230731
Nitromethane
ReagentPlus®, ≥99.0%
Synonym(s):
Nitrocarbol
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About This Item
Empirical Formula (Hill Notation):
CH3NO2
CAS Number:
Molecular Weight:
61.04
UNSPSC Code:
12352102
NACRES:
NA.21
PubChem Substance ID:
EC Number:
200-876-6
Beilstein/REAXYS Number:
1698205
MDL number:
Assay:
≥99.0%
Vapor pressure:
2.7 mmHg
InChI key
LYGJENNIWJXYER-UHFFFAOYSA-N
InChI
1S/CH3NO2/c1-2(3)4/h1H3
SMILES string
C[N+]([O-])=O
vapor density
2.1 (vs air)
vapor pressure
2.7 mmHg
product line
ReagentPlus®
assay
≥99.0%
form
liquid
autoignition temp.
784 °F
expl. lim.
7.3 %, 33 °F
dilution
(for general lab use)
Quality Level
pH
6.4 (20 °C, 0.01 g/L)
mp
−29 °C (lit.)
density
1.127 g/mL at 25 °C (lit.)
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General description
Nitromethane (CH3NO2) is the simplest nitro organic compound used for a wide range of applications, including as polar solvents to racing fuel. It serves as a solvent for organic chemistry and as a valuable building block for various useful compounds like nitroalkanes, β-nitroalcohols, nitroalkenes, carbonyl compounds, amines, and heterocycles. In industry, nitromethane can be used to stabilize halogenated hydrocarbons.
Application
Nitromethane can be used:
- As a reagent in the synthesis of 3-nitroindoles by arylation with N-(2-bromoaryl) imidates using palladium catalyst.
- As a cyanating reagent for the synthesis of thiocyanates in presence of base (KOAc) and iodine.
- In the preparation of cobalt cage complexes from polyamines and formaldehyde.
- As a solvent in the preparation of β-substituted γ-nitroaldehydes by enantioselective cross-coupling of β-arylated or γ,δ-unsaturated aldehydes using oxidizing agent DDQ (2,3-dichloro-5,6-dicyanoquinone) and catalyst diphenylprolinol silyl ether.
Features and Benefits
Nitromethane as high energy monopropellant exhibits
- Low toxicity.
- High specific impulse.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Warning
Hazard Classifications
Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 3 - Repr. 2
Storage Class
4.1A - Other explosive hazardous materials
wgk
WGK 2
flash_point_f
95.0 °F - closed cup
flash_point_c
35 °C - closed cup
Regulatory Information
易制爆化学品
危险化学品
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Metal ion encapsulation: cobalt cages derived from polyamines, formaldehyde, and nitromethane.
Geue RJ, et al.
Journal of the American Chemical Society, 106(19), 5478-5488 (1984)
The catalytic chemistry of nitromethane over Co-ZSM5 and other catalysts in connection with the methane-NOxSCR reaction.
Cowan AD, et al.
J. Catal., 176(2), 329-343 (1998)
Benedek Vakulya et al.
Organic letters, 7(10), 1967-1969 (2005-05-07)
Cinchona alkaloid-derived chiral bifunctional thiourea organocatalysts were synthesized and applied in the Michael addition between nitromethane and chalcones with high ee and chemical yields.
Junhong Shan et al.
Chemosphere, 86(4), 323-328 (2011-11-01)
In this study, the effects of pH, bromide and nitrite on the formation of halonitromethanes (HNMs) and trihalomethanes (THMs) from eight amino acids (glycine, alanine, serine, cysteine, aspartic acid, glutamic acid, lysine and histidine) and four amino sugars (glucosamine, galactosamine
Density-dependent liquid nitromethane decomposition: molecular dynamics simulations based on ReaxFF.
Naomi Rom et al.
The journal of physical chemistry. A, 115(36), 10181-10202 (2011-08-05)
The decomposition mechanism of hot liquid nitromethane at various compressions was studied using reactive force field (ReaxFF) molecular dynamics simulations. A competition between two different initial thermal decomposition schemes is observed, depending on compression. At low densities, unimolecular C-N bond
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