60628-96-8

Basic information

• Product Name: Bifonazole
• Synonyms: Bifonazole for system suitability;Bifonazole Impurity;mycospor;1-((1,1’-biphenyl)-4-ylphenylmethyl)-1h-imidazol;1-((4-biphenylyl)phenylmethyl)-1h-imidazole;1-(alpha-(4-biphenylyl)benzyl)-imidazol;1-(alpha-(4-biphenylyl)benzyl)imidazole;1-[(1,1’-biphenyl)-4-ylphenylmethyl]-1H-Imidazole
• CAS NO: 60628-96-8
• Molecular Formula: C₂₂H₁₈N₂
• Molecular Weight: 310.39
• EINECS: 262-336-6
• Product Categories: API;SARAFLOX
• Mol File: 60628-96-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 142℃
• Boiling Point: 440.55°C (rough estimate)
• Flash Point: 251.188 °C
• Appearance: white to off-white/
• Density: 1.1150 (rough estimate)
• Vapor Pressure: 2.46E-09mmHg at 25°C
• Refractive Index: 1.7620 (estimate)
• Storage Temp.: room temp
• Solubility: Soluble in DMSO
• PKA: 6.55±0.22(Predicted)
• Merck: 14,1213
• CAS DataBase Reference: Bifonazole(CAS DataBase Reference)
• NIST Chemistry Reference: Bifonazole(60628-96-8)
• EPA Substance Registry System: Bifonazole(60628-96-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 1
• RTECS: NI3517000
• Hazardous Substances Data: 60628-96-8(Hazardous Substances Data)

Usage

Chemical Description

Bifonazole is an antifungal medication, while pyrazole is a heterocyclic organic compound.

InChI:InChI=1/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

Synthetic route

(R,S)-1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarboxylic acid (162824-42-2) → bifonazole (60628-96-8)

Conditions	Yield
In diphenylether for 0.5h; Heating;	98%

1H-imidazole (288-32-4) + 4-benzylbiphenyl (613-42-3) → bifonazole (60628-96-8)

Conditions	Yield
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%

1H-imidazole (288-32-4) + C26H21N2O2S(1-)*Na(1+) → bifonazole (60628-96-8)

Conditions	Yield
With copper acetylacetonate; tetrabutylammomium bromide In toluene at 85℃; for 36h;	52%

4-phenylbenzhydrol (7598-80-3) + 1,1'-carbonyldiimidazole (530-62-1) → bifonazole (60628-96-8)

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

phenylmagnesium bromide + 1-[(4-methoxy-phenyl)-phenyl-methyl]-1H-imidazole → bifonazole (60628-96-8)

Conditions	Yield
With bis(dicyclohexylphenylphosphine)nickel(II) chloride In diethyl ether at 80℃; for 15h;

4-phenylbenzhydrol (7598-80-3) → bifonazole (60628-96-8)

Conditions	Yield
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

1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarbonitrile (162824-36-4) → bifonazole (60628-96-8)

Conditions	Yield
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

4-(chlorophenylmethyl)-1,1'-biphenyl (7515-73-3) + 1-(Trimethylsilyl)imidazole (18156-74-6) → bifonazole (60628-96-8)

Conditions	Yield
In acetonitrile

1H-imidazole (288-32-4) + 4-phenylbenzhydrol (7598-80-3) → bifonazole (60628-96-8)

Conditions	Yield
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;

trimethylphenylsilane (768-32-1) → bifonazole (60628-96-8)

Conditions

Yield

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

(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)(phenyl)methanone (1063965-82-1) → bifonazole (60628-96-8)

Conditions

Yield

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

biphenyl-4-yl-phenyl-methanone (2128-93-0) → bifonazole (60628-96-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum oxide; sodium tetrahydroborate / ethanol / 0.67 h / 20 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere 3.2: 0 - 100 °C / Inert atmosphere View Scheme

1H-imidazole (288-32-4) + [1,1'-biphenyl]-4-yl(phenyl)methyl methanesulfonate → bifonazole (60628-96-8)

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 2h; Inert atmosphere; Stage #2: [1,1'-biphenyl]-4-yl(phenyl)methyl methanesulfonate In N,N-dimethyl-formamide; mineral oil at 0 - 100℃; Inert atmosphere;	61.9 mg

