5613-46-7

Basic information

• Product Name: 2,2-BIS(4-HYDROXY-3,5-DIMETHYLPHENYL)PROPANE
• Synonyms: Phenol, 4,4'-(1-methylethylidene)bis[2,6-dimethyl-;2,2-Bis(3,5-dimethyl-4-hydroxyphenyl)propane;3,3',5,5'-TetraMethyl-4,4'-dihydroxydiphenyl-2,2-propane;4,4'-Isopropylidenedi-2,6-xylenol;Bisxylenol A;4,4'-Isopropylidenebis(2,6-dimethylphenol) Tetramethylbisphenol A;4,4'-ISOPROPYLIDENEBIS(2,6-DIMETHYLPHENOL);4,4'-(1-METHYLETHYLIDENE)BIS(2,6-DIMETHYLPHENOL)
• CAS NO: 5613-46-7
• Molecular Formula: C19H24O2
• Molecular Weight: 284.39
• EINECS: 227-033-5
• Product Categories: Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Bisphenol A type Compounds (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 5613-46-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 162-165 °C(lit.)
• Boiling Point: 420.6 °C at 760mmHg
• Flash Point: 190.2 °C
• Appearance: /
• Density: 1.074 g/cm³
• Vapor Pressure: 0Pa at 20℃
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.60±0.10(Predicted)
• Water Solubility: 3.17mg/L at 20℃
• CAS DataBase Reference: 2,2-BIS(4-HYDROXY-3,5-DIMETHYLPHENYL)PROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-BIS(4-HYDROXY-3,5-DIMETHYLPHENYL)PROPANE(5613-46-7)
• EPA Substance Registry System: 2,2-BIS(4-HYDROXY-3,5-DIMETHYLPHENYL)PROPANE(5613-46-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 5613-46-7(Hazardous Substances Data)

Usage

Uses

Tetramethylbisphenol A is a methylated congener of Bisphenol A. Tetramethylbisphenol A is a flame retardant with anti-thyroid hormonal activity. Tetramethylbisphenol A inhibits growth and interferes with microtubules in human fibroblasts in vitro.

Flammability and Explosibility

Nonflammable

Synthetic route

2.6-dimethylphenol (576-26-1) + acetone (67-64-1) → tetramethylbisphenol A (5613-46-7)

Conditions	Yield
With sulfuric acid In Petroleum ether at 27℃; for 3.75h;	94%
With silica supported perchloric acid In neat (no solvent) for 5.25h; Heating; Green chemistry;	94%
With para-dodecylbenzenesulfonic acid; 3-mercaptopropionic acid at 42 - 75℃; Temperature;	81%

2.6-dimethylphenol (576-26-1) + 2-tert.-Butyl-4-isopropenyl-phenol (32565-67-6) → 2-tert-Butylphenol (88-18-6) + tetramethylbisphenol A (5613-46-7) + 2-tert.-Butyl-2',6'-dimethyl-4,4'-isopropyliden-bisphenol (19546-24-8)

Conditions	Yield
With hydrogenchloride In toluene

2,6-xylenol sulfate (92545-08-9) → tetramethylbisphenol A (5613-46-7)

Conditions	Yield
With acetone; 1-dodecylthiol at 30℃; for 1h;

tetramethylbisphenol A (5613-46-7) + epichlorohydrin (106-89-8) → 2,2'-(4,4'-(propane-2,2-diyl)bis(2,6-dimethyl-4,1-phenylene))-bis(oxy)bis(methylene)dioxirane

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide at 20℃; for 12h;	95%

bis(p-fluorophenyl)sulfone (383-29-9) + tetramethylbisphenol A (5613-46-7) → C205H204O26S6

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 150 - 170℃; Inert atmosphere; Dean-Stark;	92.3%

tetramethylbisphenol A (5613-46-7) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C23H23O3P (1573113-21-9)

Conditions	Yield
With toluene-4-sulfonic acid at 140℃; for 12h;	92%

tetramethylbisphenol A (5613-46-7) + 2-fluoro-6-methoxybenzaldehyde (146137-74-8) → C35H36O6 (1221407-35-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 3h;	91%

