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Všechny fotografie(3)

Key Documents

S2252

Sigma-Aldrich

Sodium nitrite

ReagentPlus®, ≥99.0%

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About This Item

Lineární vzorec:
NaNO2
Číslo CAS:
Molekulová hmotnost:
69.00
EC Number:
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.21

Quality Level

product line

ReagentPlus®

assay

≥99.0%

form

powder or crystals

autoignition temp.

914 °F

pH

9 (20 °C, 100 g/L)

mp

271 °C (lit.)

SMILES string

[Na+].[O-]N=O

InChI

1S/HNO2.Na/c2-1-3;/h(H,2,3);/q;+1/p-1

InChI key

LPXPTNMVRIOKMN-UHFFFAOYSA-M

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General description

Sodium nitrite is an air-sensitive and hygroscopic solid with both reducing and oxidizing properties. It is commonly used as a reagent and catalyst in synthetic organic chemistry. It is decomposed by acids (even weak acids) with the evolution of a brown mixture of nitrogen oxides (NOx).

Application

Sodium nitrite can be used as a reagent in:      
  • In the conversion of amines into diazo compounds, which are used as key precursors to many dyes, such as diazo dyes.      
  • Nef reaction and Abidi transformations.      
  • The C–C bond cleavage reaction in the presence of TFA under aerobic conditions.      
  • The oxidative carbonitration of alkenes in the presence of K2S2O8.

It can also be used as a nitrating agent in organic synthesis.
It is used in direct C-H nitration, ipso-nitration, and nitration via transition metal-catalyzed cross-coupling reaction. NaNO2 is also used as a co-catalyst for catalytic oxidation of alcohols under aerobic, solvent-free conditions.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Eye Irrit. 2 - Ox. Sol. 3

Storage Class

5.1B - Oxidizing hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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PloS one, 15(11), e0241861-e0241861 (2020-11-07)
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Anne C Rios et al.
Cancer cell, 35(4), 618-632 (2019-04-02)
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Rustem F Dautov et al.
Nitric oxide : biology and chemistry, 40, 36-44 (2014-05-27)
Previous studies in non-human blood vessels and in platelets have demonstrated that under hypoxic conditions release of NO from nitrite (NO2(-)) is potentiated by deoxyhaemoglobin. In the current study, we characterized hypoxic potentiation of NO2(-) effects in human vasculature and
Edward H Oldfield et al.
Journal of neurosurgery, 119(3), 634-641 (2013-05-28)
Intravenous sodium nitrite has been shown to prevent and reverse cerebral vasospasm in a primate model of subarachnoid hemorrhage (SAH). The present Phase IIA dose-escalation study of sodium nitrite was conducted to determine the compound's safety in humans with aneurysmal
Paul J Shami et al.
Journal of medicinal chemistry, 49(14), 4356-4366 (2006-07-11)
The literature provides evidence that metabolic nitric oxide (NO) release mediates the cytotoxic activities (against human leukemia and prostate cancer xenografts in mice) of JS-K, a compound of structure R(2)N-N(O)=NO-Ar for which R(2)N is 4-(ethoxycarbonyl)piperazin-1-yl and Ar is 2,4-dinitrophenyl. Here

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