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3-Nitroisonicotinaldehyde

3-Nitroisonicotinaldehyde Structure
3-Nitroisonicotinaldehyde structure
CAS No.
153813-70-8
Chemical Name:
3-Nitroisonicotinaldehyde
Synonyms
3-Nitroisonicotinaldehyde;3-Nitropyridin-4-carbaldehyde;3-NITRO-4-PYRIDINECARBOXALDEHYDE;3-NITROPYRIDINE-4-CARBOXALDEHYDE;4-Pyridinecarboxaldehyde, 3-nitro-;2-forMyl-3-nitropyridine-4-carboxylic acid
CBNumber:
CB6274731
Molecular Formula:
C6H4N2O3
Molecular Weight:
152.11
MDL Number:
MFCD06253937
MOL File:
153813-70-8.mol
MSDS File:
SDS
Last updated:2026-09-12 18:54:09
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3-Nitroisonicotinaldehyde Properties

Melting point 53-54 °C
Boiling point 310.0±27.0 °C(Predicted)
Density 1.432±0.06 g/cm3(Predicted)
storage temp. Inert atmosphere,Store in freezer, under -20°C
pka -0.78±0.18(Predicted)
Appearance Light yellow to yellow Solid

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H317
Precautionary statements  P261-P272-P280g-P302+P352-P333+P313-P363-P403-P501c
HS Code  2933399990

3-Nitroisonicotinaldehyde price More Price(48)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Biosynth FN151432 3-Nitroisonicotinaldehyde 153813-70-8 0.5g $900 2026-06-04 Buy
Biosynth FN151432 3-Nitroisonicotinaldehyde 153813-70-8 5g $900 2026-06-04 Buy
Biosynth FN151432 3-Nitroisonicotinaldehyde 153813-70-8 2g $900 2026-06-04 Buy
Biosynth FN151432 3-Nitroisonicotinaldehyde 153813-70-8 1g $900 2026-06-04 Buy
Biosynth FN151432 3-Nitroisonicotinaldehyde 153813-70-8 10g $1375 2026-06-04 Buy
Product number Packaging Price Buy
FN151432 0.5g $900 Buy
FN151432 5g $900 Buy
FN151432 2g $900 Buy
FN151432 1g $900 Buy
FN151432 10g $1375 Buy

3-Nitroisonicotinaldehyde Chemical Properties, Uses, Production

Uses

3-Nitro-4-pyridinaldehyde is used in laboratory research and development and in chemical and pharmaceutical synthesis processes.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 219, 1994 DOI: 10.1016/S0040-4039(00)76515-4

