Naftifine supplier | CasNO.65472-88-0

Name
Naftifine
EINECS
CAS No. 65472-88-0
Article Data27
CAS DataBase
Density 1.082 g/cm³
Solubility
Melting Point 177 °C
Formula C₂₁H₂₁N
Boiling Point 440.1 °C at 760 mmHg
Molecular Weight 287.404
Flash Point 194.4 °C
Transport Information
Appearance
Safety
Risk Codes R22; R36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 1-Naphthalenemethanamine,N-methyl-N-(3-phenyl-2-propenyl)-, (E)-;1-Naphthalenemethanamine, N-methyl-N-[(2E)-3-phenyl-2-propenyl]-(9CI);Naftifine;Naftifungin;
PSA 3.24000
LogP 5.78700

Synthetic route

: 50-00-0
formaldehyd

: 92610-10-1
(E)-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
With sodium dihydrogen phosphate In 1,4-dioxane; water at 60℃; for 0.166667h;	100%
With sodium dihydrogenphosphate In 1,4-dioxane at 60℃; for 0.333333h;	91%
With sodium tetrahydroborate 1.) CH3OH, H2O, reflux, 30 min, 2.) CH3OH, H2O, RT, 3 h; Yield given. Multistep reaction;

: 14489-75-9
N-methyl-1-naphthalenemethylamine

: 4407-36-7
(2E)-3-phenyl-2-propen-1-ol

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Pt(COD)Cl2; bis[2-(diphenylphosphino)phenyl] ether In 1,4-dioxane for 12h; Heating;	98%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) In methanol at 20℃; for 12h; Temperature; Solvent; Inert atmosphere;	96%
With 1,10-Phenanthroline; palladium diacetate In toluene at 100℃; for 17h; Inert atmosphere; Schlenk technique; regioselective reaction;	83%
Stage #1: N-methyl-1-naphthalenemethylamine; (2E)-3-phenyl-2-propen-1-ol With manganese(IV) oxide; polymer-bound trimethyl ammonium cyanoborohydride In dichloromethane for 5h; Stage #2: With acetic acid for 17h;	72%
With triscarbonyl‐(η4–3,4‐bis(4‐methoxyphenyl)‐2,5‐diphenylcyclopenta‐2,4‐dienone)iron In nitromethane; toluene at 130℃; for 24h; Schlenk technique; Inert atmosphere;	61%

: 16519-25-8
(E)-cinnamyl phenyl ether

: 14489-75-9
N-methyl-1-naphthalenemethylamine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); Methyl formate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether In water at 20℃; for 0.333333h; chemoselective reaction;	98%

: 140-10-3
(E)-3-phenylacrylic acid

: 14489-75-9
N-methyl-1-naphthalenemethylamine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 36h; Glovebox; Molecular sieve; Schlenk technique;	96%

: 92610-10-1
(E)-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine

: 75-05-8
acetonitrile

: 65472-88-0
naftifine

Conditions

Conditions	Yield
With 18-crown-6 ether; carbon dioxide at 80℃; under 750.075 Torr; for 72h; Inert atmosphere; Schlenk technique; Glovebox;	95%

: 98977-94-7
(±)-3-(N-methyl-N-((naphthalen-5-yl)methyl)amino)-1-phenylpropan-1-ol

: 65472-88-0
naftifine

Conditions

Conditions	Yield
With hydrogenchloride In water Reflux;	90%
With hydrogenchloride for 2h; Heating;

: 4780-79-4
1-naphthalene methanol

: 60960-88-5, 93085-46-2, 83554-67-0
(E)-N-methylcinnamylamine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Stage #1: 1-naphthalene methanol; (E)-N-methylcinnamylamine With manganese(IV) oxide; polymer-bound trimethyl ammonium cyanoborohydride In dichloromethane for 5h; Stage #2: With acetic acid for 17h;	62%

: 108-86-1
bromobenzene

: 14489-75-9
N-methyl-1-naphthalenemethylamine

: 1-acetoxy-5-methyl-3,7-dioxo-9-vinyl-2,8-dioxa-5-aza-1-borabicyclo[3.3.1]nonan-5-ium-1-uide

: 65472-88-0
naftifine

Conditions

Conditions	Yield
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine In tetrahydrofuran; water at 80℃; for 16h; Sealed tube; Inert atmosphere; Schlenk technique;	62%

