35752-78-4

Basic information

• Product Name: Phenol, 4,4'-[(1E)-1-Methyl-1,2-ethenediyl]bis-
• Synonyms: Phenol, 4,4'-[(1E)-1-Methyl-1,2-ethenediyl]bis-;trans-4,4'-dihydroxy-α-methylstilbene;4,4-Dihydroxy-trans-±-methylstilbene
• CAS NO: 35752-78-4
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.27046
• Mol File: 35752-78-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 372.9±22.0 °C(Predicted)
• Appearance: /
• Density: 1.194±0.06 g/cm3(Predicted)
• PKA: 10.20±0.26(Predicted)
• CAS DataBase Reference: Phenol, 4,4'-[(1E)-1-Methyl-1,2-ethenediyl]bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 4,4'-[(1E)-1-Methyl-1,2-ethenediyl]bis-(35752-78-4)
• EPA Substance Registry System: Phenol, 4,4'-[(1E)-1-Methyl-1,2-ethenediyl]bis-(35752-78-4)

Safety Data

• Hazardous Substances Data: 35752-78-4(Hazardous Substances Data)

Usage

Uses

4,4''-Dihydroxy-trans-α-methylstilbene is an intermediate used to synthesize thermotropic liquid crystalline polymers.

Synthetic route

1,2-bis-(4-methoxy-phenyl)-propan-2-ol (79755-06-9) → trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4)

Conditions	Yield
Stage #1: 1,2-bis-(4-methoxy-phenyl)-propan-2-ol With boron tribromide In dichloromethane at -78 - 0℃; Inert atmosphere; Stage #2: With water In dichloromethane at 0℃;	51%
Multi-step reaction with 2 steps 1: KHSO4 / 190 °C 2: ethanolic KOH / 190 °C View Scheme

chloroacetone (78-95-5) + phenol (108-95-2) → trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4)

Conditions	Yield
sulfuric acid at -10℃;	15%
With sulfuric acid
With sulfuric acid In ethanol; dichloromethane; water
With sodium hydroxide; methanesulfonic acid In dichloromethane; water; isopropyl alcohol
With sulfuric acid In ethanol; dichloromethane; water

(E)-1,2-bis(4-methoxyphenyl)prop-1-ene (5912-84-5) → trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4)

Conditions	Yield
With potassium hydroxide at 190℃;
With pyridine hydrochloride Heating;

1,4-di(4-methoxyphenyl)ethanone (120-44-5) → trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether 2: KHSO4 / 190 °C 3: ethanolic KOH / 190 °C View Scheme

1,2-bis(4-hydroxyphenyl)-2-hydroxypropane (154928-56-0) → cis-4,4'-dihydroxy-α-methylstilbene + trans-1,2,4,5-tetrakis(4-hydroxyphenyl)-4-methylpentene + cis-1,2,4,5-tetrakis(4-hydroxyphenyl)-4-methylpentene + 2,3-bis(4-hydroxyphenyl)propene + trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4)

Conditions	Yield
In water; isopropyl alcohol at 50℃; for 63h;
sodium hydrogen sulfate In water; isopropyl alcohol at 50℃; for 63h;

4-methyl-pent-3-en-2-one (141-79-7) + 1,1-Dichloroacetone (513-88-2) + chloroacetone (78-95-5) + phenol (108-95-2) → trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4)

Conditions	Yield
With sulfuric acid In ethanol; dichloromethane; water; acetone

1,1-Dichloroacetone (513-88-2) + chloroacetone (78-95-5) + 1,3-Dichloroacetone (534-07-6) + phenol (108-95-2) → trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4)

Conditions	Yield
With sulfuric acid In ethanol; dichloromethane; water; acetone
With sulfuric acid In ethanol; water; acetone

1,2-dibromo-1,1,2,2-tetrafluoroethane (124-73-2) + trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) → 4,4'-Bis(2-bromotetrafluoroethoxy)-α-methylstilbene

Conditions	Yield
Stage #1: trans-4,4'-dihydroxy-α-methylstilbene With potassium hydroxide In dimethyl sulfoxide; xylene Metallation; Stage #2: 1,2-dibromo-1,1,2,2-tetrafluoroethane at 10℃; for 12h; Substitution;	50%

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) → 1c,2-bis-(4-propoxy-phenyl)-propene (36931-03-0)

Conditions	Yield
With 1-iodo-propane

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) → 4,4'-diallyloxy-α-methylstilbene

Conditions	Yield
With allyl iodid

n-tridecanoyl chloride (17746-06-4) + trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) → Tridecanoic acid 4-[(E)-1-methyl-2-(4-tridecanoyloxy-phenyl)-vinyl]-phenyl ester

pentadecanoyl chloride (17746-08-6) + trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) → Pentadecanoic acid 4-[(E)-1-methyl-2-(4-pentadecanoyloxy-phenyl)-vinyl]-phenyl ester

