13595-25-0

Basic information

• Product Name: 4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL
• Synonyms: 4,4’-[1,3-phenylenebis(1-methylethylidene)]bis-pheno;1,3-BIS[2-(4-HYDROXYPHENYL)-2-PROPYL]BENZENE;4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL;BISPHENOL M;LABOTEST-BB LT00159392;4,4-[1,3-Phenylenebis (1-Methyl-ethylidene)];1,3-BIS(4-HYDROXYCUMYL)BENZENE;4,4'-(m-Phenylenediisopropyridene)diphenol
• CAS NO: 13595-25-0
• Molecular Formula: C₂₄H₂₆O₂
• Molecular Weight: 346.46
• EINECS: 428-970-4
• Product Categories: Color Former & Related Compounds;Developer;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 13595-25-0.mol

Chemical Properties

• Melting Point: 135-139 °C(lit.)
• Boiling Point: 495.9 °C at 760 mmHg
• Flash Point: 220.1 °C
• Appearance: /
• Density: 1.107 g/cm³
• Vapor Pressure: 0.001Pa at 25℃
• Solubility: soluble in Methanol
• PKA: 10.31±0.10(Predicted)
• CAS DataBase Reference: 4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL(13595-25-0)
• EPA Substance Registry System: 4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL(13595-25-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 13595-25-0(Hazardous Substances Data)

Usage

Uses

Used in Plastics Industry:
4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL is used as a monomer for the production of polycarbonate and epoxy resins. Its chemical structure provides these resins with desirable properties such as durability, heat resistance, and transparency, making them suitable for a wide range of applications.
Used in Electronics Industry:
In the electronics industry, 4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL is used as a component in the manufacturing of various electronic components and devices. Its heat resistance and durability make it an ideal material for use in this sector.
Used in Toys:
4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL is used as a material in the production of toys due to its durability and resistance to heat and impact. This ensures that the toys made from this material are long-lasting and safe for children to play with.
Used in Food Packaging:
4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL is used in the manufacturing of food containers and bottles. Its properties, such as being resistant to heat and impact, make it an ideal material for packaging food products, ensuring their safety and durability during transportation and storage.
Used in Paper Industry:
In the paper industry, 4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL is used as a component in the production of various types of papers. Its properties contribute to the strength and durability of the paper, making it suitable for various applications.
Used in Medical Equipment:
4,4'-(1,3-PHENYLENEDIISOPROPYLIDENE)BISPHENOL is also used in the medical equipment industry, where its heat resistance and durability are essential for the production of various medical devices and equipment. This ensures the safety and reliability of the equipment used in healthcare settings.

Flammability and Explosibility

Nonflammable

Synthetic route

1,3-bis(1',1'-dimethylhydroxymethyl)benzene (1999-85-5) + phenol (108-95-2) → bisphenol M (13595-25-0)

bisphenol M (13595-25-0) + 4-picolylchloride hydrochloride (1822-51-1) → C36H36N2O2 (1020725-78-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In benzene at 80℃; for 48h;	98%

2-chloropyrazin (14508-49-7) + bisphenol M (13595-25-0) → 1,3-di(2-(4-(2-pyrazinyloxy)phenyl)prop-2-yl)benzene (1020725-53-4)

Conditions	Yield
Stage #1: bisphenol M With potassium carbonate In sulfolane; toluene at 20℃; for 0.75h; Stage #2: 2-chloropyrazin at 80℃; for 48h; Further stages.;	94%

bromocyane (506-68-3) + bisphenol M (13595-25-0) → bisphenol M cyanate

Conditions	Yield
With triethylamine; isopropyl alcohol In acetone at -15 - -10℃; for 2.5h;	93%

