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2-Phenylethylamine hydrochloride is a hydrochloride salt form of 2-Phenylethylamine, a biogenic aromatic amine that functions as a monoaminergic neuromodulator or a neurotransmitter in the human central nervous system. It is a natural monoamine alkaloid that stimulates the release of norepinephrine and dopamine and is metabolized by monoamine oxidases and other enzymes. This product is primarily intended for forensic and research applications. It is characterized by its white to light yellow powder or crystalline appearance and is soluble in water, alcohol, and ether.

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  • 99.5% High purity 2-Phenylethylamine Hydrochloride powder 99% 2-Phenylethylamine Hydrochloride powder raw material 2-Phenylethylamine Hydrochloride powder

    Cas No: 156-28-5

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  • 156-28-5 Structure
  • Basic information

    1. Product Name: 2-Phenylethylamine hydrochloride
    2. Synonyms: β-Aminoethylbenzene hydrochloride;PHENETHYLAMINEHCL;2-PHENYLETHYLAMINE HYDROCHLORIDE (BETA-) 99+%;B-PHENETHYLAMINEHYDROCHLORIDE;β-Phenylethylamine hydrochloride, Phenethylamine hydrochloride;Phenethylamine·hydrochloric acid;Nsc138569;1-phenylethan-1-aMine hydrochloride
    3. CAS NO:156-28-5
    4. Molecular Formula: C8H12N*Cl
    5. Molecular Weight: 157.64
    6. EINECS: 205-849-2
    7. Product Categories: Pharma material
    8. Mol File: 156-28-5.mol
    9. Article Data: 54
  • Chemical Properties

    1. Melting Point: 220-222 °C(lit.)
    2. Boiling Point: 196.5 °C at 760 mmHg
    3. Flash Point: 81 °C
    4. Appearance: White to off-white/Powder or Crystalline Powder
    5. Density: N/A
    6. Vapor Pressure: 0.398mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. Merck: 14,6026
    11. BRN: 3624163
    12. CAS DataBase Reference: 2-Phenylethylamine hydrochloride(CAS DataBase Reference)
    13. NIST Chemistry Reference: 2-Phenylethylamine hydrochloride(156-28-5)
    14. EPA Substance Registry System: 2-Phenylethylamine hydrochloride(156-28-5)
  • Safety Data

    1. Hazard Codes: Xn,Xi,C
    2. Statements: 22-36/37/38-34
    3. Safety Statements: 26-36-45-36/37/39
    4. RIDADR: 2811
    5. WGK Germany: 3
    6. RTECS: SH7175000
    7. HazardClass: 6.1(b)
    8. PackingGroup: III
    9. Hazardous Substances Data: 156-28-5(Hazardous Substances Data)

156-28-5 Usage

Uses

Used in Pharmaceutical Industry:
2-Phenylethylamine hydrochloride is used as a central nervous system (CNS) stimulant for its ability to stimulate the release of norepinephrine and dopamine, which are essential neurotransmitters in the human brain. This application is particularly relevant for the treatment of certain medical conditions that involve the dysregulation of these neurotransmitters.
Used in Research Applications:
In the field of research, 2-Phenylethylamine hydrochloride serves as an important compound for studying the role of monoamines in the central nervous system. It can be used to investigate the mechanisms of action of various drugs, as well as to understand the neurochemical basis of certain neurological and psychiatric disorders.
Used in Forensic Applications:
2-Phenylethylamine hydrochloride is also utilized in forensic science for the analysis and identification of substances related to criminal investigations. Its chemical properties make it a valuable tool for detecting and analyzing trace amounts of compounds in various samples.

Safety Profile

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

Check Digit Verification of cas no

The CAS Registry Mumber 156-28-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 6 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 156-28:
(5*1)+(4*5)+(3*6)+(2*2)+(1*8)=55
55 % 10 = 5
So 156-28-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N.ClH/c9-7-6-8-4-2-1-3-5-8;/h1-5H,6-7,9H2;1H

156-28-5 Well-known Company Product Price

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  • Sigma-Aldrich

  • (42681)  2-Phenylethylaminehydrochloride  certified reference material, TraceCERT®

  • 156-28-5

  • 42681-50MG

  • 816.66CNY

  • Detail
  • Aldrich

  • (P6513)  2-Phenylethylaminehydrochloride  ≥98%

  • 156-28-5

  • P6513-25G

  • 776.88CNY

  • Detail
  • Aldrich

  • (P6513)  2-Phenylethylaminehydrochloride  ≥98%

  • 156-28-5

  • P6513-100G

  • 2,329.47CNY

  • Detail

156-28-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Phenylethylamine Hydrochloride

