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130206

Sigma-Aldrich

Nitroethane

reagent grade, ≥98.0%

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About This Item

Linear Formula:
CH3CH2NO2
CAS Number:
79-24-3
Molecular Weight:
75.07
Beilstein/REAXYS Number:
1209324
MDL number:
MFCD00007404
UNSPSC Code:
12352102
PubChem Substance ID:
329749976
grade:
reagent grade
assay:
≥98.0%
bp:
114-115 °C (lit.)
vapor pressure:
15.6 mmHg ( 20 °C)

grade

reagent grade

Quality Level

100

vapor density

2.58 (vs air)

vapor pressure

15.6 mmHg ( 20 °C)

assay

≥98.0%

form

liquid

autoignition temp.

778 °F

expl. lim.

3.4 %

refractive index

n20/D 1.391 (lit.)

bp

114-115 °C (lit.)

mp

−90 °C (lit.)

solubility

acetone: soluble(lit.)
alcohol: soluble(lit.)
water: slightly soluble(lit.)

density

1.045 g/mL at 25 °C (lit.)

SMILES string

CC[N+]([O-])=O

InChI

1S/C2H5NO2/c1-2-3(4)5/h2H2,1H3

InChI key

MCSAJNNLRCFZED-UHFFFAOYSA-N

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General description

Nitroethane reacts with sodium to afford sodium-nitroethane. Solution of nitroethane in caustic potash reacts with bromine to afford monobromnitroethane. It can undergo nitroaldol (Henry) condensation reaction with various aldehydes in the presence of copper(II) arylhydrazone complexes (catalyst).[1]
pK of nitroethane is 8.60.4
Nitroethane is an aprotic solvent with high polarity[2], which on oxidation with glucose oxidase gives nitrite, acetaldehyde and hydrogen peroxide as the major products.[3]

Application

Nitroethane may be used in the synthesis of the following compounds:
  • β-nitro amine derivatives[4]
  • β-aryl nitroethylenes[5]
  • 2-alkylthio-3-alkylamino-1-aryl(hetaryl)-4-nitropentene[6]

Other Notes

major impurity is 2-nitropropane

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 1B - Flam. Liq. 3 - Muta. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

87.8 °F - closed cup

flash_point_c

31 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG5146
MKBX1943V
MKBT1339V
MKBR0849V
MKBP0489V

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Limin Xiang et al.
Nature communications, 9(1), 1435-1435 (2018-04-14)
Under ambient conditions, the behavior of a solid surface is often dominated by a molecularly thin adsorbed layer (adlayer) of small molecules. Here we develop an optical approach to unveil the nanoscale structure and composition of small-molecule adlayers on glass
Mechanism of oxidation of nitroethane by glucose oxidase
Porters.T.JD and Bright.JH
The Journal of Biological Chemistry, 252, 4361- 4370 (1977)
Volumetric and Viscometric Properties of Binary Mixtures of Aliphatic Alcohols (C1- C4) with Nitroethane from 293.15 K to 313.15 K
Tu H-C, et al.
Journal of Chemical and Engineering Data, 45(3), 450-456 (2000)
Copper (II) arylhydrazone complexes as catalysts for C-H activation in the Henry reaction in water
Ma Z, et al.
J. Mol. Catal. A: Chem. (2016)
Feng-Wu Liu et al.
Carbohydrate research, 344(18), 2439-2443 (2009-11-03)
Henry reactions of a novel higher sugar derivative, (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate (Alternate nomenclature: (1R)-(isomannid-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate), with nitromethane and nitroethane were studied. The kinetic and thermodynamic reactions with nitromethane under different conditions were carried out to afford (2S)- and (2R)-beta-nitroalcohols, respectively. But
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