Phenol,2,2'-methylenebis- supplier

Name
2,2'-METHYLENEDIPHENOL
EINECS 219-578-2
CAS No. 2467-02-9
Article Data37
CAS DataBase
Density 1.208 g/cm³
Solubility
Melting Point 113-118 °C(lit.)
Formula C₁₃H₁₂O₂
Boiling Point 362.5 °C at 760 mmHg
Molecular Weight 200.237
Flash Point 177.1 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2,2'-Dihydroxydiphenylmethane;
PSA 40.46000
LogP 2.68860

Synthetic route

: 78563-03-8
5,5'-dibromo-2,2'-dihydroxy-diphenyl-methane

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With potassium hydroxide; zinc	80%
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 5h;	62%
With aluminum nickel

: 50-00-0
formaldehyd

: 108-95-2
phenol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 2467-03-0
2-[(4-hydroxyphenyl)methyl]phenol

C: 620-92-8
bis-(4-hydroxyphenyl)methane

Conditions

Conditions	Yield
Stage #1: phenol With catalyst with modified organic framework formed from chromium trioxide and phosphotungstic acid at 80℃; for 0.25h; Stage #2: formaldehyd In water at 80℃; for 0.5h; Concentration; Time; Temperature; Reagent/catalyst;	A 7.03% B 18.73% C 74.24%
Stage #1: phenol With catalyst with modified organic framework formed from ferric nitrate and phosphotungstic acid at 80℃; for 0.25h; Stage #2: formaldehyd In water at 80℃; for 4h; Concentration; Time; Temperature; Reagent/catalyst;	A 51.19% B 33.7% C 15.11%
Stage #1: phenol With catalyst with modified organic framework formed from ferric nitrate and phosphotungstic acid at 80℃; for 0.25h; Stage #2: formaldehyd In water at 80℃; for 0.5h; Concentration; Time; Temperature; Reagent/catalyst;	A 30.11% B 50.55% C 19.34%

...Expand

: 50-00-0
formaldehyd

: 108-95-2
phenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
Stage #1: phenol With calcium silicate composite catalyst at 90℃; for 0.0833333h; Inert atmosphere; Stage #2: formaldehyd In water at 110℃; for 2h; Concentration; Reagent/catalyst; Temperature; Inert atmosphere;	56.1%

: 132980-32-6
2-(1H-1,2,3-benzotriazol-1-ylmethyl)phenol

: 108-95-2
phenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With sodium t-butanolate In tert-butyl alcohol for 72h; Heating;	40%

: 92-83-1
xanthene

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With potassium hydroxide at 260℃;

: 71-41-0
pentan-1-ol

: 53007-43-5
3-chloro-2',6-dihydroxydiphenylmethane

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With sodium

: 71-41-0
pentan-1-ol

: 78563-03-8
5,5'-dibromo-2,2'-dihydroxy-diphenyl-methane

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With sodium

: 97-23-4
2,2'-methylenebis(4-chlorophenol)

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With aluminum nickel

: 835-11-0
2,2'-dihydroxybenzophenone

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With copper oxide-chromium oxide at 175℃; under 102971 Torr; Hydrogenation;

: 5419-53-4
4,6,4'-trichloro-2,2'-methanediyl-di-phenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With aluminum nickel

: 91805-67-3
4,6-dibromo-4'-chloro-2,2'-methanediyl-di-phenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With aluminum nickel

: 90-01-7
salicylic alcohol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 4481-52-1
bis-(2-hydroxybenzyl)-ether

Conditions

Conditions	Yield
at 250℃; for 0.5h;

: 50-00-0
formaldehyd

: 108-95-2
phenol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 94-67-7
salicylaldehyde-oxime

Conditions

Conditions	Yield
With hydroxylamine sulfate; magnesium methanolate 1.) MeOH, toluene, reflux, 2.) 95 deg C, 30 min, 3.) H2O, 55 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 108-95-2
phenol

: 18885-85-3
2-phenyl-4H-benzo-1,3,2-dioxaborine

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 2467-03-0
2-[(4-hydroxyphenyl)methyl]phenol

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane for 24h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 70-30-4
hexachlorophene

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With nickel

: 90-01-7
salicylic alcohol

: 612-16-8
(2-methoxyphenyl)methanol

: 67-63-0
isopropyl alcohol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 33316-78-8
2-[(isopropyloxy)methyl]phenol

C: 2467-03-0
2-[(4-hydroxyphenyl)methyl]phenol

D: 5819-93-2
2,2'-dimethoxydiphenylmethane

E: 30567-87-4
2,4'-dimethoxydiphenylmethane

F: o-(2-propoxymethyl)anisole

Conditions

Conditions	Yield
at 201.85℃; for 1h; Rate constant;	A 62 % Chromat. B 10 % Chromat. C 24 % Chromat. D n/a E n/a F 23 % Chromat.

