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2018-90-8

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2018-90-8 Usage

General Description

1-(2-Naphthyl)methanamine is a chemical compound with the molecular formula C11H11N. It is a primary aromatic amine and belongs to the class of organic compounds known as anilines. 1-(2-NAPHTHYL)METHANAMINE is a white to light yellow crystalline solid and is primarily used in the production of pharmaceuticals and organic synthesis. It is also used as a cross-linking agent in the manufacturing of polymer materials. 1-(2-Naphthyl)methanamine is known for its reactivity and is classified as a hazardous substance, with potential health hazards including skin and eye irritation and respiratory sensitization. Due to its potential health risks and reactivity, it should be handled and stored with care in a controlled environment.

Check Digit Verification of cas no

The CAS Registry Mumber 2018-90-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,1 and 8 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2018-90:
(6*2)+(5*0)+(4*1)+(3*8)+(2*9)+(1*0)=58
58 % 10 = 8
So 2018-90-8 is a valid CAS Registry Number.
InChI:InChI=1/C11H11N/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7H,8,12H2

2018-90-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name naphthalen-2-ylmethanamine

1.2 Other means of identification

Product number -
Other names 1-(aminomethyl)naphthalene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2018-90-8 SDS

2018-90-8Synthetic route

β-naphthaldehyde
66-99-9

β-naphthaldehyde

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With piperidin-2-one; sodium tetrahydroborate; N,N-diisopropyl-4H-benzo[d][1,3,2]dioxaborinin-2-amine; ammonia In 1,2-dichloro-ethane at 20℃;99%
With ammonia; hydrogen In methanol at 120℃; under 15001.5 Torr; for 4h; Autoclave;99%
With ammonium hydroxide; hydrogen In ethanol at 130℃; under 7500.75 Torr; for 12h; Autoclave;93.6%
With ammonia; hydrogen In tert-butyl alcohol at 120℃; for 15h;90%
With ammonia; hydrogen In methanol at 120℃; under 15001.5 Torr; for 4h; Autoclave;99 %Spectr.
2-naphthalenecarbonitrile
613-46-7

2-naphthalenecarbonitrile

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 5h; Inert atmosphere; Cooling with ice;98%
With potassium hydroxide; samarium diiodide In tetrahydrofuran for 0.0666667h; Ambient temperature;86%
With boron trifluoride-tetrahydrofuran complex for 48h; Heating;84%
2-azidomethylnaphthalene
164269-42-5

2-azidomethylnaphthalene

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With hydrogenchloride; indium In tetrahydrofuran at 20℃; for 2.5h;91%
Stage #1: 2-azidomethylnaphthalene With ring-opening metathesis polymer-supported triphenylphosphine In tetrahydrofuran Staudinger reaction; Heating;
Stage #2: With ammonia In tetrahydrofuran; water Heating; Further stages.;
With water; triphenylphosphine In tetrahydrofuran Inert atmosphere; Reflux;95 mg
2-naphthalenecarbonitrile
613-46-7

2-naphthalenecarbonitrile

N-butylamine
109-73-9

N-butylamine

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

N-(2-naphthalenylmethylene)butane-1-amine
104575-54-4

N-(2-naphthalenylmethylene)butane-1-amine

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen In hexane at 80℃; under 750.075 Torr; for 18h; Autoclave; Green chemistry;A 14.9%
B 85.1%
2-[(2-naphthyl)methyl]-1H-isoindole-1,3(2H)-dione
247570-26-9

2-[(2-naphthyl)methyl]-1H-isoindole-1,3(2H)-dione

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
Stage #1: 2-[(2-naphthyl)methyl]-1H-isoindole-1,3(2H)-dione With hydrazine hydrate In ethanol for 1.5h; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride In ethanol; water at 90℃; for 15h; Inert atmosphere;
Stage #3: With sodium hydroxide In ethanol; water Inert atmosphere;
81%
With hydrazine hydrate In tetrahydrofuran; ethanol Hydrolysis;
With sodium tetrahydroborate; acetic acid In propan-1-ol; water at 80 - 90℃; for 5h;
With hydrazine hydrate In methanol for 1h; Heating;
With hydrazine In ethanol at 60℃; for 3h;
2-Naphthalenemethanol
1592-38-7

