1116-54-7 Usage
Chemical Properties
Reddish Yellow Oil
Uses
A potent liver carcinogen in several species of animals, is one of the most widespread N-nitroso compounds in the human environment.
General Description
Yellow to dark brown very viscous liquid with no distinct odor.
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)
-
NITROSATION REAGENTS AND METHODS
-
Paragraph 00158-00160; 00164; 00182; 00183; 00186-00189; ..., (2022/02/06)
Provided are compounds that can find use as nitrosation reagents. Provided are nitrosation methods that include reacting a substrate with one of the provided nitrosation reagents and thereby generating a nitrosation product. Provided are kits including a nitrosation reagent. Provided are compositions wherein the nitrosation reagent is enriched in the 15N isotope.
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.
