4-CHLOROBENZYLIDENEMALONONITRILE

Base Information

• Chemical Name: 4-CHLOROBENZYLIDENEMALONONITRILE
• CAS No.: 1867-38-5
• Molecular Formula: C10H5 Cl N2
• Molecular Weight: 188.616
• Hs Code.: 2926909090
• European Community (EC) Number: 622-481-1
• NSC Number: 637330,492
• UNII: DNV4NFK9SM
• DSSTox Substance ID: DTXSID6075148
• Nikkaji Number: J305.967G
• ChEMBL ID: CHEMBL4580653
• Mol file: 1867-38-5.mol

Synonyms:Malononitrile,(p-chlorobenzylidene)- (6CI,7CI,8CI); Propanedinitrile,[(4-chlorophenyl)methylene]- (9CI); (4-Chlorobenzylidene)malononitrile;(p-Chlorobenzylidene)malononitrile; 1-Chloro-4-(2,2-dicyanoethenyl)benzene;2-(4-Chlorobenzylidene)malononitrile; 2-(4-Chlorophenyl)-1,1-dicyanoethene;2-(p-Chlorophenyl)-1,1-dicyanoethylene; 2-[(4-Chlorophenyl)methylene]malononitrile;3-(4-Chlorophenyl)-2-cyanopropenenitrile;4-(Chlorophenyl)methylidenemalononitrile; 4-Chlorobenzalmalononitrile;4-Chlorobenzylidenemalonodinitrile; NSC 492; NSC 637330;[(4-Chlorophenyl)methylene]propanedinitrile

Chemical Property of 4-CHLOROBENZYLIDENEMALONONITRILE

Chemical Property:

• Vapor Pressure: 0.00012mmHg at 25°C
• Boiling Point: 335.4°Cat760mmHg
• Flash Point: 150.4°C
• PSA: 47.58000
• Density: 1.296g/cm³
• LogP: 2.77056
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 188.0141259
• Heavy Atom Count: 13
• Complexity: 275

Purity/Quality:

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

(4-chlorobenzylidene)malononitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=C(C#N)C#N)Cl

Technology Process of 4-CHLOROBENZYLIDENEMALONONITRILE

There total 28 articles about 4-CHLOROBENZYLIDENEMALONONITRILE 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: 100.0%

4-chlorobenzaldehyde (104-88-1) + malononitrile (109-77-3) → 4-chlorobenzylidenemalonodinitrile (1867-38-5)

Guidance literature:

at 150 ℃; for 1h;

DOI:10.1016/S0040-4020(03)00554-4

Reference yield: 97.0%

4-chlorobenzaldehyde dimethyl acetal (3395-81-1) + malononitrile (109-77-3) → 4-chlorobenzylidenemalonodinitrile (1867-38-5)

Guidance literature:

With water; In toluene; at 90 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c8nj01934g

Reference yield: 80.0%

N-(4-chlorobenzylidene)aniline (2362-79-0) + malononitrile (109-77-3) → 4-chlorobenzylidenemalonodinitrile (1867-38-5)

Guidance literature:

With Amberlite IRA-400(OH^-); In ethanol; for 4.5h; Heating;

DOI:10.1039/a800951a

upstream raw materials:

4-chlorobenzaldehyde

malononitrile

aminomethylene-malononitrile

dicyanomethylene-O,O-diethyl phosphorane

Downstream raw materials:

2-(4-chlorophenyl)-1,1,2-tricyanoethane

But-2-enyl-(4-chlor-benzyl)-but-2-enyl-malononitril

C₂₂H₃₂ClN₂P

4-chlorobenzylmalononitrile

Refernces

Anticancer and radio-sensitizing evaluation of some new thiazolopyrane and thiazolopyranopyrimidine derivatives bearing a sulfonamide moiety

10.1016/j.ejmech.2011.08.026

The research aimed to synthesize and evaluate the anticancer and radiosensitizing properties of novel thiazolo[4,5-b]pyrane and thiazolo[4,5-b]pyrano[2,3-d]pyrimidine derivatives containing a sulfonamide group. The study was motivated by the known anticancer activities of sulfonamide compounds, particularly through the inhibition of carbonic anhydrase isozymes. Key chemicals used included 4-(4-oxo-4,5-dihydrothiazol-2ylamino)benzenesulfonamide (3) as a starting material, and various reagents such as 2-(4-chlorobenzylidene)malononitrile, formic acid, acetic anhydride, and aromatic aldehydes to synthesize the target compounds. The newly synthesized compounds were tested for their in vitro anticancer activity against the human breast cancer cell line (MCF7), with several showing significant cytotoxic activity compared to the reference drug doxorubicin. Notably, compounds 5, 6, 10, and 12 exhibited higher cytotoxic activities than doxorubicin. Doxorubicin is used as a reference drug to compare the anticancer activity of the newly synthesized thiazolopyrane and thiazolopyranopyrimidine derivatives. Doxorubicin is a well-known and widely used anticancer agent, particularly effective against various types of cancer, including breast cancer. These compounds were further evaluated for their ability to enhance the cell-killing effect of gamma radiation, with compound 12 showing a synergistic decrease in IC50 value when combined with radiation. The study concluded that these new compounds not only possess significant anticancer activity but also have the potential to sensitize cancer cells to ionizing radiation, suggesting their potential use in combination therapies for cancer treatment.