2-Naphthalenemethanol

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With ammonium hydroxide; C19H37IrN4(2+)*2I(1-) at 170℃; for 20h; Sealed tube;78%

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol at 50℃; for 0.416667h;A 60%
B 35%
2-Naphthalenemethanol
1592-38-7

2-Naphthalenemethanol

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

bis((naphthalen-2-yl)methyl)amine
47304-99-4

bis((naphthalen-2-yl)methyl)amine

Conditions
ConditionsYield
With ammonium hydroxide; C15H29IrN4(2+)*2I(1-) at 170℃; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube;A 60%
B 14%
With ammonium hydroxide; C19H37IrN4(2+)*2I(1-) at 150℃; for 20h; Reagent/catalyst; Sealed tube;A 31%
B 56%
2-naphthamide
2243-82-5

2-naphthamide

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;58%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;56%
Stage #1: 2-naphthamide With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With water In tetrahydrofuran at 0℃;
56%
With lithium aluminium tetrahydride; diethyl ether
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 60℃; for 3h;

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

(±)-1,2-di(naphthalen-2-yl)ethane-1,2-diamine

(±)-1,2-di(naphthalen-2-yl)ethane-1,2-diamine

C

(1S,2R)-1,2-Di-naphthalen-2-yl-ethane-1,2-diamine

(1S,2R)-1,2-Di-naphthalen-2-yl-ethane-1,2-diamine

Conditions
ConditionsYield
With methanesulfonic acid; zinc In acetonitrile at 25℃; reduction;A 19%
B n/a
C n/a
2-naphthalenecarbonitrile
613-46-7

2-naphthalenecarbonitrile

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

bis((naphthalen-2-yl)methyl)amine
47304-99-4

bis((naphthalen-2-yl)methyl)amine

Conditions
ConditionsYield
With nickel; decalin at 190℃; under 15200 Torr; Hydrogenation;
With tetralin; nickel at 190℃; under 15200 Torr; Hydrogenation;
naphthalene-2-carbothioamide
6967-89-1

naphthalene-2-carbothioamide

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With hydrogenchloride; zinc at 30 - 40℃;
2-naphthalenecarbonitrile
613-46-7

2-naphthalenecarbonitrile

hydrogen

hydrogen

nickel

nickel

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

β-thionaphthoic acid amide

β-thionaphthoic acid amide

A

1,2-bis(2-naphthyl)ethane
21969-45-9

1,2-bis(2-naphthyl)ethane

B

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With hydrogenchloride; ethanol; zinc
N--phthalimide

N--phthalimide

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With hydrazine
thi-β-naphthoic acid amide

thi-β-naphthoic acid amide

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

α.β-di--ethane

α.β-di--ethane

Conditions
ConditionsYield
With hydrogenchloride; zinc at 30 - 40℃;
hydrogenchloride
7647-01-0

hydrogenchloride

naphthalene-2-carbothioamide
6967-89-1

naphthalene-2-carbothioamide

zinc dust

zinc dust

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal In ethanol at 20℃; for 2h;
2-naphthaloyl chloride
2243-83-6

2-naphthaloyl chloride

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3 / methanol
2: 56 percent / LAH / tetrahydrofuran / 0 - 20 °C
View Scheme
naphthalene-2-carboxylate
93-09-4

naphthalene-2-carboxylate

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 4 h / Heating
2: NH3 / methanol
3: 56 percent / LAH / tetrahydrofuran / 0 - 20 °C
View Scheme
β-naphthaldehyde
66-99-9