4-chloro-3-(trifluoromethyl)nitrobenzene (777-37-7) + tetramethylbisphenol A (5613-46-7) → 3,3',5,5'-tetramethyl-2,2-bis[4-(2-trifluoromethyl-4-nitrophenoxy)phenyl]propane

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 8h; Heating / reflux;	88%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 160℃; for 8h;	73%

tetramethylbisphenol A (5613-46-7) + (S)-(1,1'-binaphthyl-2,2'-dioxy)chlorophosphine → C59H46O6P2

Conditions	Yield
With triethylamine In toluene at -40 - 20℃; for 18h;	87%

tetramethylbisphenol A (5613-46-7) → C19H22Cl4O2P2

Conditions	Yield
With triethylamine; phosphorus trichloride In toluene at -40 - 20℃; for 18h;	86%

tetramethylbisphenol A (5613-46-7) + acetic anhydride (108-24-7) → 4-[1-(4-acetoxy-3,5-dimethylphenyl)-1-methylethyl]-2,6-dimethylphenyl ester (5769-93-7)

Conditions	Yield
With sodium periodate at 75℃; for 4h;	84%
With sodium periodate at 75℃; for 4.25h;	84%

tetramethylbisphenol A (5613-46-7) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C43H38O6P2

Conditions	Yield
Stage #1: tetramethylbisphenol A With dmap; N-ethyl-N,N-diisopropylamine In tetrachloromethane; acetonitrile at -10℃; for 0.25h; Atherton-Todd Synthesis; Inert atmosphere; Stage #2: 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide In tetrachloromethane; acetonitrile at -10 - 20℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	83%

tetramethylbisphenol A (5613-46-7) + lead(IV) tetraacetate (546-67-8) → C23H28O6 (1614247-80-1)

Conditions	Yield
In ethyl acetate at 27℃; for 0.783333h;	78%

polytetrafluoroethylene (116-14-3) + tetramethylbisphenol A (5613-46-7) → C23H24F8O2

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 60℃; for 5h; Addition;	46%

tetramethylbisphenol A (5613-46-7) → 4,4'‐(propane‐2,2‐diyl)bis(6‐hydroxy‐2,6‐dimethylcyclohexa‐2,4‐dienone)

Conditions	Yield
With Oxone; sodium hydrogencarbonate In water; acetone at 20℃; for 1h;	43%

N1,N3-bis{(S)-2-[4-(5-bromopentyloxy)phenyl]-1-(chloromethyl)ethyl}-2,2-diethylmalonamide (934559-03-2) + tetramethylbisphenol A (5613-46-7) → (14S,34S)-2,2-diethyl-132,136,14,14,153,155-hexamethyl-14,15,34,35-tetrahydro-6,12,16,22-tetraoxa-1,3(2,4)-bis(1,3-oxazola)-5,13,15,23(1,4)-tetrabenzenacyclotetracosaphane

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Heating;	41%

N1,N3-bis{(S)-2-[4-(3-bromopropoxy)phenyl]-1-(chloromethyl)ethyl}-2,2-diethylmalonamide (934559-01-0) + tetramethylbisphenol A (5613-46-7) → (14S,34S)-2,2-diethyl-112,116,12,12,133,135-hexamethyl-14,15,34,35-tetrahydro-6,10,14,18-tetraoxa-1,3(2,4)-bis(1,3-oxazola)-5,11,13,19(1,4)-tetrabenzenacycloicosaphane

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Heating;	40%

tetramethylbisphenol A (5613-46-7) + N1,N3-bis{(R)-1-[4-(4-bromobutoxy)phenyl]-2-chloroethyl}-2,2-dithylmalonamide (317373-84-5) → (14R,194R)-20,20-diethyl-92,96,10,10,113,115-hexamethyl-14,15,194,195-tetrahydro-3,8,12,17-tetraoxa-1,19(2,4)-bis(1,3-oxazola)-2,9,13,18(1,4)-tetrabenzenacycloicosaphane

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Heating;	40%

N1,N3-bis{(S)-2-[4-(2-bromoetoxy)phenyl]-1-(chloromethyl)ethyl}-2,2-diethylmalonamide (934559-00-9) + tetramethylbisphenol A (5613-46-7) → (14S,34S)-2,2-diethyl-102,106,11,11,123,125-hexamethyl-14,15,34,35-tetrahydro-6,9,13,16-tetraoxa-1,3(2,4)-bis(1,3-oxazola)-5,10,12,17(1,4)-tetrabenzenacyclooctadecaphane

