Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen In propan-1-ol; water at 60℃; under 375.038 Torr; for 18h; Flow reactor; | 100% |
Stage #1: phenylacetonitrile With water; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; Stage #2: With hydrogenchloride In water chemoselective reaction; | 99% |
Stage #1: phenylacetonitrile With ammonium hydroxide; hydrogen; cobalt(II) diacetate tetrahydrate; zinc trifluoromethanesulfonate; zinc In methanol at 120℃; under 30003 Torr; for 15h; Sealed tube; Autoclave; Stage #2: With hydrogenchloride In diethyl ether | 96% |
Conditions | Yield |
---|---|
Stage #1: phenethyl azide With triphenylphosphine at 110℃; for 20h; Staudinger Azide Reduction; Green chemistry; Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether Green chemistry; | 97% |
Stage #1: phenethyl azide With 1,3-diphenyl-disiloxane; triphenylphosphine at 20℃; for 24h; Staudinger Azide Reduction; Stage #2: With water Stage #3: With hydrogenchloride In 1,4-dioxane chemoselective reaction; | 90% |
Multi-step reaction with 2 steps 1: benzene / Ambient temperature 2: HCl / benzene / 2 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol | 90% |
With hydrogenchloride In water | |
With hydrogenchloride In methanol; diethyl ether at 20℃; Inert atmosphere; | |
With hydrogenchloride In water at 20℃; | 68.6 mg |
Conditions | Yield |
---|---|
Stage #1: 2-Phenylnitroethane With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate at 20℃; | 83% |
Conditions | Yield |
---|---|
Stage #1: 3-phenylpropionamide With tetrafluoroboric acid; iodobenzene; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at 25℃; for 48h; Hofmann rearrangement; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water Inert atmosphere; | 82% |
With hydrogenchloride; formic acid; iodosylbenzene 1.) CH3CN, H2O, 15 h, room temp.; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
Stage #1: 1-phenethyl-3,4-diphenyl-1H-pyrrole-2,5-dione With potassium hydroxide In ethanol; water at 102℃; for 0.133333h; Microwave irradiation; Green chemistry; Stage #2: With hydrogenchloride In ethanol; water pH=4; Temperature; Green chemistry; | A n/a B 82% |
Conditions | Yield |
---|---|
Stage #1: L-phenylalanine With (R)-Carvone In propan-1-ol at 190℃; under 11251.1 Torr; for 0.0833333h; Sealed tube; Stage #2: With hydrogenchloride In propan-1-ol; water at 190℃; for 0.0833333h; | 78% |
Multi-step reaction with 2 steps 1: propan-1-ol / 20 - 190 °C / Green chemistry 2: hydrogenchloride / propan-1-ol / 0.08 h / 190 °C / Green chemistry View Scheme |
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In propan-1-ol at 190℃; for 0.0833333h; Temperature; Green chemistry; | 78% |
N-phenethylbenzamide
ethylmagnesium bromide
A
2-phenylethylamine hydrochloride
B
1-phenyl-propan-1-one
Conditions | Yield |
---|---|
Stage #1: N-phenethylbenzamide With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.5h; Stage #2: ethylmagnesium bromide With cerium(III) chloride In tetrahydrofuran; dichloromethane at -78℃; for 2h; Stage #3: With hydrogenchloride In ethyl acetate | A 76% B n/a |
Conditions | Yield |
---|---|
Stage #1: Benzeneacetamide With [(aNHC)KN(SiMe3)2]2; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 40℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With water; sodium hydroxide In diethyl ether; toluene at 40℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique; Stage #3: With hydrogenchloride In diethyl ether; water Inert atmosphere; Glovebox; Schlenk technique; | 75% |
Stage #1: Benzeneacetamide With triethyl borane; phenylsilane; potassium acetate In tetrahydrofuran; tert-butyl methyl ether at 120℃; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 8h; Inert atmosphere; chemoselective reaction; | 54% |
