4-Hydroxy-5-(3-dimethylaminopropenoyl)benzenesulfonic acid chloride

Base Information

• Chemical Name: 4-Hydroxy-5-(3-dimethylaminopropenoyl)benzenesulfonic acid chloride
• CAS No.: 135251-12-6
• Molecular Formula: C₁₁H₁₂ClNO₄S
• Molecular Weight: 289.74
• DSSTox Substance ID: DTXSID301133095
• Nikkaji Number: J418.431I
• Mol file: 135251-12-6.mol

Synonyms:DTXSID301133095;AKOS000130610;135251-12-6;4-Hydroxy-5-(3-dimethylaminopropenoyl)benzenesulfonic acid chloride;Benzenesulfonyl chloride, 3-[3-(dimethylamino)-1-oxo-2-propenyl]-4-hydroxy-, (E)-

Chemical Property of 4-Hydroxy-5-(3-dimethylaminopropenoyl)benzenesulfonic acid chloride

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 289.0175567
• Heavy Atom Count: 18
• Complexity: 427

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C=CC(=O)C1=C(C=CC(=C1)S(=O)(=O)Cl)O
• Isomeric SMILES: CN(C)/C=C/C(=O)C1=C(C=CC(=C1)S(=O)(=O)Cl)O

Technology Process of 4-Hydroxy-5-(3-dimethylaminopropenoyl)benzenesulfonic acid chloride

There total 1 articles about 4-Hydroxy-5-(3-dimethylaminopropenoyl)benzenesulfonic acid chloride 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: 33.0%

(E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (1776-08-5) → 4-Hydroxy-5-(3-dimethylamino-2-propenoyl)-benzolsulfonylchlorid (135251-12-6)

Guidance literature:

With chlorosulfonic acid; for 1h; Ambient temperature; other substrate;

DOI:10.1002/ardp.19913240614

Reference yield: 40.0%

methanol (67-56-1) + 4-Hydroxy-5-(3-dimethylamino-2-propenoyl)-benzolsulfonylchlorid (135251-12-6) → 4-Hydroxy-3-(3-dimethylamino-2-propenoyl)-benzolsulfonsaeuremethylester (135251-16-0)

Guidance literature:

With pyridine; for 0.25h; Heating;

DOI:10.1002/ardp.19913240614

Reference yield: 37.0%

4-Hydroxy-5-(3-dimethylamino-2-propenoyl)-benzolsulfonylchlorid (135251-12-6) → 5-chlorosulfonyl-2-hydroxybenzoic acid (17243-13-9)

Guidance literature:

With sulfuryl dichloride; for 0.166667h; Ambient temperature;

DOI:10.1002/ardp.19953280315

upstream raw materials:

(E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one

Downstream raw materials:

4-Hydroxy-3-(3-dimethylamino-2-propenoyl)-benzolsulfonsaeuremethylester

5-chlorosulfonyl-2-hydroxybenzoic acid

Refernces

• 1、 Lowe,Braden. "Reaction of aromatic enaminones with chlorosulfuric acid". . p. 385 - 387. Retrieved 2007/10/02.