...Expand

: 50-00-0
formaldehyd

: 6783-05-7
trans-2-phenylvinylboronic acid

: 14489-75-9
N-methyl-1-naphthalenemethylamine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Mechanism; multistep reaction; other substrates, other boronic acids; E-selectivity;
1) dioxane, 90 deg C, 10 min, 2) dioxane, 90 deg C, 10 min; Yield given. Multistep reaction;

...Expand

: 118-31-0
(naphth-1-yl)methylamine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: manganese dioxide; NaBH4; 4A MS / CH2Cl2 / 17 h / Heating 1.2: 86 percent / MeOH / 0.67 h / 0 - 20 °C 2.1: 91 percent / NaH2PO4 / dioxane / 0.33 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: benzene / Heating 2: 100 percent / NaBH4 / methanol / 0.33 h / 40 °C 3: 2.) NaBH4 / 1.) CH3OH, H2O, reflux, 30 min, 2.) CH3OH, H2O, RT, 3 h View Scheme
Multi-step reaction with 3 steps 2: NaBH4 3: 100 percent / NaH2PO3 / H2O; dioxane / 0.17 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1.1: dichloro( 1,5-cyclooctadiene)platinum(ll); bis[2-(diphenylphosphino)phenyl] ether / 1,4-dioxane / 110 °C / Schlenk technique; Inert atmosphere 1.2: Schlenk technique; Inert atmosphere; Reflux 2.1: [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; diphenylsilane / N,N-dimethyl-formamide / 48 h / 50 °C / 760.05 Torr View Scheme

: 4407-36-7
(2E)-3-phenyl-2-propen-1-ol

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: manganese dioxide; NaBH4; 4A MS / CH2Cl2 / 17 h / Heating 1.2: 86 percent / MeOH / 0.67 h / 0 - 20 °C 2.1: 91 percent / NaH2PO4 / dioxane / 0.33 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1.1: dichloro( 1,5-cyclooctadiene)platinum(ll); bis[2-(diphenylphosphino)phenyl] ether / 1,4-dioxane / 110 °C / Schlenk technique; Inert atmosphere 1.2: Schlenk technique; Inert atmosphere; Reflux 2.1: [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; diphenylsilane / N,N-dimethyl-formamide / 48 h / 50 °C / 760.05 Torr View Scheme
Multi-step reaction with 3 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2: hydrazine hydrate / methanol / 20 °C / Inert atmosphere 3: 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) / methanol / 12 h / 20 °C / Inert atmosphere View Scheme

: 14371-10-9
(E)-3-phenylpropenal

yeast: yeast

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: benzene / Heating 2: 100 percent / NaBH4 / methanol / 0.33 h / 40 °C 3: 2.) NaBH4 / 1.) CH3OH, H2O, reflux, 30 min, 2.) CH3OH, H2O, RT, 3 h View Scheme

: 14489-75-9
N-methyl-1-naphthalenemethylamine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 55 percent / aq. HCl / H2O; ethanol / 2 h / Heating 2: 100 percent / NaBH4 / methanol / 0.25 h / Ambient temperature 3: 5N aq. HCl / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: bis(dibenzylideneacetone)-palladium(0); bathophenanthroline / N,N-dimethyl-formamide / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: SPGS-550M; potassium carbonate / water; toluene / 4 h / 20 °C 2: chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I); SPGS-550M; sodium hydroxide / water / 2 h / 20 °C / Green chemistry 3: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / water / 2 h / 80 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1: SPGS-550M; potassium carbonate / water; toluene / 4 h / 20 °C 2: chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I); SPGS-550M; sodium hydroxide / water / 2 h / 20 °C / Green chemistry 3: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / water / 2 h / 80 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1: triethylamine / 1,4-dioxane / Reflux 2: sodium tetrahydroborate / methanol / 0.5 h / 20 °C 3: hydrogenchloride / water / Reflux View Scheme

: 98977-93-6
3--1-phenyl-1-propanone

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / NaBH4 / methanol / 0.25 h / Ambient temperature 2: 5N aq. HCl / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C 2: hydrogenchloride / water / Reflux View Scheme

: 98977-78-7
N-(3-phenyl-2-propenylidene)-1-naphthalenemethanamine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / NaBH4 / methanol / 0.33 h / 40 °C 2: 2.) NaBH4 / 1.) CH3OH, H2O, reflux, 30 min, 2.) CH3OH, H2O, RT, 3 h View Scheme
Multi-step reaction with 2 steps 1: NaBH4 2: 100 percent / NaH2PO3 / H2O; dioxane / 0.17 h / 60 °C View Scheme