Stage #1: Benzeneacetamide With triethyl borane; phenylsilane; potassium acetate In tert-butyl methyl ether at 120℃; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 8h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube; | 54% |
Multi-step reaction with 2 steps 1: lithium 2,6-di-tert-butylphenolate / neat (no solvent) / 18 h / 60 °C / Inert atmosphere; Glovebox; Schlenk technique 2: sodium hydroxide / water; diethyl ether / 1 h View Scheme |
ethyl 3-(4-oxo-1-(2-phenylethyl)-3-piperidinyl)propionate hydrochloride
aniline
A
2,4'-diaminodiphenylmethane
B
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
In toluene for 4h; | A n/a B 69% |
1-<<(Triphenylphosphoranylidene)amino>methyl>benzotriazole
benzylmagnesium chloride
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride 1.) THF/diethyl ether, 20 min, rt.; 2.) diethyl ether, 1h; | 67% |
Conditions | Yield |
---|---|
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 0℃; for 6h; Inert atmosphere; | 51% |
Conditions | Yield |
---|---|
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 0℃; for 3.5h; | 51% |
Conditions | Yield |
---|---|
Stage #1: methyl-N-(benzyl-methyl)-formamide With pyridine; oxalyl dichloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: With propylene glycol In tetrahydrofuran at 0 - 25℃; Inert atmosphere; | 49% |
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-oxo-2-phenylethyl phenethylcarbamate With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 3h; Sealed tube; Irradiation; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere; | 49% |
methanol
Nα-diphenylphosphinyl-2-phenylethylamine
A
2-phenylethylamine hydrochloride
B
methyl diphenylphosphinate
Conditions | Yield |
---|---|
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented; |
methanol
N-(2-phenylethyl)-P,P-dimethylphosphinamide
A
dimethyl-phosphinic acid methyl ester
B
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented; |
methanol
N-(2-phenylethyl)-P,P-diethylphosphinamide
A
methyl diethylphosphinate
B
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented; |
methanol
N-(2-phenylethyl)-P,P-di-n-butylphosphinamide
A
methyl dibutylphosphinate
B
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented; |
methanol
5-dibenzophosphole-5-oxide
A
5-methoxydibenzophosphole 5-oxide
B
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented; |
methanol
N-(2-phenylethyl)-P,P-dibenzylphosphinamide
A
methyl dibenzylphosphinate
B
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented; |
1--2-phenyl-ethan
A
Hexamethyldisiloxane
B
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; water In diethyl ether Yield given; |
Nα-diphenylphosphinyl-2-phenylethylamine
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With trifluoroacetic acid for 0.166667h; |
Conditions | Yield |
---|---|
With ammonium formate; palladium on activated charcoal In methanol at 65℃; for 2h; Yield given; |
Phenethyl-phosphorimidic acid triethyl ester
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In benzene for 2h; Ambient temperature; Yield given; |
3-<(E)-(2-phenylethenyl)>-4,5-diphenyl-2(3H)oxazolone
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal 1) EtOH, H2O, HOAc, 50 deg C, 50 psi, 4h, 2) EtOH; Yield given. Multistep reaction; |
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal 1) EtOH, H2O, HOAc, 50 deg C, 50 psi, 4h, 2) EtOH; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium azide 2) ether; Multistep reaction; |
2-phenylethylamine hydrochloride
N,N-dimethyl-formamide dimethyl acetal
N,N-dimethyl-N'-phenethyl-formamidine
Conditions | Yield |
---|---|
for 2h; Reflux; | 100% |
