29968-78-3

Basic information

• Product Name: 4-Nitrophenethylamine hydrochloride
• Synonyms: 4-NITROPHENYLETHYLAMINE HCL;4-NITROPHENYLETHYLAMINE HYDROCHLORIDE;4-NITROPHENETHYLAMINE HCL;4-NITROPHENETHYLAMINE HYDROCHLORIDE;2-(P-NITROPHENYL)ETHYLAMINE HYDROCHLORIDE;2-(4-NITROPHENYL)ETHYLAMINE HYDROCHLORIDE;p-Nitrophenethylamine hydrochloride;4-Nitrophcnethylamine
• CAS NO: 29968-78-3
• Molecular Formula: C₈H₁₁N₂O₂*Cl
• Molecular Weight: 202.64
• EINECS: 249-980-3
• Product Categories: Benzene derivatives;Anilines, Aromatic Amines and Nitro Compounds;pharmacetical;API intermediates;Nitro / Nitriles
• Mol File: 29968-78-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 200 °C (dec.)(lit.)
• Boiling Point: 307.2 °C at 760 mmHg
• Flash Point: 139.6 °C
• Appearance: Yellow to yellow-green/Crystalline Powder
• Density: 1.206 g/cm³
• Vapor Pressure: 0.000737mmHg at 25°C
• Storage Temp.: 0-6°C
• Solubility: Soluble in methanol almost transparency.
• Stability: Hygroscopic
• BRN: 3568915
• CAS DataBase Reference: 4-Nitrophenethylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenethylamine hydrochloride(29968-78-3)
• EPA Substance Registry System: 4-Nitrophenethylamine hydrochloride(29968-78-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-40
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 29968-78-3(Hazardous Substances Data)

Usage

Chemical Properties

yellow to brown crystalline powder and chunks

Uses

4-Nitrophenethylamine hydrochloride was used in the synthesis of ortho-metalated primary phenethylamines complexes containing six-membered palladacycles and N-(4-nitrophenethyl)formamide.

Preparation

The preparation of 4-Nitrophenethylamine hydrochloride is as follows:Ten mL of 2M HCl was then added in a one-pot fashion, and, in all cases but threonine, the reaction vessel was heated to 190°Cover 5 min with stirring and then allowed to cool. In the case of the temperature-sensitive threonine, soxhlet extraction with toluene was performed at 80°C to remove R-carvone from the reaction mixture. The aqueous reaction mixture was washed three times with 25 mL of ether, and then water solvent was distilled off from the hydrochloride salt. The hydrochloride salt was transferred to a vacuum oven and dried overnight at 150 °C and 10 Torr.

InChI:InChI=1/C8H10N2O2/c9-6-5-7-1-3-8(4-2-7)10(11)12/h1-4H,5-6,9H2/p+1

Synthetic route

1-azido-2-(4'-nitrophenyl)ethane (70079-91-3) → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
Stage #1: 1-azido-2-(4'-nitrophenyl)ethane 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;	99%
Stage #1: 1-azido-2-(4'-nitrophenyl)ethane With triphenylphosphine at 110℃; for 20h; Staudinger Azide Reduction; Green chemistry; Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether Reagent/catalyst; Solvent; Green chemistry;	91%

N-<2-(4-nitrophenyl)ethyl>acetamide (6270-07-1) → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
With hydrogenchloride In ethanol; water for 20h; pH=1; Reflux; Large scale;	84.7%

C11H14N2O3 (250266-58-1) → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
With hydrogenchloride In methanol; water for 15h; pH=3; Solvent; pH-value; Reflux; Large scale;	82.4%

C13H18N2O3 → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
With hydrogenchloride In methanol; water for 5h; pH=1; Reflux; Large scale;	81.2%

C18H22N2O2 → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
With hydrogenchloride In propan-1-ol at 190℃; for 0.0833333h; Microwave irradiation; Green chemistry;	74%

2-phenylethylamine hydrochloride (156-28-5) → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
With nitric acid

phenethylamine (64-04-0) → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
With hydrogenchloride; sulfuric acid; nitric acid 2) ether; Multistep reaction;

4-nitro-3-phenyl-L-alanine (949-99-5) → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
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 / Microwave irradiation; Green chemistry View Scheme

2-(4-nitrophenyl)ethanol (100-27-6) → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 5.5 h / -30 - 20 °C / Inert atmosphere 2.1: sodium azide / N,N-dimethyl-formamide / 20 h / 23 °C 3.1: triphenylphosphine / 20 h / 110 °C / Green chemistry 3.2: Green chemistry View Scheme

<(p-Nitrophenyl)ethyl>-β-sulfonic ester (20020-28-4) → 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium azide / N,N-dimethyl-formamide / 20 h / 23 °C 2.1: triphenylphosphine / 20 h / 110 °C / Green chemistry 2.2: Green chemistry View Scheme

