32586-14-4

Usage

Uses

Used in Synthesis of Isotope-Labeled Compounds:
N-BUTYL-1,1-D2 ALCOHOL is used as a starting material for the synthesis of more complex isotope-labeled compounds. Its deuterium labeling allows for the incorporation of stable isotopes into organic molecules, which can be useful in various research and industrial applications.
Used in Chemical Reactions:
N-BUTYL-1,1-D2 ALCOHOL is used as a reactant in chemical reactions to produce deuterated products. The presence of deuterium can provide insights into reaction mechanisms and kinetics, as well as improve the stability and selectivity of certain reactions.
Used in Analytical Chemistry:
N-BUTYL-1,1-D2 ALCOHOL is used as an internal standard or a reference compound in analytical chemistry. Its deuterium labeling can help in the accurate quantification and identification of other compounds in complex mixtures.
Used in Pharmaceutical Industry:
N-BUTYL-1,1-D2 ALCOHOL is used as a building block in the synthesis of deuterated pharmaceutical compounds. Deuterium-labeled drugs can exhibit improved pharmacokinetic properties, such as enhanced stability, reduced metabolism, and increased bioavailability.
Used in Material Science:
N-BUTYL-1,1-D2 ALCOHOL can be used in the development of deuterated materials with unique properties. The incorporation of deuterium can lead to changes in the physical and chemical properties of materials, which can be beneficial in various applications, such as in the fields of polymers, coatings, and adhesives.

Upstream product

• 141-75-3 butyryl chloride 
• 107-92-6 butyric acid 
• 105-54-4 butanoic acid ethyl ester 
• 71-36-3 butan-1-ol 
• 27847-11-6 1,1-d2-n-butylamine 
• 64-19-7 acetic acid 
• 106-31-0 butanoic acid anhydride 
• 55538-85-7 acetic acid 1,1-dideuterio-butyl ester 
• 623-42-7 butanoic acid methyl ester 

Relevant academic research and scientific papers

NMR Spectroscopy of Organolithium Compounds, Part XVI. The Aggregation Behaviour of Butyllithium, Phenyllithium, and Lihtium Diisopropylamide in Dimethoxy- and Diethoxymethane

Keywords: Organolithium compounds, aggregation behavior, 6Li NMR, 13C NMR.The aggregation behaviour of butyllithium (BuLi), phenyllithium (PhLi), and lithium diisopropylamide (LDA) in dimethoxy- and diethoxymethane (methylal and ethylal, respectively) has been studied by NMR spectroscopy using the isotropic fingerprint method and 13C,6Li as well as 15N,6Li spin-spin coupling constants.In both solvents, LDA exists as a dimer, while BuLi forms a tetramer, PhLi forms a dimer in methylal, whereas two major aggregates exist in ethylal.Due to solvent viscosity at lower temperatures, their structure could not be determined.

Two-State Reactivity in Iron-Catalyzed Alkene Isomerization Confers σ-Base Resistance

A low-coordinate, high spin (S = 3/2) organometallic iron(I) complex is a catalyst for the isomerization of alkenes. A combination of experimental and computational mechanistic studies supports a mechanism in which alkene isomerization occurs by the allyl mechanism. Importantly, while substrate binding occurs on the S = 3/2 surface, oxidative addition to an η1-allyl intermediate only occurs on the S = 1/2 surface. Since this spin state change is only possible when the alkene substrate is bound, the catalyst has high immunity to typical σ-base poisons due to the antibonding interactions of the high spin state.

Regioselective deuteration of alcohols in D2O catalysed by homogeneous manganese and iron pincer complexes

We report a convenient and cost-effective protocol for the regioselective deuteration of primary and secondary alcohols using Earth abundant homogeneous first row transition metal pincer catalysts. D2O is utilized as both a deuterium source and a solvent, allowing for a benign inexpensive process. Depending on the metal selected (Mn or Fe), a high degree of deuterium incorporation was observed selectively either at the α and β position (Mn) or exclusively at the α position (Fe), for primary alcohols. This simple, efficient, and cost-effective protocol for alcohol C-H bond deuteration constitutes a powerful tool for the large scale synthesis of deuterated molecules.

