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Usage

Uses

Used in Chemical Synthesis:
3-methyl-1-nitrobutane is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows for the formation of new chemical bonds and the creation of a wide range of products, making it a valuable component in the chemical industry.
Used in Flavor and Fragrance Industry:
3-methyl-1-nitrobutane is used as a flavoring agent and a fragrance ingredient due to its distinct aroma. Its volatile nature and unique scent profile make it suitable for use in the development of various fragrances and flavorings, enhancing the sensory experience of consumer products.
Used in Pest Management:
As a herbivore-induced plant volatile, 3-methyl-1-nitrobutane plays a role in plant defense mechanisms against herbivores. It can be used in pest management strategies to deter or repel herbivores, protecting crops and plants from damage and contributing to sustainable agriculture practices.
Used in Environmental Monitoring:
3-methyl-1-nitrobutane, being a volatile organic compound, can be used as a biomarker for environmental monitoring. Its presence in the atmosphere can provide insights into the health of ecosystems and the presence of specific plant species, aiding in the assessment of environmental conditions and changes.

Preparation

Synthesis of 3-methyl-1-nitrobutane: Isopentyl bromide (120.84 g, 0.80 mol) was added dropwise to a mechanical stirred solution of sodium nitrite (110.39g, 1.60 mol) in DMF (500 mL) at 0°C. The reaction mixture was mechanically stirred overnight at room temperature. Water (1 L) was added to the mixture. The mixture was extracted with pet. ether (4 x 150 mL). The combined organic phases were washed with water (2 x 150 mL). The organic phase was dried with Na2SO4 then the solvent was evaporated under reduced pressure. Distillation under vacuum gave 30.2g (32%) of the colorless nitroalkane 3-methyl-1-nitrobutane (b.p. 58 - 60°C 21 mmHg)Not visible on TLC IR (neat) ν 2962, 1549, 1470, 1434, 1434, 1381, 1211, 1133, 851 cm-1 . 1H NMR (500 MHz, CDCl3) a 0.96 (d, J = 6.7 Hz, 6 H), 1.69 (h, J = 6.7Hz, 1 H), 1.91 (q, J = 7.2 Hz, 2 H), 4.41 (t, J = 7.3 Hz, 2 H). 13C NMR (125 MHz, CDCl3) a = 21.9, 25.5, 35.9, 74.2

InChI:InChI=1/C5H11NO2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3

Upstream product

• 541-28-6 isopentyl iodide 
• 107-82-4 i-pentyl bromide 
• 110-46-3 isopentyl nitrite 
• 626-90-4 isovaleraldoxime 
• 78-78-4 methylbutane 
• 27675-38-3 (E)-3-methyl-1-nitro-but-1-ene 
• 33972-66-6 3-methyl-1-nitro-but-1-ene 

Downstream Products

• 858858-73-8 (1RS,2SR)-2-Amino-4-methyl-1-phenylpentan-1-ol 
• 128114-53-4 8-Phenylmenthyl (2S,3R)-5-Methyl-3-nitro-2-((triethylsilyl)oxy)hexanoate 
• 128162-89-0 8-Phenylmenthyl (2R,3S)-2-Hydroxy-5-methyl-3-nitro-hexanoate 
• 128162-88-9 8-Phenylmenthyl (2S,3S)-2-Hydroxy-5-methyl-3-nitro-hexanoate 
• 128114-52-3 8-Phenylmenthyl (2S,3R)-2-Hydroxy-5-methyl-3-nitro-hexanoate 
• 113719-03-2 <2,4,6-tris(1,1-dimethylethyl)phenyl>-1-nitro-1-cyclopropancarboxylat 
• 541-23-1 isoamylamine hydrochloride 
• 31400-40-5 1,2,3,4-Tetrabromo-5-(3-methyl-butoxy)-benzene 
• 625-28-5 Isovaleronitrile 
• 412021-26-2 (1R,2R)-3-Methyl-2-nitromethyl-1-phenyl-butane-1-sulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 765923-83-9 (S)-1-[(R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-yl]-4-methyl-(S)-2-nitropentan-1-ol 
• 1344879-70-4 C₁₂H₁₅NO₂ 

