2167-51-3

Usage

Uses

Used in Industrial Applications:
ALPHA,ALPHA'-BIS(4-HYDROXYPHENYL)-1,4-DIISOPROPYLBENZENE is used as a chemical intermediate for the synthesis of various compounds in industrial processes. Its moderate polarity and stability contribute to its utility in the production of specialty chemicals and materials.
Used in Scientific Research:
ALPHA,ALPHA'-BIS(4-HYDROXYPHENYL)-1,4-DIISOPROPYLBENZENE is used as a research compound in the study of aryl chemistry, particularly in understanding the properties and interactions of compounds with similar structures. Its potential applications in the development of new materials or chemical processes are being explored in scientific research.

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 
• 134127-88-1 [1,4-C₆H₄(CMe₂-4-C₆H₄OCH₂CCH)2] 
• 927403-48-3 C₃₈H₅₂Br₂O₂ 
• 153775-76-9 4-{4-[1-(4-{1-[4-(3-chlorocarbonyl-propoxy)-phenyl]-1-methyl-ethyl}-phenyl)-1-methyl-ethyl]-phenoxy}-butyryl chloride 
• 153775-74-7 4-{4-[1-(4-{1-[4-(3-carboxy-propoxy)-phenyl]-1-methyl-ethyl}-phenyl)-1-methyl-ethyl]-phenoxy}-butyric acid 
• 182318-38-3 3-{4-[1-(4-{1-[4-(3-Mercapto-propoxy)-phenyl]-1-methyl-ethyl}-phenyl)-1-methyl-ethyl]-phenoxy}-propane-1-thiol 
• 182318-40-7 4-{4-[1-(4-{1-[4-(4-Mercapto-butoxy)-phenyl]-1-methyl-ethyl}-phenyl)-1-methyl-ethyl]-phenoxy}-butane-1-thiol 
• 182318-42-9 5-{4-[1-(4-{1-[4-(5-Mercapto-pentyloxy)-phenyl]-1-methyl-ethyl}-phenyl)-1-methyl-ethyl]-phenoxy}-pentane-1-thiol 

Relevant academic research and scientific papers

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

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.

Method for preparing aromatic bischloroformate compositions

Bischloroformate oligomer compositions are prepared by passing phosgene into a heterogeneous aqueous-organic mixture containing at least one dihydroxyaromatic compound, with simultaneous introduction of a base at a rate to maintain a specific pH range and to produce a specific volume ratio of aqueous to organic phase. By this method, it is possible to employ a minimum amount of phosgene. The reaction may be conducted batchwise or continuously. The bischloroformate composition may be employed for the preparation of cyclic polycarbonate oligomers or linear polycarbonate, and linear polycarbonate formation may be integrated with bischloroformate composition formation in a batch or continuous process.

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.

Cyclic monocarbonate bishaloformates

Cyclic monocarbonate bischloroformates are prepared by the reaction of a carbonyl halide such as phosgene with a bridged substituted resorcinol or hydroquinone such as bis(2,4-dihydroxy-3-methylphenyl)methane or bis(2,5-dihydroxy-3,4,6-trimethylphenyl)methane in the presence of aqueous alkali metal hydroxide. The cyclic monocarbonate bischloroformates may be used for the preparation of linear or cyclic polycarbonates containing cyclic carbonate structural units, which may in turn be converted to crosslinked polycarbonates.

Polyetherimide bisphenol compositions

Polyetherimide bisphenols and bischloroformates are prepared by the reaction of dianhydrides or certain bisimides with aminophenols or mixtures thereof with diamines. They are useful as intermediates for the preparation of cyclic heterocarbonates, which may in turn be converted to linear copolycarbonates. The bisphenols can also be converted to salts which react with cyclic polycarbonate oligomers to form block copolyetherimidecarbonates.