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Heating;	38%

N1,N3-bis{(S)-2-[4-(4-bromobutoxy)phenyl]-1-(chloromethyl)ethyl}-2,2-diethylmalonamide (934559-02-1) + tetramethylbisphenol A (5613-46-7) → (14S,34S)-2,2-diethyl-122,126,13,13,143,145-hexamethyl-14,15,34,35-tetrahydro-6,11,15,20-tetraoxa-1,3(2,4)-bis(1,3-oxazola)-5,12,14,21(1,4)-tetrabenzenacyclodocosaphane

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Heating;	37%

tetramethylbisphenol A (5613-46-7) + N1,N3-bis{(R)-1-[4-(3-bromopropoxy)phenyl]-2-chloroethyl}-2,2-dithylmalonamide (317373-83-4) → (14R,174R)-18,18-diethyl-82,86,9,9,103,105-hexamethyl-14,15,174,175-tetrahydro-3,7,11,15-tetraoxa-1,17(2,4)-bis(1,3-oxazola)-2,8,11,16(1,4)-tetrabenzenacyclooctadecaphane

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Heating;	32%

tetramethylbisphenol A (5613-46-7) + N1,N3-bis{(R)-1-[4-(5-bromopentyloxy)phenyl]-2-chloroethyl}-2,2-dithylmalonamide (317373-85-6) → (14R,214R)-22,22-diethyl-102,106,11,11,123,125-hexamethyl-14,15,214,215-tetrahydro-3,9,13,19-tetraoxa-1,21(2,4)-bis(1,3-oxazola)-2,10,15,20(1,4)-tetrabenzenacyclodocosaphane

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Heating;	32%

5-bromo-2-methoxy-1,3-dimethylbenzene (14804-38-7) + tetramethylbisphenol A (5613-46-7) → C37H44O4

Conditions	Yield
With pyridine; potassium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 165℃; for 168h; Inert atmosphere;	30.9%

tetramethylbisphenol A (5613-46-7) + N1,N3-bis{(R)-1-[4-(2-bromoethoxy)phenyl]-2-chloroethyl}-2,2-dithylmalonamide (317373-82-3) → (14R,154R)-16,16-diethyl-72,76,8,8,93,95-hexamethyl-14,15,154,155-tetrahydro-3,6,10,13-tetraoxa-1,15(2,4)-bis(1,3-oxazola)-2,7,9,14(1,4)-tetrabenzenacyclohexadecaphane

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Heating;	14%

tetramethylbisphenol A (5613-46-7) → 2.6-Dimethyl-4-isopropenyl-phenol (32565-69-8)

Conditions	Yield
With sodium (heating);

BPA (80-05-7) + dichloromethane (75-09-2) + tetramethylbisphenol A (5613-46-7) → bisphenol A-copolyformal, Mw (1E3 g/mol) = 118, Mn (1E3 g/mol) = 61; monomer(s): methylene chloride; tetramethylbisphenol A; bisphenol A

Conditions	Yield
With N-Methylpyrrole; potassium hydroxide at 75℃; for 4h;

BPA (80-05-7) + dichloromethane (75-09-2) + tetramethylbisphenol A (5613-46-7) → bisphenol A-copolyformal, Mw (1E3 g/mol) = 380, Mn (1E3 g/mol) = 188; monomer(s): methylene chloride; tetramethylbisphenol A; bisphenol A

Conditions	Yield
With N-Methylpyrrole; potassium hydroxide at 75℃; for 1.58333h;

BPA (80-05-7) + dichloromethane (75-09-2) + tetramethylbisphenol A (5613-46-7) → bisphenol A-copolyformal, Mw (1E3 g/mol) = 612, Mn (1E3 g/mol) = 240; monomer(s): methylene chloride; tetramethylbisphenol A; bisphenol A

Conditions	Yield
With N-Methylpyrrole; potassium hydroxide at 75℃; for 3h;

dichloromethane (75-09-2) + tetramethylbisphenol A (5613-46-7) → bisphenol A-polyformal, Mw (1E3 g/mol) = 100, Mn (1E3 g/mol) = 18; monomer(s): methylene chloride; tetramethylbisphenol A