Diphenylmethane (101-81-5) → bifonazole (60628-96-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: dichloromethane / -40 - 20 °C / Schlenk technique; Inert atmosphere 2: bis(tri-t-butylphosphine)palladium(0); sodium hydrogencarbonate / dichloromethane; N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere; Schlenk technique 3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 0.83 h / Inert atmosphere; Reflux 4: potassium carbonate / acetonitrile / 1 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: dichloromethane / -40 - 20 °C / Inert atmosphere; Schlenk technique 2.1: sodium hydrogencarbonate; bis(tri-t-butylphosphine)palladium(0) / dichloromethane; N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere; Schlenk technique; Sealed tube 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.83 h / Inert atmosphere; Reflux 3.2: 1 h / Reflux View Scheme

C25H19S2(1+)*CF3O3S(1-) → bifonazole (60628-96-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: bis(tri-t-butylphosphine)palladium(0); sodium hydrogencarbonate / dichloromethane; N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere; Schlenk technique 2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 0.83 h / Inert atmosphere; Reflux 3: potassium carbonate / acetonitrile / 1 h / Reflux View Scheme

1H-imidazole (288-32-4) + 4-phenyl-benzhydryl bromide (60047-92-9) → bifonazole (60628-96-8)

Conditions	Yield
With potassium carbonate In acetonitrile for 1h; Reflux;	47.9 mg

4-benzylbiphenyl (613-42-3) → bifonazole (60628-96-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 0.83 h / Inert atmosphere; Reflux 2: potassium carbonate / acetonitrile / 1 h / Reflux View Scheme

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + C25H19S2(1+)*CF3O3S(1-) → bifonazole (60628-96-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; bis(tri-t-butylphosphine)palladium(0) / dichloromethane; N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere; Schlenk technique; Sealed tube 2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.83 h / Inert atmosphere; Reflux 2.2: 1 h / Reflux View Scheme

N-trifluoromethanesulfony-4-benzylaniline → bifonazole (60628-96-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.08 h / 20 °C / Schlenk technique; Inert atmosphere 1.2: 12.03 h / 70 °C / Schlenk technique; Inert atmosphere; Glovebox 2.1: iodine; pyridine; tert.-butylhydroperoxide / water; decane / 12 h / 80 °C / Schlenk technique; Inert atmosphere 2.2: 10 h / 180 - 200 °C / Schlenk technique; Inert atmosphere View Scheme

p-benzylaniline (1135-12-2) → bifonazole (60628-96-8)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 12.5 h / -78 - 20 °C / Schlenk technique; Inert atmosphere 2.1: tetrahydrofuran / 0.08 h / 20 °C / Schlenk technique; Inert atmosphere 2.2: 12.03 h / 70 °C / Schlenk technique; Inert atmosphere; Glovebox 3.1: iodine; pyridine; tert.-butylhydroperoxide / water; decane / 12 h / 80 °C / Schlenk technique; Inert atmosphere 3.2: 10 h / 180 - 200 °C / Schlenk technique; Inert atmosphere View Scheme

tetrafluoroboric acid diethyl ether (67969-82-8) + sodium tetrafluoroborate (13755-29-8) + thianthrene-5-oxide (2362-50-7) + bifonazole (60628-96-8) → C34H25N2S2(1+)*BF4(1-)

Conditions	Yield
Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; bifonazole With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 18h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water	95%

Ethyl 4-bromobenzoate (5798-75-4) + bifonazole (60628-96-8) → ethyl 4-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)benzoate

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	90%

2,3,7,8-tetrafluorothianthrene-S-oxide + bifonazole (60628-96-8) → C34H21F4N2S2(1+)

Conditions	Yield
With trifluorormethanesulfonic acid; 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; regioselective reaction;	87%

trifluorormethanesulfonic acid (1493-13-6) + 2,3,7,8-tetrafluorothianthrene-S-oxide + sodium triflate (2926-30-9) + bifonazole (60628-96-8) → C34H21F4N2S2(1+)*CF3O3S(1-)

Conditions	Yield
Stage #1: trifluorormethanesulfonic acid; 2,3,7,8-tetrafluorothianthrene-S-oxide; bifonazole With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Sealed tube; Stage #2: sodium triflate In ethanol; dichloromethane; water	87%

4'-Bromopropiophenone (10342-83-3) + bifonazole (60628-96-8) → 1-(4-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)phenyl)propan-1-one

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	77%

4-bromo-benzaldehyde (1122-91-4) + bifonazole (60628-96-8) → 4-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)benzaldehyde

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	77%

3-bromo-1-trifluoromethylbenzene (401-78-5) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(3-(trifluoromethyl)phenyl)-1H-imidazole

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	71%

p-trifluoromethylphenyl bromide (402-43-7) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-1H-imidazole

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	66%

Dibenzothiophene sulfoxide (1013-23-6) + trifluorormethanesulfonic acid (1493-13-6) + bifonazole (60628-96-8) → C34H25N2S(1+)*CF3O3S(1-)

