sodium tetrafluoroborate
B
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With CF3COOH In dichloromethane To a soln. of complex in CH2Cl2 was added CF3CO2H, the mixt. was stirred for 10 min (N2 atm.); evapd., extd. with H2O, NaBF4 was added;; ppt. was filtered, recrystd. from CH2Cl2-hexane;; | A 98% B n/a |
isopropyl methoxyacetate
(RS)-1-(1-naphthyl)ethylamine
B
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With immobilized lipase B from Candida antarctica (Novozyme 435) In diethyl ether | A 93% B 92% |
With Novozym 435 at 47℃; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; | A 48% B 45% |
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
B
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With CF3CO2H; NaBF4 In dichloromethane addn. of CF3CO2H to Re complex soln.; stirring, 20 min.; evapn.; dissoln. in methanol; addn. of H2O and solid NaBF4; pptn.; filtration; drying (vac.); recrystn. from CH2Cl2-hexane; filtration; washing with ether; drying under vac.; elem. anal.; | A 91% B 76% |
Pyridine-2-sulfonic acid ((S)-1-naphthalen-1-yl-ethyl)-amide
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With magnesium In methanol at 0℃; for 2h; | 90% |
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With hydrogenchloride In water | 75% |
(RS)-1-(1-naphthyl)ethylamine
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
Stage #1: (RS)-1-(1-naphthyl)ethylamine With (S)-isopropylidene glycerol 3-carboxy-2-naphthoate In methanol at 20℃; Stage #2: With sulfuric acid In ethyl acetate | A n/a B 47% |
lauric acid
(RS)-1-(1-naphthyl)ethylamine
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-N-lauroyl-α-(1-naphthyl)ethylamine
C
N-((S)-1-(naphthalen-1-yl)ethyl)dodecanamide
Conditions | Yield |
---|---|
With Candida antarctica lipase B In n-heptane at 80℃; for 25h; | A 45% B n/a C n/a |
Ethyl hexanoate
(RS)-1-(1-naphthyl)ethylamine
B
(S)-1-(1-Naphthyl)ethylamine
C
(R)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With Candida antarctica lipase In di-isopropyl ether at 30℃; for 120h; | A 42% B n/a C n/a |
ethyl laurate
(RS)-1-(1-naphthyl)ethylamine
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-1-(1-Naphthyl)ethylamine
C
(R)-N-lauroyl-α-(1-naphthyl)ethylamine
Conditions | Yield |
---|---|
With Candida antarctica lipase In di-isopropyl ether at 30℃; for 120h; | A n/a B n/a C 37% |
(RS)-1-(1-naphthyl)ethylamine
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With D-(+)-camphoric acid |
methyl 1-naphthyl ketone O-methyloxime
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With (2S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol-borane In tetrahydrofuran at 30℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With hydroxylamine-O-sulfonic acid In tetrahydrofuran for 10h; Substitution; Title compound not separated from byproducts; |
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In methanol; water |
(RS)-1-(1-naphthyl)ethylamine
ethyl acetate
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-1-(1-Naphthyl)ethylamine
C
(1R)-N-acetyl-(1-naphthyl)ethylamine
D
(S)-N-(1-(naphthalen-1-yl)ethyl)acetamide
Conditions | Yield |
---|---|
With Candida antarctica lipase B at 60℃; Title compound not separated from byproducts; |
1'-naphthacetophenone
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
Stage #1: 1'-naphthacetophenone With [((R)-tol-binap)RuCl2(DMF)x]; ammonia; ammonium formate In methanol at 85℃; for 30h; Leuckart-Wallach reaction; Stage #2: With hydrogenchloride In ethanol for 1h; Heating; Title compound not separated from byproducts; | |
With pyridoxal 5'-phosphate; isopropylamine In aq. phosphate buffer at 45℃; for 24h; pH=9; Enzymatic reaction; enantioselective reaction; | A n/a B n/a |
