Phenol,4,4'-methylenebis[2,6-dimethyl]- supplier

Name
4,4'-METHYLENEBIS(2,6-DIMETHYLPHENOL)
EINECS 226-378-9
CAS No. 5384-21-4
Article Data48
CAS DataBase
Density 1.11 g/cm³
Solubility 100mg/L at 25℃
Melting Point 176 °C
Formula C₁₇H₂₀O₂
Boiling Point 414.7 °C at 760 mmHg
Molecular Weight 256.345
Flash Point 193.6 °C
Transport Information
Appearance Crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,6-Xylenol,4,4'-methylenedi- (6CI,7CI,8CI);3,3',5,5'-Tetramethyl-4,4'-dihydroxydiphenylmethane;4,4'-Dihydroxy-3,3',5,5'-tetramethyldiphenylmethane;4,4'-Methylenebis(2,6-dimethylphenol);4,4'-Methylenebis[2,6-xylenol];4,4'-Methylenedi-2,6-xylenol;Bis(3,5-dimethyl-4-hydroxyphenyl)methane;Bis(4-hydroxy-3,5-dimethylphenyl)methane;Desoxon M;NSC 128403;TMBPF;
PSA 40.46000
LogP 3.92220

Synthetic route

: 50-00-0
formaldehyd

: 576-26-1
2.6-dimethylphenol

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With silica supported perchloric acid In neat (no solvent) for 4.25h; Catalytic behavior; Reagent/catalyst; Solvent; Heating; Green chemistry;	94%
With hydrogenchloride In light petroleum; water at 27℃;	93%
With hydrogenchloride In Petroleum ether at 27℃; for 2.75h;	93%

: 4397-14-2
4-(hydroxymethyl)-2,6-dimethylphenol

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With proton exchanged montmorillonite In dichloromethane at 25℃; for 0.5h;	94%
at 140 - 155℃;
at 180℃; under 1 Torr;
With hydrogenchloride
Multi-step reaction with 2 steps 1: benzene / 50 °C / Einleiten von HBr 2: SnCl2; glacial acetic acid; water View Scheme

: 71655-87-3
4,4'-(oxybis(methylene))bis(2,6-dimethylphenol)

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With proton exchanged montmorillonite In dichloromethane at 25℃; for 0.25h;	86%

: 527-60-6
Mesitol

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With ammonium acetate; potassium hexacyanoferrate(III) In methanol; water at 45℃; for 240h;	55%
Multi-step reaction with 2 steps 1: aq. (KO3S)2NO, NaOAc / acetone 2: aq. HCl View Scheme

: 50-00-0
formaldehyd

: 576-26-1
2.6-dimethylphenol

A: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

B: 4397-14-2
4-(hydroxymethyl)-2,6-dimethylphenol

Conditions

Conditions	Yield
With sodium hydroxide for 18h; Ambient temperature; Yields of byproduct given;	A n/a B 52%

...Expand

: 576-26-1
2.6-dimethylphenol

: 75-09-2
dichloromethane

A: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

B: 3698-40-6
4-hydroxy-3,5,2',6'-tetramethyldiphenyl ether

C: 6204-16-6
4,4',4"-trihydroxy-3,3',3",5,5',5"-hexamethyltriphenylmethane

Conditions

Conditions	Yield
at 15℃; for 48h; Irradiation;	A 0.7% B 0.3% C 1.7%

...Expand

: 576-26-1
2.6-dimethylphenol

A: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

B: 3698-40-6
4-hydroxy-3,5,2',6'-tetramethyldiphenyl ether

C: 6204-16-6
4,4',4"-trihydroxy-3,3',3",5,5',5"-hexamethyltriphenylmethane

Conditions

Conditions	Yield
With dichloromethane at 15℃; for 48h; Irradiation;	A 0.7% B 0.3% C 1.7%

...Expand

: 64-17-5
ethanol

: 45952-56-5
3,5-dimethyl-4-hydroxybenzyl bromide

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 576-26-1
2.6-dimethylphenol

