2461-46-3

Basic information

• Product Name: 4,4'-bis(2,3-epoxypropoxy)biphenyl
• Synonyms: Diglycidylether of 4,4'-biphenol;Polymers of 4,4'-dihydroxy-1,1-biphenyl with (chloromethyl)oxirane;Polymers of 4,4'-dihydroxy-1,1-biphenyl with(chloromethyl)oxirane;2,2'-[(1,1'-Biphenyl)-4,4'-diyl]bis(oxymethylene)bisoxirane;2,2'-[(4,4'-Biphenylylene)bis(oxymethylene)]bisoxirane;3,3'-[Biphenyl-4,4'-diylbisoxy]bis(1,2-epoxypropane);4,4'-Bis[(oxirane-2-yl)methoxy]-1,1'-biphenyl;Biphenyl-4,4'-diylbis(glycidyl ether)
• CAS NO: 2461-46-3
• Molecular Formula: C₁₈H₁₈O₄
• Molecular Weight: 298.33312
• EINECS: 219-556-2
• Mol File: 2461-46-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 156 °C
• Boiling Point: 473.6°Cat760mmHg
• Flash Point: 171.5°C
• Appearance: /
• Density: 1.226g/cm³
• CAS DataBase Reference: 4,4'-bis(2,3-epoxypropoxy)biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-bis(2,3-epoxypropoxy)biphenyl(2461-46-3)
• EPA Substance Registry System: 4,4'-bis(2,3-epoxypropoxy)biphenyl(2461-46-3)

Safety Data

• Hazardous Substances Data: 2461-46-3(Hazardous Substances Data)

Usage

General Description

4,4'-bis(2,3-epoxypropoxy)biphenyl, is a synthetic chemical compound used primarily as a flame retardant in various industries, such as electronics, textiles, and plastics. It is a member of the class of chemicals known as bisphenol A diglycidyl ethers, which are commonly used as epoxy resins. 4,4'-bis(2,3-epoxypropoxy)biphenyl is known for its high thermal stability and its ability to resist degradation at high temperatures. However, there are concerns about its potential health and environmental impacts, as it has been found to be persistent in the environment and can bioaccumulate in organisms. Research has also suggested that it may have endocrine-disrupting properties, making it a subject of growing regulatory scrutiny.

Synthetic route

4,4'-Dihydroxybiphenyl (92-88-6) + epichlorohydrin (106-89-8) → 4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3)

Conditions	Yield
Stage #1: 4,4'-Dihydroxybiphenyl With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: epichlorohydrin In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; Stage #3: With water In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	68%
With sodium hydroxide	65%
With tetramethylammonium bromide In dimethyl sulfoxide at 80℃; for 0.666667h;	53%
Heating;
Stage #1: 4,4'-Dihydroxybiphenyl; epichlorohydrin With trimethylbenzylammonium bromide for 0.666667h; Reflux; Stage #2: With sodium hydroxide at 20℃; for 4h; Reflux;

4,4'-Dihydroxybiphenyl (92-88-6) + epichlorohydrin (106-89-8) → 1-chloro-3-[4'-(3-chloro-2-hydroxy-propoxy)-biphenyl-4-yloxy]-propan-2-ol + 4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3)

Conditions	Yield
With potassium hydroxide at 20℃; Title compound not separated from byproducts;

1,4-dioxane (123-91-1) + 4-Phenylphenol (92-69-3) → 4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3)

Conditions	Yield
With sodium sulfate; methyloxirane; potassium hydroxide In chloroform

diethylamine (109-89-7) + 4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3) + epichlorohydrin (106-89-8) → 4,4'-bis(3-N,N-diethylamino-2-hydroxypropanoxy)biphenyl

Conditions	Yield
Stage #1: 4,4'-bis(2,3-epoxypropoxy)biphenyl; epichlorohydrin With potassium hydroxide at 20℃; Stage #2: diethylamine In ethanol	50%

4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3) → 1-chloro-3-[4'-(3-chloro-2-hydroxy-propoxy)-biphenyl-4-yloxy]-propan-2-ol

Conditions	Yield
With cerium(III) chloride heptahydrate In acetonitrile for 16h; Reflux;	28%