Relevant academic research and scientific papers

Crystallization Does It All: An Alternative Strategy for Stereoselective Aza-Henry Reaction

An efficient and experimentally straightforward method for the stereoselective synthesis of a variety of β-nitro-α-amino carboxylic acids via aza-Henry (nitro-Mannich) reaction of aldimines is disclosed, yielding either anti- or a rarely reported syn-configuration. The reaction operates directly on free glyoxylic acid and generates imine species in situ. Crystallization-controlled diastereoselectivity enables isolation of the target compounds in high enantio- and diastereomeric purities by a simple filtration.

Functional-group tolerance in frustrated lewis pairs: hydrogenation of nitroolefins and acrylates

Weak Lewis acid for high nucleophilicity: Hydridoborate derived from B(2,6-F2C6H3)3 shows significant hydride character. Solid-state and solution structure analysis revealed a dihydrogen-bonded aggregate. The new frustrated Lewis pair was applied in the hydrogenation of nitroolefins and acrylates (see scheme; EWG=electron- withdrawing group). The decreased Lewis acidity provides higher reactivity and functional-group tolerance. Copyright

Catalyst-free and solventless Hantzsch ester mediated reduction of nitroolefins at elevated temperature

A catalyst-free and solventless protocol for the reduction of nitroolefins to the corresponding nitroalkanes at 100°C has been developed. Various nitroalkenes have been reduced in good to excellent yield with short reaction times.

3-(2-Aminocarbonylphenyl)propanoic acid analogs as potent and selective EP3 receptor antagonists. Part 1: Discovery and exploration of the carboxyamide side chain

A series of 3-(2-aminocarbonyl-4-phenoxymethylphenyl)propanoic acid analogs were synthesized and evaluated for their EP3 antagonist activity in the presence of additive serum albumin. Several compounds were biologically evaluated for their in vivo efficacy with respect to the PGE2-induced uterine contraction in pregnant rats as well as their pharmacokinetics. The discovery process of these potent and selective EP3 antagonists and their structure activity relationship are also presented.

Organocatalytic biomimetic reduction of conjugated nitroalkenes

A thiourea-catalyzed biomimetic reduction of conjugated nitroalkenes has been developed. Various aromatic and aliphatic conjugated nitroalkenes can be reduced to give the respective nitroalkanes with good yields under mild conditions. This protocol is not only practical, but may also provide insight into the mechanisms of redox transformations in biological systems. Georg Thieme Verlag Stuttgart.

3-Amino-2-hydroxy-propionaldehyde and 3-amino-1-hydroxypropan-2-one derivatives: New classes of aminopeptidase inhibitors

3-Amino-2-hydroxy-propionaldehydes [H2NCH(R)CHOHCHO with R = H, i-Bu, CH2Ph] were designed as metalloaminopeptidase inhibitors based on the metal active site chelation concept. These compounds were found to be micromolar inhibitors of aminopeptidase-M (AP-M, EC 3.4.11.2) with potencies similar to bestatin (K(i) = 3.5 μM). Notably, compound 5a (R = H) is a selective inhibitor of AP-M (K(i) = 7 μM) with respect to cytosolic leucine aminopeptidase (LAPc, EC 3.4.11.1) (K(i) = 385 μM). However, due to their easy oligomerization, these compounds are of low practical value. In contrast, the corresponding isomeric 3-amino-1-hydroxy-propan-2-one derivatives [H2NCH(R)COCH2OH with R = H, i-Bu, CH2Ph, i-Pr, CH2Biph] are well defined structures. These hydroxymethylketones also exhibit micromolar affinities on AP-M. Compound 6c (R = CH2Ph) was the most potent (K(i) = 1 μM). Selectivity studies of 6a (R = H) and 6b (R = i-Bu) show a preference for AP-M. Compound 6a is moderately active on AP-M (K(i) = 25 μM) and inactive on LAPc. This new class of inhibitors is proposed to bind as bidentates, analogous to hydroxamates.