759-73-9 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 759-73-9 differently. You can refer to the following data:
1. Orange Paste
2. N-Nitroso-N-ethyl urea is a pale yellow, crystalline
powder; freezing/melting point=103－104°C
(decomposes). Hazard identification (based on NFPA-704
M Rating System): Health 2; flammability 1; reactivity 0?.
Soluble in water; hydrolysis produces explosive gas.
Uses
Different sources of media describe the Uses of 759-73-9 differently. You can refer to the following data:
1. N-Nitroso-N-ethylurea has been used as a mutation-inducing agent.
2. A precursor of Diazoethane
3. Experimentally as mutagen; ethylating agent.
Definition
ChEBI: A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by ethyl and nitroso groups.
General Description
Yellow-pink crystals or off-white powder. Sensitive to light.
Air & Water Reactions
Water soluble. Sensitive to moisture--stability in aqueous solutions depends on pH.
Reactivity Profile
N-NITROSO-N-ETHYLUREA is highly reactive. Sensitive to moisture and light. Its stability in aqueous solutions is pH-dependent. Incompatible with water and nucleophilic reagents. Alkaline hydrolysis produces a highly explosive gas. .
Hazard
Tumorigen, carcinogen, neoplastigen; teratogen; poison; toxic.
Health Hazard
ACUTE/CHRONIC HAZARDS: N-NITROSO-N-ETHYLUREA is extremely unstable at high pH. It will decompose to extremely unstable decomposition products if acidic conditions are not maintained. When heated to decomposition it emits toxic fumes of nitrogen oxides. Decomposition products may be explosive.
Fire Hazard
Flash point data for N-NITROSO-N-ETHYLUREA are not available; however, N-NITROSO-N-ETHYLUREA is probably combustible.
Biochem/physiol Actions
DNA alkylating agent that is carcinogenic in many animal species. Induces benign and malignant tumors of numerous types, including the nervous tissue, stomach, esophagus, pancreas, respiratory tract, intestine, lymphoreticular tissues, skin, and kidney.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, tumorigenic, and teratogenic
data. Poison by ingestion, subcutaneous,
intraperitoneal, and intravenous routes.
Human mutation data reported. When
heated to decomposition it emits toxic
fumes of NOx. See also N-NITROSO
COMPOUNDS.
Potential Exposure
Used as a chemical intermediate for
dyes and pharmaceuticals; a polymerization inhibitor during
the manufacture of vinyl monomers such as styrene; a
precursor of diazoethane; accelerator for rubber vulcanization.
Carcinogenicity
N-Nitroso-N-ethylurea is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Shipping
Toxic solids, organic, n.o.s., Hazard Class: 6.1;
Labels: 6.1-Poisonous materials, Technical Name Required.
UN3077 Environmentally hazardous substances, solid,
n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required.
Incompatibilities
N-nitroso-N-ethylurea is highly reactive.
Sensitive to moisture and light. Its stability in aqueous
solutions is pH-dependent. Incompatible with water and
nucleophilic reagents. Alkaline hydrolysis produces a
highly explosive gas. This compound is extremely
unstable at high pH. It will decompose to extremely
unstable decomposition products if acidic conditions are
not maintained. Nitrated organics range from slight to
strong oxidizing agents. If mixed with reducing agents,
including hydrides, sulfides and nitrides, they may begin a
vigorous reaction. Reaction with
Waste Disposal
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations
governing storage, transportation, treatment, and waste
disposal.
Check Digit Verification of cas no
The CAS Registry Mumber 759-73-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,5 and 9 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 759-73:
(5*7)+(4*5)+(3*9)+(2*7)+(1*3)=99
99 % 10 = 9
So 759-73-9 is a valid CAS Registry Number.
InChI:InChI=1/C3H7N3O2/c1-2-6(5-8)3(4)7/h2H2,1H3,(H2,4,7)
759-73-9Relevant articles and documents
Metal-Free Ring-Expansion Reaction of Six-membered Sulfonylimines with Diazomethanes: An Approach toward Seven-Membered Enesulfonamides
Xia, An-Jie,Kang, Tai-Ran,He, Long,Chen, Lian-Mei,Li, Wen-Ting,Yang, Jin-Liang,Liu, Quan-Zhong
supporting information, p. 1441 - 1444 (2016/02/12)
A new metal-free, ring-expansion reaction of six-membered N-sulfonylimines with unstable diazomethanes, generated in situ from the N-tosylhydrazones, has been developed. This reaction delivers valuable seven-membered enesulfonamides by a Tiffeneau-Demjanov rearrangement and intramolecular proton transfer tautomerization process. Moreover, this ring-expansion reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using aryl aldehydes, without the need to isolate the N-tosylhydrazone. A diazo thing: The title reaction between cyclic N-sulfonylimines and diazo compounds generated in situ from the N-tosylhydrazones is simple and functional-group tolerant. It thus delivers valuable seven-membered sulfonamides in up to 95 % yield. Moreover, this reaction can be carried out in one-pot starting from the aryl aldehydes, without the need to isolate the N-tosylhydrazone (right).
Application of N-nitrosoureas in the synthesis of organophosphorus compounds
Afshar, Davood Aghaei,Islami, Mohammad Reza
scheme or table, p. 509 - 511 (2009/04/06)
N-nitrosoureas which are readily accessible from the reaction of urea derivatives with sodium nitrite and aqueous H2SO4 reacted with acetylenic esters in the presence of Ph3P in ethyl acetate at ambient pressure to give stable phosphorus ylides. This methodology is introduced as a simple and inexpensive procedure for the preparation of organophosphorus compounds in excellent yields.
The nitrosation of N-alkylureas: Evidence for a proton transfer mechanism
Casado, Iulio,Gonzalez-Alatorre, Guillermo,Izquierdo, Carmen,Brunner, Christian
, p. 307 - 313 (2007/10/03)
The kinetics of the nitrosation of methyl, ethyl, propyl, butyl, and allyl urea were studied by conventional and stopped-flow spectrophotometry in the presence or absence of acetate or mono-, di-, or trichloroacetate anions In the presence of a large excess of urea, the observed rate equation was chemical equations presented where Ka is the acidity constant of nitrous acid and KR that of the carboxylic acid The ureas exhibited the reactivity order methylurea ? (ethylurea ≈ propylurea ≈ butylureal ? allylurea. Experiments in D2O afforded values of kH2O/kD2O in general agreement with the values 4.1-5 5 predicted by a semiclassical transition state theory of kinetic isotope effects [i.e., kH2O/kD2O = exp(0.130hv/kT)]where v is the frequency of R3N - H stretching (2700-2250 cm-1) in the protonated urea. This result, the observed catalysis by carboxylate ions and the value of the Bronsted parameter β(0.45) show the rate-controlling step of these reactions to be the transfer of a proton from the protonated N-alkyl-N-nitrosourea to the solvent or to the organic anion. if present. The observed order of substrate reactivities is explicable in terms of the capacity of the protonated N-alkyl-N-nitrosourea for forming a hydrogen bond with the water molecule to which the proton will be transferred, and the degree to which the formation of such bonds is hindered by the hydrophobic alkyl chain of the nitrosourea.
