- Reactions of 3-R-5-nitropyridines with nucleophiles: Nucleophilic substitution vs conjugate additionBastrakov, Maxim A.; Nikol'skiy, Vladislav V.; Starosotnikov, Alexey M.; Fedyanin, Ivan V.; Shevelev, Svyatoslav A.; et al, Tetrahedron, 2019, 75(47),
Cas no 940-06-7 (3,5-Dinitropyridine)
3,5-Dinitropyridine is a nitrated pyridine derivative characterized by the presence of two nitro groups at the 3 and 5 positions of the pyridine ring. This compound is primarily utilized as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and energetic materials. Its high reactivity and electron-deficient nature make it a valuable building block for nucleophilic aromatic substitution reactions. The symmetrical substitution pattern enhances its stability and predictability in synthetic applications. 3,5-Dinitropyridine is also of interest in materials science due to its potential use in the development of high-energy-density compounds. Proper handling is essential due to its potential explosive properties.
3,5-Dinitropyridine structure
Product Name:3,5-Dinitropyridine
CAS No:940-06-7
MF:C5H3N3O4
MW:169.095020532608
MDL:MFCD00234030
CID:797315
PubChem ID:598054
Update Time:2025-06-07
3,5-Dinitropyridine Chemical and Physical Properties
Names and Identifiers
-
- Pyridine, 3,5-dinitro-
- 3,5-DINITROPYRIDINE
- Nicotinic Acid Impurity L (3, 5-Dinitropyridine)
- 3,5-Dinitro-pyridin
- 3,5-dinitro-pyridine
- Pyridine,3,5-dinitro
- 3,5-Dinitropyridine (ACI)
- 3,5-Dinitropyridine
-
- MDL: MFCD00234030
- Inchi: 1S/C5H3N3O4/c9-7(10)4-1-5(8(11)12)3-6-2-4/h1-3H
- InChI Key: RFSIFTKIXZLPHR-UHFFFAOYSA-N
- SMILES: [O-][N+](C1C=C([N+](=O)[O-])C=NC=1)=O
Computed Properties
- Exact Mass: 169.01200
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 1
- Heavy Atom Count: 12
- Rotatable Bond Count: 2
Experimental Properties
- PSA: 104.53000
- LogP: 1.94440
3,5-Dinitropyridine Customs Data
- HS CODE:2933399090
- Customs Data:
China Customs Code:
2933399090Overview:
2933399090. Other compounds with non fused pyridine rings in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%
Declaration elements:
Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date
Summary:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
3,5-Dinitropyridine Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | D441825-25mg |
3,5-Dinitropyridine |
940-06-7 | 25mg |
$ 276.00 | 2023-09-07 | ||
| TRC | D441825-100mg |
3,5-Dinitropyridine |
940-06-7 | 100mg |
$ 603.00 | 2023-09-07 | ||
| TRC | D441825-250mg |
3,5-Dinitropyridine |
940-06-7 | 250mg |
$1120.00 | 2023-05-18 | ||
| TRC | D441825-500mg |
3,5-Dinitropyridine |
940-06-7 | 500mg |
$2110.00 | 2023-05-18 | ||
| Chemenu | CM120607-1g |
3,5-Dinitropyridine |
940-06-7 | 95% | 1g |
$1145 | 2024-07-19 | |
| Enamine | EN300-315476-0.05g |
3,5-dinitropyridine |
940-06-7 | 95.0% | 0.05g |
$166.0 | 2025-03-19 | |
| Enamine | EN300-315476-0.1g |
3,5-dinitropyridine |
940-06-7 | 95.0% | 0.1g |
$247.0 | 2025-03-19 | |
| Enamine | EN300-315476-0.25g |
3,5-dinitropyridine |
940-06-7 | 95.0% | 0.25g |
$352.0 | 2025-03-19 | |
| Enamine | EN300-315476-0.5g |
3,5-dinitropyridine |
940-06-7 | 95.0% | 0.5g |
$554.0 | 2025-03-19 | |
| Enamine | EN300-315476-1.0g |
3,5-dinitropyridine |
940-06-7 | 95.0% | 1.0g |
$711.0 | 2025-03-19 |
3,5-Dinitropyridine Production Method
Production Method 1
Reaction Conditions
1.1 Reagents: Silver nitrate Solvents: Water ; rt → 80 °C; 1 - 2 h, 80 °C
Reference
Production Method 2
Reaction Conditions
1.1 Reagents: Silver acetate Solvents: Methanol , Water ; overnight, reflux
Reference
- Preparation of 3-(heterocyclylmethoxy)pyridines as nicotinic cholinergic agonists, United States, , ,
Production Method 3
Reaction Conditions
1.1 Reagents: Silver acetate Solvents: Methanol , Water ; overnight, reflux
Reference
- Preparation of heterocyclic ethers as neuronal nicotinic receptor ligands, World Intellectual Property Organization, , ,
Production Method 4
Reaction Conditions
