13879-32-8

Basic information

• Product Name: 1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene
• Synonyms: 1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene;Benzene, 1,1-methylenebis(oxy-2,1-ethanediyloxy)bis-;BIS(PHENOXYETHYL)FORMAL;1,1′-[Methylenbis(oxyethan-1,2-diyloxy)]bisbenzol;Desavin;1,1'-[Methylenebis(oxy-2,1-ethanediyloxy)]bisbenzene;Einecs 237-644-9
• CAS NO: 13879-32-8
• Molecular Formula: C₁₇H₂₀O₄
• Molecular Weight: 288.3383
• EINECS: 237-644-9
• Mol File: 13879-32-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 18 °C
• Boiling Point: 195-196 °C(Press: 0.6 Torr)
• Appearance: /
• Density: 1.106±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene(13879-32-8)
• EPA Substance Registry System: 1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene(13879-32-8)

Safety Data

• Hazardous Substances Data: 13879-32-8(Hazardous Substances Data)

Usage

Description

1,1'-[methylenebis(oxyethane-1,2-diyloxy)]bisbenzene is a versatile chemical compound characterized by its structure of benzene rings linked by a central chain of ethylene oxide units. It is recognized for its diverse applications across various industries due to its unique properties, making it a valuable component in chemical synthesis and material production.

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

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

Relevant articles and documents

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.