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) + trifluoroacetic anhydride (407-25-0) → 2,2,2-Trifluoro-N-(2-(4-nitrophenyl)ethyl)acetamide (24954-63-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	100%
Stage #1: 2-(4-nitrophenyl)ethylamine monohydrochloride With triethylamine In dichloromethane at 0℃; Stage #2: trifluoroacetic anhydride In dichloromethane Inert atmosphere;	100%
With triethylamine In dichloromethane at 20℃; for 2h;	90%

di-tert-butyl dicarbonate (24424-99-5) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → (tert-butoxy)-N-[2-(4-nitrophenyl)-ethyl]-carboxamide (144226-16-4)

Conditions	Yield
With triethylamine In ethyl acetate at 20℃; Inert atmosphere;	100%
With triethylamine In dichloromethane at 0 - 20℃;	99%
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 16.25h;
With hydrogenchloride; triethylamine In chloroform

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) + 1-bromomethyl-4-nitro-benzene (100-11-8) → N-(2-(4-nitrophenyl)ethyl)-N-(4-nitrobenzyl)amine

Conditions	Yield
With sodium carbonate In water; N,N-dimethyl-formamide at 20 - 40℃; for 25h; Reagent/catalyst;	99%

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) + benzaldehyde (100-52-7) → N-benzyl-2-(4-nitrophenyl)ethan-1-amine hydrochloride

Conditions	Yield
Stage #1: 2-(4-nitrophenyl)ethylamine monohydrochloride With sodium hydroxide In ethanol; water at 20℃; for 0.5h; Stage #2: benzaldehyde In ethanol at 80℃; for 16h; Inert atmosphere; Stage #3: With sodium tetrahydroborate at 20℃; for 1.5h;	99%
Stage #1: 2-(4-nitrophenyl)ethylamine monohydrochloride With sodium hydroxide In water; ethyl acetate at 25℃; for 1h; Stage #2: benzaldehyde In ethanol for 16h; Inert atmosphere; Reflux; Stage #3: With sodium tetrahydroborate In ethanol at 0 - 25℃; for 2h;	97%

tert-butyldicarbonate (34619-03-9) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → (tert-butoxy)-N-[2-(4-nitrophenyl)-ethyl]-carboxamide (144226-16-4)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃;	96%

bis-(p-nitrophenyl) carbonate (5070-13-3) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → 1,3-bis(4-nitrophenylethyl)urea

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	96%
With triethylamine In N,N-dimethyl-formamide at 58 - 62℃; for 2h; Reagent/catalyst; Solvent;	86%

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) + acrylic acid methyl ester (292638-85-8) → dimethyl 3,3'-((4-nitrophenethyl)azanediyl)dipropionate

Conditions	Yield
Stage #1: 2-(4-nitrophenyl)ethylamine monohydrochloride With sodium hydroxide In dichloromethane; water Stage #2: acrylic acid methyl ester In methanol for 16h; Reflux;	96%

pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylate (917253-02-2) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide (917253-06-6)

Conditions	Yield
With triethylamine In dichloromethane for 2h;	95%

racemic trans-1-(tert-butoxycarbonyl)pyrrolidine-3,4-dicarboxylic acid + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → tert-butyl trans-3,4-bis((4-nitrophenethyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions	Yield
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 23℃; for 16h; Inert atmosphere;	95%

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) + L-(-)-N-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidinecarboxylic acid pentafluorophenyl ester (120711-54-8) → R-2,2-dimethyl-3-(1,1-dimethylethoxycarbonyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide (917252-86-9)

Conditions	Yield
With triethylamine In dichloromethane for 2h;	93%

phosgene (75-44-5) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → 1,3-bis(4-nitrophenylethyl)urea

Conditions	Yield
With 1,2-dichloro-benzene at 120℃;	92%

4-oxo-4-{{2-[(propylamino)carbonyl]phenyl}amino}butanoic acid (815654-41-2) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → N1-[2-(4-nitrophenyl)ethyl]-N4-{2-[(propylamino)carbonyl]phenyl}butanediamide (1263363-74-1)

Conditions	Yield
With 4-methyl-morpholine; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;	91%

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) + (R)-3-chloromandelic acid (16273-37-3, 32222-43-8, 52950-16-0, 61008-98-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	91%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	91%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	91%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	91%

→ chloro-acetic acid-(4-nitro-phenethylamide) (113847-08-8)

Conditions	Yield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;	90%
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	90%

4-nitrophenyl N-(4-nitrobenzyl)carbamate (1093737-02-0) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → C16H16N4O5

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	90%

2,4-dichloropyrido[2,3-d]pyrimidine (126728-20-9) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → 2-chloro-N-(4-nitrophenethyl)pyrido[2,3-d]pyrimidin-4-amine

Conditions	Yield
With triethylamine In isopropyl alcohol at 21℃; for 5h;	89%

4-chloro-5,6-diphenylfuro[2,3-d]pyrimidine (65148-07-4) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → N-[2-(4-nitrophenyl)ethyl]-5,6-diphenylfuro[2,3-d]pyrimidin-4-amine (1235310-55-0)

Conditions	Yield
With triethylamine In ethanol at 80℃; for 8h; Inert atmosphere;	88%