β-naphthaldehyde

ethanolic KOH

ethanolic KOH

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH2OH*HCl; Na2CO3 / ethanol; H2O / 2 h / 20 °C
2: glacial AcOH; H2 / Pd/C / ethanol / 2 h / 20 °C
View Scheme
2-bromomethylnaphthyl bromide
939-26-4

2-bromomethylnaphthyl bromide

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

Fmoc-glycine loaded Wang resin

Fmoc-glycine loaded Wang resin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: propan-2-ol / 1 h / Heating
2: hydrazine hydrate / methanol / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: dimethylformamide
2: NH2NH2*H2O / tetrahydrofuran; ethanol
View Scheme
2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

Fmoc-glycine loaded Wang resin

Fmoc-glycine loaded Wang resin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-bromosuccinimide; benzoyl peroxide / CCl4 / 2 h / Heating
2: propan-2-ol / 1 h / Heating
3: hydrazine hydrate / methanol / 1 h / Heating
View Scheme
2-Naphthalenemethanol
1592-38-7

2-Naphthalenemethanol

piperazine-CO2-CH2-Wang resin

piperazine-CO2-CH2-Wang resin

A

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

B

Fmoc-glycine loaded Wang resin

Fmoc-glycine loaded Wang resin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 5.38 g / PPh3; DEAD / tetrahydrofuran / 22 h / 0 - 20 °C
2: NaBH4; AcOH / propan-1-ol; H2O / 5 h / 80 - 90 °C
View Scheme
naphthalene-2-diazonium chloride
20893-80-5

naphthalene-2-diazonium chloride

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: ammonium sulfide / 35 - 40 °C / im geschlossenen Gefaess
3: zinc; alcoholic hydrochloric acid / 30 - 40 °C
View Scheme
methyl N-(2-naphthalenylmethyl)carbamate

methyl N-(2-naphthalenylmethyl)carbamate

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; methanol at 120℃;
C16H23NO2SSi
1202001-90-8

C16H23NO2SSi

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide at 110℃; for 48h; Inert atmosphere;
C19H15NO3

C19H15NO3

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
With ethylenediamine In 1,4-dioxane; propan-1-ol; water for 24h; Reflux;20.1 mg
2-bromonaphthalene
580-13-2

2-bromonaphthalene

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane; water / 36 h / Reflux
2: ethylenediamine / 1,4-dioxane; propan-1-ol; water / 24 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 12 h / 130 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Reflux
View Scheme
flufenamic acid
530-78-9

flufenamic acid

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

C14H10F3NO2*C11H11N

C14H10F3NO2*C11H11N

Conditions
ConditionsYield
In methanol at 20℃;100%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

C17H15F3N2O3

C17H15F3N2O3

C17H15F3N2O3*C11H11N

C17H15F3N2O3*C11H11N

Conditions
ConditionsYield
In methanol at 20℃;100%
2-acetoxy-3-butene
6737-11-7

2-acetoxy-3-butene

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

(R)-N-(naphthalen-2-ylmethyl)but-3-en-2-amine

(R)-N-(naphthalen-2-ylmethyl)but-3-en-2-amine

Conditions
ConditionsYield
With [(R)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3-nitrobenzenecarboxylato] [1,2,3-eta-2-propenyl Ir(III)]; caesium carbonate In tetrahydrofuran; water at 50℃; for 18h; Inert atmosphere; Sealed tube; enantioselective reaction;99%
succinic acid anhydride
108-30-5

succinic acid anhydride

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

1-((naphthalene-2-yl)methyl)pyrrolidine-2,5-dione

1-((naphthalene-2-yl)methyl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
With dmap; acetic acid for 24h; Heating;98%
phthalic anhydride
85-44-9

phthalic anhydride

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

2-[(2-naphthyl)methyl]-1H-isoindole-1,3(2H)-dione
247570-26-9

2-[(2-naphthyl)methyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With acetic acid at 120℃; for 2h; Inert atmosphere; Schlenk technique;97%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

