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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
NACRES:
NA.22

Assay

≥99.0% (GC)

form

liquid

IVD

for in vitro diagnostic use

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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Li Chen et al.
Inorganic chemistry, 37(18), 4677-4688 (2001-10-24)
Diethylnitrosamine reacts with [(TPP)Fe(THF)(2)]ClO(4) (TPP = 5,10,15,20-tetraphenylporphyrinato dianion) in toluene to generate the bis-nitrosamine complex, [(TPP)Fe(Et(2)NNO)(2)]ClO(4), in 96% isolated yield. The related [(TTP)Fe(Et(2)NNO)(2)]SbF(6) (TTP = 5,10,15,20-tetra-p-tolylporphyrinato dianion) complex is prepared in 70% isolated yield via a similar reaction in CH(2)Cl(2).
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
Dilip V Patil et al.
Organic letters, 23(8), 3105-3109 (2021-04-02)
The generation of aminium radical cation species from N-nitrosoamines is disclosed for the first time through visible-light excitation at 453 nm. The developed visible-light-promoted photoaddition reaction of N-nitrosoamines to alkenes was combined with the o-NQ-catalyzed aerobic oxidation protocol of amines
Koichi Fujisawa et al.
PloS one, 10(6), e0129950-e0129950 (2015-06-25)
Maid is a helix-loop-helix protein that is involved in cell proliferation. In order to further elucidate its physiological functions, we studied Maid activity in two small fish model systems. We found that Maid expression was greatest in zebrafish liver and
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
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