N-Isopropylhydroxylamine
[CAS# 5080-22-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Hydroxylamine
• Name: N-Isopropylhydroxylamine
• Synonyms: N-propan-2-ylhydroxylamine
• Molecular Formula: C₃H₉NO
• Molecular Weight: 75.11
• CAS Registry Number: 5080-22-8
• EC Number: 225-791-1
• SMILES: CC(C)NO

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.411, Calc.^*
• Boiling Point: 104.9±23.0 ºC (760 mmHg), Calc.^*
• Flash Point: 44.5±13.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H312-H315-H319-H411
• Precautionary Statements: P264-P264+P265-P273-P280-P302+P352-P305+P351+P338-P317-P321-P332+P317-P337+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

N-isopropylhydroxylamine is an organic compound with the chemical formula C3H9NO. It belongs to the class of hydroxylamines, which are characterized by the presence of a nitrogen atom bound to a hydroxyl group (-OH) and an alkyl group. N-isopropylhydroxylamine is well known for its use in various chemical and industrial processes, primarily due to its reactive nature and ability to participate in a wide range of reactions, including those involving organic synthesis and catalysis.

The discovery of N-isopropylhydroxylamine was part of a larger study of the properties and applications of hydroxylamines. Hydroxylamines, in general, have been studied for their role in various chemical reactions, including those involving nitroso compounds, and for their ability to act as reducing agents. N-isopropylhydroxylamine was part of these extensive efforts, being synthesized for the first time and has since gained attention for its specific applications in synthetic and industrial chemistry.

One of the most important applications of N-isopropylhydroxylamine is in the field of organic synthesis. It is a key reagent in the preparation of nitroso compounds, which are intermediates in the production of various chemicals, including pharmaceuticals and agrochemicals. N-isopropylhydroxylamine is also used in the synthesis of other organic compounds where its ability to donate hydrogen atoms or act as a reducing agent is beneficial. This makes it a valuable tool in synthetic organic chemistry, especially in reactions that require selective reduction or the formation of specific intermediates.

In addition to its use in organic synthesis, N-isopropylhydroxylamine has been explored for its role in catalysis. It can act as a ligand in metal-catalyzed reactions, helping to promote the formation of coordination compounds, which can accelerate the reaction rate. This catalytic property has led to its use in a range of catalytic processes, including those involving the synthesis of fine chemicals and other specialty products. Its ability to stabilize metal ions and participate in catalytic cycles makes it a useful compound in a variety of industrial applications.

N-isopropylhydroxylamine has also gained interest in the field of environmental chemistry. Its reactivity allows it to participate in the removal of pollutants from wastewater or other waste streams. By acting as a reducing agent, it can help break down hazardous compounds, making it very useful in processes designed to mitigate pollution. The compound's ability to reduce certain metal and organic pollutants makes it a valuable agent in environmental remediation efforts.

While N-isopropylhydroxylamine has proven to be a versatile compound that can be used in a variety of applications, its safety and handling must be considered. Like many hydroxylamines, it is reactive and potentially hazardous, especially when exposed to strong oxidants or under certain environmental conditions. Therefore, it is imperative that proper safety procedures are followed when working with this compound to avoid any unwanted reactions or safety issues.

In summary, N-isopropylhydroxylamine is an important chemical with a variety of uses in both organic synthesis and industrial applications. Its unique properties, such as its ability to act as a reducing agent and its potential as a catalyst, make it a valuable tool in a variety of chemical processes. Ongoing research continues to explore its full range of applications, further enhancing its usefulness in various industries.

References

2008. Conformational analysis of N-isopropylbenzohydroxamic acids: crystal structure, DFT, and NMR studies. Structural Chemistry, 19(4).
DOI: 10.1007/s11224-008-9338-3

2008. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Central European Journal of Chemistry, 6(4).
DOI: 10.2478/s11532-008-0054-z

1996. Nω-Hydroxyamino-α-amino acids as a new class of very strong inhibitors of arginases. JBIC Journal of Biological Inorganic Chemistry, 1(1).
DOI: 10.1007/s007750050025