2167-51-3

Basic information

• Product Name: ALPHA,ALPHA'-BIS(4-HYDROXYPHENYL)-1,4-DIISOPROPYLBENZENE
• Synonyms: 1,4-Bis[2-(4-hydroxyphenyl)-2-propyl]benzene;1,4-Bis[2-(4-hydroxyphenyl)-2-propyl]benzene 4,4'-(1,4-Phenylenediisopropylidene)bisphenol Bisphenol P;α,α'-Bis(4-hydroxyphenyl)-1,4-diisopropylbenzene;4,4'-(1,4-Phenylenebis(propane-2,2-diyl);LABOTEST-BB LT00159393;BISPHENOL P;ALPHA,ALPHA'-BIS(4-HYDROXYPHENYL)-1,4-DIISOPROPYLBENZENE;4,4'-(1,4-PHENYLENEDIISOPROPYLIDENE)BISPHENOL
• CAS NO: 2167-51-3
• Molecular Formula: C₂₄H₂₆O₂
• Molecular Weight: 346.46
• EINECS: 200-258-5
• Product Categories: Bisphenol A type Compounds (for High-Performance Polymer Research);Color Former & Related Compounds;Developer;Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 2167-51-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 193-195 °C(lit.)
• Boiling Point: 246 °C(Press: 0.1 Torr)
• Appearance: /
• Density: 1.107±0.06 g/cm3(Predicted)
• Solubility: very faint turbidity in Methanol
• PKA: 10.31±0.10(Predicted)
• CAS DataBase Reference: ALPHA,ALPHA'-BIS(4-HYDROXYPHENYL)-1,4-DIISOPROPYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA,ALPHA'-BIS(4-HYDROXYPHENYL)-1,4-DIISOPROPYLBENZENE(2167-51-3)
• EPA Substance Registry System: ALPHA,ALPHA'-BIS(4-HYDROXYPHENYL)-1,4-DIISOPROPYLBENZENE(2167-51-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2167-51-3(Hazardous Substances Data)

Usage

General Description

Alpha, Alpha'-Bis(4-hydroxyphenyl)-1,4-diisopropylbenzene is a chemical compound with molecular formula C24H28O2. It has reportedly been used in industrial and scientific applications. The chemical is characterized by the presence of two hydroxyphenyl groups attached to a central benzene ring that is further substituted with two isopropyl groups. The hydroxyl groups make it moderately polar while the multiple aromatic rings contribute to its overall stability. As such, this compound may display properties typical of aryl compounds, like resistance to oxidation and participation in aromatic stacking interactions. Specific health, safety, or environmental effects of this molecule have not been widely reported and its specific uses or implications in different fields remains unclear. Therefore, careful handling and further research into its properties and potential effects is advised.

Synthetic route

α,α,α',α'-tetramethyl-1,4-benzenedimethanol (2948-46-1) + phenol (108-95-2) → 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3)

Conditions	Yield
With hydrogenchloride at 80℃; for 3.5h;	65%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + α,α'-bis[(5-bromopentoxy)phenyl]-1,4-di(isopropyl)benzene (182318-36-1) → C58H68O4

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 168h;	99%
With caesium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 144h;	70%

2-bromo-pyridine (109-04-6) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → C34H32N2O2 (1020725-47-6)

Conditions	Yield
Stage #1: 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol With potassium carbonate In sulfolane; toluene at 20℃; for 0.75h; Stage #2: 2-bromo-pyridine at 80℃; for 48h; Further stages.;	99%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + α,α'-di[(4-bromo-1-butoxy)phenyl]-1,4-diisopropylbenzene (625084-41-5) → C56H64O4 (625084-44-8)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 125h;	98%

1,4-dibromo-butane (110-52-1) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → α,α'-di[(4-bromo-1-butoxy)phenyl]-1,4-diisopropylbenzene (625084-41-5)

Conditions	Yield
Stage #1: 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol With potassium carbonate In acetonitrile for 1.5h; Reflux; Stage #2: 1,4-dibromo-butane In [D3]acetonitrile for 30h; Reflux;	90%

2-Chloroquinoline (612-62-4) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → C42H36N2O2 (1020725-57-8)

Conditions	Yield
Stage #1: 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol With potassium carbonate In sulfolane; toluene at 20℃; for 0.75h; Stage #2: 2-Chloroquinoline at 80℃; for 48h; Further stages.;	87%