With pyridoxal 5'-phosphate; isopropylamine In aq. phosphate buffer at 45℃; for 24h; pH=9; Enzymatic reaction; enantioselective reaction; | A n/a B n/a |
(RS)-1-(1-naphthyl)ethylamine
(1S,2S)-N-acetyl-1,2-bis(trifluoromethanesulfonamido) cyclohexane
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-1-(1-Naphthyl)ethylamine
C
(1R)-N-acetyl-(1-naphthyl)ethylamine
D
(S)-N-(1-(naphthalen-1-yl)ethyl)acetamide
Conditions | Yield |
---|---|
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at -20℃; for 24h; Title compound not separated from byproducts; | |
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at -20℃; Product distribution; Further Variations:; Temperatures; Reagents; |
N-(1-(1-Naphthyl)ethylidene)2'-methoxy-6'-methylaniline
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chiral 1,1'-bisphosphanoferrocene; H2 / {Ir(cod)Cl}2 / CH2Cl2 / 20 °C / 51714.8 Torr 2: CAN / methanol; H2O View Scheme |
1-(1-naphthalenyl)ethanone oxime
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 74.9 percent / H2, conc. ammonia / Raney nickel / aq. ethanol / 24 h / 3040 Torr / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: ammonia; hydrogen / methanol; water / 58 - 62 °C / 2574.5 - 2942.29 Torr 2: ethanol / 0.75 h / 60 - 65 °C / Resolution of racemate 3: ammonia / water; toluene View Scheme |
(Z)-1-(naphthalen-1-yl)ethanone oxime
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaH / dimethylformamide / 1.) 0 deg C, 1 h, 2.) ambient temp., 5 h 2: (S)-(-)-2-amino-3-methyl-1,1-diphenylbutanol*borane / tetrahydrofuran / 24 h / 30 °C View Scheme |
(1R)‐1‐(naphthalen‐1‐yl)ethyl methanesulfonate
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With ammonia In toluene at 87℃; under 2250.23 Torr; for 5h; | n/a |
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene pH=> 10; | n/a |
sodium tetrafluoroborate
(+)-(SS)-(η-C5H5)Re(NO)(PPH3)(CONHCH(CH3)C10H7)
B
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With CF3COOH In dichloromethane To a soln. of complex in CH2Cl2 was added CF3CO2H, the mixt. was stirred for 10 min (N2 atm.); evapd., extd. with H2O, NaBF4 was added;; ppt. was filtered, recrystd. from CH2Cl2-hexane;; |
(RS)-1-(1-naphthyl)ethylamine
A
1'-naphthacetophenone
B
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With D-amino acid oxidase; ATA-117; pyridoxal 5'-phosphate; 2-oxo-propionic acid at 30℃; for 3h; pH=8; Resolution of racemate; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
1'-naphthacetophenone
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride; sodium hydroxide / methanol; water / 20 - 35 °C / pH 6 - 6.5 2: ammonia; hydrogen / methanol; water / 58 - 62 °C / 2574.5 - 2942.29 Torr 3: ethanol / 0.75 h / 60 - 65 °C / Resolution of racemate 4: ammonia / water; toluene View Scheme | |
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; sodium carbonate / ethanol; water / pH 5 / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 18 h / 20 °C 3.1: C19H23BNO3(1-)*H(1+); borane-THF / 1,4-dioxane / 72 h / Inert atmosphere View Scheme | |
With pyridoxal 5'-phosphate; ω-transaminases from ochrobactrum anthropi mutant W58A; isopropylamine In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 300 Torr; for 15h; pH=7; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | n/a |
With dipotassium hydrogenphosphate; pyridoxal 5'-phosphate In aq. phosphate buffer; dimethyl sulfoxide at 45℃; for 48h; pH=9; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | n/a |
With pyridoxal 5'-phosphate; isopropylamine In aq. phosphate buffer at 45℃; for 24h; pH=9; Enzymatic reaction; enantioselective reaction; | n/a |
(1S)-1-(naphthalen-1-yl)ethanamine (R)-mandelate