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + n-valeryl chloride (638-29-9) → Pentanoic acid 4-[(E)-1-methyl-2-(4-pentanoyloxy-phenyl)-vinyl]-phenyl ester

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + Hexanoyl chloride (142-61-0) → Hexanoic acid 3-[(E)-2-(4-hexanoyloxy-phenyl)-1-methyl-vinyl]-phenyl ester

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + n-decanoyl chloride (112-13-0) → Decanoic acid 4-[(E)-2-(4-decanoyloxy-phenyl)-1-methyl-vinyl]-phenyl ester

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + acetyl chloride (75-36-5) → 1c.2-bis-(4-acetoxy-phenyl)-propene-(1) (65224-13-7)

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + butyryl chloride (141-75-3) → bis-n-butanoyloxy(1,4-phenylene, methylvinylene-1,4-phenylene)

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + Heptanoic acid chloride (2528-61-2) → Heptanoic acid 3-[(E)-2-(4-heptanoyloxy-phenyl)-1-methyl-vinyl]-phenyl ester

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + n-octanoic acid chloride (111-64-8) → Octanoic acid 4-[(E)-1-methyl-2-(4-octanoyloxy-phenyl)-vinyl]-phenyl ester

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + tetradecanoyl chloride (112-64-1) → Tetradecanoic acid 4-[(E)-1-methyl-2-(4-tetradecanoyloxy-phenyl)-vinyl]-phenyl ester

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid 4-[(E)-2-(4-hexadecanoyloxy-phenyl)-1-methyl-vinyl]-phenyl ester

trans-4,4'-dihydroxy-α-methylstilbene (35752-78-4) → 4,4'-Bis(trifluorovinyloxy)-α-methylstilbene (225243-38-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: KOH / dimethylsulfoxide; xylene 1.2: 50 percent / 12 h / 10 °C 2.1: 58 percent / Zn / acetonitrile / 18 h / Heating View Scheme

Upstream product

• 5912-84-5 (E)-1,2-bis(4-methoxyphenyl)prop-1-ene 
• 513-88-2 1,1-Dichloroacetone 
• 78-95-5 chloroacetone 
• 534-07-6 1,3-Dichloroacetone 
• 108-95-2 phenol 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 154928-56-0 1,2-bis(4-hydroxyphenyl)-2-hydroxypropane 
• 79755-06-9 1,2-bis-(4-methoxy-phenyl)-propan-2-ol 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 

Downstream Products

• 36931-01-8 1c,2-bis-(4-ethoxy-phenyl)-propene 
• 65224-13-7 1c.2-bis-(4-acetoxy-phenyl)-propene-⁽¹⁾ 
• 225243-38-9 4,4'-Bis(trifluorovinyloxy)-α-methylstilbene 
• 5912-84-5 (E)-1,2-bis(4-methoxyphenyl)prop-1-ene 
• 124141-05-5 1c,2-bis-[4-(2-trimethylammonio-ethoxy)-phenyl]-propene; diiodide 
• 65224-14-8 1c,2-bis-(4-propionyloxy-phenyl)-propene 
• 36931-03-0 1c,2-bis-(4-propoxy-phenyl)-propene 

Relevant articles and documents

Bibenzyl- and stilbene-core compounds with non-polar linker atom substituents as selective ligands for estrogen receptor beta

A series of structurally simple bibenzyl-diol and stilbene-diol core molecules, structural analogs of the well-known hexestrol and diethylstilbestrol non-steroidal estrogens, were prepared and evaluated as estrogen receptor (ER) subtype-selective ligands. Analysis of their ERα and ERβ binding showed that certain substitution patterns engendered binding affinities that were >100-fold selective for ERβ. When further investigated in cell-based gene transcription assays, some molecules showed similarly high relative transcriptional potency selectivity in favor of ERβ. Interestingly, the most ERβ-selective molecules were those bearing non-polar substituents on one of the internal carbon atoms. These compounds should be useful probes for determining the physiological roles of ERβ, and they might lead to the development of more selective and thus safer pharmaceuticals.

Preparation of 4,4'-dihydroxy-'alkylstiblbene with reduced dimer formation

Preparation of dihydroxy-α-alkylstilbenes with reduced undesirable by-products can be achieved by carrying out dehydrohalogenation of a substantially uniform dispersion of a halogenated intermediate of the desired product in the presence of water and a polar protic solvent.

Diglycidyl ether of 4,4'-dihydroxy-α-methylstilbene

The diglycidyl ether of 4,4'-dihydroxy-α-methylstilbene is prepared.