3-nitro-1,8-naphthalic anhydride
3027-38-1

3-nitro-1,8-naphthalic anhydride

2-(naphthalen-2-ylmethyl)-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione
1229445-61-7

2-(naphthalen-2-ylmethyl)-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
In ethanol for 2h; Reflux; Inert atmosphere;96%
In ethanol at 0 - 65℃; for 2h; Inert atmosphere;96%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

methyl chloroformate
79-22-1

methyl chloroformate

methyl N-(2-naphthalenylmethyl)carbamate

methyl N-(2-naphthalenylmethyl)carbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;96%
4-chloro-2-(4-methanesulfonylphenyl)-6-trifluoromethylpyrimidine
1018481-30-5

4-chloro-2-(4-methanesulfonylphenyl)-6-trifluoromethylpyrimidine

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

C23H18F3N3O2S
1018480-49-3

C23H18F3N3O2S

Conditions
ConditionsYield
With triethylamine93%
tert-butyl (1SR,4RS)-2-[(4-butylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hepta-2-ene-7-carboxylate

tert-butyl (1SR,4RS)-2-[(4-butylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hepta-2-ene-7-carboxylate

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

tert-butyl (1SR,2SR,3RS,4RS)-2-[(4-butylphenyl)sulfonyl]-3-[(2-naphthylmethyl)amino]-7-azabicyclo[2.2.1]heptane-7-carboxylate

tert-butyl (1SR,2SR,3RS,4RS)-2-[(4-butylphenyl)sulfonyl]-3-[(2-naphthylmethyl)amino]-7-azabicyclo[2.2.1]heptane-7-carboxylate

Conditions
ConditionsYield
at 70 - 90℃; for 14h; Inert atmosphere; Neat (no solvent); diastereoselective reaction;93%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

ethyl (S)-3-(1,1-dimethylallyloxy)glutarate

ethyl (S)-3-(1,1-dimethylallyloxy)glutarate

A

3-(1,1-dimethylallyloxy)-4-(ethoxycarbonyl)-N-(naphth-2-ylmethyl)butyramide

3-(1,1-dimethylallyloxy)-4-(ethoxycarbonyl)-N-(naphth-2-ylmethyl)butyramide

B

(S)-3-(1,1-dimethylallyloxy)-4-(ethoxycarbonyl)-N-(naphth-2-ylmethyl)butyramide

(S)-3-(1,1-dimethylallyloxy)-4-(ethoxycarbonyl)-N-(naphth-2-ylmethyl)butyramide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;A n/a
B 93%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

2-naphthalenecarbonitrile
613-46-7

2-naphthalenecarbonitrile

Conditions
ConditionsYield
With potassium hydroxide; nickel copper formate; (Bu4N)2S2O8 In dichloromethane at 20℃; for 13h; Oxidation;92%
With 1-methyl-1H-imidazole; oxygen; copper(ll) bromide In dimethyl sulfoxide at 100℃; for 24h;90%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

1-(naphthalen-2-yl)-N-(naphthalen-2-ylmethyl)methanimine

1-(naphthalen-2-yl)-N-(naphthalen-2-ylmethyl)methanimine

Conditions
ConditionsYield
With C62H72CuN2O6; oxygen In acetonitrile at 25℃; under 25.8581 Torr; for 0.5h;92%
With oxygen In acetonitrile at 40℃; for 30h; Catalytic behavior; Photolysis;81%
With titanium(IV) oxide In water under 760.051 Torr; for 9h; Time; Irradiation;
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

ethyl (S,Z)-3-(but-2-en-1-yloxy)glutarate

ethyl (S,Z)-3-(but-2-en-1-yloxy)glutarate

(S,Z)-3-(but-2-en-1-yloxy)-4-(ethoxycarbonyl)-N-(naphth-2-ylmethyl)butyramide

(S,Z)-3-(but-2-en-1-yloxy)-4-(ethoxycarbonyl)-N-(naphth-2-ylmethyl)butyramide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;91%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

