627-67-8 Usage
Description
3-methyl-1-nitrobutane, also known as a primary nitroalkane, is a chemical compound characterized by the presence of a nitro group at the 4th position of 2-methylbutane. It is a naturally occurring plant volatile found in the leaves of Oenothera biennis and serves as a plant metabolite. As a primary nitroalkane and a volatile organic compound, it possesses unique chemical properties and potential applications.
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
Check Digit Verification of cas no
The CAS Registry Mumber 627-67-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 7 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 627-67:
(5*6)+(4*2)+(3*7)+(2*6)+(1*7)=78
78 % 10 = 8
So 627-67-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3
627-67-8Relevant articles and documents
Crystallization Does It All: An Alternative Strategy for Stereoselective Aza-Henry Reaction
Mar?eková, Michaela,Ger?a, Peter,?oral, Michal,Moncol, Ján,Berke?, Du?an,Kolarovi?, Andrej,Jakubec, Pavol
supporting information, p. 4580 - 4584 (2019/06/17)
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
Chauhan, Pankaj,Kaur, Kirandeep,Bala, Neeraj,Kumar, Vikas,Chimni, Swapandeep Singh
experimental part, p. 304 - 309 (2011/05/02)
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
Zhang, Zhiguo,Schreiner, Peter R.
, p. 2559 - 2564 (2008/03/13)
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.