1.2 Other means of identification

Product number -
Other names 2-Phenylethylamine hydrochloride

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:156-28-5 SDS

156-28-5Synthetic route

phenylacetonitrile
140-29-4

phenylacetonitrile

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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%
phenethyl azide
6926-44-9

phenethyl azide

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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
phenethylamine
64-04-0

phenethylamine

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol90%
With hydrogenchloride In water
With hydrogenchloride In methanol; diethyl ether at 20℃; Inert atmosphere;
With hydrogenchloride In water at 20℃;68.6 mg
2-Phenylnitroethane
6125-24-2

2-Phenylnitroethane

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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%
3-phenylpropionamide
102-93-2

3-phenylpropionamide

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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;
1-phenethyl-3,4-diphenyl-1H-pyrrole-2,5-dione

1-phenethyl-3,4-diphenyl-1H-pyrrole-2,5-dione

A

2,3-diphenylmaleic anhydride
4808-48-4

2,3-diphenylmaleic anhydride

B

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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%
L-phenylalanine
63-91-2

L-phenylalanine

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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
C18H23N

C18H23N

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In propan-1-ol at 190℃; for 0.0833333h; Temperature; Green chemistry;78%
N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

A

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

B

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Conditions
ConditionsYield
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
Benzeneacetamide
103-81-1

Benzeneacetamide

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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
130820-32-5

ethyl 3-(4-oxo-1-(2-phenylethyl)-3-piperidinyl)propionate hydrochloride

aniline
62-53-3

aniline

A

2,4'-diaminodiphenylmethane
1208-52-2

2,4'-diaminodiphenylmethane

B

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
In toluene for 4h;A n/a
B 69%
1-<<(Triphenylphosphoranylidene)amino>methyl>benzotriazole
124316-00-3

1-<<(Triphenylphosphoranylidene)amino>methyl>benzotriazole

benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride 1.) THF/diethyl ether, 20 min, rt.; 2.) diethyl ether, 1h;67%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 0℃; for 6h; Inert atmosphere;51%
nitrostyrene
5153-67-3

nitrostyrene

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 0℃; for 3.5h;51%
methyl-N-(benzyl-methyl)-formamide
877-95-2

methyl-N-(benzyl-methyl)-formamide

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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-oxo-2-phenylethyl phenethylcarbamate

2-oxo-2-phenylethyl phenethylcarbamate

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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
67-56-1

methanol

Nα-diphenylphosphinyl-2-phenylethylamine
62056-94-4

Nα-diphenylphosphinyl-2-phenylethylamine

A

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

B

methyl diphenylphosphinate
1706-90-7

methyl diphenylphosphinate

Conditions
ConditionsYield
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented;
methanol
67-56-1

methanol

N-(2-phenylethyl)-P,P-dimethylphosphinamide
80918-98-5

N-(2-phenylethyl)-P,P-dimethylphosphinamide

A

dimethyl-phosphinic acid methyl ester
14337-77-0

dimethyl-phosphinic acid methyl ester

B

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented;
methanol
67-56-1

methanol

N-(2-phenylethyl)-P,P-diethylphosphinamide
80918-96-3

N-(2-phenylethyl)-P,P-diethylphosphinamide

A

methyl diethylphosphinate
5689-41-8

methyl diethylphosphinate

B

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented;
methanol
67-56-1

methanol

N-(2-phenylethyl)-P,P-di-n-butylphosphinamide
80918-97-4

N-(2-phenylethyl)-P,P-di-n-butylphosphinamide

A

methyl dibutylphosphinate
7163-67-9

methyl dibutylphosphinate

B

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented;
methanol
67-56-1

methanol

5-dibenzophosphole-5-oxide
80918-99-6

5-dibenzophosphole-5-oxide

A

5-methoxydibenzophosphole 5-oxide
40932-00-1

5-methoxydibenzophosphole 5-oxide

B

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented;
methanol
67-56-1

methanol

N-(2-phenylethyl)-P,P-dibenzylphosphinamide
80918-95-2

N-(2-phenylethyl)-P,P-dibenzylphosphinamide

A

methyl dibenzylphosphinate
21713-63-3

methyl dibenzylphosphinate

B

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Rate constant; Kinetics; Thermodynamic data; E, ΔS, ΔG presented;
1--2-phenyl-ethan
58367-45-6

1--2-phenyl-ethan

A

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

B

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; water In diethyl ether Yield given;
Nα-diphenylphosphinyl-2-phenylethylamine
62056-94-4

Nα-diphenylphosphinyl-2-phenylethylamine

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With trifluoroacetic acid for 0.166667h;
N,N-dibenzyl-2-phenylethan-1-amine
5636-54-4