: 86-52-2
1-Chloromethylnaphthalene

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 78 percent / ethanol / Ambient temperature 2: 55 percent / aq. HCl / H2O; ethanol / 2 h / Heating 3: 100 percent / NaBH4 / methanol / 0.25 h / Ambient temperature 4: 5N aq. HCl / 2 h / Heating View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / 24 h / 20 °C / Inert atmosphere 2: sodium hydroxide / diethyl ether; water / 0.5 h / 0 °C 3: tris-(dibenzylideneacetone)dipalladium(0); sodium acetate / benzonitrile / 1 h / 80 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / -78 - 60 °C / Inert atmosphere View Scheme

: 14371-10-9
(E)-3-phenylpropenal

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: NaBH4 3: 100 percent / NaH2PO3 / H2O; dioxane / 0.17 h / 60 °C View Scheme

: 134275-02-8
N-(naphthalen-1-ylmethyl)prop-2-en-1-amine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / diethyl ether; water / 0.5 h / 0 °C 2: tris-(dibenzylideneacetone)dipalladium(0); sodium acetate / benzonitrile / 1 h / 80 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / -78 - 60 °C / Inert atmosphere View Scheme

: 1334031-94-5
methyl allyl(naphthalen-1-ylmethyl)carbamate

: 65472-88-0
naftifine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); sodium acetate / benzonitrile / 1 h / 80 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / -78 - 60 °C / Inert atmosphere View Scheme

: 108-86-1
bromobenzene

: (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-amine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water at 80℃; for 2h; Suzuki Coupling; Green chemistry;	59 mg

: 591-50-4
iodobenzene

: (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-amine

: 65472-88-0
naftifine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water at 80℃; for 2h; Suzuki Coupling; Green chemistry;	75 mg

: 65472-88-0
naftifine

: 98977-55-0
N-methyl-N-(3-phenylpropyl)-1-naphthalenemethanamine

Conditions

Conditions	Yield
With tris(triphenylphosphine)rhodium(l) chloride; hydrogen In toluene at 70℃; for 24h; Inert atmosphere;	83%
With Wilkinson's catalyst; hydrogen In toluene at 70℃; for 24h;	83%

: 65472-88-0
naftifine

: C21H23NO2

Conditions

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 24h; Inert atmosphere;	78%

: 65472-88-0
naftifine

: C21H23NO2

Conditions

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 24h; Inert atmosphere;	78%

: 65472-88-0
naftifine

: C21H21NO

Conditions

Conditions	Yield
With sodium carbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 1h; Inert atmosphere;	60%
With sodium carbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 1h; Inert atmosphere;	60%

Naftifine Specification

The Naftifine, with the CAS registry number 65472-88-0, is also known as N-trans-Cinnamyl-N-methyl-(1-naphthylmethyl)amine. This chemical's molecular formula is C₂₁H₂₁N and molecular weight is 287.40. Its IUPAC name is called (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine. This chemical's classification codes are Anti-Infective Agents; Antifungal agents. Naftifine is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis.

Physical properties of Naftifine: (1)ACD/LogP: 5.80; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.4; (4)ACD/LogD (pH 7.4): 5.11; (5)ACD/BCF (pH 5.5): 60.47; (6)ACD/BCF (pH 7.4): 3087; (7)ACD/KOC (pH 5.5): 136.99; (8)ACD/KOC (pH 7.4): 6993.87; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.655; (13)Molar Refractivity: 97.45 cm³; (14)Molar Volume: 265.4 cm³; (15)Surface Tension: 46 dyne/cm; (16)Density: 1.082 g/cm³; (17)Flash Point: 194.4 °C; (18)Enthalpy of Vaporization: 69.71 kJ/mol; (19)Boiling Point: 440.1 °C at 760 mmHg; (20)Vapour Pressure: 6.07E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by formaldehyde and N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine. This reaction will need reagent NaH₂PO₃ and solvent H₂O, dioxane. The reaction time is 10 min with reaction temperature of 60 ℃. The yield is about 100%.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN(CC=CC1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32
(2)Isomeric SMILES: CN(C/C=C/C1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32
(3)InChI: InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+
(4)InChIKey: OZGNYLLQHRPOBR-DHZHZOJOSA-N

Product Name

Naftifine

Synthetic route

Naftifine Specification

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