(R)-Mandelic Acid (611-71-2) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide (521284-19-5)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;	86%
Stage #1: (R)-Mandelic Acid With Trimethyl borate In acetonitrile at 28 - 58℃; for 1.5h; Stage #2: 2-(4-nitrophenyl)ethylamine monohydrochloride With N-ethyl-N,N-diisopropylamine In acetonitrile at 58℃; for 12h; Reflux;	84.3%
With Trimethyl borate; N-ethyl-N,N-diisopropylamine In acetonitrile for 8h; Reflux;	82%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → N-benzyloxycarbonyl-4-nitrophenethylamine (182252-00-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 17h; Acylation;	82%

2,3-dihydro-1,4-benzodioxin-6-carboxylic acid (4442-54-0) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → N-(4-nitrophenethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-carboxamide

Conditions	Yield
Stage #1: 2,3-dihydro-1,4-benzodioxin-6-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; Stage #2: 2-(4-nitrophenyl)ethylamine monohydrochloride With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;	81%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → 2,2,2-Trifluoro-N-(2-(4-nitrophenyl)ethyl)acetamide (24954-63-0)

Conditions	Yield
With triethylamine; trifluoroacetic anhydride In methanol; water	80%
With triethylamine; trifluoroacetic anhydride In methanol; water	80%

4,5,6,7-tetrafluoroisobenzofuran-1,3-dione (652-12-0) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → C16H8F4N2O4

Conditions	Yield
With acetic acid Reflux;	80%

(R)-4-(oxiran-2-yl)-2,8-bis(trifluoromethyl)quinoline (1292282-18-8) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → (R)‐1‐(2,8‐bis(trifluoromethyl)quinolin‐4‐yl)‐2‐((4‐nitrophenethyl)amino)ethan‐1‐ol

Conditions	Yield
Stage #1: 2-(4-nitrophenyl)ethylamine monohydrochloride With sodium hydroxide Stage #2: (R)-4-(oxiran-2-yl)-2,8-bis(trifluoromethyl)quinoline In ethanol at 130℃; for 0.5h; Microwave irradiation;	78%

(S)-4-(oxiran-2-yl)-2,8-bis(trifluoromethyl)quinoline (1292282-19-9) + 2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) → (S)‐1‐(2,8‐bis(trifluoromethyl)quinolin‐4‐yl)‐2‐((4‐nitrophenethyl)amino)ethan‐1‐ol

Conditions	Yield
Stage #1: 2-(4-nitrophenyl)ethylamine monohydrochloride With sodium hydroxide Stage #2: (S)-4-(oxiran-2-yl)-2,8-bis(trifluoromethyl)quinoline In ethanol at 130℃; for 0.5h; Microwave irradiation;	78%

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) + 4-chloro-6-fluoro-quinazoline (16499-61-9) → 6-fluoro-N-(4-nitrophenethyl)quinazolin-4-amine

Conditions	Yield
With triethylamine In isopropyl alcohol at 0 - 100℃; for 15h;	78%

2-(4-nitrophenyl)ethylamine monohydrochloride (29968-78-3) + 1-phenyl-2-bromoethane (103-63-9) → N-(4-nitrophenethyl)-2-phenylethan-1-amine

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 40℃; for 2h;	77%

Upstream product

• 156-28-5 2-phenylethylamine hydrochloride 
• 64-04-0 phenethylamine 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 6270-07-1 N-<2-(4-nitrophenyl)ethyl>acetamide 
• 250266-58-1 C₁₁H₁₄N₂O₃ 
• 70079-91-3 1-azido-2-(4'-nitrophenyl)ethane 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 20020-28-4 <(p-Nitrophenyl)ethyl>-β-sulfonic ester 

Downstream Products

• 191864-43-4 N-[(2-chloroethoxy)carbonyl]-2-(4-nitrophenyl)ethylamine 
• 202740-27-0 (S)-1-{[2-(4-nitrophenyl)ethyl]amino}-3-phenoxypropan-2-ol 
• 138531-37-0 4-<2-(N,N-di-n-propylamino)ethyl>-aniline 
• 917252-86-9 R-2,2-dimethyl-3-(1,1-dimethylethoxycarbonyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 
• 917253-06-6 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 
• 917253-05-5 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-valinyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 
• 917253-24-8 S-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-valinyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 
• 917253-04-4 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-alanyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 
• 917253-03-3 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)glycyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 
• 883229-11-6 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydro-quinoline-3-carboxylic acid [2-(4-nitro-phenyl)-ethyl]-amide 
• 111437-16-2 N-[2-(4-nitrophenyl)ethyl]-4-methylbenzenesulfonamide 
• 182252-00-2 N-benzyloxycarbonyl-4-nitrophenethylamine 
• 191864-44-5 N-[2-(4-nitrophenyl)ethyl]-4-chlorobutylamide 
• 24954-67-4 2-(p-nitrophenyl)ethylamine 

Relevant articles and documents

Catalytic Staudinger Reduction at Room Temperature

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