: 100-97-0
hexamethylenetetramine

A: 527-60-6
Mesitol

B: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With water

...Expand

: 576-26-1
2.6-dimethylphenol

: 100-97-0
hexamethylenetetramine

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
at 165℃;
at 165℃;
at 130℃; for 3h;

: 45952-56-5
3,5-dimethyl-4-hydroxybenzyl bromide

: 141-52-6
sodium ethanolate

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 45952-56-5
3,5-dimethyl-4-hydroxybenzyl bromide

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With methanol; ethanol; water; sodium ethanolate weitere Reagenzien: wss. Aceton, wss. NaOH;
With water; acetic acid; tin(ll) chloride

: 92005-15-7
4,4'-dihydroxy-3,3',5,5'-tetramethylbenzophenone

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With hydrogenchloride; amalgamated zinc

: 527-60-6
Mesitol

: 94-36-0
dibenzoyl peroxide

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
ohne Loesungsmittel;

: 576-26-1
2.6-dimethylphenol

: 7205-91-6
phenylthiomethyl chloride

A: 527-60-6
Mesitol

B: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With tin(IV) chloride; nickel 1.) CH2Cl2, room temp., 1 h, 2.) acetone, ethanol, room temp., 1 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 875-83-2
sodium 2-naphtholate

: 90466-00-5
(Z)-N-nitroso-2,6-dimethyl-4-(methylaminomethyl)phenol

A: 93-04-9
2-Methoxynaphthalene

B: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

C: 1-(4-hydroxy-3,5-dimethylbenzyl)-2-naphthol

D: 1-(4-hydroxy-3,5-dimethylbenzyl)-2-methoxynaphthalene

Conditions

Conditions	Yield
With potassium hydroxide In water at 100℃; for 2h; Further byproducts given;	A 17 mg B n/a C 161 mg D 67.0 mg

...Expand

: 90466-00-5
(Z)-N-nitroso-2,6-dimethyl-4-(methylaminomethyl)phenol

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol for 4.5h; Heating; also with carbonate buffer pH 10, other substrates;	60.5 mg

: 42900-97-0
1-<(4-Hydroxy-3,5-dimethyl-phenyl)-methyl>-piperidin

NaOH-solution , diluted: NaOH-solution , diluted

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 576-26-1
2.6-dimethylphenol

: 100-97-0
hexamethylenetetramine

: 7732-18-5
water

A: 527-60-6
Mesitol

B: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

...Expand

N-<4-oxy-3.5-dimethyl-benzyl>-piperidine: N-<4-oxy-3.5-dimethyl-benzyl>-piperidine

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With sodium hydroxide

: 527-60-6
Mesitol

: 7722-84-1
dihydrogen peroxide

: iron(II) sulfate

: 64-19-7
acetic acid

A: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

B 3,5,3',5'-tetramethyl-biphenyl-2,4'-diol: 3,5,3',5'-tetramethyl-biphenyl-2,4'-diol

...Expand

: 527-60-6
Mesitol

A: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

B phenol 19 and polymeric forms: phenol 19 and polymeric forms

Conditions

Conditions	Yield
With ammonium acetate; potassium hexacyanoferrate(III) In methanol; water at 45℃; for 240h; Mechanism; Product distribution; other oxidizing agent; other phenols;

: 4397-14-2
4-(hydroxymethyl)-2,6-dimethylphenol

A: 50-00-0
formaldehyd

B: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

C: 71655-87-3
4,4'-(oxybis(methylene))bis(2,6-dimethylphenol)

D: 7732-18-5
water

Conditions

Conditions	Yield
at 140 - 155℃;

...Expand

: 45952-56-5
3,5-dimethyl-4-hydroxybenzyl bromide

: 7732-18-5
water

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 45952-56-5
3,5-dimethyl-4-hydroxybenzyl bromide

aqueous NaOH: aqueous NaOH

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 45952-56-5
3,5-dimethyl-4-hydroxybenzyl bromide

