41481-66-7

Basic information

• Product Name: Bis(3-allyl-4-hydroxyphenyl)sulfone
• Synonyms: Bis(3-allyl-4-hydroxyphenyl)sulfone;2,2'-diallyl-4,4'-sulfonyldiphenol;4,4'-Sulfonylbis(2-allylphenol);4,4'-Sulfonylbis[2-(2-propenyl)phenol];Bis(4-hydroxy-3-allylphenyl) sulfone;TGSH;4-(4-hydroxy-3-prop-2-enylphenyl)sulfonyl-2-prop-2-enylphenol;4-(4-hydroxy-3-prop-2-enylphenyl)sulfonyl-2-prop-2-enylph
• CAS NO: 41481-66-7
• Molecular Formula: C₁₈H₁₈O₄S
• Molecular Weight: 330.4
• EINECS: 411-570-9
• Mol File: 41481-66-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 138.5 °C(Solv: toluene (108-88-3))
• Boiling Point: 544.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.253±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 7.22±0.20(Predicted)
• CAS DataBase Reference: Bis(3-allyl-4-hydroxyphenyl)sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(3-allyl-4-hydroxyphenyl)sulfone(41481-66-7)
• EPA Substance Registry System: Bis(3-allyl-4-hydroxyphenyl)sulfone(41481-66-7)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-51/53
• Safety Statements: 24-37-61
• Hazardous Substances Data: 41481-66-7(Hazardous Substances Data)

Usage

Description

Bis(3-allyl-4-hydroxyphenyl)sulfone is a white to off-white solid that is synthesized through a specific chemical process involving 4,4'-diallyl diphenyl sulfone and methyl glycine diacetic acid. It is characterized by its light-thermal sensitive properties, making it a promising candidate for various applications in different industries.

Uses

Used in Imaging Systems:
Bis(3-allyl-4-hydroxyphenyl)sulfone is used as a component in the preparation of microcapsules for light-thermal sensitive imaging systems. Its light-thermal sensitivity allows for the development of advanced imaging techniques that can be utilized in various fields, such as medical diagnostics and research.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, due to its chemical properties and synthesis process, Bis(3-allyl-4-hydroxyphenyl)sulfone may also have potential applications in the pharmaceutical industry. It could be used as a starting material or intermediate in the development of new drugs or drug delivery systems, particularly those that require light-thermal sensitive properties for targeted drug release or imaging purposes.

Synthetic route

4,4'-sulfonediphenol (80-09-1) + allyl tosylate (4873-09-0) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With tetrabutyl-ammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 110 - 120℃; for 8h; Large scale;	98.5%
With potassium carbonate In N,N-dimethyl-formamide	30.4 parts (92.1%)

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With α-alanine-N-diacetic acid at 198 - 200℃; for 7h; Temperature; Inert atmosphere;	96.2%
With 1,10-Phenanthroline; ethylenediaminetetraacetic acid; sodium hydroxide In paraffin oil at 203 - 207℃; for 7h; Inert atmosphere;	93.7%
With iron(III) chloride In 1,2-dichloro-ethane at 60℃; for 15h; Reagent/catalyst; Solvent; Temperature;	93.9%

4,4'-sulfonediphenol (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With sodium carbonate; sodium hydroxide In water at 95 - 100℃; for 5h; Solvent; Reagent/catalyst; Temperature; Autoclave; Large scale;	84.4%

4,4'-sulfonediphenol (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + 4-allyloxy-4'-hydroxydiphenyl-sulfone

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium carbonate; sodium hydroxide In water; paraffin oil; kerosene at 95 - 100℃; for 5h; Autoclave; Large scale;	A 73.9% B 10.2%

4,4'-sulfonediphenol (80-09-1) + allyl tosylate (4873-09-0) + 3-chloroprop-1-ene (107-05-1) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + 4-allyloxy-4'-hydroxydiphenyl-sulfone

Conditions	Yield
Stage #1: 4,4'-sulfonediphenol; allyl tosylate With tetrabutyl-ammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 110 - 120℃; for 8h; Large scale; Stage #2: 3-chloroprop-1-ene In N,N-dimethyl-formamide at 200 - 220℃; for 6h; Large scale;	A 35.3% B 8.6%

4,4'-sulfonediphenol (80-09-1) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH, Me4NBr / toluene; H2O / 15 h / 49.9 - 59.9 °C 2: 85 percent / various solvent(s) / 30 h / 207.9 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 1.2: Reflux; Inert atmosphere 2.1: 4 h / 220 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 80 °C / Inert atmosphere 2: 1,2-dichloro-benzene / 8 h / 190 °C / Inert atmosphere View Scheme

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → 3-allyl-4,4'-dihydroxydiphenyl sulfone + 3-allyl-4'-allyloxy-4-hydroxydiphenyl sulfone (737795-84-5) + 5-(3-allyl-4-hydroxyphenylsulfonyl)-1-oxa-2-methylindane + 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With dmap at 160 - 280℃; for 0.0833333 - 0.333333h; Product distribution / selectivity; Microwave irradiation;
With 1,10-Phenanthroline; ascorbic acid In 1,2,3-trichlorobenzene at 210℃; for 7h; Product distribution / selectivity;
With 1,10-Phenanthroline; ascorbic acid at 160 - 280℃; for 0.266667h; Product distribution / selectivity; Microwave irradiation;

