627-67-8

Basic information

• Product Name: 3-methyl-1-nitrobutane
• Synonyms: 3-methyl-1-nitrobutane;1-Nitro-3-methylbutane;4-Nitro-2-methylbutane
• CAS NO: 627-67-8
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 117.14634
• EINECS: 211-008-0
• Mol File: 627-67-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 97°C
• Boiling Point: 168.95°C (estimate)
• Flash Point: 46.1°C
• Appearance: /
• Density: 0.9458
• Vapor Pressure: 2.9mmHg at 25°C
• Refractive Index: 1.4153
• PKA: 8.65±0.29(Predicted)
• CAS DataBase Reference: 3-methyl-1-nitrobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-1-nitrobutane(627-67-8)
• EPA Substance Registry System: 3-methyl-1-nitrobutane(627-67-8)

Safety Data

• Hazardous Substances Data: 627-67-8(Hazardous Substances Data)

Usage

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

Definition

ChEBI: 3-methyl-1-nitrobutane is a primary nitroalkane that is 2-methylbutane substituted by a nitro group at position 4. It is a herbivore-induced plant volatile found in the leaves of Oenothera biennis. It has a role as a plant metabolite. It is a primary nitroalkane and a volatile organic compound.

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

Upstream product

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

Downstream Products

• 858858-73-8 (1RS,2SR)-2-Amino-4-methyl-1-phenylpentan-1-ol 
• 18869-43-7 DL-leucine methyl ester 
• 499131-29-2 (R,R)-2-(1-methoxysulfonyl-1-phenylmethyl)-3-methylbutyric acid ethyl ester 
• 765923-83-9 (S)-1-[(R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-yl]-4-methyl-(S)-2-nitropentan-1-ol 
• 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 
• 625-28-5 Isovaleronitrile 
• 31400-40-5 1,2,3,4-Tetrabromo-5-(3-methyl-butoxy)-benzene 
• 541-23-1 isoamylamine hydrochloride 
• 113719-03-2 <2,4,6-tris(1,1-dimethylethyl)phenyl>-1-nitro-1-cyclopropancarboxylat 
• 128162-89-0 8-Phenylmenthyl (2R,3S)-2-Hydroxy-5-methyl-3-nitro-hexanoate 

Relevant articles and documents

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.

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.

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.