N,N-dibenzyl-2-phenylethan-1-amine

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol at 65℃; for 2h; Yield given;
Phenethyl-phosphorimidic acid triethyl ester
146039-09-0

Phenethyl-phosphorimidic acid triethyl ester

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In benzene for 2h; Ambient temperature; Yield given;
3-<(E)-(2-phenylethenyl)>-4,5-diphenyl-2(3H)oxazolone
148715-47-3

3-<(E)-(2-phenylethenyl)>-4,5-diphenyl-2(3H)oxazolone

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal 1) EtOH, H2O, HOAc, 50 deg C, 50 psi, 4h, 2) EtOH; Yield given. Multistep reaction;
3-<(E)-<2-(4-chlorophenyl)ethenyl>>-4,5-diphenyl-2(3H)oxazolone

3-<(E)-<2-(4-chlorophenyl)ethenyl>>-4,5-diphenyl-2(3H)oxazolone

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal 1) EtOH, H2O, HOAc, 50 deg C, 50 psi, 4h, 2) EtOH; Yield given. Multistep reaction;
3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium azide 2) ether; Multistep reaction;
2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N,N-dimethyl-N'-phenethyl-formamidine
15795-36-5

N,N-dimethyl-N'-phenethyl-formamidine

Conditions
ConditionsYield
for 2h; Reflux;100%
2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

2,2-dideuterio-2-phenylethylamine hydrochloride

2,2-dideuterio-2-phenylethylamine hydrochloride

Conditions
ConditionsYield
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%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

C17H18N2O3*HCl

C17H18N2O3*HCl

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 8h; Mannich reaction; Heating;98%
2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

phenylacetylene
536-74-3

phenylacetylene

N-phenethyl-2-phenylacetamide
5460-60-6

N-phenethyl-2-phenylacetamide

Conditions
ConditionsYield
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%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

para-methylacetophenone
122-00-9

para-methylacetophenone

C18H21NO*HCl

C18H21NO*HCl

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 8h; Mannich reaction; Heating;97%
With hydrogenchloride In ethanol; water Mannich reaction; Reflux;24%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

para-bromoacetophenone
99-90-1

para-bromoacetophenone

C17H18NOBr*HCl

C17H18NOBr*HCl

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 14h; Mannich reaction; Heating;97%
(1RS,5RS)-8-benzyl-6-ethyl-2-oxa-8-azabicyclo[3.4.0]nonan-3-one

(1RS,5RS)-8-benzyl-6-ethyl-2-oxa-8-azabicyclo[3.4.0]nonan-3-one

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

(3'SR,4'RS,5'RS)-2-(1-benzyl-3-ethyl-5-hydroxypiperidin-4-yl)-N-phenethylacetamide

(3'SR,4'RS,5'RS)-2-(1-benzyl-3-ethyl-5-hydroxypiperidin-4-yl)-N-phenethylacetamide

Conditions
ConditionsYield
With sodium 2-ethylhexanoic acid In tetrahydrofuran at 20℃; for 144h;96%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

para-chloroacetophenone
99-91-2

para-chloroacetophenone

C17H18NOCl*HCl

C17H18NOCl*HCl

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 16h; Mannich reaction; Heating;96%
In isopropyl alcohol Mannich reaction; Heating; Acidic conditions;35%
2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

benzoic acid
65-85-0

benzoic acid

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
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
109-09-1

2-chloropyridine

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

4-trifluoromethylbenzoic acid
455-24-3

4-trifluoromethylbenzoic acid

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline
757880-98-1

1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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
710-11-2

2-oxo-4-phenylbutyric acid

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

N-phenethyl-3-phenylpropanamide
10264-31-0

N-phenethyl-3-phenylpropanamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide In water; acetonitrile at 20℃; for 1h; Reagent/catalyst; Sealed tube; Darkness; chemoselective reaction;96%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

acetophenone
98-86-2

acetophenone

3-(benzylmethylamino)-1-phenylpropane-1-one hydrochloride

3-(benzylmethylamino)-1-phenylpropane-1-one hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 7h; Mannich reaction; Heating;95%
With hydrogenchloride In ethanol; water Mannich reaction; Reflux;18%
sodium 3,5-bis(ethoxycarbonyl)pyrazolate

sodium 3,5-bis(ethoxycarbonyl)pyrazolate

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

2C8H11N*2C9H12N2O4

2C8H11N*2C9H12N2O4

Conditions
ConditionsYield
In chloroform at 25℃; for 24h;95%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

