Product Name

  • Name

    Bis(4-cyanophenyl)methanol

  • EINECS
  • CAS No. 134521-16-7
  • Article Data7
  • CAS DataBase
  • Density 1.27 g/cm3
  • Solubility
  • Melting Point 158-159 °C
  • Formula C15H10N2O
  • Boiling Point 473.5 °C at 760 mmHg
  • Molecular Weight 234.257
  • Flash Point 240.1 °C
  • Transport Information
  • Appearance White or off-white crystalline powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 134521-16-7 (Bis(4-cyanophenyl)methanol)
  • Hazard Symbols
  • Synonyms Bis(p-cyanophenyl)methanol;CGP 44645;4,4'-(hydroxymethanediyl)dibenzonitrile;benzonitrile, 4,4'-(hydroxymethylene)bis-;
  • PSA 67.81000
  • LogP 2.51166

Synthetic route

4,4'-dicyanobenzophenone
32446-66-5

4,4'-dicyanobenzophenone

4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;100%
With aluminium amalgam; ammonia
With sodium tetrahydroborate In methanol
With sodium tetrahydroborate In methanol
Stage #1: 4,4'-dicyanobenzophenone With sodium tetrahydroborate In methanol at 0 - 30℃; for 0.5h;
Stage #2: With methanol; water; acetic acid pH=6.33;
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

A

4,4'-dicyanobenzophenone
32446-66-5

4,4'-dicyanobenzophenone

B

4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

C

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With rhodium(II) acetate; 1,3-bis-(diphenylphosphino)propane In toluene at 200℃; for 5.5h; Temperature;A 10%
B 6%
C 30%
...Expand
4,4'-diaminobenzophenone
611-98-3

4,4'-diaminobenzophenone

4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium nitrite; aqueous hydrochloric acid; water / weiteres Reagens: Natriumcarbonat
2: amalgamated aluminium; ethanolic ammonia
View Scheme
bis(p-methylphenyl)-methanone
611-97-2

bis(p-methylphenyl)-methanone

4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dihydrogen peroxide; hydrogen bromide / water; tetrachloromethane / 2 h / 20 °C / Irradiation
1.2: 48 h / 20 - 60 °C
2.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
View Scheme
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

Conditions
ConditionsYield
Stage #1: 4-bromobenzenecarbonitrile With TurboGrignard In tetrahydrofuran at -15 - 20℃; for 2.25h;
Stage #2: 4-cyanobenzaldehyde In tetrahydrofuran at -15 - 0℃; for 1.16667h;		0.72 g
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

4,4'-dicyanodiphenylbromomethane
69545-39-7

4,4'-dicyanodiphenylbromomethane

Conditions
ConditionsYield
With hydrogen bromide In water; toluene at 60℃; for 2h; Heating / reflux;92%
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

4-(alpha-chloro-4'-cyanobenzyl)-benzonitrile
112809-57-1

4-(alpha-chloro-4'-cyanobenzyl)-benzonitrile

Conditions
ConditionsYield
With hydrogenchloride; zinc(II) chloride In water; toluene at 40 - 65℃; for 4h;85%
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

4,4'-dicyanobenzophenone
32446-66-5

4,4'-dicyanobenzophenone

Conditions
ConditionsYield
With manganese(IV) oxide In chloroform at 20℃; for 5.5h;85%
With nickel(II) triflate; cyclohexanone; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 110℃; for 12h; Schlenk technique;59%
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

4,4'-hydroxymethanediyl-bis-benzamidine; dihydrochloride

4,4'-hydroxymethanediyl-bis-benzamidine; dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride; nitrobenzene weiteres Reagens: Aethanol; Behandeln des nach mehreren Tagen isolierten Reaktionsprodukts mit aethanol. Ammoniak;
With hydrogenchloride; chloroform weiteres Reagens: Aethanol; Behandeln des nach mehreren Tagen isolierten Reaktionsprodukts mit aethanol. Ammoniak;
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

C15H10N2O(1-)

C15H10N2O(1-)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; Kinetics; electron pulse irradiation;
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

toluene-4-sulfonic acid bis-(4-cyano-phenyl)-methyl ester
935477-95-5

toluene-4-sulfonic acid bis-(4-cyano-phenyl)-methyl ester

Conditions
ConditionsYield
Stage #1: 4,4'-Methanol-bisbenzonitrile; p-toluenesulfonyl chloride In acetone at 0 - 5℃; for 0.0833333h;
Stage #2: With sodium hydroxide In water; acetone at 0 - 5℃; for 1.25h;
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

