(1R)-1-(2-methoxyphenyl)-2-nitroethanol

Base Information

• Chemical Name: (1R)-1-(2-methoxyphenyl)-2-nitroethanol
• CAS No.: 610758-06-0
• Molecular Formula: C9H11NO4
• Molecular Weight: 197.191
• DSSTox Substance ID: DTXSID80460143
• Nikkaji Number: J1.963.081A
• Mol file: 610758-06-0.mol

Synonyms:610758-06-0;(1R)-1-(2-methoxyphenyl)-2-nitroethanol;Benzenemethanol, 2-methoxy-alpha-(nitromethyl)-, (alphaR)- (9CI);DTXSID80460143;Benzenemethanol, 2-methoxy-alpha-(nitromethyl)-, (alphaR)-(9CI)

Chemical Property of (1R)-1-(2-methoxyphenyl)-2-nitroethanol

Chemical Property:

• PSA: 75.28000
• LogP: 1.52850
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 197.06880783
• Heavy Atom Count: 14
• Complexity: 192

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1C(C[N+](=O)[O-])O
• Isomeric SMILES: COC1=CC=CC=C1[C@H](C[N+](=O)[O-])O

Technology Process of (1R)-1-(2-methoxyphenyl)-2-nitroethanol

There total 9 articles about (1R)-1-(2-methoxyphenyl)-2-nitroethanol 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%

nitromethane (75-52-5) + ortho-anisaldehyde (135-02-4) → (R)-1-(2-methoxyphenyl)-2-nitroethan-1-ol (610758-06-0)

Guidance literature:

With 4-methyl-N-[(1R)-2-{[(1S,2S)-2-{[(2R)-2-(4-methylbenzenesulfonamido)-2-phenylethyl]amino}-1,2-diphenylethy]amino}-1-phenylethyl]benzene-1-sulfonamido; copper(II) acetate monohydrate; In ethanol; at 20 ℃; for 96h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201000964

Reference yield: 77.0%

nitromethane (75-52-5) + ortho-anisaldehyde (135-02-4) → (1S)-1-(2-methoxyphenyl)-2-nitroethanol + (R)-1-(2-methoxyphenyl)-2-nitroethan-1-ol (610758-06-0)

Guidance literature:

nitromethane; With copper(II) acetate monohydrate; N¹-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)-N²-((2R,3R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)ethane-1,2-diamine; In propan-1-ol; dichloromethane; at 22 ℃; for 6.5h; Inert atmosphere;

ortho-anisaldehyde; In propan-1-ol; dichloromethane; at 22 ℃; for 2h; Reagent/catalyst; Inert atmosphere;

DOI:10.1039/c4ra00193a

Reference yield: 75.0%

1-(2-methoxyphenyl)-2-nitroethan-1-one (46270-50-2) → (R)-1-(2-methoxyphenyl)-2-nitroethan-1-ol (610758-06-0)

Guidance literature:

With formic acid; {Cp*Ir[(R,R)-Me-CF₃-DPEN](H₂O)}(SO₄); In methanol; water; at 20 - 70 ℃; Product distribution / selectivity;

upstream raw materials:

nitromethane

ortho-anisaldehyde

1-(2-methoxyphenyl)-2-nitroethan-1-one

2-Methoxybenzoic acid

Downstream raw materials:

(R)-2-Amino-1-(2-methoxy-phenyl)-ethanol