Conditions	Yield
With N-Methylpyrrole; potassium hydroxide at 75℃; for 4h;

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 32565-67-6 2-tert.-Butyl-4-isopropenyl-phenol 
• 67-64-1 acetone 
• 92545-08-9 2,6-xylenol sulfate 

Downstream Products

• 32565-73-4 1-(3,5-dimethyl-4-hydroxyphenyl)-6-hydroxy-1,3,3,5,7-pentamethyl-1,2-dihydroindene 
• 65962-46-1 2,2-bis-(3,5-dimethyl-4-aminocyclohexyl)-propane 
• 1221407-35-7 C₃₅H₃₆O₆ 
• 5769-93-7 4-[1-(4-acetoxy-3,5-dimethylphenyl)-1-methylethyl]-2,6-dimethylphenyl ester 
• 1614247-80-1 C₂₃H₂₈O₆ 
• 1614247-90-3 C₂₃H₂₈O₆ 
• 1614247-91-4 C₂₁H₂₆O₄ 

Relevant articles and documents

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Preparation method of tetramethyl bisphenol A

The invention discloses a preparation method of tetramethyl bisphenol A. The preparation method comprises the following steps: 1) mixing 2, 6-dimethylphenol, acetone, a main catalyst, an auxiliary catalyst and a mixed solvent to obtain a reaction solution, and reacting the reaction solution at 20-60 DEG C until the reaction is finished; (2) adding a hydrophobic solvent into the reaction liquid, performing heating and dissolving, separating out an oil layer, adjusting the pH value of the oil layer to be neutral, and performing washing until the conductivity is less than 50 mu S/cm; 3) cooling the oil layer treated in the step 2) to obtain tetramethyl bisphenol A crystal mush, and performing cooling, centrifuging, washing, drying and discharging to obtain tetramethyl bisphenol A; (4) treating the crystallization mother liquor in the step (3), recovering excessive and unreacted raw material 2, 6-dimethylphenol, adding a hydrophobic solvent into the remaining residues, and repeating the steps (2)-(3) to obtain the tetramethyl bisphenol A. The method disclosed by the invention is low in impurity conversion rate and high in product purity, and realizes low emission of the preparation process.

BISPHENOL COMPOSITION CONTAINING AROMATIC ALCOHOL SULFONATE AND METHOD FOR PRODUCING SAME, POLYCARBONATE RESIN AND METHOD FOR PRODUCING SAME, AND BISPHENOL PRODUCTION METHOD

A bisphenol composition including a specific amount of aromatic alcohol sulfonate, and a simple method of producing it are provided. Also provided is a method of producing a polycarbonate resin in which, by using the bisphenol composition including a specific amount of aromatic alcohol sulfonate, melt polymerization reaction can be efficiently allowed to proceed to produce a polycarbonate resin having an excellent color tone. A bisphenol composition including an aromatic alcohol sulfonate at not less than 0.1 ppb by mass with respect to a bisphenol. A method of producing a bisphenol composition, including reacting a ketone or an aldehyde with an aromatic alcohol in the presence of sulfuric acid to produce a bisphenol composition. A method of producing a polycarbonate resin, including producing a polycarbonate resin using the bisphenol composition. A polycarbonate resin including a specific amount of aromatic alcohol sulfonate.

Method for producing a bisphenol, and, production of polycarbonate resin (by machine translation)

[Problem] aromatic alcohols and ketone or aldehyde from reaction of bisphenol a, bisphenol to shorten the reaction time, produced bisphenol selectivity is improved, having good color tone bisphenol production can be obtained. [Solution] aromatic alcohols containing organic phase, the aqueous phase is separated from the oil and water containing sulfuric acid, wherein the organic phase in the aromatic alcoholic sulfone acid, aromatic alcoholic sulfone acid (1) to obtain a liquid reaction product containing, a reaction liquid containing the aromatic alcoholic sulfone acid, ketone or aldehyde mixture, the aromatic alcoholic sulfone in the presence of acid, the aromatic alcohol, wherein said step (2) produced from a ketone or aldehyde to bisphenol a, bisphenol a production. [Drawing] no (by machine translation)