5-Acetyl-2-aminobenzonitrile

Base Information

• Chemical Name: 5-Acetyl-2-aminobenzonitrile
• CAS No.: 33720-71-7
• Molecular Formula: C9H8N2O
• Molecular Weight: 160.175
• Hs Code.: 29269090
• DSSTox Substance ID: DTXSID20446340
• Nikkaji Number: J2.111.496K
• Wikidata: Q72434509
• Mol file: 33720-71-7.mol

Synonyms:5-Acetyl-2-aminobenzonitrile;33720-71-7;2-Amino-5-acetylbenzonitrile;4'-Amino-3'-cyanoacetophenone;MFCD18379155;5-acetyl-2-amino-benzonitrile;5-Acetyl-anthranilonitrile;Benzonitrile, 5-acetyl-2-amino-;Benzonitrile,5-acetyl-2-amino-;5-Acetylanthranilonitrile;SCHEMBL3734286;DTXSID20446340;SJXQSPLLUXAJQJ-UHFFFAOYSA-N;CL8661;AKOS015841049;SB76550;AS-46067;CS-0040846;FT-0661132;A856681;J-019303

Chemical Property of 5-Acetyl-2-aminobenzonitrile

Chemical Property:

• Appearance/Colour: Yellow Solid
• Melting Point: 159-161 °C
• Boiling Point: 374.536 °C at 760 mmHg
• PKA: -0.62±0.10(Predicted)
• Flash Point: 180.313 °C
• PSA: 66.88000
• Density: 1.202 g/cm³
• LogP: 1.92428
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 160.063662883
• Heavy Atom Count: 12
• Complexity: 228

Purity/Quality:

99% ^*data from raw suppliers

5-Acetyl-2-aminobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC(=C(C=C1)N)C#N
• Uses: Cimaterol intermediate.

Technology Process of 5-Acetyl-2-aminobenzonitrile

There total 8 articles about 5-Acetyl-2-aminobenzonitrile 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%

dicyanozinc (557-21-1) + 4-acetyl-2-iodoaniline (97776-06-2) → 4-amino-3-cyanoacetophenone (33720-71-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; for 0.5h;

DOI:10.1080/00397919408011310

Reference yield: 85.0%

1-(4-amino-3-bromophenyl)-ethanone (56759-32-1) + potassium ferrocyanide → 4-amino-3-cyanoacetophenone (33720-71-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; tert-butyl alcohol; for 16h; Inert atmosphere; Reflux;

Reference yield: 80.0%

→ 4-amino-3-cyanoacetophenone (33720-71-7)

Guidance literature:

upstream raw materials:

1-(4-amino-3-bromophenyl)-ethanone

copper(I) cyanide

4-acetyl-2-iodoaniline

dicyanozinc

Downstream raw materials:

4'-amino-3'-chloro-5'-cyano-2-tert.butylamino-acetophenone

4'-amino-3'-bromo-2-tert-butylamino-5'-cyano-acetophenone

4'-amino-3'-chloro-5'-cyano-2-tert-pentylaminoacetophenone

4'-amino-3'-bromo-5'-cyano-2-tert-pentylaminoacetophenone

Refernces

• 1、 -. "Phenylethanolamine β receptor agonist synthetic method". . . Retrieved 2019/07/04.
• 2、 -. "NOVEL PHENYLETHANOLAMINE COMPOUNDS HAVING BETA2-ACCEPTOR EXCITATORY FUNCTION AND THEIR PREPARATION METHOD". Page 5. . Retrieved 2010/02/07.