Synthesis

N,N-Dimethyl-N-[(E)-2-(3-nitropyridin-4-yl)vinyl]amine

908847-23-4

3-NITROISONICOTINALDEHYDE

153813-70-8

General procedure for the synthesis of 3-nitropyridine-4-carbaldehyde from the compound (CAS: 908847-23-4): 1. Preparation of intermediate 12: (3R/S)-3-Amino-L-FF(4R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl-3,4-dihydro-1,7-naphthyridin-2(1H)-one (1.43 g, 10.36 mmol) was dissolved in anhydrous DMF (5 mL), and dimethylformamide dimethyl acetal (2.0 g. 16.8 mmol). The mixture was heated at 140 °C for 2 h under nitrogen protection and evaporated under reduced pressure to give (E)-N,N-dimethyl-2-(3-nitropyridin-4-yl)ethylideneamine as a dark red solid. 2. Oxidation reaction: The above product was added to a stirred THF/water (1:1, 100 mL) solution of sodium periodate (6.61 g, 31 mmol) in one go at room temperature. After stirring for 2 h at room temperature, the reaction mixture was filtered and the solid was washed with ethyl acetate (100 mL). The washings and filtrate were combined and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (100 mL), the organic layers were combined and washed sequentially with saturated aqueous sodium bicarbonate solution (100 mL) and brine (100 mL), dried (MgSO) and evaporated under reduced pressure to give a brown solid. Purification by column chromatography (DCM) gave 3-nitroisonicotinaldehyde (960 mg, 61%). 3. 1H NMR data: δ 7.8 (d, 1H); 9.15 (d, 1H); 9.4 (s, 1H); 10.4 (s, 1H). 4. methyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate (1.73 g, 5.82 mmol) was dissolved in anhydrous THF (20 mL) and cooled to -78 °C under nitrogen protection. Tetramethylguanidine (638 mg, 5.55 mmol) was added and stirred at -78 °C for 10 min. Anhydrous THF (5 mL) solution of 3-nitroisonicotinic acid hydrazide (804 mg, 5.29 mmol) was added dropwise. The dark red solution was stirred at -78 °C for 2 h and poured into a mixture of ethyl acetate (100 mL) and water (50 mL). The organic layer was separated, washed with water (2 x 50 mL) and brine (25 mL), dried (MgSO) and evaporated under reduced pressure to give a yellow oil. Purification by column chromatography (EtOAc:isohexane 1:1) afforded methyl-2-[(tert-butoxycarbonyl)amino]-3-(3-nitropyridin-4-yl)acrylate as a 10:1 mixture of Z/E isomers (1.57 g, 92%). 5. 1H NMR data: δ 1.3 (s, 9H); 1.4 (s, 0.9H); 3.55 (s, 0.3H); 3.8 (s, 3H); 6.6 (s, 0.1H); 7.2 (s, 1H); 7.25 (d, 0.1H); 7.5 (d, 1H); 8.75 (d, 0.1H); 8.8 (s, 1.1H); 8.85 (d, 1H); 9.2 (s, 0.1H); 9.25 (s, 1H); MS m/z 322. 6. 2-[(tert-butoxycarbonyl)amino]-3-(3-nitropyridin-4-yl)acrylic acid methyl ester (10:1 mixture of Z/E isomers) (1.57 g, 4.83 mmol) was dissolved in ethanol and 10% palladium/carbon catalyst (250 mg) was added. The mixture was stirred for 6 h at room temperature under 1 atm hydrogen. After diatomaceous earth filtration to remove the catalyst, the filtrate was concentrated under reduced pressure to give a yellow oil. Purification by column chromatography (eluent DCM/MeOH gradient 0-10%) afforded tert-butyl (2-oxo-1,2,3,4-tetrahydro-1,7-diazanaphthalen-3-yl) carbamate (284 mg, 22%). 7. 1H NMR data: δ 1.4 (s, 9H); 3.0 (m, 2H); 4.2 (m, 1H); 7.0 (d, 1H); 7.2 (d, 1H); 8.1 (m, 2H); 10.36 (s, 1H); MS m/z 264. 8. tert-Butyl (2-oxo-1,2,3,4-tetrahydro-1,7-diazanaphthalen-3-yl) carbamate (284 mg) was dissolved in DCM (10 mL) and trifluoroacetic acid (5 mL) was added. After stirring at room temperature for 1 h, the reaction mixture was evaporated under reduced pressure and the residue was ground with ether (20 mL) to give a light brown solid. It was collected by filtration, washed with ether and dried to give 3-amino-3,4-dihydro-1,7-diazanaphthalen-2(1H)-one (346 mg, 82%) as trifluoroacetic acid bis salt. 9. 1H NMR data: δ 3.2 (m, 2H); 4.3 (m, 1H); 7.4 (d, 1H); 8.2 (s, 1H); 8.25 (d, 1H); 8.6 (b, 3H); 11.0 (s, 1H). 10. Sodium hydride (1.18 g, 60% dispersion in oil, 29.4 mmol) was added to a solution of (3R/S)-3-amino-3,4-dihydro-1,7-diazanaphthalen-2(1H)-one (2.24 g, 9.4 mmol) in anhydrous DMF (40 mL), and the mixture was heated to 80 °C and stirred for 30 min. [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl] methyl methanesulfonate (2 mL, 10.4 mmol) was added and the reaction was stirred at 80 °C for 19 hours. After cooling, the mixture was diluted with DCM (450 mL) and purified by fast column chromatography (SiO, eluent: DCM to DCM:MeOH, 85:15 to DCM:MeOH:NHOH, 80:20:0.7), and the solvent was removed under reduced pressure to give 3-nitropyridine-4-carbaldehyde (1.1 g, 42%) as an oil. 11. 1H NMR data: δ 1.23 (m, 3H), 1.26 (s, 1.8H), 1.28 (s, 1.2H), 3.52 (m, 1H), 3.68 (m, 1H), 4.02 (m, 2H), 4.15 (m, 1H), 4.31 (m, 1H), 7.27 (br d, 1H), 8.21 (d, 1H). 8.55 (d, 1H); MS m/z 278.

