85290-51-3

Basic information

• Product Name: Benzenepropanol, a-(nitromethyl)-
• Synonyms: (S)-1-nitro-4-phenyl-2-butanol;(S)-(-)-1-nitro-4-phenylbutan-2-ol;(S)-2-Hydroxy-1-nitro-4-phenylbutane;(S)-1-nitro-4-phenyl-2-nitrobutanol;(S)-1-nitro-4-phenylbutan-2-ol;(S)-(-)-1-nitro-4-phenylbutanol
• CAS NO: 85290-51-3
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• Mol File: 85290-51-3.mol

Chemical Properties

• Boiling Point: 359.2±35.0 °C(Predicted)
• Density: 1.176±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzenepropanol, a-(nitromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanol, a-(nitromethyl)-(85290-51-3)
• EPA Substance Registry System: Benzenepropanol, a-(nitromethyl)-(85290-51-3)

Safety Data

• Hazardous Substances Data: 85290-51-3(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 75-52-5 nitromethane 
• 108-30-5 succinic acid anhydride 
• 141377-53-9 1-nitro-4-phenylbutan-2-ol 
• 108-05-4 vinyl acetate 
• 55628-83-6 1-(1H-imidazol-1-yl)-3-phenylpropan-1-one 
• 501-52-0 3-Phenylpropionic acid 
• 67333-73-7 1-nitro-4-phenylbutan-2-one 
• 66-99-9 β-naphthaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 51146-35-1 trimethylsilyl ester of aci-nitromethane 
• 563-70-2 bromonitromethane 
• 768-56-9 4-Phenylbut-1-ene 

Downstream Products

• 85290-51-3 (S)-1-nitro-4-phenyl-2-butanol 
• 85290-51-3 (R)-1-nitro-4-phenylbutan-2-ol 
• 80922-14-1 (E)-(4-nitrobut-3-enyl)benzene 
• 432042-89-2 tert-butyl (2S)-(2-hydroxy-4-phenylbutyl)carbamate 
• 68844-69-9 (2R)-2-Hydroxy-4-phenylbutyric acid methyl ester 
• 129990-77-8 (2S)-2-Hydroxy-4-phenylbutyric acid methyl ester 
• 1033598-98-9 (2S)-1-amino-4-phenylbutan-2-ol 
• 115016-95-0 (S)-2-hydroxy-4-phenylbutanoic acid 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 1243250-51-2 1-acetamido-4-phenylbutan-2-yl acetate 

Relevant articles and documents

Application of asymmetric Henry reaction by copper(II) complexes containing (R,R)-1,2-diaminocyclohexane with naphthyl and thiophenyl substituents

A series of Cu(II) complexes containing C1-symmetric thiophene derivatives of (1R,2R)-N1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine, namely L1, L2 and L3 were synthesized and characterized. These complexes h

Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions

We have developed a practical, general protocol for denitration of readily available α-nitroketones with sulfur and amines to access a broad range of α-ketothioamides under mild conditions. Such a reaction proceeds under metal-, oxidant-, and catalyst-free conditions to provide synthetically useful α-ketothioamides. Furthermore, the mild reaction conditions tolerate a wide range of substrates especially for the synthesis of aliphatic α-ketothioamides which are rarely reported.

An efficient synthetic approach towards a single diastereomer of (2R,3R)-N 2,N 3-bis((S)-1-phenylethyl)butane-2,3-diamine via metalation and demetalation

Abstract: A facile synthetic approach has been adopted towards the synthesis of (2R,3R)-N2,N3-bis((S)-1-phenylethyl)butane-2,3-diamine via demetalation of its dichloro Zn(II) complex, which itself was separated from a mixture of dias

Synthesis and structures of copper complexes bearing unsymmetric derivatives of (R,R)-1,2-diaminocyclohexane: An efficient catalyst for asymmetric Henry reaction

A series of Cu (II) complexes bearing asymmetric derivatives of (R,R)-1,2-diaminocyclohexane were synthesised and characterised. The X-ray structures of the complexes showed distorted square planar geometry. The catalytic activities of in situ-generated c

Microwave-assisted synthesis of urea-containing zirconium metal-organic frameworks for heterogeneous catalysis of Henry reactions

Here we report the facile preparation of a urea-containing UiO-68 isoreticular zirconium metal-organic framework (MOF) with mixed dicarboxylate struts by utilizing a microwave-assisted heating method. It can work as an efficient hydrogen-bond-donating heterogeneous catalyst for Henry reactions of benzaldehydes and nitroalkanes. This mixed strut MOF exhibits improved catalytic activity compared to the pure urea-functionalized linker based analogue.

Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones

We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.

Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.

Base-catalyzed reactions enhanced by solid acids: Amine-catalyzed nitroaldol (Henry) reactions enhanced by silica gel or mesoporous silica SBA-15

The reactions of various aldehydes with CH3NO2 catalyzed by Et3N, n-C6H13NH2, and Me2N(CH2)2NH2 were accelerated by the addition of silica gel to give aromatic (aliphatic) β-nitroalcohols, aromatic nitroalkenes, and aromatic 1,3-dinitroalkanes, respectively. Mesoporous silica SBA-15 showed higher activity than silica gel for the synthesis of aromatic nitroalkenes by the reactions of the corresponding aldehydes with CH3NO2 catalyzed by n-C6H13NH2.

Double bond formation based on nitroaldol reaction and radical elimination: A prototype segment connection method for the total synthesis of nigricanoside A dimethyl ester

During the course of our studies toward the total synthesis of nigricanoside A dimethyl ester, a prototype method for the connection of the left- and right-half segments at the C9′–C10′ double bond was developed using a model system. The method was based

The synthesis of chiral tridentate ligands from L-proline and their application in the copper(II)-catalyzed enantioselective Henry reaction

A series of chiral tridentate ligands derived from readily available enantiopure L-proline were designed and synthesized. The ligands together with Cu(OAc)2 were successfully used in asymmetric Henry reactions. Various structurally divergent aldehydes and nitromethane were converted into versatile β-nitro alcohols in MeOH at room temperature with very good yields (up to 85%) and enantioselectivities (up to 86%).