4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine supplier

Name
4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine
EINECS
CAS No. 79560-20-6
Article Data9
CAS DataBase
Density 1.251 g/cm³
Solubility DMSO: ~26 mg/mL
Melting Point 243-247 °C
Formula C₁₇H₁₅Cl₂N
Boiling Point 390.529 °C at 760 mmHg
Molecular Weight 304.219
Flash Point 190 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms N-[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine;
PSA 12.36000
LogP 5.33800

Synthetic route

: 79560-19-3
4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one

: 74-89-5
methylamine

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
In ethanol at 0℃; Solvent; Heating; Industrial scale; Large scale;	95%
With formic acid In methanol	95%
With thionyl chloride In tetrahydrofuran at -10 - 20℃;	93%

: 4-(2,3-dichlorophenyl)-3,4-dihydro-1(2H)-naphthone

: 79560-19-3
4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one

: 74-89-5
methylamine

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
methanesulfonic acid In ethanol at 0 - 70℃; for 4h;	88%
methanesulfonic acid In acetonitrile at 0 - 70℃; for 4h;	88%
In triethylamine at 0 - 90℃; for 10h;	87%
toluene-4-sulfonic acid In triethylamine at 0 - 50℃; for 4h;	82%

...Expand

: 6284-79-3
3,4-dichlorobenzophenone

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: potassium tert-butoxide / 2-methyl-propan-2-ol / 16 h / Heating 2: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 3: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 4: SOCl2 / toluene / 1.25 h 5: AlCl3 / CS2 / 16 h / Ambient temperature 6: TiCl4 / toluene / 17 h / Ambient temperature View Scheme

: 79560-18-2
4-(3,4-dichlorophenyl)-4-phenylbutanoic acid

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / toluene / 1.25 h 2: AlCl3 / CS2 / 16 h / Ambient temperature 3: TiCl4 / toluene / 17 h / Ambient temperature View Scheme

: 79560-17-1
4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 2: SOCl2 / toluene / 1.25 h 3: AlCl3 / CS2 / 16 h / Ambient temperature 4: TiCl4 / toluene / 17 h / Ambient temperature View Scheme

: 149620-65-5
4-(3,4-dichlorophenyl)-4-phenylbutyric acid

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3 / CS2 / 16 h / Ambient temperature 2: TiCl4 / toluene / 17 h / Ambient temperature View Scheme

: 79560-16-0
3-(ethoxycarbonyl)-4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 3: SOCl2 / toluene / 1.25 h 4: AlCl3 / CS2 / 16 h / Ambient temperature 5: TiCl4 / toluene / 17 h / Ambient temperature View Scheme

: 4-(2,3-dichlorophenyl)-3,4-dihydro-1(2H)-naphthone

: 79560-19-3
4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one

: 74-89-5
methylamine

A: 340830-05-9
2,3-dichlorosertraline-imine

B: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
methanesulfonic acid In ethanol at 0 - 70℃; for 4h;
toluene-4-sulfonic acid at 60℃; under 3750.38 - 7500.75 Torr; for 5h;

...Expand

: 79560-19-3
4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
With formic acid; methylamine In N,N-dimethyl-formamide

: 95-50-1
1,2-dichloro-benzene

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride 2: ethanol / 0 °C / Heating; Industrial scale; Large scale View Scheme

: 90-15-3
α-naphthol

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride 2: ethanol / 0 °C / Heating; Industrial scale; Large scale View Scheme

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: cis-1-methylamino-4-(3,4-dichlorophenyl)tetralin

: trans-1-methylamino-4-(3,4-dichlorophenyl)tetralin

Conditions

Conditions	Yield
With hydrogen; 5 % alumina-supported palladium In methanol at 26 - 29℃; Product distribution / selectivity; Autoclave;	A 91.52% B 6.54%

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: cis-1-methylamino-4-(3,4-dichlorophenyl)tetralin

Conditions

Conditions	Yield
With hydrogen; CuCrBa oxide In ethanol at 130 - 150℃; under 9000.9 Torr; for 1h;	83%
With hydrogen; CuCrBa oxide In butan-1-ol
With hydrogen; CuCrBa oxide In isopropyl alcohol
With hydrogen; CuCrBa oxide In methanol

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 140631-53-4
sertraline

Conditions

Conditions	Yield
With tris(pentafluorophenyl)borate; 1,1'-[1-methyl-3-(2,6-dimethylpiperidinyl)-1,3-propyl]ferrocene; hydrogen In toluene at 80℃; under 15001.5 Torr;	83%
With tris(pentafluorophenyl)borate; diisopropylamine at 100℃; for 24h; Neat (no solvent);	90 %Spectr.
With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; tert-butyl alcohol In chloroform-d1	83 %Spectr.

