924-16-3 Usage
Chemical Properties
N-Nitrosodi-n-butylamine is a yellow, oily
liquid.
Uses
Different sources of media describe the Uses of 924-16-3 differently. You can refer to the following data:
1. N-Nitrosodi-n-butylamine is used primarily as a research chemical (IARC 1974). It has also been used as an intermediate in the synthesis of di-n-butylhydrazine.
2. N-Nitroso-di-n-butylamine is a pollutant that can be found in water network systems.
Reactivity Profile
N-NITROSODIBUTYLAMINE is a nitrated amine derivative. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Health Hazard
Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution.
Fire Hazard
Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
tumorigenic, and neoplastigenic data.
Moderately toxic by ingestion,
subcutaneous, and intraperitoneal routes.
Experimental teratogenic effects. Human
mutation data reported. When heated to
decomposition it emits toxic fumes of NOx.
See also NITROSAMINES.
Potential Exposure
N-Nitrosodi-n-butylamine is a carcinogenic
nitrosamine. It is found or used in various
manufacturing industries, including chemical, rubber,
metal, etc., and in research.
Carcinogenicity
N-Nitrosodi-n-butylamine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Incompatibilities
N-Nitrosodi-n-butylamine is light sensitive.
Nitrosamines can be strong oxidizers; contact with
these materials may cause fires or explosions. Keep away
from combustible materials, alkaline materials, strong
acids, strong bases. 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. Amines are a chemical base: will neutralize
acids to form salts plus water with an exothermic
reaction. May be incompatible with isocyanates, halogenated
organics, peroxides, phenols (acidic), epoxides, anhydrides,
and acid halides. Flammable gaseous hydrogen
is generated by amines in combination with strong reducing
agents such as hydrides, nitrides, alkali metals, and
sulfides.
Check Digit Verification of cas no
The CAS Registry Mumber 924-16-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 4 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 924-16:
(5*9)+(4*2)+(3*4)+(2*1)+(1*6)=73
73 % 10 = 3
So 924-16-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H18N2O/c1-3-5-7-10(9-11)8-6-4-2/h3-8H2,1-2H3
924-16-3Relevant articles and documents
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.
A combined experimental and DFT mechanistic study for the unexpected nitrosolysis of: N -hydroxymethyldialkylamines in fuming nitric acid
Zhang, Yu,Zou, Po,Han, Yingbin,Geng, Yongliang,Luo, Jun,Zhou, Baojing
, p. 19310 - 19316 (2018/05/31)
The reaction of dimorpholinomethane in fuming HNO3 was investigated. Interestingly, the major product was identified as N-nitrosomorpholine and a key intermediate N-hydroxymethylmorpholine was detected during the reaction by 1H-NMR tracking which indicates that the reaction proceeds via an unexpected nitrosolysis process. A plausible nitrosolysis mechanism for N-hydroxymethyldialkylamine in fuming nitric acid involving a HNO3 redox reaction is proposed, which is supported by both experimental results and density functional theory (DFT) calculations. The effects of ammonium nitrate and water on the nitrosolysis were studied using different ammonium salts as additives and varying water content, respectively. Observations show the key role of ammonium ions and a small amount of water in promoting the nitrosolysis reaction. Furthermore, DFT calculations reveal an essential point that ammonia, merged from the decomposition of the ammonium salts, acts as a Lewis base catalyst, and the hydroxymethyl group of the substrate participates in a hydrogen-bonding interaction with the NH3 and H2O molecules.