...Expand

: 90-01-7
salicylic alcohol

: 108-95-2
phenol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 2467-03-0
2-[(4-hydroxyphenyl)methyl]phenol

C: 21243-69-6
2,2'-dihydroxy-3-(hydroxymethyl)diphenylmethane

Conditions

Conditions	Yield
at 150.85℃; for 1h; Rate constant;	A 50 % Chromat. B 31 % Chromat. C n/a

...Expand

: 108-88-3
toluene

: 108-95-2
phenol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 28994-41-4
o-Benzylphenol

C: 95-48-7
ortho-cresol

D xylols, cresols: xylols, cresols

Conditions

Conditions	Yield
zeolite CaY type at 300℃; for 0.4h; Product distribution; Mechanism; in the presence of HDPM and DHDPM;

...Expand

: 106-41-2
4-bromo-phenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2SO4 / 60 - 70 °C 2: sodium View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / methanol / 6 h / -10 - -5 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 25 °C View Scheme

: 4186-54-3
2-(bromomethyl)-4,6-dibromophenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: H2O; acetone 3: nickel-aluminium-alloy View Scheme

: 90-01-7
salicylic alcohol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4-chloro-phenol; concentrated aqueous HCl / 30 °C 2: sodium View Scheme

: 6641-02-7
3,5-dichloro-2-hydroxybenzyl alcohol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3 2: nickel-aluminium-alloy View Scheme

: 2183-54-2
2-hydroxy-3,5-dibromobenzenemethanol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: nickel-aluminium-alloy View Scheme

: 106-48-9
4-chloro-phenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3 2: nickel-aluminium-alloy View Scheme

: 95-95-4
2,4,5-trichlorophenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / methanol; H2O 2: Raney-Ni View Scheme

: 90-01-7
salicylic alcohol

: 108-95-2
phenol

: 2467-02-9
Bis(2-hydroxyphenyl)methane

Conditions

Conditions	Yield
With sulfuric acid at 100℃; for 17h;

: 13352-76-6
POMM5

: 108-95-2
phenol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 2467-03-0
2-[(4-hydroxyphenyl)methyl]phenol

C: 620-92-8
bis-(4-hydroxyphenyl)methane

Conditions

Conditions	Yield
With phosphoric acid In water at 80℃; for 4h; Overall yield = 74.8 %;

...Expand

: 13352-77-7
CH3-(OCH2)6-OCH3

: 108-95-2
phenol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 2467-03-0
2-[(4-hydroxyphenyl)methyl]phenol

C: 620-92-8
bis-(4-hydroxyphenyl)methane

Conditions

Conditions	Yield
With phosphoric acid In water at 80℃; for 4h; Overall yield = 66.2 %;

...Expand

: 13353-04-3
CH3-(OCH2)7-OCH3

: 108-95-2
phenol

A: 2467-02-9
Bis(2-hydroxyphenyl)methane

B: 2467-03-0
2-[(4-hydroxyphenyl)methyl]phenol

C: 620-92-8
bis-(4-hydroxyphenyl)methane

Conditions

Conditions	Yield
With phosphoric acid In water at 80℃; for 4h; Overall yield = 60.3 %;

...Expand

: 127-88-8
N,N-di(2-chloroethyl)amidophosphoric acid dichloride

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: Bis-(2-chloro-ethyl)-(6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-amine

Conditions

Conditions	Yield
With triethylamine In ethyl acetate at 34℃; for 2h;	89%

: 676-97-1
methylphosphonic acid dichloroanhydride

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 2-methyl-4,5;7,8-dibenzo-1,3,2λ5-dioxaphosphocine 2-oxide

Conditions

Conditions	Yield
With triethylamine In diethyl ether at -6℃; for 3h;	89%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 3385-78-2
trimethyl indium

: 1187925-68-3
[Me5In3)(2,2'-methylenediphenolate)2]

