4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile

Base Information

• Chemical Name: 4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile
• CAS No.: 119580-81-3
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.137
• DSSTox Substance ID: DTXSID201259965
• Nikkaji Number: J1.723.527C
• Mol file: 119580-81-3.mol

Synonyms:4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile;119580-81-3;1H-Pyrrole-2-carbonitrile,4-formyl-1-methyl-(9CI);4-FORMYL-1-METHYLPYRROLE-2-CARBONITRILE;5-cyano-1-methylpyrrole-3-carbaldehyde;SCHEMBL6650884;CILGDZPSMMRNIB-UHFFFAOYSA-N;DTXSID201259965;MFCD12923604;AKOS015832752;SB62383;BS-37066;CS-0117603;EN300-171771;W19143;J-004156;Z1235967810;4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile, AldrichCPR

Chemical Property of 4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile

Chemical Property:

• Boiling Point: 232.2±20.0 °C(Predicted)
• PKA: -12.07±0.70(Predicted)
• PSA: 45.79000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 0.70928
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 134.048012819
• Heavy Atom Count: 10
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C=C1C#N)C=O

Technology Process of 4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile

There total 2 articles about 4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile 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%

1-methyl-1H-pyrrole-2-carbonitrile (34884-10-1) + Dichloromethyl methyl ether (4885-02-3) → 4-formyl-1-methyl-1H-pyrrol-2-carbonitrile (119580-81-3)

Guidance literature:

With aluminium trichloride; In nitromethane; dichloromethane;

DOI:10.1016/S0960-894X(03)00347-0

Reference yield:

N-Methylpyrrole (96-54-8) → 4-formyl-1-methyl-1H-pyrrol-2-carbonitrile (119580-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / CSI / dimethylformamide / -78 - 20 °C

2: 91 percent / AlCl₃ / nitromethane; CH₂Cl₂

With aluminium trichloride; isocyanate de chlorosulfonyle; In nitromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00347-0

Reference yield: 40.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 4-formyl-1-methyl-1H-pyrrol-2-carbonitrile (119580-81-3) → 2-cyano-1-methyl-4-vinylpyrrole (119580-84-6)

Guidance literature:

With sodium hydride; 1.) THF, 20 deg C, 2 h, 2.) reflux, 5 h; 20 deg C, 10 h;

upstream raw materials:

1-methyl-1H-pyrrole-2-carbonitrile

Dichloromethyl methyl ether

N-Methylpyrrole

Downstream raw materials:

2-cyano-1-methyl-4-vinylpyrrole

(S)-2-hydroxy-2-(5-cyano-1-methyl-3-pyrrolyl)acetonitrile

(R)-(+)-2-hydroxy-2-(5-cyano-1-methyl-3-pyrrolyl)acetonitrile

2-hydroxy-2-(5-cyano-1-methyl-3-pyrrolyl)acetonitrile

Refernces

• 1、 Lange, Udo E. W.,Baucke, Dorit,Hornberger, Wilfried,Mack, Helmut,Seitz, Werner,Hoeffken, H. Wolfgang. "D-Phe-Pro-Arg type thrombin inhibitors: Unexpected selectivity by modification of the P1 moiety". . p. 2029 - 2033. Retrieved 2007/10/03.