Synthesis of sequentially deuterated 1-n-Butyl-3-methylimidazolium ionic liquids

Deuterium isotopologues of the ionic liquid (IL) 1-n-butyl-3- methylimidazolium chloride ([C4mim]Cl) sequentially labeled on the C-1″, C-1′, C-2′, C-3′, and C-4′ positions of the N-alkyl groups were prepared following a strategy that minimizes

Experimental and theoretical study of tunable 1,3-lithium shift of proparglie/allem lie species, transmetallation and Pd-catalyzed crosscoupling reactions

The highly selective tuning of the isomerization from 1-arylalka1,2-dien-l- yllithium to l-arylalka-1,2dien-3-yllithium has been realized in the deprotonation of 1-arylalk-l-yne (conditions A and B) and carbolithiation of l-arylbut-3-en-l-yne with alkyllithium (conditions C and D). Subsequent transmetallation and Pd-catalyzed Negishi coupling reactions afforded 1,1-diaryl or 1,3-diaryl alienes with high selectivity. Deuterium-labeling cross experiments indicated that an intermolecular lithiation process occurred in both 1,3-lithium shift conditions (conditions B and D). 1-Arylalka1,2-diene was confirmed experimentally to be the intermediate. A computational study at the B3LYP level for the isomerization indicated that the acidity of H at the 3-position is higher than that of the H at the 1-position of 1phenyl-l,2-butadiene. Under conditions B, (Pr2NH acts as a proton carrier to finish the 1,3-lithium shift. The overall activation barrier for the rate-determining step in the solvated models is ≈ 21.0 kcal mol-1, indicating that the isomerization is reasonable at room temperature. For the isomerization under conditions D, DFT calculations indicated that the addition of TMEDA (tetramethylethylenediamine) and HMPA (hexamethylphosphoramide) changes the global minimum of the system; among the possible mechanisms (P1-P5) considered, the mechanism catalyzed by dilithiated species (P5) is the most probable one. The overall activation barriers for isomerization in THF and TMEDA solvated models are 22.6 and 19.7 kcal mol-1, respectively, proving that the isomerization may proceed at RT in THF or at -78°C with TMEDA, due to the fact that the solvation of the additives may increase the concentration of 1-phenyl1,2-butadienyllithium monomer by a deaggregation effect.

Cryptoregiochemistry of a Brassica napus fatty acid desaturase (FAD3): A kinetic isotope effect study

α-Linolenic acid ((Z,Z,Z)-octadeca-9,12,15-trienoic acid) is biosynthesized by a series of regio- and stereoselective dehydrogenation reactions which are catalyzed by a set of enzymes known as fatty acid desaturases. As part of ongoing research into the mechanism of these remarkable catalysts, we have examined the cryptoregiochemistry (site of initial oxidation) of extraplastidial ω - 3 desaturation as it occurs in the commercially important plant Brassica napus (oilseed rape or canola). The individual deuterium kinetic isotope effects associated with the C-H bond cleavages at C-15 and C-16 of a thiaoleoyl analogue were measured using a convenient in vivo yeast expression system. Competition experiments using appropriately deuterium-labelled 7-thia substrates revealed a large kinetic isotope effect (KIE) (kH/kD = 7.5 ± 0.4) for the C-H bond-breaking step at C-15 while the C-H bond cleavage at C-16 was found to be insensitive to deuterium substitution (kH/kD = 1.0 ± 0.14). These results point to C-15 as the site of initial oxidation in ω - 3 desaturation since the first chemical step in this type of reaction is rupture of a strong, unactivated C-H bond - an energetically difficult process which typically exhibits a large KIE.

Site-selective deuterium labeling of the tetrabutylammonium cation

Four separate selectively deuterated samples of tetrabutylammonium iodide have been prepared in which each one of the four nonequivalent alkyl carbons is separately and fully deuterated. These samples were prepared for nuclear magnetic resonance (NMR) studies of the aggregation of ion pairs in low polarity solvents.

Intermediacy of ion neutral complexes in the fragmentation of short-chain dialkyl sulfides

The main fragmentation processes after electron ionization of butyl methyl and butyl ethyl sulfides are rationalized by the intermediacy of the ion neutral complex [RSH · methylcyclopropane](+·) as demonstrated by extensive labeling and collision activation studies.

Tritiated chiral alkanes as substrates for soluble methane monooxygenase from Methylococcus capsulatus (Bath): Probes for the mechanism of hydroxylation

The tritiated chiral alkanes (S)-[1-2H1, 1-3H]ethane, (R)-[1-2H1, 1-3H]ethane, (S)-[1-2H1, 1-3H]butane, (R)[1-2H1, 1-3H]but

Side-chain Effects on the Fragmentation Behaviour of Alkylthiophenes

The processes leading to the fragment ions formed from alkylthiophene molecule ions by benzylic cleavage without and with transfer of one hydrogen from the side-chain to the ring and the influence of additional methyl groups on the relative importance of these two fragmentation reactions were investigated.