: 64-19-7
acetic acid

SnCl2: SnCl2

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

...Expand

: 576-26-1
2.6-dimethylphenol

: 41763-16-0
tris-(4-hydroxy-3,5-dimethyl-benzyl)-amine

of sulfate of tris-<4-hydroxy-3.5-dimethyl-benzyl>-amine: of sulfate of tris-<4-hydroxy-3.5-dimethyl-benzyl>-amine

sodium carbonate: sodium carbonate

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
at 160℃;

...Expand

: 107140-21-6
2,6-dimethyl-4-(3,5-dimethyl-4-hydroxybenzylidene)-2,5-cyclohexadien-1-one

: 64-19-7
acetic acid

zinc: zinc

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

...Expand

: N-methyl-4-benzoyloxy-3,5-dimethylbenzylammonium chloride

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq.NaNO2, glac.AcOH / 5 h 2: n-PrNH2 / 24 h / Heating 3: KOH / H2O / 2 h / 100 °C View Scheme

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 65962-45-0
2,2′,6,6′-tetramethyl-4,4′-methylenebis(cyclohexylamine)

Conditions

Conditions	Yield
With ammonia; Ni-Cr-Ba-Zn	96.9%
With ammonia; Ni-Cr-Al-Cu In hydrogen

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 51762-67-5
3-nitrobenzene-1,2-dicarbonitrile

: C33H24N4O2

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 24h;	95%

: [V(N-2,6-Me2C6H3)(CH2SiMe3)3]

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: C49H80N2O2Si4V2

Conditions

Conditions	Yield
In toluene at -5 - 20℃; for 12h; Inert atmosphere;	87%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 107140-21-6
2,6-dimethyl-4-(3,5-dimethyl-4-hydroxybenzylidene)-2,5-cyclohexadien-1-one

Conditions

Conditions	Yield
With silver(l) oxide In diethyl ether at 20℃; for 12h; Inert atmosphere;	86%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 546-67-8
lead(IV) tetraacetate

: bis-(3,5-dimethyl-3-acethoxy-4-oxocyclohexa-1,5-dienyl)methane

Conditions

Conditions	Yield
In ethyl acetate at 27℃; for 0.75h;	82%
In benzene at 27℃; for 1h;	45%
In toluene at 27℃;	45%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 106-89-8
epichlorohydrin

: 93705-66-9
4,4’-methylenebis(2,6-dimethylphenol) diglycidyl ether

Conditions

Conditions	Yield
Stage #1: bis(4-hydroxy-3,5-dimethylphenyl)methane; epichlorohydrin In isopropyl alcohol at 80℃; Stage #2: With sodium hydroxide In water; isopropyl alcohol at 80℃; for 2h;	60%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 18162-48-6
tert-butyldimethylsilyl chloride

: 4-(4-(tert-butyldimethylsilyloxy)-3,5-dimethylbenzyl)-2,6-dimethylphenol

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 50℃; for 48h; Inert atmosphere;	53%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 106-95-6
allyl bromide

: 4-(4-(allyloxy)-3,5-dimethylbenzyl)-2,6-dimethylphenol

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	52%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	28%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 108-24-7
acetic anhydride

: bis(4-acethoxy-3,5-dimethylphenyl)methyl acetate

Conditions

Conditions	Yield
With sodium periodate at 75 - 80℃; for 5h;	51.28%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 74-88-4
methyl iodide

: 2,6-dimethyl-4-[(4'-methoxy-3',5'-dimethylphenyl)methyl]phenol

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	50%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

A: 2423-71-4
2,6-dimethyl-4-nitro phenol

B: 527-61-7
2,6-dimethyl-1,4-benzoquinone

Conditions

Conditions	Yield
With sulfuric acid; nitric acid In nitromethane at 2℃; for 1h; Product distribution;	A 22% B 41%

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 637-61-6
benzoquinone N-chloroimine

: 30128-02-0
2,6-dimethyl-[1,4]benzoquinone-4-(4-hydroxy-phenylimine)

Conditions

Conditions	Yield
With sodium hydroxide; sodium chloride

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 59079-37-7
2,6,2',6'-tetramethyl-4,4'-methanediyl-bis-cyclohexanol

Conditions

Conditions	Yield
With acetic acid; platinum Hydrogenation;