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With ammonia In water; toluene |
A
(S)-1-(1-Naphthyl)ethylamine
B
(R)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With potassium hydroxide Inert atmosphere; |
Phenylselenyl chloride
(S)-1-(1-Naphthyl)ethylamine
N-<(S)-1-(1-Naphthyl)-ethyl>benzeneselenamide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0℃; for 2h; | 100% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd In toluene for 0.5h; cooling; Stage #2: (S)-1-(1-Naphthyl)ethylamine With tetrafluoroboric acid In water; toluene at 0℃; for 0.25h; Stage #3: Glyoxal In water; toluene at 20 - 40℃; for 12.5h; | 100% |
bromobenzene
(S)-1-(1-Naphthyl)ethylamine
(S)-N-(1-(1-naphthyl)ethyl)aniline
Conditions | Yield |
---|---|
With sodium t-butanolate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; | 100% |
With potassium tert-butylate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80℃; for 12h; Inert atmosphere; | 97% |
(S)-1-(1-Naphthyl)ethylamine
Boc-Arg(MTS)-OH
[4-(N'-2,4,6-trimethylphenylsulfonyl-guanidino)-1(S)-(1-naphthalen-1(S)-yl-ethylcarbamoyl)-butyl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 12h; | 100% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane |
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
In tetrahydrofuran room temp.; | 100% |
In tetrahydrofuran N2-atmosphere; addn. of 3-fold excess of amine to suspension of Ru-complex, stirring (1 h, in dark); evapn., pptn. on addn. of petroleum ether, recrystn. (CH2Cl2:petroleum ether); elem. anal.; | 90% |
(1α,5α,6α)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
Stage #1: (1α,5α,6α)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid; (S)-1-(1-Naphthyl)ethylamine With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 4h; | 100% |
Multi-step reaction with 2 steps 1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 4 h / 20 °C View Scheme |
(2R)-2-tert-butyloxy-4-(9-fluorenylmethoxy)carbonylaminobutyric acid
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; | 99% |
(2S)-2-tert-butyloxy-4-(9-fluorenylmethoxy)carbonylaminobutyric acid
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; | 99% |
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
In ethanol 1 equiv. of amine was added to EtOH soln. of Co-complex at 45 °C,30 min; solid was filtered off, further product was recovered after partial evapn. of solvent at room temp.; | 99% |
Conditions | Yield |
---|---|
With triethylamine In chloroform at 20℃; for 72h; | 99% |
(S)-1-(1-Naphthyl)ethylamine
ortho-diphenylphosphinobenzoic acid
C31H26NOP
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 24℃; for 12h; | 99% |
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-methoxybenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere; Stage #2: (S)-1-(1-Naphthyl)ethylamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; | 99% |
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile at 0 - 20℃; for 4h; | 99% |
With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile at 20℃; for 2h; Cooling with ice; | 99% |
(S)-1-(1-Naphthyl)ethylamine
benzenesulfonyl chloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1.08333h; | 99% |
(S)-1-(1-Naphthyl)ethylamine
o-hydroxyacetophenone
2-{1-[(E)-(S)-1-Naphthalen-1-yl-ethylimino]-ethyl}-phenol
Conditions | Yield |
---|---|
With dibutyltin diacetate In toluene for 96h; Reflux; Inert atmosphere; | 98% |
With toluene-4-sulfonic acid In benzene for 24h; Heating; |
(S)-1-(1-Naphthyl)ethylamine
3-acetamino-3-methyltridecanoic acid
Conditions | Yield |
---|---|
Stage #1: 3-acetamino-3-methyltridecanoic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 1h; Stage #2: (S)-1-(1-Naphthyl)ethylamine In dichloromethane for 3h; | 98% |
