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Bifonazole

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Name

Bifonazole

EINECS 262-336-6
CAS No. 60628-96-8 Density 1.077 g/cm3
PSA 17.82000 LogP 5.18780
Solubility N/A Melting Point 142℃
Formula C22H18N2 Boiling Point 491.728 °C at 760 mmHg
Molecular Weight 310.398 Flash Point 251.188 °C
Transport Information N/A Appearance N/A
Safety Risk Codes 22
Molecular Structure Molecular Structure of 60628-96-8 (Bifonazole) Hazard Symbols Xn
Synonyms

1-[4-Biphenylyl(phenyl)methyl]-1H-imidazole;

Article Data 15

Bifonazole Synthetic route

162824-42-2

(R,S)-1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarboxylic acid

60628-96-8

bifonazole

Conditions
ConditionsYield
In diphenylether for 0.5h; Heating;98%
288-32-4

1H-imidazole

613-42-3

4-benzylbiphenyl

60628-96-8

bifonazole

Conditions
ConditionsYield
Stage #1: 4-benzylbiphenyl With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 0.833333h; Inert atmosphere; Reflux;
Stage #2: 1H-imidazole With potassium carbonate In acetonitrile for 1h; Reflux;
77%
Stage #1: 4-benzylbiphenyl With pyridine; tert.-butylhydroperoxide; iodine In decane; water at 80℃; for 12h; Schlenk technique; Inert atmosphere;
Stage #2: 1H-imidazole With formic acid; toluene-4-sulfonic acid In water at 180 - 200℃; for 10h; Schlenk technique; Inert atmosphere;
66%
288-32-4

1H-imidazole

C26H21N2O2S(1-)*Na(1+)

60628-96-8

bifonazole

Conditions
ConditionsYield
With copper acetylacetonate; tetrabutylammomium bromide In toluene at 85℃; for 36h;52%
7598-80-3

4-phenylbenzhydrol

530-62-1

1,1'-carbonyldiimidazole

60628-96-8

bifonazole

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one Heating;12%

phenylmagnesium bromide

1-[(4-methoxy-phenyl)-phenyl-methyl]-1H-imidazole

60628-96-8

bifonazole

Conditions
ConditionsYield
With bis(dicyclohexylphenylphosphine)nickel(II) chloride In diethyl ether at 80℃; for 15h;
7598-80-3

4-phenylbenzhydrol

60628-96-8

bifonazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 96 percent / DEAD, Ph3P / tetrahydrofuran / 24 h / Ambient temperature
2: 85 percent / NaOH / ethanol / 24 h / Heating
3: 98 percent / diphenyl ether / 0.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere
2.2: 0 - 100 °C / Inert atmosphere
View Scheme
162824-36-4

1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarbonitrile

60628-96-8

bifonazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / NaOH / ethanol / 24 h / Heating
2: 98 percent / diphenyl ether / 0.5 h / Heating
View Scheme
7515-73-3

4-(chlorophenylmethyl)-1,1'-biphenyl

18156-74-6

1-(Trimethylsilyl)imidazole

60628-96-8

bifonazole

Conditions
ConditionsYield
In acetonitrile
288-32-4

1H-imidazole

7598-80-3

4-phenylbenzhydrol

60628-96-8

bifonazole

Conditions
ConditionsYield
Stage #1: 1H-imidazole; 4-phenylbenzhydrol With ammonium bromide In water at 125 - 130℃; for 2h; Industrial scale;
Stage #2: With ammonium bromide In water at 190 - 195℃; for 2h; Temperature; Industrial scale;
768-32-1

trimethylphenylsilane

60628-96-8

bifonazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: silver(I) 4-methylbenzenesulfonate; dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); [bis(acetoxy)iodo]benzene / 1,1,1-trichloroethane / 2 h / 110 °C / Inert atmosphere; Schlenk technique
2.1: aluminum oxide; sodium tetrahydroborate / ethanol / 0.67 h / 20 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere
4.2: 0 - 100 °C / Inert atmosphere
View Scheme

Bifonazole Specification

The Bifonazole, with the CAS registry number 60628-96-8, is also known as 1-[4-Biphenylyl(phenyl)methyl]-1H-imidazole. It belongs to the classification codes of Anti-Infective Agents; Antifungal; Antifungal Agents; Drug / Therapeutic Agent; Reproductive Effect. Its EINECS registry number is 262-336-6. This chemical's molecular formula is C22H18N2 and molecular weight is 310.39. What's more, its IUPAC name is called 1-[Phenyl-(4-phenylphenyl)methyl]imidazole. It should be stored in a cool, dry and well-ventilated place. Bifonazole is topical imidazole antifungal drug for the treatment of a variety of dermatophytoses, such as tinea corporis, tinea cruris, hand, foot and ringworm.

Physical properties about Bifonazole are: (1)ACD/LogP: 4.689; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.62; (4)ACD/LogD (pH 7.4): 4.63; (5)ACD/BCF (pH 5.5): 182.76; (6)ACD/BCF (pH 7.4): 1890.91; (7)ACD/KOC (pH 5.5): 717.78; (8)ACD/KOC (pH 7.4): 7426.47; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 17.82 Å2; (13)Index of Refraction: 1.616; (14)Molar Refractivity: 100.752 cm3; (15)Molar Volume: 288.133 cm3; (16)Polarizability: 39.941×10-24cm3; (17)Surface Tension: 43.15 dyne/cm; (18)Density: 1.077 g/cm3; (19)Flash Point: 251.188 °C; (20)Enthalpy of Vaporization: 72.969 kJ/mol; (21)Boiling Point: 491.728 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Bifonazole: this chemical can be prepared by imidazole with thionyl chloride. This reaction needs reagent acetonitrile at ambient temperature. The reaction time is 15 hours.

Bifonazole can be prepared by imidazole with thionyl chloride.

You can still convert the following datas into molecular structure:
(1) SMILES: n1ccn(c1)C(c3ccc(c2ccccc2)cc3)c4ccccc4
(2) InChI: InChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H
(3) InChIKey: OCAPBUJLXMYKEJ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 500mg/kg (500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 739, 1983.
mouse LD50 intravenous 57mg/kg (57mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 23, 1984.
mouse LD50 oral 2629mg/kg (2629mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 739, 1983.
mouse LD50 subcutaneous > 15gm/kg (15000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 23, 1984.
rabbit LD50 oral 4gm/kg (4000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 739, 1983.
rat LD50 intravenous 63mg/kg (63mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 23, 1984.
rat LD50 oral 1463mg/kg (1463mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 23, 1984.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 23, 1984.

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