55-18-5 Usage
Chemical Properties
N-Nitrosodiethylamine is a yellow liquid.
Uses
Different sources of media describe the Uses of 55-18-5 differently. You can refer to the following data:
1. N-Nitrosodiethylamine (DEN) is a widely occurring nitrosamine that is one of the most important environmental carcinogens primarily inducing tumors of liver.
2. Gasoline and lubricant additive; antioxidant; stabilizer in plastics.
3. N,N-diethylnitrous Amide is a useful research reagent for organic synthesis.
Definition
ChEBI: A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.
General Description
Clear slightly yellow liquid. Boiling point 175-177°C. Can reasonably be anticipated to be a carcinogen. Used as a gasoline and lubricant additive and as an antioxidant and stabilizer in plastics.
Air & Water Reactions
Water soluble.
Reactivity Profile
N-NITROSODIETHYLAMINE reacts with strong oxidizing agents. Incompatible with reducing agents. Can be hydrolyzed by hydrogen bromide in acetic acid .
Hazard
Possible carcinogen; mutagen; neoplastigen; tumorigen; poison; teratogen.
Health Hazard
Different sources of media describe the Health Hazard of 55-18-5 differently. You can refer to the following data:
1. ACUTE/CHRONIC HAZARDS: When heated to decomposition N-NITROSODIETHYLAMINE emits toxic fumes of nitrogen oxides.
2. The acute toxicity of diethylnitrosamine is classified as moderate. Other
nitrosamines of higher molecular weight are somewhat less toxic. Harmful exposure
to nitrosamines can occur by inhalation and ingestion and may cause nausea,
vomiting, and fever. This substance does not have adequate warning properties.
Chronic exposure to nitrosamines can cause severe liver damage. Diethylnitrosamine
is listed in IARC Group 2A ("probable human carcinogen") and is classified as an
OSHA "select carcinogen." Nitrosamines are suspected of causing cancers of the
lung, nasal sinuses, brain, esophagus, stomach, liver, bladder, and kidney.
Diethylnitrosamine is mutagenic and teratogenic.
Fire Hazard
Different sources of media describe the Fire Hazard of 55-18-5 differently. You can refer to the following data:
1. Volatilization during combustion produces hazardous vapors. Combustion products
contain nitrogen oxides.
2. N-NITROSODIETHYLAMINE is combustible.
Flammability and Explosibility
Volatilization during combustion produces hazardous vapors. Combustion products contain nitrogen oxides.
Biochem/physiol Actions
N-Nitrosodiethylamine (NDMA) is carcinogenic in all animal species tested. The main target organs are the nasal cavity, trachea, lung, esophagus and liver. NDMA is acted upon by the cytochrome P450 system resulting in the formation of carcinogenic methyldiazonium ion. However microbes like Pseudomonas metabolize NDMA into N-nitromethylamine (NTMA) and formaldehyde.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data. Poison
by ingestion, intravenous, intraperitoneal,
and subcutaneous routes. An experimental
teratogen. Other experimental reproductive
effects. Human mutation data reported. A
transplacental carcinogen. When heated to
decomposition it emits toxic fumes of NOx.
See also N-NITROSO COMPOUNDS and
AMINES.
Potential Exposure
An additive in gasoline and lubricants;
an antioxidant and stabilizer in plastics. Used in research.
Incompatibilities: Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Contact with reducing
agents may form hydrazine; hydrogen bromide. Light sensitive;
rapidly decomposes.
Carcinogenicity
N-Nitrosodiethylamine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
storage
work with diethylnitrosamine should be conducted in a fume hood to prevent exposure by inhalation, and appropriate impermeable gloves and splash goggles should be worn at all times to prevent skin and eye contact.
Shipping
UN2810 Toxic liquids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. UN3082 Environmentally hazardous
substances, liquid, n.o.s., Hazard Class: 9; Labels:
9-Miscellaneous hazardous material, Technical Name
Required.
Incompatibilities
An additive in gasoline and lubricants;
an antioxidant and stabilizer in plastics. Used in research.
Incompatibilities: Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Contact with reducing
agents may form hydrazine; hydrogen bromide. Light sensitive;
rapidly decomposes.
Check Digit Verification of cas no
The CAS Registry Mumber 55-18-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 5 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 55-18:
(4*5)+(3*5)+(2*1)+(1*8)=45
45 % 10 = 5
So 55-18-5 is a valid CAS Registry Number.
InChI:InChI=1S/C4H10N2O/c1-3-6(4-2)5-7/h3-4H2,1-2H3
55-18-5Relevant articles and documents
Synthesis of N,N-diethylhydrazine and its reactions with carboxylic acids and alkyl halides
Akhmedov,Tadzhimukhamedov,Akhmedov
, p. 1720 - 1722 (2005)
N,N-Diethylhydrazine was synthesized by a modified procedure via nitrosation of diethylamine, followed by reduction of the resulting N-nitrosodiethylamine with zinc amalgam in a hydrochloric acid medium. Reactions of N, N-diethylhydrazine with carboxylic acids and alkyl halides resulted in formation of the corresponding hydrazinium salts.
A method for the demonstration of nitrosamines
Sander
, p. 852 - 854 (1967)
-
Polyakov,A.I.,Spiridonova,L.N.
, (1973)
Visible-Light-Induced Photoaddition of N-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines
Patil, Dilip V.,Si, Tengda,Kim, Hun Young,Oh, Kyungsoo
supporting information, p. 3105 - 3109 (2021/05/05)
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 to telescope the direct handling of harmful N-nitroso compounds, where the desired α-amino oxime derivatives were obtained in a one-pot tandem N-nitrosation and photoaddition sequence.
Facile N-nitrosation of secondary amines using poly(N,N'-dibromo-Nethylene- benzene-1,3-disulfonamide) and N,N,N′,N′-tetrabromobenzene-1,3- disulfonamide/NaNO2 under mild conditions
Ghorbani-Vaghei, Ramin,Shiri, Lotfi,Ghorbani-Choghamarani, Arash
, p. 204 - 208 (2013/07/26)
In this research project, a combination of poly(N,N′-dibromo-N- ethylene-benzene-1,3-disulfonamide) [PBBS] and/or (N,N,N′,N′- tetrabromobenzene-1,3-disulfonamide) [TBBDA] with sodium nitrite in the presence of wet SiO2 (50% w/w) was used as an efficient nitrosating agent for the conversion of secondary amines to their corresponding nitroso compounds. N-Nitrosation reaction has been performed in dichloromethane at room temperature under mild and heterogeneous conditions. The reaction is operationally simple and corresponding products were achieved in good to excellent yields.
1-butyl-3-methylimidazolium nitrite as a reagent for the efficient n-nitrosation of secondary amines
Valizadeh,Gholipour
experimental part, p. 857 - 861 (2012/06/18)
1-Butyl-3-methylimidazolium nitrite, [bmim]NO2 was used as a new effective reagent for the preparation of N-nitrosamines from the corresponding secondary amines at 0 °C to room temperature, under mild conditions in good to excellent yields.
