2-Amino-5-nitro-4-picoline Chemical Properties

Melting point:

223-225 °C (lit.)

Boiling point:

276.04°C (rough estimate)

Density 

1.3682 (rough estimate)

refractive index 

1.6500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in DMSO.

pka

3.44±0.24(Predicted)

form 

Powder

color 

Orange to yellow-brown

BRN 

137695

InChI

InChI=1S/C6H7N3O2/c1-4-2-6(7)8-3-5(4)9(10)11/h2-3H,1H3,(H2,7,8)

InChIKey

GRBBNZYMXKTQAI-UHFFFAOYSA-N

SMILES

C1(N)=NC=C([N+]([O-])=O)C(C)=C1

CAS DataBase Reference

21901-40-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-36/37/39-22-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

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

2-Amino-5-nitro-4-picoline Usage And Synthesis

Chemical Properties

orange to yellow-brown powder

Uses

2-Amino-4-methyl-5-nitropyridine was used in the preparation of matrix mixture required to study new technical developments for the direct tissue analysis of peptides.

General Description

The crystal structure of 2-amino-4-methyl-5-nitropyridine was elucidated.

Synthesis

Example 9: Synthesis of 2-(1-aziridinyl)-4-carbamoyl-5-nitropyridine (Compound VI) Reagents and conditions: (i) HNO3/H2SO4; (ii) NaNO2; (iii) POCl3; (iv) Na2Cr2O7; (v) SOCl2/DMF, followed by NH4OH treatment; (vi) aziridine. Synthesis steps for compound 30: 1. cool concentrated sulfuric acid (240 mL) in an ice bath and slowly add raw compound 29 (2-amino-4-methylpyridine, 50 g, 0.462 mol), keeping the temperature at 0°C. 2. slowly add acid mixture prepared from concentrated sulfuric acid (98%, 55 mL) and concentrated nitric acid (72%, 55 mL) in a 1:1 volume ratio. 3. slowly heat to 50°C and react for 24 hours to ensure complete reaction. 4. Pour the reaction solution into 2 L of ice water, adjust the pH to 7 with a strong base, and filter to collect the precipitate. 5. Dry the filter cake to give 54 g of crude product. 6. The by-product 4-methyl-3-nitro-2-aminopyridine was removed by wet distillation and subsequently recrystallized in 95% ethanol to give 33 g of Compound 30 (2-amino-4-methyl-5-nitropyridine) with a melting point of 220-222 °C (Literature value: 220-222 °C). Yield: 46.6%.

References

[1] Patent: EP2366691, 2011, A1. Location in patent: Page/Page column 12-13
[2] Patent: CN105906621, 2016, A. Location in patent: Paragraph 0044
[3] Patent: WO2005/97129, 2005, A2. Location in patent: Page/Page column 176
[4] Patent: WO2012/103806, 2012, A1. Location in patent: Page/Page column 43

2-Amino-5-nitro-4-picoline(21901-40-6)Related Product Information

• 4-Methylpyridine
• 2-Bromo-5-nitropyridine
• 3-Amino-4-methylpyridine
• METSULFURON METHYL
• 2-Aminopyridine
• 4-Dimethylaminopyridine
• Methyl salicylate
• 2-Methyl-5-nitropyridine
• 4-Methylpyridin-2-amine
• Kresoxim-methyl
• Methylparaben
• 2-Amino-5-nitropyridine
• 3-Aminopyridine
• Methyl acetate
• Bensulfuron methyl
• Thiophanate-methyl
• Tris(hydroxymethyl)aminomethane
• Methyl