nitromethane

• ChemBase ID: 128625
• Molecular Formular: CH3NO2
• Molecular Mass: 61.04002
• Monoisotopic Mass: 61.01637834
• SMILES: C[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)C
• InChI: InChI=1S/CH3NO2/c1-2(3)4/h1H3
• InChIKey: LYGJENNIWJXYER-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: nitromethane
• IUPAC Traditional name: nitromethane
• Synonyms: Nitrocarbol; Nitromethane; Nitromethane; 硝基甲烷

Database IDs

• CAS Number: 75-52-5
• EC Number: 200-876-6
• MDL Number: MFCD00007400
• Beilstein Number: 1698205
• Merck Index: 146611
• PubChem SID: 24862170; 24856374; 24853835; 162222932; 24886573; 24845304; 24846653; 24849317
• PubChem CID: 6375
• CHEMBL: 276924
• Chemspider ID: 6135
• KEGG ID: C19275
• Wikipedia Title: Nitromethane

CALCULATED PROPERTIES

• Acid pKa: 8.882173
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.028654944
• LogD (pH = 7.4): 0.0147883715
• Log P: 0.028834643
• Molar Refractivity: 11.5834 cm^3
• Polarizability: 4.645152 Å^3
• Polar Surface Area: 43.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ca. 10 g/100 mL in water
• Apperance: APHA: ≤10; colorless liquid
• Melting Point: -29 °C (244.15 K); -29 °C(lit.); -29°C
• Boiling Point: 100–103 °C (373-376 K); 101.2 °C; 101.2 °C(lit.); 101°C
• Flash Point: 35 °C; 35°C(95°F); 36 °C; 96.8 °F
• Auto Ignition Point: 784 °F
• Density: 1.127 g/mL at 25 °C(lit.); 1.130; 1.1371 g/cm3, liquid
• Refractive Index: 1.3820; n20/D 1.382; n20/D 1.382(lit.)
• Vapor Pressure: 2.7 mmHg ( 20 °C); 27.3 mmHg ( 20 °C)
• Vapor Density: 2.1 (vs air)
• Absorption Wavelength: λ: 380 nm Amax: 1.0; λ: 380 nm Amax: 1.00; λ: 386 nm Amax: 0.50; λ: 395 nm Amax: 0.20; λ: 400 nm Amax: 0.1; λ: 400 nm Amax: 0.10; λ: 405 nm Amax: 0.05; λ: 430 nm Amax: 0.01; λ: 430-700 nm Amax: 0.01
• pKa: 10.2
• Viscosity: 0.61 mPa·s at 25 °C

Safety Information

• RTECS: PA9800000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 1261; UN1261
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 5-10-22; R5 R10 R22
• Safety Statements: 41; S41
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• Main Hazard: Flammable, harmful
• NFPA704:
  

  3

  2

  4
• Explode Limits: 7.3 %, 33 °F
• GHS Hazard statements: H226-H302
• GHS Precautionary statements: P260-P370+P380+P375
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1261 3/PG 2

Product Information

• Purity: ≥90.0%; ≥95%; ≥95.0% (GC); ≥96%; ≥97.0% (GC); ≥98.5% (GC); ≥99.0%; ≥99.0% (GC); 96%; 98+%
• Grade: absolute; ACS reagent; analytical standard; CHROMASOLV®; for HPLC; puriss.; purum; reagent grade; ReagentPlus®; SAJ first grade; spectrophotometric grade
• Impurities: <0.030% water; <0.050% water; ≤0.03% water; ≤0.05% water; ≤0.5% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality: over molecular sieve (H2O ≤0.01%)
• Solvent Strength(ε Al2O3): 0.64
• λ: 1 cm path, H2O reference; H2O reference
• Appearance: clear
• Empirical Formula (Hill Notation): CH3NO2

DETAILS

Sigma Aldrich - 360554

Packaging
1, 2, 2.5, 4×4 L in glass bottle
20 L in steel drum
500, 6×500 mL in glass bottle

Sigma Aldrich - 270423

Packaging
1, 2 L in glass bottle
100 mL in glass bottle
Legal Information
CHROMASOLV is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 230731

Packaging
25, 100 mL in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 108170

Packaging
1, 4 L in glass bottle
20 L in steel drum

Sigma Aldrich - 154946

Packaging
1 L in glass bottle

REFERENCES

• For conditions for the Henry (nitro-aldol) condensation of nitroalkanes with carbonyl compounds, see 1-Nitropropane, A11975. In the Tiffeneau-Demjanov ring expansion of ketones, the nitro aldol is reduced to the ?-hydroxyamine before diazotization; see, e.g. (cyclohexanone to cycloheptanone): Org. Synth. Coll., 4, 221 (1963); review: Org. React., 11, 157 (1960).
• For a review of the use of nitro compounds as alkyl anion synthons, including methods for removing the nitro group from the resulting carbon skeletons, see: Synthesis, 833 (1988).
• For reaction with TosMIC adducts to give pyrroles, see p-Toluenesulfonylmethyl isocyanide, A14312.
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 1174 (2007).