25182-84-7

Usage

Definition

ChEBI: The nitro compound formed from propan-1-ol by nitration at C-3.

Safety Profile

A poison by ingestion,intraperitoneal, and subcutaneous routes. When heated todecomposition it emits toxic vapors of NOx.

InChI:InChI=1/C3H7NO3/c5-3-1-2-4(6)7/h5H,1-3H2

Upstream product

• 109-70-6 1.3-chlorobromopropane 
• 627-18-9 1-bromo-3-propanol 
• 58657-26-4 3-nitropropionaldehyde 
• 21461-49-4 3-acetoxy-1-nitropropane 
• 504-88-1 3-nitropropionic acid 
• 627-32-7 1-iodopropan-3-ol 
• 60-29-7 diethyl ether 

Downstream Products

• 295365-79-6 ethyl (Z)-2-(N-benzyloxycarbonylamino)-5-hydroxy-2-pentenoate 
• 482580-70-1 3-nitro-O-diphenylmethyl-1-propanol 
• 482580-71-2 3-nitro-O-triisopropylsilyl-1-propanol 
• 357204-56-9 3-nitro-O-benzyl-1-propanol 
• 107833-76-1 2-(3-Nitropropoxy)-tetrahydropyran 
• 16694-52-3 3-chloro-1-nitropropane 
• 156-87-6 propan-1-ol-3-amine 

Relevant academic research and scientific papers

Synthesis of 3-nitropropanol homologues

Several high yielding routes to oxygenated nitropropanes have been developed that include a palladium catalyzed nitro allylation of allylic carbonates, nitration of brominated compounds and a nitro aldol condensation/hydrogenation sequence. Georg Thieme Verlag Stuttgart.

Synthesis of Novel Polynitrodiols

The synthesis of a number of polynitroalkanediols of widely varying structure is reported.Several of the synthesis methods described constitute novel variations or improvements of known reactions: some polynitroaliphatic carboxylic acids were found to undergo the Schmidt reaction only in triflic acid as reaction medium; 3-nitropropyl acetate was advantageously prepared by a variation of the Kornblum reaction with aqueous Me2SO as solvent; 3,3-dinitropropanol was obtained by an intramolecular variant of the alkaline nitration method.

Quinine-Based Trifunctional Organocatalyst for Tandem Aza-Henry Reaction-Cyclization: Asymmetric Synthesis of Spiroxindole-Pyrrolidine/Piperidines

A quinine-derived trifunctional sulphonamide catalyst has been developed for the effective asymmetric organocatalytic tandem aza-Henry reaction-cyclization of isatin-derived ketimines and nitroalkane-mesylates for the synthesis of spiro-pyrrolidine/piperidine-oxindoles. Demethylation of traditional bifunctional catalyst to incorporate an additional hydrogen bonding C6′-OH group plays the key role toward remarkable enantioselectivity.

Catalytic Asymmetric Synthesis of Isoxazolines from Silyl Nitronates

1,3-Dipolar cycloadditions of triisopropylsilyl nitronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%. (Chemical Equation Presented).

Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine

The formation of amides and peptides often necessitates powerful yet mild reagent systems. The reagents used, however, are often expensive and highly elaborate. New atom-economical and practical methods that achieve such goals are highly desirable. Ideally, the methods should start with substrates that are readily available in both chiral and non-chiral forms and utilize cheap reagents that are compatible with a wide variety of functional groups, steric encumberance, and epimerizable stereocenters. A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2CO3 under O2. Contrary to expectations, a 1:1 halogen-bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form α-iodo nitroalkanes as precursors to the amides.

Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II

In our continued efforts to develop α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists as novel antidepressants having a unique mechanism of action, structure-activity relationship (SAR) exploration of certain isoxazolylpyridine ethers is presented. In particular, modifications to both the azetidine ring present in the starting structure 4 and its metabolically liable hydroxyl side chain substituent have been explored to improve compound druggability. The pharmacological characterization of all new compounds has been carried out using [3H]epibatidine binding studies together with functional assays based on 86Rb+ ion flux measurements. We found that the deletion of the metabolically liable hydroxyl group or its replacement by a fluoromethyl group not only maintained potency and selectivity but also resulted in compounds showing antidepressant-like properties in the mouse forced swim test. These isoxazolylpyridine ethers appear to represent promising lead candidates in the design of innovative chemical tools containing reporter groups for imaging purposes and of possible therapeutics.

Reactions of hydroxylated sodium nitronates with acetic anhydride/pyridine

Reactions with Ac2O/Py of sodium nitronate salts derived from primary or secondary nitroalkanes bearing hydroxyl groups at γ or more remote positions have been studied. In all cases, the results could be explained through an acetic nitronic anhydride intermediate, whose evolution depends on conformational factors, and also on the type of the hydroxyl group.

A new and convenient method for the synthesis of dehydroamino acids starting from ethyl N-Boc- and N-Z-α-tosylglycinates and various nitro compounds

Ethyl N-Boc- and N-Z-α-tosylglycinates, which were readily available from t-butyl or benzyl carbamate, ethyl glyoxylate, and sodium p- toluenesulfinate in formic acid, were reacted with a variety of nitro compounds in the presence of a base to afford the corresponding α,β- didehydroamino acid derivatives in good yields. Eventually, it was found that the (Z)-isomer was predominantly formed in the present method.

Regioselective synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates from benzyl isocyanoacetate

A general synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates was developed based on the reaction of β-nitroacetates with benzyl isocyanoacetate. The advantage of this route over other pyrrole syntheses was the regiochemical control of the substitution pattern on the pyrrole ring.

3-Nitropropanal and 3-Nitropropanol: Preparation of the Parent Compounds and Derivatives

3-Nitropropanal has been prepared for the first time by 1,4-nitrite addition to acrolein.Several acetals of 3-nitropropanal are described, as well as 3-nitropropanol and some of its ethers. 3-Nitropropanol has been obtained by borane-dimethyl sulfide reduction of both 3-nitropropanal and 3-nitropropanoic acid.These reactions make available a variety of nitro compounds known as, or expected to become, highly useful and versatile building blocks for organic syntheses.