4-Aminophenylacetonitrile

Base Information

• Chemical Name: 4-Aminophenylacetonitrile
• CAS No.: 3544-25-0
• Molecular Formula: C8H8N2
• Molecular Weight: 132.165
• Hs Code.: 29269095
• European Community (EC) Number: 222-587-4
• DSSTox Substance ID: DTXSID50188923
• Nikkaji Number: J184H
• Wikidata: Q63396122
• Mol file: 3544-25-0.mol

Synonyms:3544-25-0;4-Aminobenzyl cyanide;4-Aminophenylacetonitrile;2-(4-aminophenyl)acetonitrile;(4-aminophenyl)acetonitrile;Benzeneacetonitrile, 4-amino-;p-Aminobenzyl cyanide;4-aminobenzylcyanide;EINECS 222-587-4;MFCD00007912;(4-amino-phenyl)-acetonitrile;4-aminobenzyl;4-cyanomethylaniline;4-amino-benzylcyanide;p-amino benzyl cyanide;p-Aminophenylacetonitrile;4-aminobenzeneacetonitrile;4-amino phenylacetonitrile;4-aminophenyl acetonitrile;(p-Aminophenyl)acetonitrile;4-AMINOBENZYL CYANID;4-Aminobenzyl cyanide, 99%;BIDD:GT0095;SCHEMBL141424;Acetonitrile, (p-aminophenyl)-;2-(4-aminophenyl)-acetonitrile;DTXSID50188923;HMS1728C10;STR01806;STK259228;AKOS000277480;CS-W002037;PS-4131;AC-10549;SY015676;FT-0617596;EN300-18737;4-Aminobenzyl cyanide 4-Aminophenylacetonitrile;W-106671;Q63396122;Z90122117

Chemical Property of 4-Aminophenylacetonitrile

Chemical Property:

• Appearance/Colour: yellow to brown crystalline powder, crystals
• Melting Point: 45-48 °C(lit.)
• Refractive Index: 1.6231 (estimate)
• Boiling Point: 312 °C at 760 mmHg
• PKA: 4.25±0.10(Predicted)
• Flash Point: 136.3 °C
• PSA: 49.81000
• Density: 1.12 g/cm³
• LogP: 1.91608
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: soluble in Methanol
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 132.068748264
• Heavy Atom Count: 10
• Complexity: 137

Purity/Quality:

99.9% ^*data from raw suppliers

4-Aminobenzyl Cyanide >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC#N)N
• Uses: 4-Aminobenzyl Cyanide can be used to prevent or treat influenza.

Technology Process of 4-Aminophenylacetonitrile

There total 12 articles about 4-Aminophenylacetonitrile 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-Nitrophenylacetonitrile (555-21-5,34512-13-5,174848-08-9) → p-aminophenylacetonitrile (3544-25-0)

Guidance literature:

With hydrazine hydrate; palladium on activated charcoal; In ethanol; at 20 - 25 ℃; Product distribution; Other nitroarylalkylnitriles, higher temperature. Object: selective reduction of the nitro group in larger scale.;

DOI:10.1016/S0040-4039(01)81568-9

Reference yield: 94.0%

4,4'-di(cyanomethyl)azobenzene → p-aminophenylacetonitrile (3544-25-0)

Guidance literature:

With polystyrene-CH₂-NH₃(+)HCO₂(-); magnesium; In methanol; at 20 ℃; for 0.266667h;

Reference yield: 74.0%

4-isoxazoleboronic acid pinacol ester (928664-98-6) + 4-bromo-aniline (106-40-1) → p-aminophenylacetonitrile (3544-25-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; water; In dimethyl sulfoxide; at 130 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja201743j

upstream raw materials:

4-Nitrophenylacetonitrile

tetralin

hydrogenchloride

1-nitro-2-(4-nitrophenyl)-1-ethoxycarbonylethene

Downstream raw materials:

4-(2-piperidin-1-yl-ethyl)-phenylamine

1-(4-amino-benzyl)-[5]isoquinolylamine

2-((4-diethylamino)phenyl)acetonitrile

(4-dimethylamino-phenyl)-acetonitrile

Refernces

• 1、 Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.. "A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride". supporting information. p. 3565 - 3589. Retrieved 2021/10/12.
• 2、 Bento, Ian,Bernaldez, Mabel,Noguchi, Ryden,Kawakami, Joel. "Ultrasound-assisted rapid reduction of nitroaromatics to anilines using gallium metal". supporting information. p. 1404 - 1407. Retrieved 2020/03/31.