utilized as a crosslinking agent for the production of epoxy resins, enhancing their mechanical properties and durability.
Used in Polyurethane Foam Manufacturing:
1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene also serves as a crosslinking agent in the creation of polyurethane foams, contributing to their stability and performance characteristics.
Used in Plastic Material Stabilization:
1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene is used as a stabilizer in plastic materials to improve their resistance to degradation and extend their service life.
Used in Personal Care Products:
As an additive in personal care products, 1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene helps to enhance the texture, consistency, and performance of formulations, ensuring a better consumer experience.

Synthetic route

2-Phenoxyethanol (122-99-6) + 1,2-dibromomethane (74-95-3) → bis-[(2-phenoxyethyl)oxy]methane (13879-32-8)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In benzene for 5h; Reflux;	59%

2-Phenoxyethanol (122-99-6) + dimethyl sulfoxide (67-68-5) → bis-[(2-phenoxyethyl)oxy]methane (13879-32-8) + 2-chloroethoxybenzene (622-86-6)

Conditions	Yield
With 2,4-Dichloro-6-methoxy-1,3,5-triazine In toluene at 80℃; for 4h;	A 52% B 35%

bis(2-chloroethoxy)methane (111-91-1) + sodium phenoxide (139-02-6) → bis-[(2-phenoxyethyl)oxy]methane (13879-32-8)

Conditions	Yield
at 180℃;

bis-[(2-phenoxyethyl)oxy]methane (13879-32-8) + 6-(3,5-dimethylbenzyl)-5-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (171048-65-0) → 6-(3,5-dimethylbenzyl)-5-ethyl-1-[(2-phenoxyethyl)oxymethyl]uracil

Conditions	Yield
Stage #1: 6-(3,5-dimethylbenzyl)-5-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 0.166667h; Inert atmosphere; Stage #2: bis-[(2-phenoxyethyl)oxy]methane With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -50 - 20℃; Inert atmosphere;	63%

bis-[(2-phenoxyethyl)oxy]methane (13879-32-8) + 6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione (176519-55-4) → 6-benzyl-5-isopropyl-1-[(2-phenoxyethyl)oxymethyl]uracil

Conditions	Yield
Stage #1: 6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 0.166667h; Inert atmosphere; Stage #2: bis-[(2-phenoxyethyl)oxy]methane With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -50 - 20℃; Inert atmosphere;	59%

bis-[(2-phenoxyethyl)oxy]methane (13879-32-8) + 6-benzyl-5-ethylpyrimidine-2,4(1H,3H)-dione (171048-63-8) → 6-benzyl-5-ethyl-1-[(2-phenoxyethyl)oxymethyl]uracil

Conditions	Yield
Stage #1: 6-benzyl-5-ethylpyrimidine-2,4(1H,3H)-dione With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 0.166667h; Inert atmosphere; Stage #2: bis-[(2-phenoxyethyl)oxy]methane With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -50 - 20℃; Inert atmosphere;	48%

bis-[(2-phenoxyethyl)oxy]methane (13879-32-8) + 6-(3,5-dimethylbenzyl)-5-isopropyl-2,4-pyrimidinedione (171048-69-4) → 6-(3,5-dimethylbenzyl)-5-isopropyl-1-[(2-phenoxyethyl)oxymethyl]uracil

Conditions	Yield
Stage #1: 6-(3,5-dimethylbenzyl)-5-isopropyl-2,4-pyrimidinedione With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 0.166667h; Inert atmosphere; Stage #2: bis-[(2-phenoxyethyl)oxy]methane With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -50 - 20℃; Inert atmosphere;

bis-[(2-phenoxyethyl)oxy]methane (13879-32-8) + 5-ethyl-6-(3,5-dimethoxybenzyl)uracil → 6-(3,5-dimethoxybenzyl)-5-ethyl-1-[(2-phenoxyethyl)oxymethyl]uracil

Conditions	Yield
Stage #1: 5-ethyl-6-(3,5-dimethoxybenzyl)uracil With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 0.166667h; Inert atmosphere; Stage #2: bis-[(2-phenoxyethyl)oxy]methane With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -50 - 20℃; Inert atmosphere;

bis-[(2-phenoxyethyl)oxy]methane (13879-32-8) + 5-isopropyl-6-(3,5-dimethoxybenzyl)uracil → 6-(3,5-dimethoxybenzyl)-5-isopropyl-1-[(2-phenoxyethyl)oxymethyl]uracil

Conditions	Yield
Stage #1: 5-isopropyl-6-(3,5-dimethoxybenzyl)uracil With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 0.166667h; Inert atmosphere; Stage #2: bis-[(2-phenoxyethyl)oxy]methane With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -50 - 20℃; Inert atmosphere;

Upstream product

• 122-99-6 2-Phenoxyethanol 
• 67-68-5 dimethyl sulfoxide 
• 74-95-3 1,1-dibromomethane 
• 111-91-1 bis(2-chloroethoxy)methane 
• 139-02-6 sodium phenoxide 

Relevant academic research and scientific papers

Synthesis and Antiviral Evaluation of 1-[(2-Phenoxyethyl)oxymethyl] and 6-(3,5-Dimethoxybenzyl) Analogues of HIV Drugs Emivirine and TNK-651

Novel emivirine analogues 6a, b were synthesized by reacting chloromethyl ethyl ether with 5-ethyl/isopropyl-6-(3,5-dimethoxybenzyl)uracils 5e, f. On the other hand, A series of new TNK-651 analogues 10a-f substituted at N-1 with phenoxyethoxymethyl moiety was prepared on treatment of the corresponding uracils 5a-f with bis(phenoxyethoxy)methane (9). The newly synthesized non-nucleosides were tested for antiviral activity against wild type HIV-1 IIIB as well as the resistant strains N119 (Y181C), A17 (K103N+Y181C), and the triple mutant EFVR (K103R+V179D+P225H) in MT-4 cells. Most of the tested compounds showed good activities. Among them 6-(3,5-dimethylbenzyl)-5-ethyl-1-[(2-phenoxyethyl)oxymethyl]uracil (10c) and 6-(3,5-dimethylbenzyl)-5-isopropyl-1-[(2-phenoxyethyl)oxymethyl]uracil (10d) that showed inhibitory potency higher than emivirine against both wild type HIV-1 and the tested mutant strains, as well as higher activity than efavirenz against EFVR.

A new and more efficient synthesis of methylene acetals

A new and efficient synthesis of benzyl chlorides and methylene acetals by use of 2,4-dichloro-6-methoxy[l,3,5]triazine (MeOTCT) and dimethyl sulfoxide has been developed. Chlorides are the major products for benzyl alcohols, while methylene acetals are the major products for secondary alcohols. This procedure provides the highest yields so far for methylene acetals of steroids. A plausible mechanism is proposed on the basis of the experiments. Georg Thieme Verlag Stuttgart.