Conditions

Conditions	Yield
In methanol; diethyl ether byproducts: CH4; (N2); std. Schlenk technique; soln. of MeOH in Et2O was added to stirredsoln. of Me3In in Et2O at -76°C; warmed to room temp.; soln. of ligand in Et2O was added at -76°C; warmed to room temp.; cooled to 0°C; elem. anal.;	87%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 74-95-3
1,1-dibromomethane

: 256-48-4
12H-dibenzo<1,3>dioxocin

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide; butanone at 110℃; for 13h;	81%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 105-36-2
ethyl bromoacetate

: 824424-46-6
bis-(ethylphenoxy acetate)

Conditions

Conditions	Yield
With caesium carbonate In acetone Heating;	75%
With caesium carbonate In acetone Heating / reflux;	75%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 106-95-6
allyl bromide

: 71355-88-9
bis(2-allyloxyphenyl)-methane

Conditions

Conditions	Yield
With potassium carbonate In acetone for 5h; Reflux;	73%

: 75-77-4
chloro-trimethyl-silane

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: C19H28O2Si2

Conditions

Conditions	Yield
Stage #1: Bis(2-hydroxyphenyl)methane With n-butyllithium In tetrahydrofuran; cyclohexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: chloro-trimethyl-silane at 20℃; for 20h; Inert atmosphere;	71%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 4708-04-7
propylphosphonic dichloride

: 6-Propyl-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-oxide

Conditions

Conditions	Yield
With triethylamine In dichloromethane; toluene for 1h; Ambient temperature;	69%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 106-89-8
epichlorohydrin

: 54208-63-8
ortho,ortho-bisphenol F diglycidyl ether

Conditions

Conditions	Yield
Stage #1: Bis(2-hydroxyphenyl)methane With sodium hydride In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: epichlorohydrin In N,N-dimethyl-formamide at 20℃; for 42h; Inert atmosphere;	64%
With tetrabutylammomium bromide; potassium hydroxide	52%
With sodium hydroxide

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 777067-25-1
[(S,S)-bis(α-methylbenzyl)amino]phosphorous dichloride

: (S,S)-(CH2(C6H4O)2)PN(CH(CH3)Ph)2

Conditions

Conditions	Yield
Stage #1: Bis(2-hydroxyphenyl)methane With triethylamine In toluene at 23℃; for 0.0833333h; Inert atmosphere; Stage #2: [(S,S)-bis(α-methylbenzyl)amino]phosphorous dichloride In toluene at 23℃; for 6h; Inert atmosphere;	64%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: C14H21IrO4*H2O

: C33H38Ir2O2

Conditions

Conditions	Yield
In toluene at 100℃; for 14.5h; Inert atmosphere; Schlenk technique;	60%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 178056-86-5
1-phenylprop-2-yn-1-yl benzoate

: (Z)-6-benzylidene-7,13-dihydro-6H-dibenzo[e,h][1,4]dioxonine

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; BPPFA; caesium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Schlenk technique; Reflux; stereoselective reaction;	59%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

A: 97-23-4
2,2'-methylenebis(4-chlorophenol)

B: 1940-43-8
2,2'-methylenebis(4,6-dichlorophenol)

Conditions

Conditions	Yield
With sulfuryl dichloride; acetic acid	A 9% B 58%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

A: 1009647-10-2
C13H11BrO2

B: 78563-03-8
5,5'-dibromo-2,2'-dihydroxy-diphenyl-methane

Conditions

Conditions	Yield
With bromine; acetic acid In dichloromethane at 20℃; for 2h;	A 41% B 53%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

A: 133704-82-2
3-chloro-2,2'-dihydroxydiphenylmethane

B: 53007-43-5
3-chloro-2',6-dihydroxydiphenylmethane

Conditions

Conditions	Yield
With sulfuryl dichloride; acetic acid In dichloromethane	A 38% B 51%

: 37860-51-8
tetraethylene glycol di(p-toluenesulfonate)

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 85248-34-6
<18>5-(2,2')diphenylmethano-24-coronand-5>

Conditions

Conditions	Yield
With cesium fluoride In acetonitrile at 65℃; for 48h; under nitrogen;	49%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 113137-79-4
12H-Dibenzo<1,3,2>dioxathiocin 6-Oxide