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With hydrogen; water-d2; palladium on activated charcoal at 20℃; for 72h; | 99% |
With hydrogen; water-d2; palladium on activated charcoal at 110℃; under 760.051 Torr; for 24h; | 94% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 8h; Mannich reaction; Heating; | 98% |
2-phenylethylamine hydrochloride
phenylacetylene
N-phenethyl-2-phenylacetamide
Conditions | Yield |
---|---|
With potassium hexafluorophosphate; 4-methylpyridine-1-oxide; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); potassium carbonate In 1,2-dichloro-ethane at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; | 98% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 8h; Mannich reaction; Heating; | 97% |
With hydrogenchloride In ethanol; water Mannich reaction; Reflux; | 24% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 14h; Mannich reaction; Heating; | 97% |
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
With sodium 2-ethylhexanoic acid In tetrahydrofuran at 20℃; for 144h; | 96% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 16h; Mannich reaction; Heating; | 96% |
In isopropyl alcohol Mannich reaction; Heating; Acidic conditions; | 35% |
Conditions | Yield |
---|---|
Stage #1: benzoic acid With 1,1'-carbonyldiimidazole In neat (no solvent) for 0.0833333h; Milling; Stage #2: 2-phenylethylamine hydrochloride In neat (no solvent) for 0.166667h; Milling; | 96% |
Stage #1: benzoic acid With 1,1'-carbonyldiimidazole for 0.0833333h; Milling; Green chemistry; Stage #2: 2-phenylethylamine hydrochloride for 0.166667h; Milling; Green chemistry; | 96% |
2-chloropyridine
trifluoromethylsulfonic anhydride
4-trifluoromethylbenzoic acid
2-phenylethylamine hydrochloride
1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Stage #1: 4-trifluoromethylbenzoic acid; 2-phenylethylamine hydrochloride With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 17h; Stage #2: 2-chloropyridine; trifluoromethylsulfonic anhydride at -78 - 20℃; for 37h; Stage #3: With sodium tetrahydroborate In methanol at 20℃; for 13h; | 96% |
2-oxo-4-phenylbutyric acid
2-phenylethylamine hydrochloride
N-phenethyl-3-phenylpropanamide
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In water; acetonitrile at 20℃; for 1h; Reagent/catalyst; Sealed tube; Darkness; chemoselective reaction; | 96% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 7h; Mannich reaction; Heating; | 95% |
With hydrogenchloride In ethanol; water Mannich reaction; Reflux; | 18% |
2-phenylethylamine hydrochloride
Conditions | Yield |
---|---|
In chloroform at 25℃; for 24h; | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 13h; Mannich reaction; Heating; | 94% |
Stage #1: 2-phenylethylamine hydrochloride; 1-(4-methoxyphenyl)ethanone In ethanol Mannich reaction; Heating; Stage #2: formaldehyd In ethanol; water for 9h; Mannich reaction; Heating; Stage #3: With hydrogenchloride In diethyl ether |
potassium cyanide
2-phenylethylamine hydrochloride
3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one
3,7-dimethyl-9-phenethylamino-3,7-diazabicyclo<3.3.1>nonane-9-carbonitrile
Conditions | Yield |
---|---|
In methanol; water for 72h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 19h; Mannich reaction; Heating; | 93% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 7h; Mannich reaction; Heating; | 93% |
formaldehyd
2-phenylethylamine hydrochloride
1-(2,4-dichlorophenyl)ethan-1-one
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 26h; Mannich reaction; Heating; | 91% |
2-phenylethylamine hydrochloride
acetyl chloride
methyl-N-(benzyl-methyl)-formamide
Conditions | Yield |
---|---|
Stage #1: 2-phenylethylamine hydrochloride With triethylamine In dichloromethane for 0.5h; Stage #2: acetyl chloride In dichloromethane at 0 - 20℃; for 18.5h; | 90% |