C18H21NO2*HCl

C18H21NO2*HCl

Conditions
ConditionsYield
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
151-50-8

potassium cyanide

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one
14789-54-9

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
144054-89-7

3,7-dimethyl-9-phenethylamino-3,7-diazabicyclo<3.3.1>nonane-9-carbonitrile

Conditions
ConditionsYield
In methanol; water for 72h; Ambient temperature;93%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

C17H19NO2*HCl

C17H19NO2*HCl

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 19h; Mannich reaction; Heating;93%
2-Acetylthiophene
88-15-3

2-Acetylthiophene

formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

C15H17NOS*HCl

C15H17NOS*HCl

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 7h; Mannich reaction; Heating;93%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

C17H17NOCl2*HCl

C17H17NOCl2*HCl

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 26h; Mannich reaction; Heating;91%
2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

acetyl chloride
75-36-5

acetyl chloride

methyl-N-(benzyl-methyl)-formamide
877-95-2

methyl-N-(benzyl-methyl)-formamide

Conditions
ConditionsYield
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
156-28-5

2-phenylethylamine hydrochloride

2,5-di-O-acetyl-3-azido-1-(6-chloropurin-9-yl)-β-D-1,3-dideoxyribofuranose
889126-06-1

2,5-di-O-acetyl-3-azido-1-(6-chloropurin-9-yl)-β-D-1,3-dideoxyribofuranose

C5H6(OCOCH3)2ON3C5H2N4NHCH2CH2C6H5

C5H6(OCOCH3)2ON3C5H2N4NHCH2CH2C6H5

Conditions
ConditionsYield
With triethylamine In ethanol at 50℃;90%
2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

bismuth(III) oxide
1304-76-3

bismuth(III) oxide

3C6H5CH2CH2NH3(1+)*[BiCl6](3-)=[C6H5CH2CH2NH3]3BiCl6

3C6H5CH2CH2NH3(1+)*[BiCl6](3-)=[C6H5CH2CH2NH3]3BiCl6

Conditions
ConditionsYield
In hydrogenchloride; water 80°C; cooling (room temp.), pptn., filtn., washing (aq. HCl), recrystn. (aq. HCl); elem. anal.;89%
2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

benzaldehyde
100-52-7

benzaldehyde

N-phenethylbenzamide
3278-14-6

N-phenethylbenzamide

Conditions
ConditionsYield
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%
formaldehyd
50-00-0

formaldehyd

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

1-(4-fluorophenyl)ethanone
403-42-9

1-(4-fluorophenyl)ethanone

C17H18NOF*HCl

C17H18NOF*HCl

Conditions
ConditionsYield
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
1169605-26-8

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
156-28-5

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
1383554-58-2

(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
ConditionsYield
With triethylamine In methanol at 20℃; Inert atmosphere;84%
N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

2-phenylethylamine hydrochloride
156-28-5

2-phenylethylamine hydrochloride

Cbz-L-Phe-NHCH2CH2Ph
187678-28-0

Cbz-L-Phe-NHCH2CH2Ph

Conditions
ConditionsYield
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%

156-28-5Relevant articles and documents

Regio- and stereoselective hydroamination of alkynes using an ammonia surrogate: Synthesis of N -Silylenamines as reactive synthons

Lui, Erica K. J.,Brandt, Jason W.,Schafer, Laurel L.

, p. 4973 - 4976 (2018)

An anti-Markovnikov selective hydroamination of alkynes with N-silylamines to afford N-silylenamines is reported. The reaction is catalyzed by a bis(amidate)bis(amido)Ti(IV) catalyst and is compatible with a variety of terminal and internal alkynes. Stoichiometric mechanistic studies were also performed. This method easily affords interesting N-silylenamine synthons in good to excellent yields and the easily removable silyl protecting group enables the catalytic synthesis of primary amines.

Hydroborative reduction of amides to amines mediated by La(CH2C6H4NMe2-: O)3

Gong, Mingliang,Guo, Chenjun,Luo, Yunjie,Xie, Hongzhen,Zhang, Fangcao

, p. 779 - 791 (2022/01/22)

The deoxygenative reduction of amides to amines is a great challenge for resonance-stabilized carboxamide moieties, although this synthetic strategy is an attractive approach to access the corresponding amines. La(CH2C6H4NMe2-o)3, a simple and easily accessible lanthanide complex, was found to be highly efficient not only for secondary and tertiary amide reduction, but also for the most challenging primary reduction with pinacolborane. This protocol exhibited good tolerance for many functional groups and heteroatoms, and could be applied to gram-scale synthesis. The active species in this catalytic cycle was likely a lanthanide hydride.