1.1 Reagents: Nitrogen dioxide
Reference
- Ozone-mediated C-nitration of pyridine and methylpyridines with nitrogen dioxideSuzuki, Hitomi; Kozai, Iku; Murashima, Takashi, Journal of Chemical Research, 1993, (4), 156-7
Production Method 5
Reaction Conditions
1.1 Reagents: Acetic acid, silver salt Solvents: Water
Reference
- Synthesis of 3,5-dinitropyridinePlazek, Edwin, Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, 1953, 72, 569-75
Production Method 6
Reaction Conditions
1.1 Reagents: Hydrazine Solvents: Dichloromethane ; 0 °C; 18 h, rt
1.2 Reagents: Silver nitrate Solvents: Water ; 3 h, reflux; reflux → rt
1.3 Solvents: tert-Butyl methyl ether ; rt
1.2 Reagents: Silver nitrate Solvents: Water ; 3 h, reflux; reflux → rt
1.3 Solvents: tert-Butyl methyl ether ; rt
Reference
- 3,5-Pyridyne-A Heterocyclic meta-Benzyne DerivativeWinkler, Michael; Cakir, Bayram; Sander, Wolfram, Journal of the American Chemical Society, 2004, 126(19), 6135-6149
Production Method 7
Reaction Conditions
1.1 Reagents: Silver nitrate Solvents: Water ; rt; rt → reflux; 5 h, reflux
Reference
- Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in OxidationsSturala, Jiri; Bohacova, Sona; Chudoba, Josef; Metelkova, Radka; Cibulka, Radek, Journal of Organic Chemistry, 2015, 80(5), 2676-2699
Production Method 8
Reaction Conditions
1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Methanol ; 10 min, 0 °C; overnight, rt
1.2 Reagents: Silver acetate Solvents: Water ; 3 h, reflux
1.3 Reagents: Sodium hydroxide Solvents: Water ; pH 9, reflux → rt
1.2 Reagents: Silver acetate Solvents: Water ; 3 h, reflux
1.3 Reagents: Sodium hydroxide Solvents: Water ; pH 9, reflux → rt
Reference
- Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity ScaleMayer, Robert J. ; Hampel, Nathalie; Ofial, Armin R., Chemistry - A European Journal, 2021, 27(12), 4070-4080
Production Method 9
Reaction Conditions
Reference
- Product class 1: pyridinesSpitzner, D., Science of Synthesis, 2005, 15, 11-284
Production Method 10
Reaction Conditions
Reference
- Thermal Decomposition Pathways of 1,3,3-Trinitroazetidine (TNAZ), Related 3,3-Dinitroazetidium Salts, and 15N, 13C, and 2H IsotopomersOxley, Jimmie; Smith, James; Zheng, Weiyi; Rogers, Evan; Coburn, Michael, Journal of Physical Chemistry A, 1997, 101(24), 4375-4383
Production Method 11
Reaction Conditions
Reference
- Preparation of 2-(3-pyridyloxyalkyl)azetidines and -pyrrolidines as nicotinic receptor ligands, World Intellectual Property Organization, , ,
Production Method 12
Reaction Conditions
Reference
- Mineral acid-free preparation of nitro compounds from pyridine or its derivatives, Japan, , ,
Production Method 13
Reaction Conditions
Reference
- Pyrimidines. LXIV. Ring transformations in reactions of heterocyclic compounds with nucleophiles. XX. Conversion of 5-nitropyrimidine into 3,5-dinitropyridine. A novel ring transformationVan der Plas, H. C.; Jongejan, H.; Koudijs, A., Journal of Heterocyclic Chemistry, 1978, 15(3), 485-7
Production Method 14
Reaction Conditions
1.1 Reagents: p-Toluenesulfonic acid Solvents: Ethanol ; 20 h, 80 °C
Reference
- Construction of 3,5-dinitrated 1,4-dihydropyridines modifiable at 1,4-positions by a reaction of β-formyl-β-nitroenamines with aldehydesAsahara, Haruyasu; Hamada, Mai; Nakaike, Yumi; Nishiwaki, Nagatoshi, RSC Advances, 2015, 5(110), 90778-90784
3,5-Dinitropyridine Raw materials
- Pyridine, 2-hydrazinyl-3,5-dinitro-
- 2-Propenal, 3-[(1,1-dimethylethyl)amino]-2-nitro-
- Benzaldehyde
- 2-Chloro-3,5-dinitropyridine
- 5-Nitropyrimidine
3,5-Dinitropyridine Preparation Products
3,5-Dinitropyridine Related Literature
-
Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
-
Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu Junkang New J. Chem., 2015,39, 5240-5248
-
Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143
-
Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
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