N-propyl-1,3,2-benzodithiazole S-oxide
145025-18-9

N-propyl-1,3,2-benzodithiazole S-oxide

N-(2-naphthylmethyl)-1,3,2-benzodithiazole S-oxide

N-(2-naphthylmethyl)-1,3,2-benzodithiazole S-oxide

Conditions
ConditionsYield
In toluene for 16h; Heating;90%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

N-naphthylidene(2-naphthalene)methylamine

N-naphthylidene(2-naphthalene)methylamine

Conditions
ConditionsYield
With iodine; mercury(II) oxide In dichloromethane at 20℃; for 1h; Oxidation;90%
carbon disulfide
75-15-0

carbon disulfide

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

methyl iodide
74-88-4

methyl iodide

methyl n-(2-naphthalenylmethyl)dithiocarbamate

methyl n-(2-naphthalenylmethyl)dithiocarbamate

Conditions
ConditionsYield
Stage #1: carbon disulfide; naphthalen-2-ylmethylamine With pyridine; triethylamine at 0℃; for 0.333333h;
Stage #2: methyl iodide at 0℃; for 0.5h;
90%
Stage #1: carbon disulfide; naphthalen-2-ylmethylamine With triethylamine In methanol at 0℃; for 0.5h;
Stage #2: methyl iodide In methanol at 0 - 20℃;
54%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

2-naphthalen-1-yl-benzooxazole
3164-18-9

2-naphthalen-1-yl-benzooxazole

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; copper(II) ferrite; oxygen at 130℃; for 16h; Schlenk technique; Green chemistry;90%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

2-Bromobenzamide
4001-73-4

2-Bromobenzamide

2-(naphthalen-2-yl)quinazolin-4(3Η)-one
18818-43-4

2-(naphthalen-2-yl)quinazolin-4(3Η)-one

Conditions
ConditionsYield
With potassium carbonate; dimethyl sulfoxide at 80℃; for 2h;90%
4-Methylpyrimidine
3438-46-8

4-Methylpyrimidine

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

(E)-4-(2-(naphthalen-2-yl)vinyl)pyrimidine

(E)-4-(2-(naphthalen-2-yl)vinyl)pyrimidine

Conditions
ConditionsYield
With 1,10-phenanthroline-5,6-dione; trifluorormethanesulfonic acid; oxygen In chlorobenzene at 80℃; under 760.051 Torr; for 24h;90%
4-Amino-2,6-dihydroxypyrimidine
873-83-6

4-Amino-2,6-dihydroxypyrimidine

formaldehyd
50-00-0

formaldehyd

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

5,8-diallyl-5,6,8,9-tetrahydro-4H,7H-2,5,6a,8,9a-penta-azaphenalene-1,3-dione

5,8-diallyl-5,6,8,9-tetrahydro-4H,7H-2,5,6a,8,9a-penta-azaphenalene-1,3-dione

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 65℃; for 1.5h; Microwave irradiation;89%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

N-(naphthyl-2-methyl)-N'-phenylthiourea

N-(naphthyl-2-methyl)-N'-phenylthiourea

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.25h;88%
2-methyl-3-phenylacrylic acid
1895-97-2

2-methyl-3-phenylacrylic acid

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

chloroacetone
78-95-5

chloroacetone

N-(2-chloro-1-methyl-1-{5-[(E)-1-methyl-2-phenyl-1-ethenyl]-1,3,4-oxadiazol-2-yl}ethyl)-N-(2-naphthylmethyl)amine