Lithium compound catalyzed deoxygenative hydroboration of primary, secondary and tertiary amides

Bisai, Milan Kumar,Gour, Kritika,Das, Tamal,Vanka, Kumar,Sen, Sakya S.

supporting information, p. 2354 - 2358 (2021/03/03)

A selective and efficient route for the deoxygenative reduction of primary to tertiary amides to corresponding amines has been achieved with pinacolborane (HBpin) using simple and readily accessible 2,6-di-tert-butyl phenolate lithium·THF (1a) as a catalyst. Both experimental and DFT studies provide mechanistic insight. This journal is

Reduction of Amides to Amines with Pinacolborane Catalyzed by Heterogeneous Lanthanum Catalyst La(CH2C6H4NMe2- o)3@SBA-15

Guo, Chenjun,Zhang, Fangcao,Yu, Chong,Luo, Yunjie

supporting information, p. 13122 - 13135 (2021/08/31)

Hydroboration of amides is a useful synthetic strategy to access the corresponding amines. In this contribution, it was found that the supported lanthanum benzyl material La(CH2C6H4NMe2-o)3@SBA-15 was highly active for the hydroboration of primary, secondary, and tertiary amides to amines with pinacolborane. These reactions selectively produced target amines and showed good tolerance for functional groups such as -NO2, -halogen, and -CN, as well as heteroatoms such as S and O. This reduction procedure exhibited the recyclable and reusable property of heterogeneous catalysts and was applicable to gram-scale synthesis. The reaction mechanisms were proposed based on some control experiments and the previous literature. This is the first example of hydroborative reduction of amides to amines mediated by heterogeneous catalysts.

Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia-Borane

Sarkar, Koushik,Das, Kuhali,Kundu, Abhishek,Adhikari, Debashis,Maji, Biplab

, p. 2786 - 2794 (2021/03/03)

Herein we report the synthesis of primary and secondary amines by nitrile hydrogenation, employing a borrowing hydrogenation strategy. A class of phosphine-free manganese(I) complexes bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia-borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled by changing the catalyst structure and the polarity of the reaction medium. The significant advantage of this method is that the protocol operates without externally added base or other additives as well as obviates the use of high-pressure dihydrogen gas required for other nitrile hydrogenation reactions. Utilizing this method, a wide variety of primary and symmetric and asymmetric secondary amines were synthesized in high yields. A mechanistic study involving kinetic experiments and high-level DFT computations revealed that both outer-sphere dehydrogenation and inner-sphere hydrogenation were predominantly operative in the catalytic cycle.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

Bera, Jitendra K.,Pandey, Pragati

supporting information, p. 9204 - 9207 (2021/09/20)

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming

supporting information, p. 1618 - 1629 (2021/01/25)

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Green method for catalyzing reduction reaction of aliphatic nitro derivative

-

Paragraph 0005-0006; 0081-0084, (2021/07/31)

The invention relates to a green method for catalyzing reduction reaction of aliphatic nitro derivatives. According to the method, non-transition metal compounds, namely triethyl boron and potassium tert-butoxide, are used as a catalytic system for the first time, an aliphatic nitro derivative and pinacolborane which is low in price and easy to obtain are catalyzed to be subjected to a reduction reaction under mild conditions, and an aliphatic amine hydrochloride product is synthesized after acidification with a hydrochloric acid aqueous solution. Compared with a traditional method, the method generally has the advantages that the catalyst is cheap and easy to obtain, operation is convenient, and reaction is safe. The selective reduction reaction of the aliphatic nitro derivative catalyzed by the non-transition metal catalyst and pinacol borane is realized for the first time, and the aliphatic amine hydrochloride product is synthesized through acidification treatment of the hydrochloric acid aqueous solution, so that a practical new reaction strategy is provided for laboratory preparation or industrial production.

Silicon hydrogenation reaction method of organic boron and inorganic alkali catalysis amide (by machine translation)

-

Paragraph 0134-0140; 0170-0173, (2020/08/18)

The method is characterized in that organic boron and inorganic bases are used as catalysts, silane is used as a reducing agent, primary amide is reduced to primary amine or dehydration dinitrile, the secondary amide is reduced to a secondary amine or aldimine, and the tertiary amide is reduced to tertiary amine. The method has the advantages of simple operation, mild reaction conditions, wide substrate universality, good functional group compatibility and the like, and has the characteristics of good stability, cheap and accessible catalyst, simple and convenient operation, high practicality and the like. (by machine translation)

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

Wang, Yong,Cao, Xinyi,Zhao, Leyao,Pi, Chao,Ji, Jingfei,Cui, Xiuling,Wu, Yangjie

supporting information, p. 4119 - 4129 (2020/08/10)

A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).

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