4-Nitrophthalonitrile (31643-49-9) + bisphenol M (13595-25-0) → C40H30N4O2

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere;	91.3%

bisphenol M (13595-25-0) + 3-chloromethylpyridinium chloride (6959-48-4) → 1,3-di(2-(4-(3-pyridylmethoxy)phenyl)prop-2-yl)benzene (1020725-73-8)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In benzene at 80℃; for 48h;	90.4%

bisphenol M (13595-25-0) + 2-chloromethylpyridine hydrochloride (6959-47-3) → C36H36N2O2 (1020725-68-1)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In benzene at 80℃; for 48h;	84%

bisphenol M (13595-25-0) → C72H72O6P2 + C72H72O6P2

Conditions	Yield
With TEA; phosphorus trichloride In toluene at 25℃; for 24h;	A n/a B 18%

bisphenol M (13595-25-0) → C72H72O6P2 + C72H72O6P2

Conditions	Yield
With TEA; phosphorus trichloride In toluene at 25℃; for 24h;	A n/a B 18%

bisphenol M (13595-25-0) → C72H72O8P2 + C72H72O8P2

Conditions	Yield
Stage #1: bisphenol M With TEA; phosphorus trichloride In toluene at 25℃; for 24h; Stage #2: With Cumene hydroperoxide In toluene at 20℃; for 1h;	A n/a B 1.37 g

bisphenol M (13595-25-0) + 4-chlorobenzonitrile (100-00-5) → 1,3-bis[4-(4-nitrophenoxy)-α,α-dimethylbenzyl]benzene (135672-39-8)

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide; toluene

meta-dinitrobenzene (99-65-0) + bisphenol M (13595-25-0) → 1,3-bis[4-(3-nitrophenoxy)-α,α-dimethylbenzyl]benzene (135654-83-0)

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide; toluene

formaldehyd (50-00-0) + bisphenol M (13595-25-0) → 4,4'-[1,3-phenylenebis(1-methylethylidene)]bis(3,5-dihydroxymethylphenol)

Conditions	Yield
Stage #1: bisphenol M With sodium hydroxide In methanol; water at 20℃; for 0.166667h; Stage #2: formaldehyd In water at 30℃; for 9h;

bisphenol M (13595-25-0) → 3-(4-(2-(3-(2-(4-(3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenyl)propan-2-yl)phenoxy)propane-1,2-diol (1403962-95-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 20 °C / Inert atmosphere 1.2: 40 h / 70 - 80 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 20 °C / Inert atmosphere 2.2: 22 h / 20 °C / Inert atmosphere 3.1: cerium(III) chloride heptahydrate / acetonitrile / 22 h / Reflux View Scheme

5-chloromethyl-2,2-dimethyl-1,3-dioxolane (4362-40-7) + bisphenol M (13595-25-0) → 2,2-dimethyl-4-((4-(2-(3-(2-(4-(oxiran-2-ylmethoxy)phenyl)propan-2-yl)phenyl)propan-2-yl)phenoxy)methyl)-1,3-dioxolane (1403962-94-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 20 °C / Inert atmosphere 1.2: 40 h / 70 - 80 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 20 °C / Inert atmosphere 2.2: 22 h / 20 °C / Inert atmosphere View Scheme

bisphenol M (13595-25-0) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → C40H40N2O8S2

Conditions	Yield
With triethylamine In tetrahydrofuran at 30 - 40℃; for 3h; Inert atmosphere;

bisphenol M (13595-25-0) + 3-fluoro-6-nitrotoluene (446-33-3) → 1,3-bis{2-[4-(3-methyl-4-nitrophenoxy)phenyl]-2-propyl}benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 9h;	6.0 g

bisphenol M (13595-25-0) + 3-fluoro-6-nitrotoluene (446-33-3) → 1,3-bis{2-[4-(4-amino-3-methylphenoxy)phenyl]-2-propyl}benzene

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 9 h / 120 °C 2: 5%-palladium/activated carbon; 2-methoxy-ethanol; hydrogen / 90 °C / 6000.6 Torr / Autoclave View Scheme

