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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:
1209324
MDL number:
MFCD00007404
UNSPSC Code:
12352102
PubChem Substance ID:
329749976
grade:
reagent grade
bp:
114-115 °C (lit.)
vapor pressure:
15.6 mmHg ( 20 °C)

grade

reagent grade

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).
pK of nitroethane is 8.60.4
Nitroethane is an aprotic solvent with high polarity, which on oxidation with glucose oxidase gives nitrite, acetaldehyde and hydrogen peroxide as the major products.

Application

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

Other Notes

major impurity is 2-nitropropane

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

87.8 °F - closed cup

Flash Point(C)

31 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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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
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)
Annie Héroux et al.
Biochemistry, 48(15), 3407-3416 (2009-03-07)
The flavoenzyme nitroalkane oxidase is a member of the acyl-CoA dehydrogenase superfamily. Nitroalkane oxidase catalyzes the oxidation of neutral nitroalkanes to nitrite and the corresponding aldehydes or ketones. Crystal structures to 2.2 A resolution or better of enzyme complexes with
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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