816-57-9

Basic information

• Product Name: propylnitrosourea
• Synonyms: propylnitrosourea;NITROSOPROPYLUREA;N-PROPYLNITROSOUREA;PNU;N-PROPYL-N-NITROSOUREA;NPU;N-Nitroso-N-propyl Urea, Contains 40% Water, 1.8% Acetic Acid;1-Nitroso-1-propylurea
• CAS NO: 816-57-9
• Molecular Formula: C₄H₉N₃O₂
• Molecular Weight: 131.16
• Product Categories: Aliphatics;Amines;Nitric Oxide Reagents
• Mol File: 816-57-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 242.43°C (rough estimate)
• Flash Point: 74.9°C
• Appearance: /
• Density: 1.3227 (rough estimate)
• Vapor Pressure: 0.327mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility: DMSO, Methanol
• Stability: Unstable at RT, Contains 40% Water, 1.8% Acetic Acid
• CAS DataBase Reference: propylnitrosourea(CAS DataBase Reference)
• NIST Chemistry Reference: propylnitrosourea(816-57-9)
• EPA Substance Registry System: propylnitrosourea(816-57-9)

Safety Data

• Hazardous Substances Data: 816-57-9(Hazardous Substances Data)

Usage

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic data. An experimental teratogen. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also NNITROSO COMPOUNDS.

InChI:InChI=1/C4H9N3O2/c1-2-3-7(6-9)4(5)8/h2-3H2,1H3,(H2,5,8)

Upstream product

• 627-06-5 n-propylurea 
• 107-10-8 propylamine 

Downstream Products

• 71-23-8 propan-1-ol 
• 47007-32-9 NBP-Pr 
• 10250-52-9 1,1-diiodopropane 

Relevant articles and documents

Steric effect in alkylation reactions by N-alkyl-N-nitrosoureas: A kinetic approach

The alkylation reactions of 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilic characteristics similar to DNA base by five N-alkyl-N-nitrosoureas (methyl-, ethyl-, propyl-, butyl-, and allylnitrosourea) were investigated in 7.3 (v/v) water/dioxane medium in the 5.0-6.5 pH range. Decomposition of alkylnitrosoureas (ANU) gives rise to alkyldiazonium ions that yield NBP-R adducts directly or through carbocations in certain instances. The NBP alkylation rate constants by these species were determined. The following sequence of alkylating potential was found: methyl- > ethyl- > allyl- > propyl- > butyl group. Application of Ingold-Taft correlation analysis to the kinetic results revealed that the NBP alkylation reactions occur mainly through steric control. The values of the molar absorption coefficients of the NBP-R adducts also reveal the determinant influence of a steric effect in the formation of alkylation adducts. The kinetic results are consistent with the biological activity of ANU. Copyright

The nitrosation of N-alkylureas: Evidence for a proton transfer mechanism

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.