4-bromoethylbutanoate (2969-81-5) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → 4-{4-[1-(4-{1-[4-(3-ethoxycarbonyl-propoxy)-phenyl]-1-methyl-ethyl}-phenyl)-1-methyl-ethyl]-phenoxy}-butyric acid ethyl ester (153775-72-5)

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;	85%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + subphthalocyanine (36530-06-0) → (B(N6C24H12))2O2C6H4C(CH3)2C6H4C(CH3)2C6H4

Conditions	Yield
In 1,2-dichloro-benzene at 180.5℃; for 39h; Inert atmosphere;	85%
In 1,2-dichloro-benzene (Ar) chloro boron subphthalocyanine and bisphenol in 1,2-dichlorobenzenewere heated at reflux (180.5°C) for 39 h; react. mixt. was cooled, solvent was totary evapd., purification from hot toluene;	85%

4-Nitrophthalonitrile (31643-49-9) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → 4,4′-bis[1,3-propylbenzene-2-p-phenoxy]phthalonitrile

Conditions	Yield
With potassium carbonate In acetonitrile at 90℃; for 72h; Inert atmosphere;	84.44%
With potassium carbonate In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere;	83.9%

1,8-dibromooctane (4549-32-0) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → C40H56Br2O2

Conditions	Yield
With potassium carbonate In acetone for 5h; Heating;	84%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + 3-chloromethylpyridinium chloride (6959-48-4) → C36H36N2O2 (1020725-72-7)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In benzene at 80℃; for 48h;	82%

1,7-dibromoheptane (4549-31-9) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → C38H52Br2O2 (927403-48-3)

Conditions	Yield
With potassium carbonate In acetone for 5h; Heating;	81%

1,5-dibromo-pentane (111-24-0) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → α,α'-bis[(5-bromopentoxy)phenyl]-1,4-di(isopropyl)benzene (182318-36-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;	80%
With potassium carbonate In water; acetone for 48h; Heating;	71%
With potassium carbonate In water; acetone	65%
Stage #1: 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol With potassium carbonate In acetonitrile for 1.5h; Reflux; Stage #2: 1,5-dibromo-pentane In [D3]acetonitrile for 30h; Reflux;	60%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + 2-chloromethylpyridine hydrochloride (6959-47-3) → C36H36N2O2 (1020725-67-0)

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

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + Hexafluoroacetone (684-16-2) → C27H20F18O4 (1422464-20-7)

Conditions	Yield
With methanesulfonic acid at 20 - 55℃; for 8h; Autoclave;	80%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + acetic anhydride (108-24-7) → C26H28O3 (1107651-70-6)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 1.75h; Inert atmosphere;	72%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + α,α'-di[(3-bromo-1-propoxy)phenyl]-1,4-diisopropylbenzene → C54H60O4 (199340-65-3)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 120h;	71%

3-iodopropyl methyl diisopropoxy silane (515136-37-5) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → C44H70O6Si2

Conditions	Yield
Stage #1: 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol With potassium isopropoxide In isopropyl alcohol at 20℃; Stage #2: 3-iodopropyl methyl diisopropoxy silane In N,N-dimethyl-formamide at 70℃; for 1h; Stage #3: With potassium iodide In N,N-dimethyl-formamide at 25℃; for 1h;	70%

2-chloropyrazin (14508-49-7) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → C32H30N4O2 (1020725-52-3)

Conditions	Yield
Stage #1: 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol With potassium carbonate In sulfolane; toluene at 20℃; for 0.75h; Stage #2: 2-chloropyrazin at 80℃; for 48h; Further stages.;	69%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + 4-picolylchloride hydrochloride (1822-51-1) → C36H36N2O2 (1020725-77-2)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In benzene at 80℃; for 48h;	68%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + 1,4-dichlorobutane (110-56-5) → C32H40Cl2O2

Conditions	Yield
With sodium hydroxide In butan-1-ol	66%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + triphenylacetyl chloride (6068-70-8) + 11'-(tert-butyl)-5',17',23',35',38',40'43',45'-octamethyldispiro[cyclohexane-1,2'-[7,15,25,33]tetraazaheptacyclo[32.2.2.2.2(3,6).2(16,19).2(21,24).1(3,13).1(27,31)]hexatetraconta[3,5,9,11,13(44),16,18,21,23,27,29,31(39),34,36,37,40,42,45]octadecaene..]. (169179-44-6) → C64H72N4O4*C64H54O4