48%-caustic soda + 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With 1,2,3-trichlorobenzene In water	14.0 parts (93.3%)

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + 3-dibutylamino-6-methyl-7-anilinofluoran → C35H36N2O3*C18H18O4S

Conditions	Yield
In hexane; acetone at 5℃; for 336h;	41.7%

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C18H16O4S(2-)*2Na(1+)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C32H42O8S5 (1636900-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 1.2: Reflux; Inert atmosphere 2.1: 2,2'-azobis(isobutyronitrile) / tetrahydrofuran / 16.5 h / 20 - 65 °C / Inert atmosphere View Scheme

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C24H34O4S5 (1636900-15-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 1.2: Reflux; Inert atmosphere 2.1: 2,2'-azobis(isobutyronitrile) / tetrahydrofuran / 16.5 h / 20 - 65 °C / Inert atmosphere 3.1: hydrogenchloride; water / tetrahydrofuran; methanol / 24 h / 60 °C / Inert atmosphere View Scheme

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + allyl bromide (106-95-6) → 4,4’-sulfonylbis(2-allyl-1-(allyloxy)benzene) (122438-87-3)

Conditions	Yield
Stage #1: 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone With potassium carbonate In acetone for 1h; Inert atmosphere; Reflux; Stage #2: allyl bromide In acetone Reflux; Inert atmosphere;	47.5 g

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → C24H34O4SSi2

Conditions	Yield
In 1,4-dioxane for 2h;	6.5 g

di-tert-butyl dicarbonate (24424-99-5) + 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C28H34O8S

Conditions	Yield
In 1,4-dioxane for 4h;	6.5 g

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C36H58O12S3Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / isopropyl alcohol; water / 3 h / 60 °C / Inert atmosphere 2: 2,2-dimethoxy-2-phenylacetophenone / 24 h / 20 °C / Inert atmosphere; Darkness View Scheme

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + epichlorohydrin (106-89-8) → C24H26O6S

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol at 60℃; for 3h; Inert atmosphere;

Upstream product

• 41481-63-4 4,4’-sulfonylbis((allyloxy)benzene) 
• 80-09-1 4,4'-sulfonediphenol 
• 4873-09-0 allyl tosylate 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 1636900-13-4 C₃₂H₄₂O₈S₅ 
• 1636900-15-6 C₂₄H₃₄O₄S₅ 
• 122438-87-3 4,4’-sulfonylbis(2-allyl-1-(allyloxy)benzene) 

Relevant articles and documents

Synthesis method of thermosensitive color developing agent 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol

The invention provides a synthesis method of a thermosensitive color developing agent 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol, which comprises the following step: directly heating and rearranging 4, 4'-diallyl diphenyl sulfone in an organic solvent under the action of a catalyst to obtain the 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol. In the process of preparing 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol, a Lewis acid catalyst is used, so that a high-temperature reaction at 200 DEG C or above can be avoided, safety accidents are greatly reduced, energy is saved, consumption is reduced, andequipment investment is greatly reduced. The catalysts zinc chloride, aluminum trichloride, ferric trichloride and titanium tetrachloride used in the preparation process of the 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol are low in cost and convenient to post-treat. In the process of preparing the 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol, the use of a high-boiling-point solvent and heat conduction oil can be avoided, and the production cost is greatly reduced.

PROCESS FOR PRODUCING ALLYL-SUBSTITUTED BISPHENOL COMPOUND

The present invention relates to a process for producing an allyl-substituted bisphenol compound including a step of subjecting a diallyl etherified bisphenol compound represented by the following general formula (I) to a thermal rearrangement reaction in the presence of a specific phosphine compound [in the formula, A represents a single bond, —SO2—, —S—, —O—, a divalent group represented by the following formula (i-1), or a divalent group represented by —CY1Y2—(Y1 and Y2 each independently represent hydrogen, a linear, branched, or cyclic alkyl group having 6 or less carbon atoms, a phenyl group, or an aralkyl group having 7 or 8 carbon atoms), B1 and B2 each independently represent a linear, branched, or cyclic alkyl group having 6 or less carbon atoms, an allyl group, a phenyl group, or an aralkyl group having 7 or 8 carbon atoms, and n1 and n2 each independently represent an integer from 0 to 2,

METHOD OF CONSISTENTLY PRODUCING DIALLYLBISPHENOLS

The purpose of the present invention is to provide a method of consistently producing high-quality diallylbisphenols with high yields from bisphenols. This method involves steps (1) through (3) below, and enables the consistent production of diallylbisphenols from bisphenols. (1) A step for reacting allyl halides and bisphenols or alkali metal salts thereof in a cellosolve solvent in the presence or absence of basic alkali metal salts, (2) a step for separating inorganic salt by-products from a reaction solution obtained in step (1), and (3) a step for heating and subjecting to a rearrangement reaction the reaction solution obtained in step (2).