(1-Naphthylmethyl)phosphonic acid

Base Information

• Chemical Name: (1-Naphthylmethyl)phosphonic acid
• CAS No.: 4730-77-2
• Molecular Formula: C11H11 O3 P
• Molecular Weight: 222.18
• NSC Number: 78906
• DSSTox Substance ID: DTXSID10197096
• Nikkaji Number: J50.301K
• Wikidata: Q83070066
• ChEMBL ID: CHEMBL37851
• Mol file: 4730-77-2.mol

Synonyms:(1-Naphthylmethyl)phosphonic acid;4730-77-2;1-NAPHTHYLMETHYLPHOSPHONIC ACID;naphthalen-1-ylmethylphosphonic acid;Phosphonic acid, (1-naphthylmethyl)-;Phosphonic acid, (1-naphthalenylmethyl)-;NSC 78906;BRN 2938979;1-naphthalenemethylphosphonate;CHEMBL37851;4-16-00-01102 (Beilstein Handbook Reference);1-Naphthylmethylphosphonic Acid 98+%;1-NAPHTHYLMETHYLPHOSPHONICACID;NCIOpen2_004339;WLN: L66J B1PQQO;SCHEMBL233333;C11H11O3P;DTXSID10197096;NSC78906;BDBM50080269;C11-H11-O3-P;MFCD00015567;NSC-78906;Naphthalen-1-ylmethyl-phosphonic acid;AKOS017345041;[(naphthalen-1-yl)methyl]phosphonic acid;LS-106709;FT-0608136

Chemical Property of (1-Naphthylmethyl)phosphonic acid

Chemical Property:

• Vapor Pressure: 6.02E-10mmHg at 25°C
• Melting Point: 212-213°C
• Boiling Point: 478°Cat760mmHg
• Flash Point: 242.9°C
• PSA: 67.34000
• Density: 1.397g/cm³
• LogP: 2.51750
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 222.04458121
• Heavy Atom Count: 15
• Complexity: 261

Purity/Quality:

99% ^*data from raw suppliers

1-naphthylmethylphosphonic acid AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R34:Causes burns.
• Hazard Codes: R34:Causes burns.
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2CP(=O)(O)O

Technology Process of (1-Naphthylmethyl)phosphonic acid

There total 4 articles about (1-Naphthylmethyl)phosphonic acid 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: 75.0%

1-naphthalene methanol (4780-79-4) → naphthalen-1-ylmethylphosphonic acid (4730-77-2)

Guidance literature:

1-naphthalene methanol; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; hypophosphorous acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 110 ℃; for 15h; Inert atmosphere;

In N,N-dimethyl-formamide; at 110 ℃; for 8h;

DOI:10.1002/ejoc.200800581

Reference yield: 23.0%

diethyl 1-naphthylmethylphosphonate (53575-08-9) → naphthalen-1-ylmethylphosphonic acid (4730-77-2)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmcl.2008.10.125

Reference yield:

1-Chloromethylnaphthalene (86-52-2) → naphthalen-1-ylmethylphosphonic acid (4730-77-2)

Guidance literature:

Multistep reaction; (i) P(OEt)3, (ii) aq. HCl;

upstream raw materials:

diethyl 1-naphthylmethylphosphonate

1-Chloromethylnaphthalene

1-naphthalene methanol

Refernces

• 1、 Coudray, Laetitia,Montchamp, Jean-Luc. "Green, palladium-catalyzed synthesis of benzylic H-phosphinates from hypophosphorous acid and benzylic alcohols". supporting information; experimental part. p. 4101 - 4103. Retrieved 2009/05/07.