Benzenemethanol, alpha-methyl-3-nitro-, (alphaS)- (9CI)

Base Information

• Chemical Name: Benzenemethanol, alpha-methyl-3-nitro-, (alphaS)- (9CI)
• CAS No.: 103966-65-0
• Molecular Formula: C8H9 N O3
• Molecular Weight: 167.164
• Mol file: 103966-65-0.mol

Synonyms:Benzenemethanol,a-methyl-3-nitro-, (S)-;(S)-1-(3-Nitrophenyl)ethanol

Chemical Property of Benzenemethanol, alpha-methyl-3-nitro-, (alphaS)- (9CI)

Chemical Property:

• Melting Point: 84-85℃
• Boiling Point: 281℃
• Flash Point: 124℃
• PSA: 66.05000
• Density: 1.263
• LogP: 2.17130

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-1-(3-Nitrophenyl)ethanol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenemethanol, alpha-methyl-3-nitro-, (alphaS)- (9CI)

There total 20 articles about Benzenemethanol, alpha-methyl-3-nitro-, (alphaS)- (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3-Nitroacetophenone (121-89-1) → (S)-1-(3-nitrophenyl)ethan-1-ol (103966-65-0)

Guidance literature:

With (R)-2,2',6,6'-tetramethoxy-4,4'-bis(di-3,5-dimethylphenylphosphine)3,3'-bipyridine; phenylsilane; cobalt(II) diacetate tetrahydrate; In toluene; at 40 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Molecular sieve; Under air;

DOI:10.1039/c1ob05494e

Reference yield: 49.0%

vinyl acetate (108-05-4,9003-20-7) + 1-(3-nitrophenyl)ethanol (5400-78-2) → (R)-1-(3-nitrophenyl)ethyl acetate (103966-64-9) + (S)-1-(3-nitrophenyl)ethan-1-ol (103966-65-0)

Guidance literature:

With novozyme-435; In diethyl ether; at 20 ℃; for 24h; Resolution of racemate; Enzymatic reaction;

DOI:10.1039/d0nj04802j

Reference yield: 48.0%

1-(3-nitrophenyl)ethanol (5400-78-2) → 3-Nitroacetophenone (121-89-1) + (S)-1-(3-nitrophenyl)ethan-1-ol (103966-65-0)

Guidance literature:

With Arthrobacter atrocyaneus; In aq. phosphate buffer; at 32 ℃; for 72h; enantioselective reaction; Microbiological reaction;

DOI:10.1016/j.molcatb.2012.06.013

upstream raw materials:

1-(3-nitrophenyl)ethanol

(-)-(S)-N,N-dimethyl-1-phenylethylamine

acetic anhydride

3-Nitroacetophenone

Downstream raw materials:

(S)-1-(3-nitrophenyl)ethyl tosylate

Refernces

• 1、 Pa?a, Salih,Arslan, Nevin,Meri??, Nermin,Kayan, Cezmi,Bingül, Murat,Durap, Feyyaz,Aydemir, Murat. "Boron containing chiral Schiff bases: Synthesis and catalytic activity in asymmetric transfer hydrogenation (ATH) of ketones". . . Retrieved 2020.
• 2、 Sz?ll?si, Gy?rgy,Kolcsár, Vanessza Judit. "Highly Enantioselective Transfer Hydrogenation of Prochiral Ketones Using Ru(II)-Chitosan Catalyst in Aqueous Media". . p. 820 - 830. Retrieved 2019.
• 3、 ?olak, Nida Sezin,Kalay, Erbay,?ahin, Engin. "Asymmetric reduction of prochiral aromatic and hetero aromatic ketones using whole-cell of Lactobacillus senmaizukei biocatalyst". . p. 2305 - 2315. Retrieved 2021.
• 4、 Zhang, Xi-Chang,Wu, Yan,Yu, Feng,Wu, Fei-Fei,Wu, Jing,Chan, Albert S. C.. "Application of copper(II)-dipyridylphosphine catalyst in the asymmetric hydrosilylation of simple ketones in air". . p. 5888 - 5891. Retrieved 2009.
• 5、 Barros-Filho, Bartholomeu A.,Nunes, Fatima M.,de Oliveira, Maria da Conceicao F.,Lemos, Telma L.G.,de Mattos, Marcos C.,de Gonzalo, Gonzalo,Gotor-Fernandez, Vicente,Gotor, Vicente. "Bioreduction of prochiral ketones by growing cells of Lasiodiplodia theobromae: Discovery of a versatile biocatalyst for asymmetric synthesis". . p. 37 - 40. Retrieved 2010.
• 6、 Tsuji, Yutaka,Richard, John P.. "When does an intermediate become a transition state? Degenerate isomerization without competing racemization during solvolysis of (S)-1-(3-nitrophenyl)ethyl tosylate". . p. 17139 - 17145. Retrieved 2006.
• 7、 Kolcsár, Vanessza Judit,Sz?ll?si, Gy?rgy. "Mechanochemical, Water-Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst". . . Retrieved 2022/01/04.