Conditions	Yield
With dibenzo-18-crown-6; potassium carbonate In dichloromethane at 20℃; for 168h; Acylation; Threading synthesis;	65%

formaldehyd (50-00-0) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + dimethyl amine (124-40-3) → 2,5,2',5'-tetra(dimethylaminemethylene)-α,α'-bis(4-hydroxyphenyl)-1,4-diisopropylbenzene (912474-61-4)

Conditions	Yield
In ethanol; water for 3h; Mannich reaction; Heating;	63%

bromocyane (506-68-3) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → 1,4-bis(2-(4-cyanatophenyl)propan-2-yl)benzene (133685-37-7)

Conditions	Yield
With triethylamine In acetone at -5 - 20℃; for 2h;	63%

ethyl bromide (74-96-4) + 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) → α,α'-bis(4-ethoxyphenyl)-1,4-di(isopropyl)benzene

Conditions	Yield
With potassium carbonate In acetone Heating;	62%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + 1,3-dibromo-propane (109-64-8) → α,α'-di[(3-bromo-1-propoxy)phenyl]-1,4-diisopropylbenzene

Conditions	Yield
Stage #1: 4,4'-(1,4-phenylene-diisopropylidene)-bisphenol With potassium carbonate In acetonitrile for 1.5h; Reflux; Stage #2: 1,3-dibromo-propane In [D3]acetonitrile for 30h; Reflux;	61%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + tri(p-bromomethylphenyl)phosphane oxide (1107651-69-3) → C69H67O5P + C114H108O8P2 + C228H216O16P4

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃; for 60h; Inert atmosphere;	A 1% B 58% C 8%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + propyl bromide (106-94-5) → α,α'-bis(4-propyloxyphenyl)-1,4-di(isopropyl)benzene

Conditions	Yield
With potassium carbonate In acetone Heating;	55%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + propargyl bromide (106-96-7) → [1,4-C6H4(CMe2-4-C6H4OCH2CCH)2] (134127-88-1)

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;	48%

4,4'-(1,4-phenylene-diisopropylidene)-bisphenol (2167-51-3) + 2,6-di-tert-butyl-4-methylphenoxydichlorophosphine (789-54-8) → C78H94O6P2

Conditions	Yield
With triethylamine In toluene at 25℃; for 24h;	46%

Upstream product

• 2948-46-1 α,α,α',α'-tetramethyl-1,4-benzenedimethanol 
• 108-95-2 phenol 

Downstream Products

• 182318-36-1 α,α'-bis[(5-bromopentoxy)phenyl]-1,4-di(isopropyl)benzene 
• 153775-72-5 4-{4-[1-(4-{1-[4-(3-ethoxycarbonyl-propoxy)-phenyl]-1-methyl-ethyl}-phenyl)-1-methyl-ethyl]-phenoxy}-butyric acid ethyl ester 
• 625084-41-5 α,α'-di[(4-bromo-1-butoxy)phenyl]-1,4-diisopropylbenzene 

Relevant articles and documents

Synthesis and evaluation of new ditopic cyclophane receptors for benzoic acid

As potential receptors for a benzoic acid guest, new ditopic cyclophane host molecules, each with a π electron-rich portion and a pyridine ring-containing portion, are synthesized. Complexation of benzoic acid guest by the potential molecular receptors is probed by infrared spectroscopy, proton magnetic resonance titration experiments and solid-state structure determination. Copyright

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.

Bischoloroformate preparation method with phosgene removal and monochloroformate conversion

Aqueous bischloroformates are prepared by the reaction of a dihydroxyaromatic compound (e.g., bisphenol A) with phosgene in a substantially inert organic liquid (e.g., methylene chloride) and in the presence of an aqueous alkali metal or alkaline earth metal base, at a pH below about 8. After all solid dihydroxyaromatic compound has been consumed, the pH is raised to a higher value in the range of about 7-12, preferably 9-11, and maintained in said range until a major proportion of the unreacted phosgene has been hydrolyzed. At the same time, any monochloroformate in the product may be converted to bischloroformate.