Diethyl(3-aminophenyl)phosphonate

Base Information

• Chemical Name: Diethyl(3-aminophenyl)phosphonate
• CAS No.: 89277-85-0
• Molecular Formula: C10H16NO3P
• Molecular Weight: 229.216
• NSC Number: 141177
• DSSTox Substance ID: DTXSID601008742
• Nikkaji Number: J2.724.409B
• Wikidata: Q83005304
• ChEMBL ID: CHEMBL160608
• Mol file: 89277-85-0.mol

Synonyms:diethyl(3-aminophenyl)phosphonate;89277-85-0;diethyl (3-aminophenyl)phosphonate;NSC141177;CHEMBL160608;SCHEMBL2034316;Diethyl 3-aminophenylphosphonate;AXAVRCDPAKQEMV-UHFFFAOYSA-N;DTXSID601008742;NSC-141177

Chemical Property of Diethyl(3-aminophenyl)phosphonate

Chemical Property:

• Vapor Pressure: 3.62E-05mmHg at 25°C
• Boiling Point: 353.3°Cat760mmHg
• Flash Point: 167.5°C
• Density: 1.15g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 229.08678037
• Heavy Atom Count: 15
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C1=CC=CC(=C1)N)OCC

Technology Process of Diethyl(3-aminophenyl)phosphonate

There total 9 articles about Diethyl(3-aminophenyl)phosphonate 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%

phosphonic acid diethyl ester (762-04-9) + m-Bromoaniline (591-19-5) → (3-aminophenyl)phosphonate de diethyle (89277-85-0)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In ethanol; for 30h; Reflux; Inert atmosphere;

DOI:10.1246/cl.2009.738

Reference yield: 90.0%

phosphonic acid diethyl ester (762-04-9) + 3-Iodoaniline (626-01-7) → (3-aminophenyl)phosphonate de diethyle (89277-85-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; acetonitrile; at 25 ℃; for 2.5h; Irradiation;

Reference yield: 80.0%

3-aminophenyl methanesulfonate (38164-50-0) + phosphonic acid diethyl ester (762-04-9) → (3-aminophenyl)phosphonate de diethyle (89277-85-0)

Guidance literature:

With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; N-ethyl-N,N-diisopropylamine; In ethanol; tert-butyl alcohol; at 110 ℃; for 18h; chemoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03104

upstream raw materials:

diethyl (3-nitrophenyl)phosphonate

phosphonic acid diethyl ester

3-Iodoaniline

(m-nitrophenyl)phosphonic acid

Downstream raw materials:

(3-hydroxy-phenyl)-phosphonic acid diethyl ester

m-aminophenylphosphonic acid

diethyl 3-(n-octylsulfonamido)phenylphosphonate

(3-{[6-(3-nitrophenyl)pyrimidin-4-yl]amino}phenyl)phosphonic acid

Refernces

• 1、 Németh, Gábor,Greff, Zoltán,Sipos, Anna,Varga, Zoltán,Székely, Rita,Sebestyén, Mónika,Jászay, Zsuzsa,Béni, Szabolcs,Nemes, Zoltán,Pirat, Jean-Luc,Volle, Jean-No?l,Virieux, David,Gyuris, ágnes,Kelemenics, Katalin,áy, éva,Minarovits, Janos,Szathmary, Susan,Kéri, Gy?rgy,Orfi, László. "Synthesis and evaluation of phosphorus containing, specific CDK9/CycT1 inhibitors". . p. 3939 - 3965. Retrieved 2014/06/09.
• 2、 Wang, Ping,Lu, Jie,Zhang, Zhan-Hui. "An improved procedure for the synthesis of aryl phosphonates by palladium-catalysed cross-coupling of aryl halides and diethyl phosphite in polyethylene glycol". . p. 359 - 361. Retrieved 2013/07/26.