2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde

Base Information

• Chemical Name: 2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde
• CAS No.: 83-18-1
• Deprecated CAS: 1989657-82-0
• Molecular Formula: C13H13 N O
• Molecular Weight: 199.252
• Hs Code.: 2933990090
• European Community (EC) Number: 201-458-6
• NSC Number: 68230
• UNII: PW8ELR8SUD
• DSSTox Substance ID: DTXSID2058887
• Nikkaji Number: J192.606C
• Wikidata: Q72471406
• ChEMBL ID: CHEMBL2113933
• Mol file: 83-18-1.mol

Synonyms:83-18-1;2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde;2,5-Dimethyl-1-Phenylpyrrole-3-Carboxaldehyde;2,5-dimethyl-1-phenylpyrrole-3-carbaldehyde;1H-Pyrrole-3-carboxaldehyde, 2,5-dimethyl-1-phenyl-;PW8ELR8SUD;EINECS 201-458-6;NSC 68230;NSC-68230;Pyrrole-3-carboxaldehyde, 2,5-dimethyl-1-phenyl-;NSC68230;2,5-dimethyl-1-phenyl-1H-Pyrrole-3-carboxaldehyde;UNII-PW8ELR8SUD;SCHEMBL645648;OSM-S-28;CHEMBL2113933;DTXSID2058887;MFCD00051494;STK297810;AKOS000113216;AM83083;AS-66693;BB 0237624;CS-0186511;FT-0610426;EN300-01173;10.14272/LNROIXNEIZSESG-UHFFFAOYSA-N;2,5-dimethyl-1-phenyl-3-pyrrolecarboxaldehyde;3-FORMYL-2,5-DIMETHYL-1-PHENYLPYRROLE;Pyrrole-3-carboxaldehyde,5-dimethyl-1-phenyl-;W18717;2,5-Dimethyl-1-phenyl pyrrole-3-carboxaldehyde;2,5-dimethyl-1-phenyl-1H-pyrrol-3-carbaldehyd;1-Phenyl-2,5-dimethyl-1H-pyrrole-3-carbaldehyde;10.14272/LNROIXNEIZSESG-UHFFFAOYSA-N.1;1H-Pyrrole-3-carboxaldehyde,5-dimethyl-1-phenyl-;doi:10.14272/LNROIXNEIZSESG-UHFFFAOYSA-N;2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbalde hyde;doi:10.14272/LNROIXNEIZSESG-UHFFFAOYSA-N.1;W-203889;Z56759012;F1029-0024;2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde, AldrichCPR;4-(5-{[(3-chloro-4-fluorophenyl)sulfonyl]amino}-1-methyl-1H-benzimidazol-2-yl)-N-ethylbenzamide

Chemical Property of 2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde

Chemical Property:

• Vapor Pressure: 6E-05mmHg at 25°C
• Melting Point: 89-90°C
• Boiling Point: 345.8°C at 760 mmHg
• PKA: -5.56±0.70(Predicted)
• Flash Point: 163°C
• PSA: 22.00000
• Density: 1.04
• LogP: 2.90660
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 199.099714038
• Heavy Atom Count: 15
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(N1C2=CC=CC=C2)C)C=O
• Uses: 2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde is a reagent that is used in the discovery of pyrrolone antimalarials.

Technology Process of 2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde

There total 9 articles about 2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde 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%

2,5-dimethyl-1-phenyl-1H-pyrrole (83-24-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (83-18-1)

Guidance literature:

With trichlorophosphate; at 110 ℃; for 6h;

DOI:10.3987/COM-12-12446

Reference yield: 29.0%

2,5-dimethyl-1-phenyl-1H-pyrrole (83-24-9) → 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (83-18-1)

Guidance literature:

2,5-dimethyl-1-phenyl-1H-pyrrole; With N,N-dimethyl-formamide; trichlorophosphate; In toluene; at 80 ℃; for 3h;

With water; sodium carbonate; In toluene; at 20 ℃; Product distribution / selectivity;

Reference yield:

N-(3′-methylphenyl)-2,5-dimethylpyrrole (32570-10-8) → 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (83-18-1)

Guidance literature:

With trichlorophosphate; In N,N-dimethyl-formamide; at 110 ℃;

DOI:10.1021/acscatal.6b02953

upstream raw materials:

2,5-dimethyl-1-phenyl-1H-pyrrole

formamide

N,N-dimethyl-formamide

2,5-hexanedione

Downstream raw materials:

1-ethyl-2-[2-(2,5-dimethyl-1-phenyl-pyrrol-3-yl)-vinyl]-6,7-dihydro-4H-pyrano[4,3-d]thiazolium; iodide

(E)-2-(2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)-6-(dimethylamino)-1-methylquinolin-1-ium iodide

Refernces

Organotin(IV) 4-nitrophenylethanoates: Synthesis, structural characteristics and intercalative mode of interaction with DNA

10.1016/j.jorganchem.2009.06.036

The research investigates the synthesis, structural properties, and DNA-binding behavior of four new organotin(IV) carboxylates, namely [Bu2SnL2] (1), [Et2SnL2] (2), [Bu3SnL]n (3), and [Me3SnL]n (4), where L represents the 4-nitrophenylethanoates ligand. The purpose of this study is to provide insights into the drug-DNA interaction mechanism and potential drug design applications, particularly in the context of anticancer activity. The researchers synthesized these compounds using organotin(IV) precursors and characterized them through elemental analysis, FT-IR, multinuclear NMR, and X-ray single crystal analysis. Dibutyltin(IV) dichloride was used as a precursor for the synthesis of complex 1. The study found that the ligand coordinated to the organotin moiety via the COO group, with different coordination modes observed in the complexes. Cyclic voltammetry was employed to evaluate the electrochemical, kinetic, and thermodynamic parameters of these complexes interacting with DNA, revealing diffusion-controlled processes and binding constants indicating the order of binding strength as 2 < 1 < 4 < 3. Additionally, compounds 1 and 2 demonstrated anticancer activity against prostate cancer cell lines (PC-3), consistent with their voltammetric behavior. The research concludes that these organotin(IV) derivatives show potential as chemotherapeutic agents due to their intercalative interaction with DNA and their anticancer activity, suggesting further exploration for drug development.