4-Nitrobenzylamine hydrochloride Chemical Properties

Melting point:

~265 °C (dec.)(lit.)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

methanol:glacial acetic acid (1:1): soluble25mg/mL, clear, colorless to light yellow

form 

powder to crystal

color 

White to Light yellow

Water Solubility 

almost transparency

BRN 

3629994

Stability:

Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents.

InChI

InChI=1S/C7H8N2O2.ClH/c8-5-6-1-3-7(4-2-6)9(10)11;/h1-4H,5,8H2;1H

InChIKey

SMIXZZMSWYOQPW-UHFFFAOYSA-N

SMILES

C1([N+]([O-])=O)C=CC(CN)=CC=1.Cl

CAS DataBase Reference

18600-42-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

2811

WGK Germany 

3

RTECS 

DP6705000

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29214990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Nitrobenzylamine hydrochloride Usage And Synthesis

Chemical Properties

light brown crystalline solid

Uses

4-Nitrobenzylamine hydrochloride was used in chemical modification of graphite powder and multiwalled carbon nanotubes. It was also used in the preparation of 2-fluoro-6-(4-nitrohenzylamino)purine.

Uses

4-Nitrobenzylamine hydrochloride was used in chemical modification of graphite powder and multiwalled carbon nanotubes. It was also used in the preparation of 2-fluoro-6-(4-nitrohenzylamino)purine.

Synthesis

General procedure for the synthesis of 4-nitrobenzylamine hydrochloride from p-nitrobenzonitrile: To a 6.0 mL solution of toluene containing p-nitrobenzonitrile (1.0 g, 5.1 mmol, 1.0 eq.) under nitrogen protection was added TMDS (900 μL, 5.1 mmol, 1.0 eq.) or PMHS (610 μL, 10.2 mmol, 2.0 eq.) and Ti(Oi-Pr)4 (1.5 mL, 5.1 mmol, 1.0 eq.). The reaction mixture was heated at 60 °C for 24 h, during which the colorless solution gradually changed to black, and the reaction progress could be monitored by TLC or 1H NMR. Upon completion of the reaction, the mixture was cooled to room temperature and acidified with 1 M aqueous HCl (7.7 mL, 1.5 eq.) to obtain a clarified solution. Subsequently, the crude product was concentrated under reduced pressure, and the resulting solid was filtered and washed with pentane (3 x 50 mL). The washed solid was dissolved in ethanol and finally the filtrate was concentrated under reduced pressure to give the target product 4-nitrobenzylamine hydrochloride.

References

[1] Tetrahedron, 2014, vol. 70, # 4, p. 975 - 983
[2] Tetrahedron Letters, 2009, vol. 50, # 50, p. 7005 - 7007
[3] Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 1, p. 22 - 28
[4] Journal of Organic Chemistry, 2015, vol. 80, # 14, p. 7281 - 7287

4-Nitrobenzylamine hydrochloride(18600-42-5)Related Product Information

• 4-Fluorobenzylamine
• Topotecan hydrochloride
• Dibenzylamine
• 4-Hydroxybenzylamine
• Trimethoprim
• 3-Iodobenzylamine
• Phenoxybenzamine hydrochloride
• Benzylamine hydrochloride
• 4-Nitrobenzyl alcohol
• (S)-ALPHA-METHYL-4-NITROBENZYLAMINE HYDROCHLORIDE
• (S)-1-(4-Nitrophenyl)ethylamine hydrochloride
• 4-Chloro-5-nitrophthalimide
• 2-CHLORO-4-NITROBENZAMIDE
• 4-Nitrophthalimide
• N-(N-PROPYL)-4-NITROBENZYLAMINE HYDROCHLORIDE,N-PROPYL-4-NITROBENZYLAMINE HYDROCHLORIDE,N-(n-Propyl)-4-nitrobenzylamine hydrochloride, 98+%
• N-METHYL-4-NITROBENZYLAMINE HYDROCHLORIDE
• 4-NITROBENZAMIDINE, HYDROCHLORIDE
• 2-CHLORO-4-NITROBENZHYDRAZIDE