References

[1] Tetrahedron Letters, 1994, vol. 35, # 2, p. 219 - 222
[2] Patent: WO2005/20987, 2005, A1. Location in patent: Page/Page column 58
[3] Patent: WO2003/74532, 2003, A1. Location in patent: Page/Page column 112

3-Nitroisonicotinaldehyde Preparation Products And Raw materials

Raw materials

N,N-Dimethylformamide Tetrahydrofuran Ethyl acetate Sodium bicarbonate Dichloromethane
Sodium periodate N,N-Dimethylformamide dimethyl acetal 4-Methyl-3-nitropyridine N,N-diMethyl-2-(3-nitropyridin-4-yl)ethenaMine N,N-Dimethyl-N-[(E)-2-(3-nitropyridin-4-yl)vinyl]amine

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Preparation Products

3-Nitroisonicotinaldehyde Suppliers

Global Suppliers ( 91)
Supplier Tel Email Country ProdList Advantage
Capot Chemical Co., Ltd +86 (0) 571 85 58 67 18 China 18187 66
Nanjing Chemlin Chemical Co., Ltd 025-83697070 13770331960 info@chemlin.com.cn China 16306 64
Heterochem 027-88041443 13072715837 sales@hetero-chem.com China 695 58
Wuhan TCASChem Technology Co., Ltd. 027-86697669 13986148687 sales@tcaschem.com China 3997 55
Shanghai Jian Chao Chemical Technology Co., Ltd. 150-2103-5486 18017383231 983544897@qq.com China 9335 55
SynAsst Chemical. 021-60343070 China 12731 55
Shanghai Raise Chemical Technology Co.,Ltd +86-021-50935922 China 7854 55
Shanghai Leto Pharmatech Co.,Ltd. 86-021-5821 5861; 18016401466 sales@letopharm.com China 235 58
Shanghai JONLN Reagent Co., Ltd. 400-0066400 13621662912 422131432@qq.com China 9970 55
Bide Pharmatech Ltd. 400-164-7117 18317119277 product02@bidepharm.com China 40000 60
Supplier Advantage
Capot Chemical Co., Ltd 66
Nanjing Chemlin Chemical Co., Ltd 64
Heterochem 58
Wuhan TCASChem Technology Co., Ltd. 55
Shanghai Jian Chao Chemical Technology Co., Ltd. 55
SynAsst Chemical. 55
Shanghai Raise Chemical Technology Co.,Ltd 55
Shanghai Leto Pharmatech Co.,Ltd. 58
Shanghai JONLN Reagent Co., Ltd. 55
Bide Pharmatech Ltd. 60

View Latest Price from 3-Nitroisonicotinaldehyde manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
3-NITROISONICOTINALDEHYDE pictures 2020-03-08 3-NITROISONICOTINALDEHYDE
153813-70-8
 $2.00 1KG 96%-99% 200kg Career Henan Chemical Co

3-Nitroisonicotinaldehyde Spectrum

3-NITROISONICOTINALDEHYDE(153813-70-8)1HNMR

153813-70-8 (3-Nitroisonicotinaldehyde) Related Search:

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2-forMyl-3-nitropyridine-4-carboxylic acid 4-Pyridinecarboxaldehyde, 3-nitro- 3-NITROPYRIDINE-4-CARBOXALDEHYDE 3-NITRO-4-PYRIDINECARBOXALDEHYDE 3-Nitropyridin-4-carbaldehyde 3-Nitroisonicotinaldehyde 153813-70-8 C6H4N2O3 Aldehydes Pyridines