20575-40-0

Usage

Uses

2-Nitro-3-pentanol (cas# 20575-40-0) is a compound useful in organic synthesis.

InChI:InChI=1/C5H11NO3/c1-3-5(7)4(2)6(8)9/h4-5,7H,3H2,1-2H3

Upstream product

• 79-24-3 Nitroethane 
• 123-38-6 propionaldehyde 

Downstream Products

• 13485-58-0 2-Nitro-3-pentanone 
• 152796-95-7 3-ethyl-4-methyl-2-(p-toluenesulfonyl)-1H-pyrrole 
• 250380-42-8 5-bromo-4-methyl-3-ethyl-2-tosyl-pyrrole 
• 152796-98-0 4-ethyl-3-methyl-5-(p-toluenesulfonyl)-1,5-dihydro-1H-pyrrolin-2-one 
• 5866-56-8 2-benzyloxycarbonyl-3-ethyl-4-methylpyrrole 
• 6065-19-6 2-nitro-2-pentene 
• 108895-19-8 1,4-bis<5-<2,8,12,18-tetraethyl-15-(2,5-dimethoxyphenyl)-3,7,13,17-tetramethylporphyrinyl>>benzene 
• 108869-80-3 1,3-bis<5-<2,8,12,18-tetraethyl-15-(2,5-dimethoxyphenyl)-3,7,13,17-tetramethylporphyrinyl>>benzene 
• 108869-78-9 bis(4-ethyl-3-methyl-2-pyrryl)(2,5-dimethoxyphenyl)methane 
• 131012-34-5 C₂₄H₃₂N₂O₃ 
• 108895-17-6 bis(4-ethyl-5-formyl-3-methyl-2-pyrryl)(2,5-dimethoxyphenyl)methane 
• 131012-35-6 bis(4-ethyl-5-formyl-3-methyl-2-pyrryl)(2,4,6-trimethoxyphenyl)methane 
• 131012-32-3 Bis(5-ethoxycarbonyl-4-ethyl-3-methyl-2-pyrryl)(2,5-dimethoxyphenyl)methan 
• 102586-95-8 1,3-bisbenzene 

Relevant academic research and scientific papers

Nanoporous lanthanide metal-organic frameworks as efficient heterogeneous catalysts for the Henry reaction

A series of self-assembled lanthanide coordination polymers formulated as [La(L1)2]n·1n(DMF)H·3n(DMF) (1), [Ce(L1)2]n·1n(DMF)H·2n(DMF) (2), [Sm(L1)2]n·1n(HCONH2)H·2n(HCONH2) (3), [La(L2)(HL2)(H2O)(DMF)2]n (4) and [Ce(L2)(HL2)(H2O)(DMF)2]n (5) [H2L1: 2-acetamidoterephthalic acid and H2L2: 2-benzamidoterephthalic acid] has been synthesized from the reactions of H2L1 or H2L2 with different lanthanide salts under hydrothermal conditions and characterized by elemental analysis, IR spectroscopy, X-ray single-crystal diffraction, powder X-ray diffraction, thermogravimetry and photoluminescence spectroscopy. X-ray diffraction analyses reveal that frameworks 1-3 have similar types of three-dimensional structures, composed of L12- ligands and trinuclear lanthanide nodes, in which two crystallographically independent lanthanide atoms are present. Frameworks 4 and 5 are isostructural, featuring a double chain-type one-dimensional coordination polymer which expands to 3D by means of H-bond interactions. These frameworks act as heterogeneous polymeric solid catalysts for the nitroaldol (Henry) reaction of different aldehydes with nitroalkanes, in water, and can be recycled without losing appreciable activity.

Synthesis of 2,2′-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines

Facile, versatile, and cost-effective synthetic routes for the preparation of a range of new 3-alkyl-, 4-alkyl-, 3,4-dialkyl-, and 3-halo-4-alkyl-2, 2′-bipyrrole-5-carboxaldehydes have been developed. These 2,2′-bipyrrole-5-carboxaldehydes offer interesting potential as building blocks for making bioactive natural and unnatural products, as demonstrated by the synthesis of B-ring functionalized prodiginines (PGs) and tambjamines.

