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73861

Sigma-Aldrich

N-Nitrosodiethylamine

≥99.0% (GC)

Synonym(s):

Diethylnitrosamine

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About This Item

Linear Formula:
(C2H5)2NNO
CAS Number:
55-18-5
Molecular Weight:
102.14
Beilstein:
1744991
EC Number:
200-226-1
MDL number:
MFCD00013890
UNSPSC Code:
12352100
PubChem Substance ID:
57652493

Quality Level

100

Assay

≥99.0% (GC)

form

liquid

bp

177 °C (lit.)

density

0.95 g/mL (lit.)

SMILES string

CCN(CC)N=O

InChI

1S/C4H10N2O/c1-3-6(4-2)5-7/h3-4H2,1-2H3

InChI key

WBNQDOYYEUMPFS-UHFFFAOYSA-N

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Application

N-Nitrosodiethylamine can be used as a reactant to synthesize:
  • α-Amino oxime derivatives from alkenes via visible-light-induced photoaddition in the presence of HCl.
  • Diethylnitrosamine metalloporphyrin complexes from metalloporphyrins in the presence of dichloromethane.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301 - H350 - H412

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 3 - Carc. 1B

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Changyu Zhu et al.
Journal of hepatology, 74(3), 613-626 (2020-10-11)
The hepatocyte Notch pathway is a pathogenic factor in non-alcoholic steatohepatitis (NASH)-associated fibrosis, but its role in hepatocellular carcinoma (HCC) is less well defined. Herein, we aimed to characterize the molecular and clinical features of Notch-active human HCC, and to
Maria José Rodríguez et al.
International journal of molecular sciences, 21(22) (2020-12-04)
Liver fibrosis is a complex process associated to most types of chronic liver disease, which is characterized by a disturbance of hepatic tissue architecture and the excessive accumulation of extracellular matrix. Resolvin E1 (RvE1) is a representative member of the
L Verna et al.
Pharmacology & therapeutics, 71(1-2), 57-81 (1996-01-01)
N-Nitrosodiethylamine (NDEA) is DNA reactive after bioactivation and produces tumors in every animal species tested. Bioactivation is effected by several P450 isozymes including CYP2E1, which is ethanol inducible. Tumor formation in rat liver was proportional to O4-ethyldeoxythymidine formation in DNA
Esther Bertran et al.
Hepatology (Baltimore, Md.), 58(6), 2032-2044 (2013-07-03)
Transforming growth factor-beta (TGF-β) is an important regulatory suppressor factor in hepatocytes. However, liver tumor cells develop mechanisms to overcome its suppressor effects and respond to this cytokine by inducing other processes, such as the epithelial-mesenchymal transition (EMT), which contributes
Masaaki Miyakoshi et al.
Molecular carcinogenesis, 53(1), 67-76 (2012-08-23)
STAT3 activation is involved in development and progression of hepatocellular carcinoma (HCC). We investigated STAT3 activation during hepatocarcinogenesis induced by neonatal diethylnitrosamine (DEN) treatment in mice. Nuclear accumulation and phosphorylation of STAT3 were detected in altered hepatocyte foci in the
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