With sodium hydroxide In dichloromethane for 3h; | 65% |
2-phenylethylamine hydrochloride
2,5-di-O-acetyl-3-azido-1-(6-chloropurin-9-yl)-β-D-1,3-dideoxyribofuranose
Conditions | Yield |
---|---|
With triethylamine In ethanol at 50℃; | 90% |
Conditions | Yield |
---|---|
In hydrogenchloride; water 80°C; cooling (room temp.), pptn., filtn., washing (aq. HCl), recrystn. (aq. HCl); elem. anal.; | 89% |
Conditions | Yield |
---|---|
With copper(l) iodide; calcium carbonate In water; acetonitrile at 40℃; for 6h; | 88% |
Stage #1: benzaldehyde With 1-hydroxy-pyrrolidine-2,5-dione; oxygen; cobalt(II) diacetate tetrahydrate; sodium hydrogencarbonate In acetonitrile at 20℃; under 760.051 Torr; for 1h; Molecular sieve; Stage #2: 2-phenylethylamine hydrochloride In acetonitrile at 20℃; Molecular sieve; | 80% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 12h; Mannich reaction; Heating; | 87% |
6-chloro-9-((3aR,3bR,4aS,5R,5aS)-hexahydro-2,2dimethylbicyclo[3.1.0]hex-1(5)-eno[3,2-d] [1,3]dioxol-5-yl)-2-iodo-9H-purine
2-phenylethylamine hydrochloride
(1R,2R,3S,4R,5S)-4-(2-iodo-6-(2-phenylethylamino)-9H-purin-9-yl)-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexane
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
Stage #1: N-Cbz-L-Phe With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-phenylethylamine hydrochloride In tetrahydrofuran; water at 0℃; for 0.5h; | 84% |
The molecular structure of 2-Phenylethylamine hydrochloride (CAS NO.156-28-5):
IUPAC Name: 2-Phenylethanamine hydrochloride
Molecular Weight: 157.64058 g/mol
Molecular Formula: C8H12ClN
Melting Point: 220-222 °C(lit.)
Flash Point: 90.6 °C
Enthalpy of Vaporization: 43.27 kJ/mol
Boiling Point: 196.5 °C at 760 mmHg
Vapour Pressure: 0.398 mmHg at 25 °C
H-Bond Donor: 2
H-Bond Acceptor: 1
Rotatable Bond Count: 2
Exact Mass: 157.065827
MonoIsotopic Mass: 157.065827
Topological Polar Surface Area: 26
Heavy Atom Count: 10
Canonical SMILES: C1=CC=C(C=C1)CCN.Cl
InChI: InChI=1S/C8H11N.ClH/c9-7-6-8-4-2-1-3-5-8;/h1-5H,6-7,9H2;1H
InChIKey: SKHIBNDAFWIOPB-UHFFFAOYSA-N
EINECS: 205-849-2
Classification Code: Drug / Therapeutic Agent; Human Data; Skin / Eye Irritant
1. | eye-man 50 mg SEV | AIMDAP Archives of Internal Medicine. 39 (1927),404. | ||
2. | orl-hmn TDLo:714 mg/kg:CVS | AIMDAP Archives of Internal Medicine. 39 (1927),404. | ||
3. | orl-hmn TDLo:45 mg/kg:CNS | KLWOAZ Klinische Wochenscrift. 17 (1938),1580. | ||
4. | scu-rat LDLo:160 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 71 (1941),62. | ||
5. | scu-mus LD50:470 mg/kg | JPPMAB Journal of Pharmacy and Pharmacology. 15 (1963),472. | ||
6. | ivn-rbt LDLo:50 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 36 (1929),363. | ||
7. | skn-gpg LDLo:200 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 32 (1927),121. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xn, Xi
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
RIDADR: 2811
WGK Germany: 3
RTECS: SH7175000
HazardClass: 6.1(b)
PackingGroup: III
Poison by skin contact, subcutaneous, and intravenous routes. A human eye irritant. A skin irritant and possible sensitizer. Human systemic effects by ingestion: blood pressure lowering, anorexia. When heated to decomposition it emits very toxic fumes of NOx and HCl.
2-Phenylethylamine hydrochloride (CAS NO.156-28-5) is also named as 1-Phenyl-2-aminoethane hydrochloride ; Benzeneethanamine hydrochloride ; NSC 138569 ; Phenethylammonium chloride ; UNII-VOF61XW69D ; USAF EL-76 ; beta-Phenethylamine hydrochloride ; beta-Phenylathylaminhydrochlorid ; beta-Phenylathylaminhydrochlorid [German] ; beta-Phenylethylamine hydrochloride .
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