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 1125-51-5
dibromo-3,4 dimethylphenol-2,6

Conditions

Conditions	Yield
With bromine; acetic acid

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 64-19-7
acetic acid

: 1125-51-5
dibromo-3,4 dimethylphenol-2,6

Conditions

Conditions	Yield
bei der Bromierung;

: 5384-21-4
bis(4-hydroxy-3,5-dimethylphenyl)methane

: 77-78-1
dimethyl sulfate

A: 16271-22-0
3,3',5,5'-Tetramethyl-4,4'-dimethoxydiphenylmethane

B: 2,6-dimethyl-4-[(4'-methoxy-3',5'-dimethylphenyl)methyl]phenol

...Expand

Phenol,4,4'-methylenebis[2,6-dimethyl]- Specification

The Phenol,4,4'-methylenebis[2,6-dimethyl]-, with the CAS registry number 5384-21-4, is also known as Bis(3,5-dimethyl-4-hydroxyphenyl)methane. Its EINECS number is 226-378-9 and its systematic name is 4,4'-Methanediylbis(2,6-dimethylphenol). This chemical's molecular formula is C₁₇H₂₀O₂ and molecular weight is 256.34. What's more, it belongs to the product categories of Diphenylmethanes (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research. The product is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place.

Physical properties of Phenol,4,4'-methylenebis[2,6-dimethyl]- are: (1)ACD/LogP: 4.58; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.57; (4)ACD/LogD (pH 7.4): 4.57; (5)ACD/BCF (pH 5.5): 1765.06; (6)ACD/BCF (pH 7.4): 1763.39; (7)ACD/KOC (pH 5.5): 7338.83; (8)ACD/KOC (pH 7.4): 7331.85; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 18.46 Å²; (13)Index of Refraction: 1.596; (14)Molar Refractivity: 78.63 cm³; (15)Molar Volume: 230.7 cm³; (16)Polarizability: 31.17×10^-24cm³; (17)Surface Tension: 45.3 dyne/cm; (18)Density: 1.11 g/cm³; (19)Flash Point: 193.6 °C; (20)Enthalpy of Vaporization: 69.36 kJ/mol; (21)Boiling Point: 414.7 °C at 760 mmHg; (22)Vapour Pressure: 1.81E-07 mmHg at 25°C; (23)XLogP3-AA: 4.6; (24)Rotatable Bond Count: 2; (25)Tautomer Count: 3; (26)Topological Polar Surface Area: 40.5; (27)Heavy Atom Count: 19; (28)Complexity: 239; (29)Covalently-Bonded Unit Count: 1.

Preparation: this chemical can be prepared by 2,4,6-trimethyl-phenol at the temperature of 45 °C. This reaction will need reagents ammonium acetate, potassium ferricyanide and solvent H₂O with the reaction time of 10 days. The yield is about 55%.

Phenol,4,4'-methylenebis[2,6-dimethyl- can be prepared by 2,4,6-trimethyl-phenol at the temperature of 45 °C

Uses of Phenol,4,4'-methylenebis[2,6-dimethyl-]: it can be used to produce 2,6-dimethyl-[1,4]benzoquinone at the temperature of 2 °C. It will need reagent conc. HNO₃ or conc. H₂SO₄ and solvent nitromethane with the reaction time of 1 hour. The yield is about 22%.

Phenol,4,4'-methylenebis[2,6-dimethyl- can be used to produce 2,6-dimethyl-[1,4]benzoquinone at the temperature of 2 °C

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=CC(=CC(=C1O)C)CC2=CC(=C(C(=C2)C)O)C
(2)InChI: InChI=1S/C17H20O2/c1-10-5-14(6-11(2)16(10)18)9-15-7-12(3)17(19)13(4)8-15/h5-8,18-19H,9H2,1-4H3
(3)InChIKey: AZZWZMUXHALBCQ-UHFFFAOYSA-N

Product Name

4,4'-METHYLENEBIS(2,6-DIMETHYLPHENOL)

Synthetic route

Phenol,4,4'-methylenebis[2,6-dimethyl]- Specification

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