1116-54-7 Usage
Description
N-NITROSODIETHANOLAMINE is a potent liver carcinogen found in several species of animals and is one of the most widespread N-nitroso compounds in the human environment. It is a yellow to dark brown very viscous liquid with no distinct odor and has reddish-yellow oil as its chemical property.
Uses
Used in Research and Development:
N-NITROSODIETHANOLAMINE is used as a research chemical for studying the effects of N-nitroso compounds on various species of animals and their potential impact on human health.
Used in Environmental Monitoring:
N-NITROSODIETHANOLAMINE is used as an indicator for the presence of N-nitroso compounds in the human environment, helping to monitor and control exposure to these potentially harmful substances.
Air & Water Reactions
Water soluble.
Reactivity Profile
N-NITROSODIETHANOLAMINE can react with alkoxides. N-NITROSODIETHANOLAMINE reacts with sulfuric acid at temperatures above 311° F.
Health Hazard
ACUTE/CHRONIC HAZARDS: N-NITROSODIETHANOLAMINE may be harmful by eye or skin contact, inhalation or ingestion. It is an irritant and, when heated to decomposition, it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides.
Fire Hazard
Flash point data for N-NITROSODIETHANOLAMINE are not available; however, N-NITROSODIETHANOLAMINE is probably combustible.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data.Mildly
toxic by ingestion. Mutation data reported.
When heated to decomposition it emits
toxic fumes of NOx. See also N-NITROSO
COMPOUNDS and ALCOHOLS.
Carcinogenicity
N-Nitrosodiethanolamine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Purification Methods
Purify NDELA by dissolving the amine (0.5g) in 1-propanol (10mL) and 5g of anhydrous Na2SO4 added with stirring. After standing for 1-2hours, it is filtered and passed through a chromatographic column packed with 10mL of AG 50W x 8 (H+form 50-100mesh, a strongly acidic cation exchanger). The eluent and washings (50 mL EtOH) are combined and evaporated to dryness at 35o. It has also been extracted with EtOH from the nitrosation mixture of ethanolamine, filtered and distilled under high vacuum. [Fukuda et al. Anal Chem 53 2000 1981, Jones & Wilson J Chem Soc 550, 1949, Beilstein 1 III 721, see Spiegelhalder et al. N-Nitroso Compounds: Occurrence Biological Effects and Relevance in Human Cancer (eds. O’Neill et al. IARC Scientific Publications No 57; IARC Lyon p943 1984.] Possible
Check Digit Verification of cas no
The CAS Registry Mumber 1116-54-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,1 and 6 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1116-54:
(6*1)+(5*1)+(4*1)+(3*6)+(2*5)+(1*4)=47
47 % 10 = 7
So 1116-54-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H10N2O3/c7-3-1-6(5-9)2-4-8/h7-8H,1-4H2
1116-54-7Relevant articles and documents
Facile Formation of N-Nitrosamines from Bromonitromethane and Secondary Amines
Challis, Brian C.,Yousaf, Taher I.
, p. 1598 - 1599 (1990)
Bromonitromethane readily converts secondary amines to N-nitrosamines in aqueous and organic solvents at room temperature via reaction of an iminium ion intermediate with nitrite ion.
Carcinogenic nitrosamines: Hundred-gram preparations of N-nitrosodiethylamine and α-ureidodimethylnitrosamine
Johnston,McCaleb
, p. 311 - 313 (1984)
-
Versatile new reagent for nitrosation under mild conditions
Galloway, Jordan D.,Sarabia, Cristian,Fettinger, James C.,Hratchian, Hrant P.,Baxter, Ryan D.
supporting information, p. 3253 - 3258 (2021/05/06)
Here we report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures and is effective for transnitrosation in multiple solvents. Compared with traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirm that two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization effects.
Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation
Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
, p. 9216 - 9221 (2019/10/08)
ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.