4-(Aminomethyl)benzonitrile

Base Information

• Chemical Name: 4-(Aminomethyl)benzonitrile
• CAS No.: 10406-25-4
• Molecular Formula: C8H8N2
• Molecular Weight: 132.165
• Hs Code.: 2926909090
• European Community (EC) Number: 233-877-5
• UNII: SG5W3N5HYJ
• DSSTox Substance ID: DTXSID40146234
• Nikkaji Number: J30.857I
• Wikidata: Q72457934
• Pharos Ligand ID: XWQHXGY6S9TC
• ChEMBL ID: CHEMBL4068773
• Mol file: 10406-25-4.mol

Synonyms:4-Cyanobenzylamine;4-(Aminomethyl)benzonitrile;10406-25-4;Benzonitrile, 4-(aminomethyl)-;p-cyanobenzylamine;4-cyanobenzyl amine;4-aminomethyl benzonitrile;SG5W3N5HYJ;(4-Cyanophenyl)methanamine;4-(Aminomethyl)benzonitrile HCl;CHEMBL4068773;EINECS 233-877-5;MFCD00025578;4-Cyan-benzylamin;4-cyano-benzylamine;4-(cyano)benzylamine;4-cyano-benzyl amine;a-Amino-p-tolunitrile;p-aminomethylbenzonitrile;4-aminomethylbenzonitrile;4-cyanobenzenemethanamine;alpha-Amino-p-tolunitrile;UNII-SG5W3N5HYJ;4-aminomethyl-benzonitrile;4-(aminomethyl) benzonitrile;SCHEMBL297224;P-CYANOPHENYLMETHYLAMINE;4-Cyanobenzylamine, AldrichCPR;LFIWXXXFJFOECP-UHFFFAOYSA-;DTXSID40146234;.ALPHA.-AMINO-P-TOLUNITRILE;BCP33970;BDBM50232691;AKOS000139186;CS-W022002;PS-6134;AC-16387;BP-24095;SY012258;METHYL3,4-DI-O-ACETYL-D-GLUCURONAL;FT-0600790;EN300-33164;A800887;W-200714;1-(4-chlorophenyl)pyrazolo[3,4-d]pyrimidin-4-amine;4-(AMINOMETHYL)BENZONITRILE

Chemical Property of 4-(Aminomethyl)benzonitrile

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.0051mmHg at 25°C
• Melting Point: 274-279 °C(lit.)
• Refractive Index: 1.573
• Boiling Point: 275.4 °C at 760 mmHg
• PKA: 8.47±0.10(Predicted)
• Flash Point: 120.4 °C
• PSA: 49.81000
• Density: 1.1 g/cm³
• LogP: 1.71728
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.9
• 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:

98%,99%, ^*data from raw suppliers

4-Cyanobenzylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CN)C#N
• Uses: Intermediate in the preparation of Ximelagatran.

Technology Process of 4-(Aminomethyl)benzonitrile

There total 33 articles about 4-(Aminomethyl)benzonitrile 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: 95.0%

4-(azidomethyl)benzonitrile (84466-87-5) → 4-aminobenzyl cyanide (10406-25-4)

Guidance literature:

4-(azidomethyl)benzonitrile; With triphenylphosphine; In tetrahydrofuran; Heating;

With sodium hydroxide; In ethanol; at 60 - 65 ℃; for 0.666667h;

DOI:10.1002/jhet.5570400206

Reference yield: 94.2%

terephthalonitrile (623-26-7) → 4-aminobenzyl cyanide (10406-25-4)

Guidance literature:

With carbon dioxide; Rh/Al₂O₃; hydrogen; at 80 ℃; for 6h; chemoselective reaction;

DOI:10.1002/adsc.201000514

Reference yield: 94.0%

4-aminomethyl-benzaldehyde → 4-aminobenzyl cyanide (10406-25-4)

Guidance literature:

With (2-hydroxyethyl)trimethylazanium urea chloride; hydroxylamine hydrochloride; In neat (no solvent); at 140 ℃; for 0.166667h; Microwave irradiation; Green chemistry;

DOI:10.1055/s-0033-1339904

upstream raw materials:

4-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]benzonitrile

4-cyanobenzyl chloride

C₁₄H₁₃NO

4-cyanobenzaldehyde oxime

Downstream raw materials:

(4-Cyano-benzyl)-carbamic acid 3-methylsulfanylcarbonylamino-phenyl ester

N-(4-Cyano-benzyl)-guanidine

C₁₄H₁₃NO

C₁₅H₁₉N₅

Refernces

• 1、 Delcaillau, Tristan,Boehm, Philip,Morandi, Bill. "Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers". . p. 3723 - 3728. Retrieved 2021/04/07.
• 2、 Nguyen, Dat P.,Sladek, Rudolph N.,Do, Loi H.. "Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions". supporting information. . Retrieved 2020/07/15.