Conditions	Yield
With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 2h; Schlenk technique; Glovebox; Inert atmosphere;	65%

4-bromoisoquinoline (1532-97-4) + bifonazole (60628-96-8) → 4-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)isoquinoline

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	63%

4-bromobenzenecarbonitrile (623-00-7) + bifonazole (60628-96-8) → 4-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)-benzonitrile

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	61%

3-cyanobromobenzene (6952-59-6) + bifonazole (60628-96-8) → 3-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)benzonitrile

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	61%

2-Acetyl-5-bromothiophene (5370-25-2) + bifonazole (60628-96-8) → 1-(5-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)thiophen-2-yl)ethan-1-one

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	59%

o-cyanobromobenzene (2042-37-7) + bifonazole (60628-96-8) → 2-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)benzonitrile

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	58%

para-bromotoluene (106-38-7) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-2,5-di-p-tolyl-1H-imidazole + C29H24N2

Conditions	Yield
With cesium acetate; palladium diacetate at 150℃; for 48h; Inert atmosphere; Schlenk technique;	A 58% B n/a

1-bromo-4-methoxy-benzene (104-92-7) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-2,5-bis(4-methoxyphenyl)-1H-imidazole + 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(4-methoxyphenyl)-1H-imidazole

Conditions	Yield
With cesium acetate; palladium diacetate at 150℃; for 48h; Inert atmosphere; Schlenk technique;	A 57% B n/a

bromobenzene (108-86-1) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-2,5-diphenyl-1H-imidazole + C28H22N2

Conditions	Yield
With cesium acetate; palladium diacetate at 150℃; for 48h; Inert atmosphere; Schlenk technique;	A 55% B n/a

[(Co(C20H8N4(C6H5)3(C6H4CONH2)))2] + bifonazole (60628-96-8) → Co(O(C4NH2C(C6H5))3H(OH)C4NH2C6H4C2NO)(bifonazole)

Conditions	Yield
With air In chloroform treatment of Co-complex with rac-bifonazole; XRD, UV-Vis;	46%

o-trifluoromethylphenyl bromide (392-83-6) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(2-(trifluoromethyl)phenyl)-1H-imidazole

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	45%

3-Chloropyridine (626-60-8) + bifonazole (60628-96-8) → 3-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)pyridine

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	45%

bifonazole (60628-96-8) + para-nitrophenyl bromide (586-78-7) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(4-nitrophenyl)-1H-imidazole

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	43%

1-Bromonaphthalene (90-11-9) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(naphthalen-1-yl)-1H-imidazole

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	42%

5-bromopyrimidine (4595-59-9) + bifonazole (60628-96-8) → 5-(1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-1H-imidazol-5-yl)pyrimidine

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	41%

2-bromonaphthalene (580-13-2) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(naphthalen-2-yl)-1H-imidazole

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	39%

1-bromo-4-tert-butylbenzene (3972-65-4) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(4-(tert-butyl)-phenyl)-1H-imidazole

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	34%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + bifonazole (60628-96-8) → 1-([1,1′-biphenyl]-4-yl(phenyl)methyl)-5-(benzo[d][1,3]-dioxol-5-yl)-1H-imidazole

Conditions	Yield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	28%

Upstream product

• 162824-42-2 (R,S)-1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarboxylic acid 
• 288-32-4 1H-imidazole 
• 7598-80-3 4-phenylbenzhydrol 
• 162824-36-4 1-<α-(4-Biphenylyl)benzyl>imidazole-4,5-dicarbonitrile 
• 7515-73-3 4-(chlorophenylmethyl)-1,1'-biphenyl 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 530-62-1 1,1'-carbonyldiimidazole 
• 768-32-1 trimethylphenylsilane 
• 1063965-82-1 (4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)(phenyl)methanone 
• 2128-93-0 biphenyl-4-yl-phenyl-methanone 
• 101-81-5 Diphenylmethane 
• 60047-92-9 4-phenyl-benzhydryl bromide 
• 613-42-3 4-benzylbiphenyl 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 

Downstream Products

• 66600-14-4 1-[α-(4-biphenylyl)-benzyl]-3-benzoylmethyl-imidazolium bromide 
• 66600-13-3 1,3-bis-[α-(4-biphenylyl)-benzyl]imidazolium chloride 
• 91487-86-4 (S)-(+)-1-[α-(4-biphenylyl)benzyl]-1H-imidazole 
• 91487-86-4 (R)-(-)-1-[α-(4-biphenylyl)benzyl]-1H-imidazole 

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