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2-Methoxy-5-nitropyridine

2-Methoxy-5-nitropyridine

CAS: 5446-92-4

Molecular Formula: C6H6N2O3

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2-Methoxy-5-nitropyridine - Names and Identifiers

Name 2-Methoxy-5-nitropyridine
Synonyms 2-Methoxy-5-nitropyridine
2-METHOXY-5-NITROPYRIDINE
6-Methoxy-3-nitropyridine
5-NITRO-2-METHOXY PYRIDINE
METHOXY(2-)-5-NITROPYRIDINE
Pyridine,2-methoxy-5-nitro-
CAS 5446-92-4
EINECS 226-661-7
InChI InChI=1/C6H6N2O3/c1-11-6-3-2-5(4-7-6)8(9)10/h2-4H,1H3

2-Methoxy-5-nitropyridine - Physico-chemical Properties

Molecular FormulaC6H6N2O3
Molar Mass154.12
Density0.45
Melting Point104-108°C(lit.)
Boling Point277.46°C (rough estimate)
Flash Point130 °C
Water Solubilityinsoluble
Vapor Presure0.0216mmHg at 25°C
AppearanceSolid
ColorClear colorless to yellow
BRN126991
pKa-0?+-.0.10(Predicted)
Storage ConditionSealed in dry,Room Temperature
Refractive Index1.5100 (estimate)
MDLMFCD00006263
Physical and Chemical PropertiesCrystal. Melting point 110 °c.
UseUsed as a drug Intermediate

2-Methoxy-5-nitropyridine - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk Codes36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39 - Wear suitable gloves and eye/face protection
S36 - Wear suitable protective clothing.
WGK Germany3
HS Code29333990
Hazard ClassIRRITANT

2-Methoxy-5-nitropyridine - Reference Information

preparation (1) synthesis of 2-amino -5-nitropyridine 18.82g(0.2mol) of 2-aminopyridine and 75.3g of dichloroethane are added into the reactor, stirred and dissolved, 43.29g of mixed acid composed of fuming nitric acid/concentrated sulfuric acid with a mass ratio of 1:1.3 is slowly added dropwise below 10 ℃, after dropping, react at 58 ℃ for 10 hours, and the reaction solution changes from light yellow to wine red. After the reaction, the temperature is reduced to room temperature, the water is washed to PH5.5, the organic layer is reduced to recover dichloroethane, the residue is slowly poured into ice water, deep yellow precipitate is precipitated, filtered, washed and dried to obtain 25.64g of 2-amino -5-nitropyridine, the HPLC purity is 98.57%, and the yield is 90.85%. (2) Synthesis of 2-Hydroxy -5-Nitropyridine 13.9g(0.1mol) of 2-amino -5-nitropyridine is dissolved in 55.6g of dilute hydrochloric acid with a mass concentration of 15%, 48.3g of 20% NaNO2 aqueous solution is added dropwise below 0 ℃, after dropping, heat preservation at 5 ℃ for 30min, reaction solution is concentrated under reduced pressure, light yellow solid is precipitated by cooling, ice water washing and drying, 12.48g of 2-hydroxy -5-nitropyridine was obtained with HPLC purity of 98.35% and yield of 87.61%.
use for organic synthesis. The product is reduced to obtain 5-amino-2-methoxypyridine, which is an intermediate of the drug. For example, it is used to produce the first-aid antimalarial drug, pyronidine.
Used as a pharmaceutical intermediate
Production method From 2-chloro-5-nitropyridine through etherification. Sodium methoxide is added dropwise to the mixed solution of 2-chloro-5-nitropyridine and methanol under stirring, and crystals are precipitated in crushed ice after adding sulfur for 1h. Filter, dry, and recrystallize with methanol to obtain the finished product. The yield was 92%.
Last Update:2024-04-09 21:01:54
2-Methoxy-5-nitropyridine
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View History
2-Methoxy-5-nitropyridine
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