Nitroaldol-reaction of aldehydes in the presence of non-activated Mg:Al 2:1 hydrotalcite; A possible new mechanism for the formation of 2-aryl-1,3-dinitropropanes

Commercially available, non-activated 2:1 Mg:Al hydrotalcite catalyzes the nitroaldol reaction between a variety of aromatic and aliphatic aldehydes and simple nitroalkanes such as nitromethane and nitroethane. A new mechanism is proposed for the formation of the 1,3-dinitropropanes. The threo/erythro diastereoselectivity of the nitroethane-adducts was determined by 1H NMR spectroscopy and was found to range from 50:50 to 70:30. The substituents of the aromatic aldehydes influenced the isomer ratio.

Method of producing organic compounds in presence of oxyethylene ether catalyst and in a solvent minimized environment

A process of producing organic compounds, such as acetaminophen, nitroalcohols and indoles, employs a catalyst system of an oxyethylene ether and a metal containing inorganic or organic reagent. The oxyethylene ether at least partially complexes the metal of the inorganic or organic reagent. As such, the reactions may be conducted neat. The processes are environmentally friendly and operationally simple.

Potassium Phosphate Catalyzed Nitroaldol Reaction

Potassium phosphate was found to catalyze condensation of nitroalkanes with various aliphatic and aromatic aldehydes to form nitroaldols in excellent yields in acetonitrile medium at room temperature.

Ionic liquid catalyzed Henry reactions

The 1,1,3,3-tetramethyl guanidine (TMG)-based ionic liquid was used as a recyclable catalyst for Henry reactions to produce 2-nitroalcohols. Good yields were obtained even after 15 reactions.

Synthesis of a 10-oxo-bilirubin: Effects of the oxo group on conformation, transhepatic transport, and glucuronidation

Bilirubin, the yellow pigment of jaundice, is a linear tetrapyrrole with a methylene group at its center, C(10), a position of crucial importance to its conformation and metabolism. The presence of the central methylene group allows the bilirubin to fold into an intramolecularly hydrogen-bonded conformation. This paper describes the first synthesis of a bilirubin analogue with an oxo group at C(10). The change from CH2 to C=O, from sp3 to sp2, is designed to stress the molecule at its hinge and relax its conformation. Such compounds have been suggested as potential oxidative metabolites of bilirubin in vivo. 10-Oxo-mesobilirubin-XIIIα (1) is a red crystalline solid, unlike its parent, mesobilirubin-XIIIα, which is a bright yellow solid. It is surprisingly polar, relative to the parent, yet it does not exhibit a significantly larger bicarbonate/chloroform partition coefficient. Like the parent, 1 appears to adopt an intramolecularly hydrogen-bonded ridge-tile-like conformation. In normal rats, 1 is metabolized to acylglucuronides, which are secreted into bile, but a portion of the administered dose is secreted into bile intact. In mutant rats (Gunn rats) lacking bilirubin glucuronyl transferase, 1 was excreted efficiently in bile in unchanged form, unlike the parent with a methylene group at C(10). Thus, introduction of the oxygen function at C(10) has little effect on hepatic uptake but a dramatic effect on canalicular secretion into bile.

Fast nitroaldol reaction using powdered KOH in dry media

β-Nitroalkanols are easily obtained within a few minutes, through the nitroaldol (Henry) reaction, catalyzed by a stoichiometric amount of powdered potassium hydroxide, in dry media. Satisfactory to excellent yields are obtained both with primary and seco

Potassium Exchanged Layered Zirconium Phosphate as Base Catalyst in the Synthesis of 2-Nitroalkanols

The synthesis of 2-nitroalkanols from nitroalkanes and aldehydes occurs efficiently, in mild conditions without solvent, when mediated by layered Zr(KOPO3)2.The reaction has been tested in the preparation of ten different nitroalkanols and the data obtain

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.