4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3) → C30H50N2O4(2+)*2Br(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aq. KOH / 20 °C 1.2: 50 percent / ethanol 2.1: 87 percent / acetone / 6 h / Heating View Scheme

acrylic acid (79-10-7) + 4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3) → C24H26O8 (166596-79-8)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; hydroquinone Heating;

4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3) → C30H45NO9Si

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; tetraethylammonium bromide / tetrahydrofuran; acetonitrile / 2.5 h / 26 °C 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 65 °C View Scheme

ethanol (64-17-5) + 4,4'-bis(2,3-epoxypropoxy)biphenyl (2461-46-3) → C20H24O5

Conditions	Yield
With tetraethylammonium bromide; sodium hydroxide In tetrahydrofuran; acetonitrile at 26℃; for 2.5h;

Upstream product

• 92-88-6 4,4'-Dihydroxybiphenyl 
• 106-89-8 epichlorohydrin 
• 123-91-1 1,4-dioxane 
• 92-69-3 4-Phenylphenol 

Relevant articles and documents

Liquid crystalline epoxy resin based on biphenyl mesogen: Thermal characterization

An epoxy monomer of 4,4′-diglycidyloxybiphenyl (BP) was synthesized and cured with a tetra-functional amine, sulfanilamide (SAA), to produce novel liquid crystalline epoxy resins (LCERs). The thermal properties, liquid crystalline morphologies, and cure behavior of the monomer were studied using differential scanning calorimetry, wide angle X-ray diffraction, and polarized optical microscopy. The effects of curing condition on the glass transition temperature, coefficient of thermal expansion, and dynamic mechanical properties of the resins were determined through thermomechanical analysis and dynamic mechanical analysis, respectively. The effects of cure condition on the formation of the liquid crystalline phase were also examined. The results show that BP is not a liquid crystalline epoxy monomer and an irreversible crystal transition exists in the temperature range of 120 C-140 C. The use of SAA results in the formation of a smectic liquid crystalline phase. Compared to the resins cured into an amorphous network, the LCERs exhibited a polydomain structure with individual liquid crystalline domain distributed in the resin matrix, which results in better thermomechanical properties.

Using the liquid crystalline epoxy resin thermoset aromatic diamine

PROBLEM TO BE SOLVED: To provide an aromatic diamine that gives a heat-cured product useful as an electric insulation material for radiating the heat generated from a semiconductor element and the like, and a liquid crystalline epoxy resin heat-cured product prepared therewith.SOLUTION: This invention relates to an aromatic diamine represented by formula (1), and a heat-cured product of the diamine and a liquid crystalline bisepoxide represented by formula (2) (where R-Rindependently represent a hydrogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group, m is an integer of 2-14, and Xis a divalent aromatic group).SELECTED DRAWING: None

Synthesis, characterization, and thermal properties of diacrylic/ divinylbenzene copolymers

In this article, synthesis, characterization, and thermal properties of diacrylic/divinylbenzene copolymers based on the new aromatic tetrafunctional acrylate monomers are presented. The new monomers were generated by treatment of epoxides derived from various aromatic diols: naphthalene-2,3-diol (NAF), biphenyl-4,4′-diol (BIF), bis(4-hydroxyphenyl)methanone (BEP) or 4,4′-thiodiphenol (BES), and epichlorohydrin with acrylic acid. The addition reaction was carried out by a ratio of 0.5 mol of suitable epoxy derivative and 1 mol of acrylic acid in the presence of 0.7 wt% of triethylbenzylammonia chloride (TEBAC) as a catalyst and 0.045 wt% of hydroquinone as a polymerization inhibitor. The chemical structure of the prepared acrylate monomers was confirmed by 13C NMR and GC MS spectra. The emulsion-suspension polymerization of acrylate monomers with divinylbenzene (DVB) in the presence of pore-forming diluents (toluene + decan-1-ol) allowed obtaining microspheres containing pendant functional groups (hydroxyl groups). This process was carried out at constant mol ratio of acrylate monomers: DVB (1:1), and constant volume ratio of pore-forming diluents to monomers (1:1). The different concentrations of toluene in the mixture with decan-1-ol were used for qualifying the effect of the diluents on the microsphere characteristics. The influence of synthesis's parameters on the properties of copolymer beads, e.g., pore size and surface area by BET method, the surface texture by AFM, swelling behavior in polar and non-polar solvents as well as thermal stability by differential scanning calorimetry (DSC), and thermogravimetric analysis (TG) was studied and discussed.