4-isocyano-N,N-dimethylaniline

Base Information

• Chemical Name: 4-isocyano-N,N-dimethylaniline
• CAS No.: 7050-85-3
• Molecular Formula: C9H10N2
• Molecular Weight: 146.192
• DSSTox Substance ID: DTXSID00377961
• Nikkaji Number: J640.985G
• Wikidata: Q82167371
• Mol file: 7050-85-3.mol

Synonyms:4-isocyano-N,N-dimethylaniline;7050-85-3;Benzenamine, 4-isocyano-N,N-dimethyl- (9CI);N,N-Dimethyl-4-isocyanoaniline;SCHEMBL13007736;DTXSID00377961;4-(dimethylamino)-phenyl isocyanide;AKOS006278031;EN300-1855915

Chemical Property of 4-isocyano-N,N-dimethylaniline

Chemical Property:

• PSA: 3.24000
• LogP: 1.53410
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 146.084398327
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

99%min ^*data from raw suppliers

N-(4-ISOCYANOPHENYL)-N,N-DIMETHYLAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)[N+]#[C-]

Technology Process of 4-isocyano-N,N-dimethylaniline

There total 7 articles about 4-isocyano-N,N-dimethylaniline 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: 90.0%

N-(4-(dimethylamino)phenyl)formamide (18606-63-8) → 4-(dimethylamino)phenyl isocyanide (7050-85-3)

Guidance literature:

With triethylamine; trichlorophosphate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/cmdc.201402244

Reference yield: 72.0%

sodium chlorodifluoroacetate (1895-39-2) + 4-amino-N,N-dimethylaniline (99-98-9) → 4-(dimethylamino)phenyl isocyanide (7050-85-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1021/acs.orglett.0c03472

Reference yield: 70.0%

3-phenyl-5-isoxazolone (7713-79-3) + p-dimethylaminonitrosobenzene (138-89-6) → 4-(dimethylamino)phenyl isocyanide (7050-85-3)

Guidance literature:

3-phenyl-5-isoxazolone; p-dimethylaminonitrosobenzene; In ethanol; for 0.25h; Heating;

In toluene; at 90 ℃; for 30h;

DOI:10.1134/S1070363210120303

upstream raw materials:

N-(4-(dimethylamino)phenyl)formamide

chloroform

4-amino-N,N-dimethylaniline

3-phenyl-5-isoxazolone

Downstream raw materials:

N-(4-Dimethylamino-phenyl)-formimidic acid 1,1-dimethyl-octadecyl ester

C₃₀H₃₂N₄O₄S

C₂₉H₃₀N₄O₄S

C₂₇H₂₈N₄O₄S

Refernces

• 1、 Ghorai, Sourav,Lin, Yongjia,Xia, Yuanzhi,Wink, Donald J.,Lee, Daesung. "Silver-Catalyzed Selective Multicomponent Coupling Reactions of Arynes with Nitriles and Isonitriles". supporting information. p. 642 - 647. Retrieved 2020/01/31.
• 2、 Ghorai, Sourav,Lee, Daesung. "Synthesis of Imides, Imidates, Amidines, and Amides by Intercepting the Aryne-Isocyanide Adduct with Weak Nucleophiles". supporting information. p. 7390 - 7393. Retrieved 2019/10/02.