1-Chloro-2,3-dimethoxy-5-[(E)-2-nitroethenyl]benzene

Base Information

• Chemical Name: 1-Chloro-2,3-dimethoxy-5-[(E)-2-nitroethenyl]benzene
• CAS No.: 871126-37-3
• Molecular Formula: C₁₀H₁₀ClNO₄
• Molecular Weight: 243.647
• Hs Code.: 2909309090
• European Community (EC) Number: 621-584-9
• DSSTox Substance ID: DTXSID20584559
• Wikidata: Q76511210
• Mol file: 871126-37-3.mol

Synonyms:871126-37-3;1-Chloro-2,3-dimethoxy-5-[(E)-2-nitroethenyl]benzene;trans-3-Chloro-4,5-dimethoxy-beta-nitrostyrene;DTXSID20584559;EN300-1966663;trans-3-Chloro-4,5-dimethoxy-beta-nitrostyrene, 97%;1-CHLORO-2,3-DIMETHOXY-5-(2-NITROETHENYL)BENZENE

Chemical Property of 1-Chloro-2,3-dimethoxy-5-[(E)-2-nitroethenyl]benzene

Chemical Property:

• Melting Point: 163-167 °C(lit.)
• PSA: 64.28000
• LogP: 3.12780
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 243.0298355
• Heavy Atom Count: 16
• Complexity: 266

Purity/Quality:

99% ^*data from raw suppliers

trans-3-Chloro-4,5-dimethoxy-β-nitrostyrene 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=CC(=C1)C=C[N+](=O)[O-])Cl)OC
• Isomeric SMILES: COC1=C(C(=CC(=C1)/C=C/[N+](=O)[O-])Cl)OC

Technology Process of 1-Chloro-2,3-dimethoxy-5-[(E)-2-nitroethenyl]benzene

There total 4 articles about 1-Chloro-2,3-dimethoxy-5-[(E)-2-nitroethenyl]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: 92.0%

nitromethane (75-52-5) + 5-chloroveratraldehyde (18268-68-3) → 5-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene (27164-13-2,871126-37-3)

Guidance literature:

With ammonium acetate; In acetic acid; at 90 - 100 ℃; for 1h; Molecular sieve;

DOI:10.1055/s-0034-1379481

Reference yield:

5-chlorovanillin (19463-48-0) → 5-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene (27164-13-2,871126-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 12 h / 20 °C

2: ammonium acetate / acetic acid / 1 h / 90 - 100 °C / Molecular sieve

With ammonium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; acetic acid; 2: |Henry Nitro Aldol Condensation;

DOI:10.1055/s-0034-1379481

Reference yield:

vanillin (121-33-5,8014-42-4) → 5-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene (27164-13-2,871126-37-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuryl dichloride / acetic acid / 2 h / 0 - 2 °C

2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 12 h / 20 °C

3: ammonium acetate / acetic acid / 1 h / 90 - 100 °C / Molecular sieve

With sulfuryl dichloride; ammonium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; acetic acid; 3: |Henry Nitro Aldol Condensation;

DOI:10.1055/s-0034-1379481

upstream raw materials:

nitromethane

5-chloroveratraldehyde

5-chlorovanillin

vanillin

Downstream raw materials:

2-(2-chloro-3,4-dimethoxyphenyl)ethylamine

2-chlorodopamine