Conditions

Conditions	Yield
With pyridine; thionyl chloride In diethyl ether 1) 2h, between -2 and 0 deg C, 2) 2h, without cooling;	47%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 41024-91-3
penta(ethylene glycol) bis(p-toluenesulfonate)

: 97990-42-6
<21>6(2,2')Diphenylmethano.25coronand-6>

Conditions

Conditions	Yield
With cesium fluoride In acetonitrile at 65℃; for 48h; under nitrogen;	45%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 52830-49-6
tris(2,6-dimethylphenyl) phosphite

: 128471-51-2
tris(2,6-dimethylphenoxy)phosphorane

Conditions

Conditions	Yield
With chloro-diisopropyl-amine In diethyl ether at 20℃; for 10h;	42%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 75-78-5
dimethylsilicon dichloride

: dimethylsilane

Conditions

Conditions	Yield
With triethylamine In toluene at 55℃; for 24h;	41.3%
With triethylamine

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 591-78-6
n-hexan-2-one

: 6-butyl-6-methyl-12H-dibenzo(d,g)(1,3)dioxocin

Conditions

Conditions	Yield
With indium(III) chloride for 0.5h;	40%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 16297-07-7
2,3,5,6-tetrafluoro-4-pyridinecarbonitrile

: C32H20N2O4

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 150℃; for 0.416667h;	34%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

A: C13H10Cl4N3O2P3

B: C13H10Cl4N3O2P3

C: C26H21Cl3N3O4P3

D: C26H20Cl2N3O4P3

E: C39H32Cl2N3O6P3

Conditions

Conditions	Yield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 5h; Inert atmosphere;	A 14% B 12% C 11% D 33% E 8%

...Expand

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 57602-02-5
1,14-dibromo-3,6,9,12-tetraoxatetradecane

: 97990-42-6
<21>6(2,2')Diphenylmethano.25coronand-6>

Conditions

Conditions	Yield
With potassium hydroxide In butan-1-ol for 12h; Heating;	31%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 141-97-9
ethyl acetoacetate

: 12H-dibenzo(d,g)(1,3)dioxocin-6-methyl-6-acetic acid ethyl ester

Conditions

Conditions	Yield
With indium(III) chloride for 20h;	30%

: 2467-02-9
Bis(2-hydroxyphenyl)methane

: 98-86-2
acetophenone

: 6-methyl-6-phenyl-12H-dibenzo(d,g)(1,3)dioxocin

Conditions

Conditions	Yield
With indium(III) chloride for 0.5h;	30%

Phenol,2,2'-methylenebis- Specification

The Phenol,2,2'-methylenebis-, with the CAS registry number of 2467-02-9, is also known as 2,2'-Dihydroxydiphenylmethane. This chemical's molecular formula is C₁₃H₁₂O₂ and molecular weight is 200.233180. What's more, its IUPAC name is 2-[(2-Hydroxyphenyl)methyl]phenol.

Physical properties about the Phenol,2,2'-methylenebis- are: (1)ACD/LogP: 2.73; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.73; (4)ACD/LogD (pH 7.4): 2.73; (5)ACD/BCF (pH 5.5): 70.49; (6)ACD/BCF (pH 7.4): 70.22; (7)ACD/KOC (pH 5.5): 731.95; (8)ACD/KOC (pH 7.4): 729.15; (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: 1.635; (14)Molar Refractivity: 59.33 cm³; (15)Molar Volume: 165.6 cm³; (16)Surface Tension: 53.6 dyne/cm; (17)Density: 1.208 g/cm³; (18)Flash Point: 177.1 °C; (19)Enthalpy of Vaporization: 63.24 kJ/mol; (20)Boiling Point: 362.5 °C at 760 mmHg; (21)Vapour Pressure: 9.22E-06 mmHg at 25 °C.

Uses: it is used to produce other chemicals. For example, it is used to produce 2-Methyl-phenol. The reaction time is 0.5 h with reaction temperature of 430 °C. The yield is about 21.5 %.

You can still convert the following datas into molecular structure:
(1) SMILES: Oc1ccccc1Cc2ccccc2O
(2) InChI: InChI=1/C13H12O2/c14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)15/h1-8,14-15H,9H2
(3) InChIKey: MQCPOLNSJCWPGT-UHFFFAOYAP

Product Name

2,2'-METHYLENEDIPHENOL

Synthetic route

Phenol,2,2'-methylenebis- Specification

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