Reaxys ID: 11723384

Reaxys ID: 11723384

Conditions
ConditionsYield
In toluene
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

trichloroacetonitrile
545-06-2

trichloroacetonitrile

trichloroacetimidate bis-(4-cyanophenyl)methyl ester
1161570-94-0

trichloroacetimidate bis-(4-cyanophenyl)methyl ester

Conditions
ConditionsYield
Stage #1: 4,4'-Methanol-bisbenzonitrile; trichloroacetonitrile In acetone at 10 - 20℃; for 0.166667 - 0.25h;
Stage #2: With sodium hydroxide In water; acetone for 2 - 3h; pH=~ 7.00;
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

bis(4-cyanophenyl)methylmethanesulfonate
134521-17-8

bis(4-cyanophenyl)methylmethanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 8h;
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

4-[6-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexan-6-yl]benzonitrile

4-[6-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexan-6-yl]benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: manganese(IV) oxide / chloroform / 5.5 h / 20 °C
2: hydrazine hydrate / ethanol / 16 h / 80 °C
3: manganese(IV) oxide / chloroform / 1 h
4: chloroform / 17.5 h / 20 - 60 °C
View Scheme
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

rac-4-[(1S,5S)-6-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-3-azabicyclo[3.1.0]hexan-6-yl]benzonitrile

rac-4-[(1S,5S)-6-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-3-azabicyclo[3.1.0]hexan-6-yl]benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: manganese(IV) oxide / chloroform / 5.5 h / 20 °C
2: hydrazine hydrate / ethanol / 16 h / 80 °C
3: manganese(IV) oxide / chloroform / 1 h
4: chloroform / 17 h / 60 °C
View Scheme
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

4-[(4-cyanophenyl)methanehydrazonoyl]benzonitrile
64568-34-9

4-[(4-cyanophenyl)methanehydrazonoyl]benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: manganese(IV) oxide / chloroform / 5.5 h / 20 °C
2: hydrazine hydrate / ethanol / 16 h / 80 °C
View Scheme
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

4-[(4-cyanophenyl)(diazo)methyl]benzonitrile
64568-33-8

4-[(4-cyanophenyl)(diazo)methyl]benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: manganese(IV) oxide / chloroform / 5.5 h / 20 °C
2: hydrazine hydrate / ethanol / 16 h / 80 °C
3: manganese(IV) oxide / chloroform / 1 h
View Scheme
4,4'-Methanol-bisbenzonitrile
134521-16-7

4,4'-Methanol-bisbenzonitrile

cyclohexanone
108-94-1

cyclohexanone

A

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

B

4,4'-dicyanobenzophenone
32446-66-5

4,4'-dicyanobenzophenone

Conditions
ConditionsYield
Stage #1: 4,4'-Methanol-bisbenzonitrile; cyclohexanone With N-hydroxyphthalimide; 2,2'-azobis(isobutyronitrile); oxygen In ethyl acetate at 75℃; for 22h; Baeyer-Villiger Ketone Oxidation;
Stage #2: With ammonium cerium (IV) nitrate; 1,1,1,3',3',3'-hexafluoro-propanol In ethyl acetate at 45℃; for 10h; Baeyer-Villiger Ketone Oxidation;
...Expand

Bis(4-cyanophenyl)methanol Specification

The Bis(4-cyanophenyl)methanol, with the CAS registry number 134521-16-7, has the systematic name of 4,4'-(hydroxymethanediyl)dibenzonitrile. It is a kind of organics, and should be stored in the dry and cool environment. And the molecular formula of the chemical is C15H10N2O.

The characteristics of Bis(4-cyanophenyl)methanol are as followings: (1)ACD/LogP: 1.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 10; (6)ACD/BCF (pH 7.4): 10; (7)ACD/KOC (pH 5.5): 180; (8)ACD/KOC (pH 7.4): 180; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 67.81 Å2; (13)Index of Refraction: 1.644; (14)Molar Refractivity: 66.738 cm3; (15)Molar Volume: 184.393 cm3; (16)Polarizability: 26.457×10-24cm3; (17)Surface Tension: 67.115 dyne/cm; (18)Density: 1.27 g/cm3; (19)Flash Point: 240.139 °C; (20)Enthalpy of Vaporization: 77.598 kJ/mol; (21)Boiling Point: 473.458 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: N#Cc1ccc(cc1)C(O)c2ccc(C#N)cc2
(2InChI: InChI=1/C15H10N2O/c16-9-11-1-5-13(6-2-11)15(18)14-7-3-12(10-17)4-8-14/h1-8,15,18H
(3)InChIKey: JNJWXPZHWUOYRZ-UHFFFAOYAQ

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