N-(2-chloro-1-methyl-1-{5-[(E)-1-methyl-2-phenyl-1-ethenyl]-1,3,4-oxadiazol-2-yl}ethyl)-N-(2-naphthylmethyl)amine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12.25h;88%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

ethyl (S)-3-(benzyloxymethoxy)glutarate

ethyl (S)-3-(benzyloxymethoxy)glutarate

(S)-3-(benzyloxymethoxy)-4-(ethoxycarbonyl)-N-(naphth-2-ylmethyl)butyramide

(S)-3-(benzyloxymethoxy)-4-(ethoxycarbonyl)-N-(naphth-2-ylmethyl)butyramide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;88%
tert-butyl (1SR,4RS)-2-{[4-(pentyloxy)phenyl]sulfonyl}-7-azabicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

tert-butyl (1SR,4RS)-2-{[4-(pentyloxy)phenyl]sulfonyl}-7-azabicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

tert-butyl 3-exo-[(naphth-2-ylmethyl)amino]-2-endo-{[4-(pentyloxy)phenyl]sulfonyl}-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate

tert-butyl 3-exo-[(naphth-2-ylmethyl)amino]-2-endo-{[4-(pentyloxy)phenyl]sulfonyl}-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate

Conditions
ConditionsYield
In dichloromethane at 25℃; for 15h; Inert atmosphere; Autoclave; Schlenk technique;87%
2,6-Dichloropyrimidine
3934-20-1

2,6-Dichloropyrimidine

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

2-chloro-N-(naphthalen-2'-ylmethyl)pyrimidin-4-amine

2-chloro-N-(naphthalen-2'-ylmethyl)pyrimidin-4-amine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 0℃; Microwave irradiation;87%
carbon disulfide
75-15-0

carbon disulfide

naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

α-bromoacetophenone
70-11-1

α-bromoacetophenone

3-(2-naphthylmethyl)-4-phenyl-1,3-thiazole-2(3H)-thione
1372541-13-3

3-(2-naphthylmethyl)-4-phenyl-1,3-thiazole-2(3H)-thione

Conditions
ConditionsYield
Stage #1: carbon disulfide; naphthalen-2-ylmethylamine In methanol at 25℃; for 1h;
Stage #2: α-bromoacetophenone In methanol at 25℃; for 24h;
86%
naphthalen-2-ylmethylamine
2018-90-8

naphthalen-2-ylmethylamine

8-bromoadenosine
2946-39-6

8-bromoadenosine

8-(2-naphthylmethylamino)adenosine

8-(2-naphthylmethylamino)adenosine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 120℃; for 101h; Sealed tube;86%

2018-90-8Relevant articles and documents

A simple anion chemosensor based on a naphthalene-thiouronium dyad

Kubo, Yuji,Tsukahara, Masahiko,Ishihara, Shinji,Tokita, Sumio

, p. 653 - 654 (2000)

A fluorescent-active molecular dyad comprising a naphthalene moiety covalently attached, via a methylene spacer, to a thiouronium receptor is described where selective anion-induced fluorescence changes make it of potential use as an anion chemosensor material.

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong

, p. 2059 - 2067 (2021/09/02)

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

Benzimidazole fragment containing Mn-complex catalyzed hydrosilylation of ketones and nitriles

Ganguli, Kasturi,Mandal, Adarsha,Sarkar, Bidisha,Kundu, Sabuj

supporting information, (2020/08/13)

The synthesis of a new bidentate (NN)–Mn(I) complex is reported and its catalytic activity towards the reduction of ketones and nitriles is studied. On comparing the reactivity of various other Mn(I) complexes supported by benzimidazole ligand, it was observed that the Mn(I) complexes bearing 6-methylpyridine and benzimidazole fragments exhibited the highest catalytic activity towards monohydrosilylation of ketones and dihydrosilylation of nitriles. Using this protocol, a wide range of ketones were selectively reduced to the corresponding silyl ethers. In case of unsaturated ketones, the chemoselective reduction of carbonyl group over olefinic bonds was observed. Additionally, selective dihydrosilylation of several nitriles were also achieved using this complex. Mechanistic investigations with radical scavengers suggested the involvement of radical species during the catalytic reaction. Stoichiometric reaction of the Mn(I) complex with phenylsilane revealed the formation of a new Mn(I) complex.

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