3-Allylrhodanine

Base Information

• Chemical Name: 3-Allylrhodanine
• CAS No.: 1457-47-2
• Molecular Formula: C6H7NOS2
• Molecular Weight: 173.26
• Hs Code.: 29341000
• European Community (EC) Number: 215-941-4
• NSC Number: 43395
• DSSTox Substance ID: DTXSID60163140
• Nikkaji Number: J37.308G
• Wikidata: Q72437399
• Mol file: 1457-47-2.mol

Synonyms:3-Allylrhodanine;1457-47-2;Rhodanine, 3-allyl-;N-Allylrhodanine;Allyl-4-oxo-2-thioxothiazolidin;3-Allyl-2-thioxothiazolidin-4-one;4-Thiazolidinone, 3-(2-propenyl)-2-thioxo-;NSC43395;3-allyl-2-thioxo-thiazolidin-4-one;3-(prop-2-en-1-yl)-2-sulfanylidene-1,3-thiazolidin-4-one;3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one;EINECS 215-941-4;NSC 43395;3-Allyl-2-thioxo-1,3-thiazolidin-4-one;3-(prop-2-en-1-yl)-2-thioxo-1,3-thiazolidin-4-one;3-allyl rhodanine;3-Allylrhodanine, 99%;4-Thiazolidinone, 3-(2-propen-1-yl)-2-thioxo-;SCHEMBL181568;DTXSID60163140;3-Allyl-2-thioxo-4-thiazolidinone;BAA45747;BBL023052;MFCD00044700;NSC-43395;STL363690;AKOS000120446;NS-01424;CS-0214910;FT-0614897;EN300-20377;D88434;SR-01000396030;J-650280;SR-01000396030-1;Z104477926

Chemical Property of 3-Allylrhodanine

Chemical Property:

• Appearance/Colour: yellow crystals
• Vapor Pressure: 0.0238mmHg at 25°C
• Melting Point: 46-48 °C(lit.)
• Refractive Index: 1.651
• Boiling Point: 248.8 °C at 760 mmHg
• Flash Point: 104.3 °C
• PSA: 77.70000
• Density: 1.35g/cm³
• LogP: 0.97060
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 172.99690619
• Heavy Atom Count: 10
• Complexity: 190

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Allylrhodanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCN1C(=O)CSC1=S
• Uses: 3-Allylrhodanine exhibits anticonvulsive activity. An intermediate for the synthesis of useful sensitizers for silver halide photograph emissions.

Technology Process of 3-Allylrhodanine

There total 10 articles about 3-Allylrhodanine 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: 91.0%

carbon disulfide (75-15-0,12122-00-8) + 1-amino-2-propene (107-11-9,30551-89-4) + methyl N-(chloroacetyl)carbamate (13558-70-8) → 3-allylrhodanine (1457-47-2)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.3390/molecules25051138

Reference yield: 82.0%

carbon disulfide (75-15-0,12122-00-8) + sodium monochloroacetic acid (3926-62-3) + 1-amino-2-propene (107-11-9,30551-89-4) → 3-allylrhodanine (1457-47-2)

Guidance literature:

carbon disulfide; 1-amino-2-propene; With sodium hydroxide; In water; at 100 ℃; for 0.0833333h; Microwave irradiation;

sodium monochloroacetic acid; In water; at 40 - 100 ℃; for 0.0833333h; Microwave irradiation;

DOI:10.1007/s00044-016-1545-7

Reference yield: 77.0%

carbon disulfide (75-15-0,12122-00-8) + chloroacetic acid (79-11-8) + 1-amino-2-propene (107-11-9,30551-89-4) → 3-allylrhodanine (1457-47-2)

Guidance literature:

carbon disulfide; 1-amino-2-propene; With sodium hydroxide; In water; at 100 ℃; Microwave irradiation;

chloroacetic acid; In water; at 100 ℃; for 0.0833333h; Microwave irradiation;

With hydrogenchloride; In water; at 120 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.tetlet.2012.07.002

upstream raw materials:

mercaptoacetic acid

N-allyl isothiocyanate

thiocyanato-acetic acid

Methyl thioglycolate

Downstream raw materials:

3-Allyl-5-(6-methyl-pyrid-2-yl-methylen)-rhodanin

3-Allyl-5-(5-brom-indolyl-(3)-methylen)-rhodanin

3-Allyl-5-(3-iodbenzyliden)rhodanin

3-allyl-5-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylmethylene)-2-thioxo-thiazolidin-4-one

Refernces

• 1、 Ali Muhammad, Sulaiman,Ravi, Subban,Thangamani, Arumugam. "Synthesis and evaluation of some novel N-substituted rhodanines for their anticancer activity". . p. 994 - 1004. Retrieved 2016.
• 2、 Nitsche, Christoph,Schreier, Verena N.,Behnam, Mira A. M.,Kumar, Anil,Bartenschlager, Ralf,Klein, Christian D.. "Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture". . p. 8389 - 8403. Retrieved 2013/12/04.