n-(4-Cyanophenyl)glycine

Base Information

• Chemical Name: n-(4-Cyanophenyl)glycine
• CAS No.: 42288-26-6
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.175
• Hs Code.: 2926909090
• European Community (EC) Number: 459-560-3,815-989-1
• UNII: G95LDV9GQ2
• DSSTox Substance ID: DTXSID80355883
• Nikkaji Number: J759.801G
• Wikidata: Q72458840
• Mol file: 42288-26-6.mol

Synonyms:n-(4-cyanophenyl)glycine;42288-26-6;2-((4-Cyanophenyl)amino)acetic acid;2-(4-Cyanophenylamino)acetic acid;N-(4-CYANO-PHENYL)-GLYCINE;2-(4-cyanoanilino)acetic acid;N-(4-cyanophenyl)-Glycine;2-[(4-cyanophenyl)amino]acetic Acid;Glycine, N-(4-cyanophenyl)-;MFCD01464022;[(4-cyanophenyl)amino]acetic acid;n-(p-cyanophenyl)glycine;N-(p-cyanophenyl)-glycine;G95LDV9GQ2;Oprea1_114543;SCHEMBL361315;(4-cyano-phenylamino)acetic acid;DTXSID80355883;(4-Cyano-phenylamino)-acetic acid;BCP04527;CS-D0913;2-(4-cyanophenylamino) acetic acid;SC3501;AKOS000218605;AC-7903;FS-3199;4-(((Carboxy)methyl)amino)benzonitrile;HY-77519;SY021403;A6910;AM20090750;BB 0253985;C2771;FT-0647115;EN300-52080;Q-102527;Z331870794

Chemical Property of n-(4-Cyanophenyl)glycine

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 8.8E-09mmHg at 25°C
• Melting Point: 237 °C(dec.)
• Refractive Index: 1.593
• Boiling Point: 447.2 °C at 760 mmHg
• PKA: 3.81±0.10(Predicted)
• Flash Point: 224.3 °C
• PSA: 73.12000
• Density: 1.3 g/cm³
• LogP: 1.12778
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 176.058577502
• Heavy Atom Count: 13
• Complexity: 223

Purity/Quality:

99.0%min. ^*data from raw suppliers

N-(4-Cyanophenyl)-glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)NCC(=O)O
• Description: Dabigatran etexilate is a novel synthetic direct thrombin inhibitor, a prodrug of dabigatran, a non-peptide thrombin inhibitor. Dabigatran etexilate intermediate II is an impurity produced during the preparation of dabigatran etexilate.
• Physical properties: N-(4-Cyanophenyl)glycine is a off-white Solid.
• Uses: N-(4-Cyanophenyl)-glycine (cas# 42288-26-6) is a compound useful in organic synthesis.

Technology Process of n-(4-Cyanophenyl)glycine

There total 7 articles about n-(4-Cyanophenyl)glycine 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: 88.0%

bromoacetic acid (79-08-3) + 4-Aminobenzonitrile (873-74-5) → (4-cyanophenyl)glycine (42288-26-6)

Guidance literature:

In water; at 100 - 110 ℃; for 3h;

Reference yield: 88.0%

4-bromobenzenecarbonitrile (623-00-7) + glycine (56-40-6,18875-39-3,25718-94-9) → (4-cyanophenyl)glycine (42288-26-6)

Guidance literature:

With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid; In water; dimethyl sulfoxide; at 25 ℃; for 48h; chemoselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1002/ejoc.201500279

Reference yield: 73.2%

sodium monochloroacetic acid (3926-62-3) + 4-Aminobenzonitrile (873-74-5) → (4-cyanophenyl)glycine (42288-26-6)

Guidance literature:

In water; for 6.5h; Product distribution / selectivity; Reflux;

upstream raw materials:

chloroacetic acid

4-Aminobenzonitrile

(4-cyanophenylamino)-acetic acid tert-butyl ester

bromoacetic acid

Downstream raw materials:

1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide acetate salt

dabigatran etexilate

3-({2-[(4-carbamimidoylphenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid ethyl ester

N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl] amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-β-alanine ethyl ester methanesulfonate

Refernces

• 1、 Pétry, Nicolas,Vanderbeeken, Thibaut,Malher, Astrid,Bringer, Yoan,Retailleau, Pascal,Bantreil, Xavier,Lamaty, Frédéric. "Mechanosynthesis of sydnone-containing coordination complexes". supporting information. p. 9495 - 9498. Retrieved 2019/08/15.
• 2、 Ren, Weixin,Ren, Yujie,Wang, Shuai. "Design, synthesis, anticoagulant activity evaluation and molecular docking studies of a class of N -ethyl dabigatran derivatives". . p. 148 - 159. Retrieved 2016/05/24.