837-08-1

Basic information

• Product Name: o-[1-(4-hydroxyphenyl)-1-methylethyl]phenol
• Synonyms: o-[1-(4-hydroxyphenyl)-1-methylethyl]phenol;Phenol, 2-1-(4-hydroxyphenyl)-1-methylethyl-;2-[1-(4-hydroxyphenyl)-1-methylethyl]-Phenol;2,4'-(1-methylethylidene)phenol;2-(o-Hydroxyphenyl)-2-(p-hydroxyphenyl)propane;2,4'-(1-Methylethylidene)diphenol;2,4'-Bisphenol A;2,4'-Isopropylidenediphenol
• CAS NO: 837-08-1
• Molecular Formula: C₁₅H₁₆O₂
• Molecular Weight: 228.28634
• EINECS: 212-650-4
• Product Categories: Aromatics, Mutagenesis Research Chemicals
• Mol File: 837-08-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 110.5 °C
• Boiling Point: 381.8°C at 760 mmHg
• Flash Point: 181.5°C
• Appearance: /
• Density: 1.143g/cm³
• Vapor Pressure: 2.25E-06mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.28±0.30(Predicted)
• CAS DataBase Reference: o-[1-(4-hydroxyphenyl)-1-methylethyl]phenol(CAS DataBase Reference)
• NIST Chemistry Reference: o-[1-(4-hydroxyphenyl)-1-methylethyl]phenol(837-08-1)
• EPA Substance Registry System: o-[1-(4-hydroxyphenyl)-1-methylethyl]phenol(837-08-1)

Safety Data

• Hazardous Substances Data: 837-08-1(Hazardous Substances Data)

Usage

Uses

o-[1-(4-hydroxyphenyl)-1-methylethyl]phenol can be used for the preparation of low-molecular-weight epoxy resins. It is a derivative of Bisphenol A (B519495), used as a building block in polycarbonate bottles and in the epoxy-resin liners of metal cans.

InChI:InChI=1/C15H16O2/c1-15(2,11-7-9-12(16)10-8-11)13-5-3-4-6-14(13)17/h3-10,16-17H,1-2H3

Synthetic route

acetone (67-64-1) + phenol (108-95-2) → BPA (80-05-7) + 4-methyl-pent-3-en-2-one (141-79-7) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1)

Conditions	Yield
beta zeolite acidic form at 120℃; under 760.051 Torr; for 12h;	A 63.2% B 0.01% C 11.43%

acetone (67-64-1) + phenol (108-95-2) → BPA (80-05-7) + 2,2-bis(2-hydroxyphenyl)-propane (7559-72-0) + 2-(2-hydroxyphenyl)-2,4,4-trimethylchroman (5026-12-0) + 4'-hydroxy-2,4,4-trimethylflavan (63661-69-8) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1)

Conditions	Yield
With aluminium(III) phenoxide at 140 - 160℃; for 1h; Product distribution; oth. temperature, oth. ratio of reactants, solvents;	A 8.1% B 1.5% C 7% D 21.6% E 50.3%

acetone (67-64-1) + phenol (108-95-2) → BPA (80-05-7) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1)

Conditions	Yield
With hydrogenchloride In water at 19.9℃; Rate constant; varying concentrations of reagents;
With MCM-41 silica anchored at 70℃; for 24h; Product distribution; Further Variations:; Reagents; Temperatures; atmospheric pressure;
With EPMO at 85℃; for 24h; Product distribution; Further Variations:; Reagents;

methylthiol (74-93-1) + acetone (67-64-1) + phenol (108-95-2) → BPA (80-05-7) + C27H30O3 (287110-79-6) + 2,2-bis(methylthio)propane (6156-18-9) + 2,2-bis(2-hydroxyphenyl)-propane (7559-72-0) + 5-hydroxy-3-(4-hydroxyphenyl)-1,1,3-trimethylindane (10527-11-4) + 2,4-bis[1-(4-hydroxyphenyl)-1-methylethyl]phenol (2300-15-4) + 4-methyl-4-methylthio-2-pentanone (23550-40-5) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) + 5-hydroxy-1-(4'-hydroxyphenyl)-1,3,3-trimethylindan (109252-41-7)

Conditions	Yield
strongly acidic 2percent cross linked sulfonated styrene divinylbenzene cationic gel exchange resin CT122 In water at 75℃; for 3h; Product distribution / selectivity;