(S)-1-(1-Naphthyl)ethylamine
N-methyl-2-imidazolcarboxaldehyde
Conditions | Yield |
---|---|
With magnesium sulfate In chloroform for 24h; Inert atmosphere; Reflux; | 98% |
Conditions | Yield |
---|---|
Stage #1: C11H16O3 With triethylsilane; Wilkinson's catalyst In toluene at 20℃; Inert atmosphere; Stage #2: With sodium hydroxide In methanol; water at 70℃; for 1h; Stage #3: (S)-1-(1-Naphthyl)ethylamine In ethanol for 2h; | 98% |
(S)-1-(1-Naphthyl)ethylamine
1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-one
Conditions | Yield |
---|---|
Stage #1: 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-one With toluene-4-sulfonic acid In ethanol at 5 - 15℃; Inert atmosphere; Stage #2: (S)-1-(1-Naphthyl)ethylamine In ethanol at 10℃; Inert atmosphere; | 97.7% |
Conditions | Yield |
---|---|
Stage #1: m-bromobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1h; Stage #2: (S)-1-(1-Naphthyl)ethylamine With pyridine In dichloromethane at 0 - 20℃; for 2h; | 97% |
1-(3-iodopropyl)-3-(trifluoromethyl)benzene
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 70℃; for 12h; | 97% |
With potassium carbonate In acetonitrile | 95% |
Glyoxal
(S)-1-(1-Naphthyl)ethylamine
N,N'-bis[(S)-1-naphthyl-ethyl]ethanediimine
Conditions | Yield |
---|---|
With formic acid; magnesium sulfate In dichloromethane; water at 20℃; for 16h; | 96% |
With formic acid; magnesium sulfate In dichloromethane at 20℃; for 5h; |
carbon disulfide
(S)-1-(1-Naphthyl)ethylamine
Conditions | Yield |
---|---|
at 48℃; | 96% |
Conditions | Yield |
---|---|
With sodium t-butanolate; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride In 1,2-dimethoxyethane at 50℃; for 48h; Product distribution / selectivity; Buchwald-Hartwig Reaction; | 96% |
3-chloroquinoline
(S)-1-(1-Naphthyl)ethylamine
(S)-N-(1-(naphthalene-1-yl)ethyl)isoquinolin-3-amine
Conditions | Yield |
---|---|
With [(1,3-(2,6-diisopropylphenyl)imidazol-2-ylidene)(3-chloropyridyl)palladium(II) dichloride]; caesium carbonate In 1,2-dimethoxyethane at 80℃; for 24h; Buchwald-Hartwig amination; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 96% |
IUPAC Name: 1-Naphthalen-1-ylethanamine
Empirical Formula: C12H13N
Molecular Weight: 171.2383 g/mol
Index of Refraction: 1.629
Density: 1.064 g/cm3
Flash Point: 144.3 °C
Storage tempreture: 2-8 °C
Sensitive: Air sensitive
alpha: -60 °(c=2, MeOH)
Appearance: Colorless to light yellow liqui
Enthalpy of Vaporization: 52.92 kJ/mol
Boiling Point: 289.9 °C at 760 mmHg
Vapour Pressure: 0.00214 mmHg at 25 °C
Product Category of (S)-(-)-1-(1-Naphthyl)ethylamine (CAS NO.10420-89-0): Amines (Chiral); Analytical Chemistry; Chiral Building Blocks; Enantiomer Excess & Absolute Configuration Determination; Optical Resolution; Synthetic Organic Chemistry; Miscellaneous
(S)-(-)-1-(1-Naphthyl)ethylamine (CAS NO.10420-89-0) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65.
Safety Information of (S)-(-)-1-(1-Naphthyl)ethylamine (CAS NO.10420-89-0):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
(S)-(-)-1-(1-Naphthyl)ethylamine , its cas register number is 10420-89-0. It also can be called (S)-(-)-alpha-(1-Naphthyl)ethylamine ; and 1-(1-Naphthyl)ethylamine . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. While, it's inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.
In addition, (S)-(-)-1-(1-Naphthyl)ethylamine (CAS NO.10420-89-0) could be stable under normal temperatures and pressures. It is not compatible with incompatible materials, acids, acid chlorides, acid anhydrides, chloroformates, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: irritating and toxic fumes and gases.
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