(E)-1,2-Dimethoxy-3-(2-nitrovinyl)benzene

Base Information

• Chemical Name: (E)-1,2-Dimethoxy-3-(2-nitrovinyl)benzene
• CAS No.: 2815-67-0
• Molecular Formula: C10H11 N O4
• Molecular Weight: 209.202
• European Community (EC) Number: 621-793-5
• NSC Number: 184401,93685
• Nikkaji Number: J445.188K,J996.321I
• Wikidata: Q76305929
• Mol file: 2815-67-0.mol

Synonyms:37630-20-9;(E)-1,2-Dimethoxy-3-(2-nitrovinyl)benzene;2815-67-0;1,2-Dimethoxy-3-(2-nitrovinyl)benzene;1,2-dimethoxy-3-[(E)-2-nitroethenyl]benzene;TRANS-2 3-DIMETHOXY-beta-NITROSTYRENE;2,3-Dimethoxy-w-nitrostyrene;NSC93685;SCHEMBL1011167;2,3-dimethoxy-beta-nitrostyrene;beta-Nitro-2,3-dimethoxystyrene;HMS562G22;Styrene,3-dimethoxy-.beta.-nitro-;ANM100769;CCG-45139;MFCD00068082;NSC-93685;NSC184401;AKOS000277008;AKOS015913625;trans-2,3-Dimethoxy-beta-nitrostyrene;MS-9820;NSC-184401;CID 5380390;trans-2,3-Dimethoxy- beta -nitrostyrene;Benzene,1,2-dimethoxy-3-(2-nitroethenyl)-;CS-0246042;trans-2,3-Dimethoxy-beta-nitrostyrene, 97%;2,3-Dimethoxy-1-[(E)-2-nitroethenyl]benzene;EN300-315530;1,2-dimethoxy-3-[(1e)-2-nitroethenyl]benzene;EN300-1865309;CID 5380390, >=98% (HPLC);SR-01000634925;SR-01000634925-1;SR-01000634925-2

Chemical Property of (E)-1,2-Dimethoxy-3-(2-nitrovinyl)benzene

Chemical Property:

• Vapor Pressure: 0.000366mmHg at 25°C
• Melting Point: 80-84oC(lit.)
• Boiling Point: 328.3°Cat760mmHg
• Flash Point: 148.2°C
• PSA: 64.28000
• Density: 1.197g/cm³
• LogP: 2.47440
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 209.06880783
• Heavy Atom Count: 15
• Complexity: 236

Purity/Quality:

98%min ^*data from raw suppliers

1,2-Dimethoxy-3-(2-nitrovinyl)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36-50/53
• Safety Statements: 26-36-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1OC)C=C[N+](=O)[O-]
• Isomeric SMILES: COC1=CC=CC(=C1OC)/C=C/[N+](=O)[O-]

Technology Process of (E)-1,2-Dimethoxy-3-(2-nitrovinyl)benzene

There total 2 articles about (E)-1,2-Dimethoxy-3-(2-nitrovinyl)benzene 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: 94.0%

nitromethane (75-52-5) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 2,3-dimethoxynitrostyrene (2815-67-0)

Guidance literature:

With (2-hydroxyethyl)ammonium formate; at 20 ℃; for 1.3h; Ionic liquid;

DOI:10.1021/jo101696z

Reference yield:

1-(2,3-dimethoxyphenyl)-2-nitroethan-1-ol (76048-88-9) → 2-(2,3-dimethoxyphenyl)-1-nitroethane (14255-59-5) + 2,3-dimethoxynitrostyrene (2815-67-0)

Guidance literature:

With triethylsilane; trifluoroacetic acid; at 0 - 20 ℃; for 5h; Title compound not separated from byproducts.;

DOI:10.1016/j.tetlet.2007.07.098

Reference yield: 98.0%

2,3-dimethoxynitrostyrene (2815-67-0) + diethyl malonate (105-53-3) → (R)-ethyl 2-carboethoxy-4-nitro-3-(2,3-dimethoxyphenyl)butyrate + (S)-ethyl-2-carboethoxy-4-nitro-3-(2,3-dimethoxyphenyl)butyrate

Guidance literature:

With C₅₅H₄₃CuF₁₂N₇O₃S; triethylamine; In acetonitrile; at 20 ℃; enantioselective reaction;

DOI:10.1039/c5sc02144h

upstream raw materials:

nitromethane

2,3-dimethyoxybenzaldehyde

1-(2,3-dimethoxyphenyl)-2-nitroethan-1-ol

Downstream raw materials:

2,3-dimethoxyphenethylamine

7-[1-(2,3-dimethoxy-phenyl)-2-nitro-ethyl]-5H-[1,3]dioxolo[4,5-f]indole

7-[1-(2,3-dimethoxy-phenyl)-2-nitro-ethyl]-6-methyl-5H-[1,3]dioxolo[4,5-f]indole

2-(2,3-dimethoxyphenyl)-1-nitroethane

Refernces

• 1、 Pottie, Eline,Kupriyanova, Olga V.,Shevyrin, Vadim A.,Stove, Christophe P.. "Synthesis and Functional Characterization of 2-(2,5-Dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine (25H-NBF) Positional Isomers". . p. 1667 - 1673. Retrieved 2021/05/31.
• 2、 Alizadeh, Abdolhamid,Khodaei, Mohammad M.,Eshghi, Ali. "Ambiphilic dual activation role of a task-specific ionic liquid: 2-hydroxyethylammonium formate as a recyclable promoter and medium for the green synthesis of β-nitrostyrenes". scheme or table. p. 8295 - 8298. Retrieved 2011/03/17.