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 79617-95-1
cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine

: 79836-45-6
trans-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol for 1.5h; Ambient temperature;
With palladium on activated charcoal; hydrogen	A n/a B n/a

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 79617-95-1
cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine

Conditions

Conditions	Yield
With hydrogen; 5 wt% palladium on calcium carbonate In methanol; water at 20 - 35℃; for 3.5h;
With Lindlar's catalyst; hydrogen; pyrographite In ethanol at 20 - 40℃; Solvent; Industrial scale; Large scale;	n/a

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 79617-98-4
(1R,4R)-sertraline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 91797-60-3
trans-(1S,4R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 79951-46-5
trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 79617-96-2
Sertraline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme
Stage #1: With hydrogen; G-69 (Ni/Kieselguhr) at 150℃; for 2h; Stage #2: N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine With hydrogen In tetrahydrofuran at 90℃; under 6080.41 Torr;	86 %Chromat.

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

A: 871838-58-3
cis-(1S,4S)-N-methyl-(3-chlorophenyl)-1,2,3,4-tetrahydro-1-naphtalenamine

B: 91797-63-6
(1S)-cis-N-methyl-4-(4-chlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

C: 79560-19-3
4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one

D: 91797-60-3
trans-(1S,4R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

E: 79617-96-2
Sertraline

Conditions

Conditions	Yield
With hydrogen; SA-3135 support, Co(NO3)2, H2O; dried and calcined ones or twice (Co 11 - 25percent); reduction with H2 In tetrahydrofuran at 120 - 150℃; under 6000.6 Torr;	A n/a B n/a C 0.2 - 0.7 %Chromat. D 7 - 9.4 %Chromat. E 87 - 91 %Chromat.

...Expand

: 101-02-0
triphenyl phosphite

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 140631-53-4
sertraline

Conditions

Conditions	Yield
palladium on graphite In N-methyl-acetamide; methanol

palladium on graphite: palladium on graphite

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 140631-53-4
sertraline

Conditions

Conditions	Yield
With phosphorous acid trimethyl ester In methanol

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine hydrochloride

B: 79559-97-0
sertraline hydrochloride

Conditions

Conditions	Yield
Stage #1: N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine With hydrogen; pyridine hydrochloride; 50% Pd/C In methanol at 25 - 35℃; for 6h; Stage #2: With hydrogenchloride In methanol; water pH=1 - 2; Product distribution / selectivity;
Stage #1: N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine With hydrogen; pyridine hydrochloride; platinum on carbon In methanol at 25 - 35℃; for 0.5h; Stage #2: With hydrogenchloride In methanol; water pH=1 - 2; Product distribution / selectivity;
Stage #1: N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine With hydrogen; N,N-dimethylacetamide hydrochloride; 50% Pd/C In methanol at 25 - 35℃; for 4h; Stage #2: With hydrogenchloride In methanol; water pH=1 - 2; Product distribution / selectivity;

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

A: 79617-98-4
(1R,4R)-sertraline

B: 91797-60-3
trans-(1S,4R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

C: 79951-46-5
trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

D: 79617-96-2
Sertraline

Conditions

Conditions	Yield
With C32H12BF24(1-)*C36H44IrNOP(1+); hydrogen at 20℃; under 15201 Torr; for 12h; optical yield given as %ee; enantioselective reaction;

...Expand

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

A: 79617-98-4
(1R,4R)-sertraline

B: 79951-46-5
trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

C: 79617-96-2
Sertraline

Conditions

Conditions	Yield
With R,S-[Ir(1,5-cyclooctadiene)(PPh2(C9H10)(C3H3NO-i-Bu))] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; hydrogen at 20℃; under 15201 Torr; for 12h; optical yield given as %ee; enantioselective reaction;

...Expand

: 79560-20-6
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

: 244223-89-0, 79617-97-3
(cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyrographite; hydrogen; Lindlar's catalyst / ethanol / 20 - 40 °C / Industrial scale; Large scale 2: ethanol / Reflux; Industrial scale; Large scale View Scheme

4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine Chemical Properties

Molecular Structure of 4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine (CAS NO.79560-20-6):

Empirical Formula: C₁₇H₁₅Cl₂N
Molecular Weight: 304.2137
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 12.36Å²
Index of Refraction: 1.619
Molar Refractivity: 85.315 cm³
Molar Volume: 243.202 cm³
Surface Tension: 41.23 dyne/cm
Density: 1.251 g/cm³
Flash Point: 189.985 °C
Enthalpy of Vaporization: 61.501 kJ/mol
Boiling Point: 390.529 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Melting point: 243-247°C
Solubility DMSO: ~26 mg/mL

4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine Safety Profile

Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: QJ0352070

4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine Specification

4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine , with CAS number of 79560-20-6, can be called methanamine, N-[(1E)-4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]- ; N-[(1E)-4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine ; N-[(1E)-4-(3,4-Dichlorphenyl)-3,4-dihydronaphthalen-1(2H)-yliden]methanamin . It is a white to light yellow crystal powde.

Product Name

4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine

Synthetic route

4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine Chemical Properties

4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine Safety Profile

4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenimine Specification

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