...Expand

2,2-bis(methylthio)propane (6156-18-9) + acetone (67-64-1) + phenol (108-95-2) → BPA (80-05-7) + C27H30O3 (287110-79-6) + methylthiol (74-93-1) + 2,2-bis(2-hydroxyphenyl)-propane (7559-72-0) + 5-hydroxy-3-(4-hydroxyphenyl)-1,1,3-trimethylindane (10527-11-4) + 2,4-bis[1-(4-hydroxyphenyl)-1-methylethyl]phenol (2300-15-4) + 4-methyl-4-methylthio-2-pentanone (23550-40-5) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) + 5-hydroxy-1-(4'-hydroxyphenyl)-1,3,3-trimethylindan (109252-41-7)

Conditions	Yield
strongly acidic 2percent cross linked sulfonated styrene divinylbenzene cationic gel exchange resin CT122 In water at 75℃; for 3h; Product distribution / selectivity;

...Expand

acetone (67-64-1) + phenol (108-95-2) → BPA (80-05-7) + 2,2-bis(2-hydroxyphenyl)-propane (7559-72-0) + 5-hydroxy-3-(4-hydroxyphenyl)-1,1,3-trimethylindane (10527-11-4) + 2,4-bis[1-(4-hydroxyphenyl)-1-methylethyl]phenol (2300-15-4) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) + 5-hydroxy-1-(4'-hydroxyphenyl)-1,3,3-trimethylindan (109252-41-7) + C27H30O3

Conditions	Yield
Stage #1: phenol With water at 75℃; Autoclave; Stage #2: acetone; 2,2-bis(methylthio)propane In water for 3h; Product distribution / selectivity;
Stage #1: phenol With water at 75℃; Autoclave; Stage #2: acetone; methylthiol In water for 3h; Product distribution / selectivity;

...Expand

technical CHP + acetone (67-64-1) + phenol (108-95-2) → BPA (80-05-7) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1)

Conditions	Yield
Stage #1: technical CHP; acetone; zirconia, sulfated at 55 - 65℃; Stage #2: phenol at 75℃; for 12h;	A 94 %Chromat. B n/a
Stage #1: technical CHP; acetone; zirconia, sulfated at 50 - 90℃; under 0 - 517.162 Torr; for 24h; Stage #2: phenol at 75℃; for 12h;	A 92.1 %Chromat. B n/a

4'-hydroxy-2,4,4-trimethylflavan (63661-69-8) + phenol (108-95-2) → BPA (80-05-7) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1)

Conditions	Yield
ion exchange T-66 resin at 93℃; Product distribution / selectivity;

BPA (80-05-7) + 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine (940-71-6) → 4-isopropenylphenol (4286-23-1) + 5-hydroxy-3-(4-hydroxyphenyl)-1,1,3-trimethylindane (10527-11-4) + 2,4-bis[1-(4-hydroxyphenyl)-1-methylethyl]phenol (2300-15-4) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) + phenol (108-95-2)

Conditions	Yield
With potassium carbonate In chlorobenzene at 170℃; for 2h;

diazomethane (186581-53-3, 908094-01-9) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) → C17H20O2

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) → C21H32O2Si2

Conditions	Yield
at 50℃; for 0.5h; Yield given;

2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) → C15H14(2)H2O2

Conditions	Yield
With deuteromethanol

BPA (80-05-7) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) → phenol (108-95-2)

Conditions	Yield
sulfuric acid at 180 - 210℃; for 18.8 - 120h; Product distribution / selectivity;

2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) → BPA (80-05-7)

Conditions	Yield
DIAION SK-104H at 75℃; for 200 - 8000h; Conversion of starting material;
LEWATIT K2649 in the hydrogen form at 65℃; Product distribution / selectivity;

BPA (80-05-7) + 2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) → 4-isopropenylphenol (4286-23-1) + phenol (108-95-2)

Conditions	Yield
sodium hydroxide at 190℃; under 120 Torr; Product distribution / selectivity;

2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol (837-08-1) + acetone (67-64-1) + phenol (108-95-2) → BPA (80-05-7)

Conditions	Yield
2percent cross-linked A121 ion exchange resin with 22percent attached dimethylthiazolidine at 65℃; Product distribution / selectivity;

Upstream product

• 67-64-1 acetone 
• 108-95-2 phenol 
• 80-05-7 BPA 
• 940-71-6 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine 
• 6156-18-9 2,2-bis(methylthio)propane 
• 74-93-1 methylthiol 
• 63661-69-8 4'-hydroxy-2,4,4-trimethylflavan 

Downstream Products

• 80-05-7 BPA 
• 4286-23-1 4-isopropenylphenol 
• 108-95-2 phenol 

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