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2-Methyl-5-nitropyridine

2-Methyl-5-nitropyridine structure

CAS No:
21203-68-9
Formula:
C6H6N2O2
Chemical Name:
2-Methyl-5-nitropyridine
Synonyms:
2-METHYL-5-NITROPYRIDINE;5-NITRO-2-PICOLINE;AURORA KA-6797;Pyridine, 2-methyl-5-nitro- (9CI);2-METHYL-5-NITROPYRIDINE, 95+%;2-METHYL-5-NITROPYRIDINE/5-NITRO-2-PICOLINE;2-Methyl-5-nitropyridine Hydrochloride;21203-68-92-Methyl-5-nitropyridine
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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2-Methyl-5-nitropyridine Basic Attributes

Molecular Weight：

138.12

Exact Mass：

138.042923

EC Number：

-0

DSSTox ID：

DTXSID90383213

HScode：

2933399090

Characteristics

PSA：

58.7

XLogP3：

Appearance：

Solid

Density：

1.2±0.1 g/cm3

Melting Point：

112 C

Boiling Point：

238°C at 760 mmHg

Flash Point：

97.2±21.8 °C

Refractive Index：

1.558

Water Solubility：

Slightly soluble in water.

Safety Information

hazard class code：

36/37/38

safety instructions：

26-36

Marks：

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

Hazard Statements：

H302+H312+H332

GHS Classification：

|Warning|H302+H312+H332 (93.02%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-Methyl-5-nitropyridine Use and Manufacturing

To a stirred solution of Step 1 To a stirred solution of A mixture of To a 250mL autoclave was added100mLMeOH, Step 3 5-Amino-2-picoline The product of Step 2, 20a. 5-Amino-2-methylpyridine A slurry of diethyl malonate (42 mL) and sodium (4.71 g) were warmed slowly to 90 C. and stirred at 90 C. for 2 hours and 120 C. for 30 minutes before being cooled to room temperature. Toluene (200 mL) and 2-chloro-5-nitropyridine (25.0 g) were added and the mixture was heated at 110 C. for 1.5 hours and ambient temperature for 17 h. After removal of the volatiles in vacuo, 6 N HCl (200 mL) was added and the mixture was heated to reflux for 4 h and cooled to room temperature. The solution was neutralized with solid sodium carbonate, extracted with ethyl acetate (6×100 mL), dried over solid magnesium sulfate, and concentrated to a dark solid. This material was purified by flash chromatography using 20% ethyl acetate in petroleum ether as the eluent. Concentration in vacuo of the product-rich fractions afforded Preparation 90; 6-methyl-pyridin-3-vlamine; Iron powder (10g) was added to a well-stirred solution of 2-methyl-5-nitro- pyridine, [ (46g, 330mmol) Monatshefte fur chemie, 1950 81 (4) 479] dissolved in acetic acid (500mL). The mixture was heated under reflux for 1.5 hours, cooled, and a further portion of iron powder (2g) was added. The reaction mixture was stirred under reflux for an additional 5 hours, cooled and left to stand for 18 hours. The iron powder was then filtered off and the filtrate was evaporated under reduced pressure. The residue was taken up in water and chloroform and was treated with potassium carbonate. The organic phase was washed with water, dried over magnesium sulfate and concentrated in vacuo to produce the title compound as a semi-solid (17. 2g). BPt. 130C 1 mmHgIn some specific embodiments, an isopropyl acetate (15 V) solution of 2-Methyl-5- nitropyridine (NPYR) is washed with a 1 N aqueous NaOH solution (2 V) and water (2 V). The solution is optionally circulated through charcoal capsules until the color-of-solution (COS) in-process control is met (COS 99 LC area%.

Computed Properties

Molecular Weight:138.12
XLogP3:1
Hydrogen Bond Acceptor Count:3
Exact Mass:138.042927438
Monoisotopic Mass:138.042927438
Topological Polar Surface Area:58.7
Heavy Atom Count:10
Complexity:132
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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