1-(Benzo[D][1,3]dioxol-6-YL)-2-nitroethanol

Base Information

• Chemical Name: 1-(Benzo[D][1,3]dioxol-6-YL)-2-nitroethanol
• CAS No.: 40288-64-0
• Molecular Formula: C9H9NO5
• Molecular Weight: 211.174
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID80521869
• Nikkaji Number: J2.499.820G
• Mol file: 40288-64-0.mol

Synonyms:40288-64-0;1-(BENZO[D][1,3]DIOXOL-6-YL)-2-NITROETHANOL;1-(Benzo[d][1,3]dioxol-5-yl)-2-nitroethanol;1-(1,3-benzodioxol-5-yl)-2-nitroethanol;SCHEMBL5522615;DTXSID80521869;AB3053;MFCD00247460;1-(2H-1,3-Benzodioxol-5-yl)-2-nitroethan-1-ol

Chemical Property of 1-(Benzo[D][1,3]dioxol-6-YL)-2-nitroethanol

Chemical Property:

• PSA: 84.51000
• LogP: 1.24860
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 211.04807239
• Heavy Atom Count: 15
• Complexity: 241

Purity/Quality:

1-(Benzo[d][1,3]dioxol-5-yl)-2-nitroethanol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C(C[N+](=O)[O-])O

Technology Process of 1-(Benzo[D][1,3]dioxol-6-YL)-2-nitroethanol

There total 4 articles about 1-(Benzo[D][1,3]dioxol-6-YL)-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: 88.0%

piperonal (120-57-0,30024-74-9) + nitromethane (75-52-5) → 1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethanol (40288-64-0)

Guidance literature:

With polystyryl-diphenylphosphine-ethyl acrylate complex; In neat (no solvent); at 20 ℃; for 4h; Green chemistry;

DOI:10.1139/cjc-2012-0164

Reference yield: 31.3%

piperonal (120-57-0,30024-74-9) + nitromethane (75-52-5) → 5-((E)-2-nitroethenyl)-1,3-benzodioxole (1485-00-3,22568-48-5) + 1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethanol (40288-64-0)

Guidance literature:

With CaO modified benzyl bromide; at 102 ℃; for 5h;

DOI:10.1007/s11164-012-0875-4

Reference yield:

5-(2-nitrovinyl)benzo[1,3]dioxole (1485-00-3) → 1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethanol (40288-64-0)

Guidance literature:

With hydrogenchloride; sulfuric acid-d2; In methanol; water-d2; at 25 ℃; Rate constant; var. pH or pD, var. buffer, var. molarity, solv. H₂O or HDO; isotope effect (KSIE);

DOI:10.1021/jo00167a026

upstream raw materials:

piperonal

nitromethane

5-(2-nitrovinyl)benzo[1,3]dioxole

Downstream raw materials:

2-amino-1-benzo[1,3]dioxol-5-yl-ethanol; hydrochloride

1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenyloxy]-1-(3,4-methylenedioxyphenyl)-2-nitro-1-propanol

1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenyloxy]-1-(3,4-methylenedioxyphenyl)-2-nitroethane

3-cinnamyloxy-3-(3,4-methylenedioxyphenyl)-2-nitro-1-propanol

Refernces

• 1、 Otevrel, Jan,Bobal, Pavel. "Biphenyl-Based Bis(thiourea) Organocatalyst for Asymmetric and syn -Selective Henry Reaction". supporting information. p. 593 - 603. Retrieved 2017/01/25.
• 2、 Surneni, Naresh,Barua, Nabin C.,Saikia, Bishwajit. "Application of natural feedstock extract: The Henry reaction". supporting information. p. 2814 - 2817. Retrieved 2016/06/09.