Upstream product

• 1999-85-5 1,3-bis(1',1'-dimethylhydroxymethyl)benzene 
• 108-95-2 phenol 

Downstream Products

• 1417523-36-4 C₃₀H₂₉O₃P 
• 1403962-94-6 2,2-dimethyl-4-((4-(2-(3-(2-(4-(oxiran-2-ylmethoxy)phenyl)propan-2-yl)phenyl)propan-2-yl)phenoxy)methyl)-1,3-dioxolane 
• 1403962-93-5 4-(2-(3-(2-(4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenyl)propan-2-yl)phenol 
• 1403962-95-7 3-(4-(2-(3-(2-(4-(3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenyl)propan-2-yl)phenoxy)propane-1,2-diol 
• 1020725-73-8 1,3-di(2-(4-(3-pyridylmethoxy)phenyl)prop-2-yl)benzene 
• 1020725-68-1 C₃₆H₃₆N₂O₂ 
• 1020725-78-3 C₃₆H₃₆N₂O₂ 
• 1020725-53-4 1,3-di(2-(4-(2-pyrazinyloxy)phenyl)prop-2-yl)benzene 
• 1020725-48-7 C₃₄H₃₂N₂O₂ 
• 135654-83-0 1,3-bis[4-(3-nitrophenoxy)-α,α-dimethylbenzyl]benzene 
• 135672-39-8 1,3-bis[4-(4-nitrophenoxy)-α,α-dimethylbenzyl]benzene 

Relevant articles and documents

MEDICAL DEVICE USING SULFONATED NEUTRALIZED POLYMERS WITH REDUCED ADHESION OF BIOLOGICAL FLUIDS

A medical article having neutralized sulfonic acid groups on its surface, is disclosed. The article has reduced interaction with biological fluids such as insulin, human growth hormone and human serum albumin.

Process for production of 1,3-di(2-p-hydroxyphenyl-2-propyl)benzene

The invention provides a process for production of 1,3-di(2-p-hydroxyphenyl-2-propyl)benzene which comprises: reacting 1,3-di(2-hydroxy-2-propyl)benzene with phenol in an amount of 4-6 times in mols the amount of the 1,3-di(2-hydroxy-2-propyl)benzene in the presence of an acid catalyst at a temperature of 10-55° C. thereby crystallizing adducts formed of phenol and the resulting 1,3-di(2-p-hydroxyphenyl-2-propyl)benzene so that the reaction is effected in a slurry, and then recovering 1,3-di(2-p-hydroxyphenyl-2-propyl)benzene from the adduct.

Production process of bisphenol compounds

A process for the production of a bisphenol compound comprising: a step for reacting a phenolic compound (a) with at least one compound (b) selected from the group consisting of dialkenylbenzene compounds, bis(hydroxyalkyl)benzene compounds and (hydroxyalkyl)-alkenylbenzene compounds or at least one compound (c) selected from the group consisting of monoalkenylphenolic compounds and mono(hydroxyalkyl)phenolic compounds in the presence of an acidic catalyst to obtain a reaction mixture containing said bisphenol compound, a step for neutralizing the reaction mixture with an anion exchange resin, a step for removing a remaining phenolic compound from the reaction mixture to concentrate the neutralized reaction mixture, and a step for isolating the bisphenol compound from the resulting concentrated mixture. This process enables to produce a bisphenol compound, which is useful for preparing raw materials of thermoplastic polymers, surface-active agents and stabilizers.

Salicylic acid derivatives

The heat-sensitive recording material disclosed comprises a colorless or pale colored dyestuff precursor, one or more salicylic acid derivative of the formula (1) or metal salt of the derivative and an aliphatic amide compound having 18?60 carbon atoms in molecular structure, and is excellent in thermal response and preservation stability of white portions and images. STR1 wherein X1 and X2 are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aralkyl group or an aryl group, Y1 and Y2 are an oxygen atom or a sulfur atom, R1 is a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R2 is an alkyl group, an alkenyl group, an aralkyl group or an aryl group.

Phenolic compounds

A phenolic compound having formula (I): STR1 wherein X represents a chlorine atom or a methyl group, and a recording material comprising a coloress or light-colored leuco dye and the above phenolic compound serving as a color developer for the leuco dye are disclosed.