Phenylphosphonic acid

Base Information

• Chemical Name: Phenylphosphonic acid
• CAS No.: 1571-33-1
• Molecular Formula: C6H7O3P
• Molecular Weight: 158.094
• Hs Code.: 29319090
• European Community (EC) Number: 216-388-1
• NSC Number: 145
• UNII: BYD76T2868
• DSSTox Substance ID: DTXSID2044399
• Nikkaji Number: J40.748H
• Wikidata: Q26841314
• Pharos Ligand ID: Z57DXHSHQ261
• ChEMBL ID: CHEMBL179801
• Mol file: 1571-33-1.mol

Synonyms:benzenephosphonic acid;phenylphosphonate;phenylphosphonic acid;phenylphosphonic acid, aluminum salt;phenylphosphonic acid, calcium salt;phenylphosphonic acid, cerium (3+) salt (3:2);phenylphosphonic acid, copper salt;phenylphosphonic acid, dipotassium salt;phenylphosphonic acid, disodium salt;phenylphosphonic acid, dysposium (3+) salt;phenylphosphonic acid, dysposium (3+) salt (3:2), dihydrate;phenylphosphonic acid, erbium (3+) salt (3:2);phenylphosphonic acid, erbium (3+) salt (3:2), dihydrate;phenylphosphonic acid, europium (3+) salt (3:2);phenylphosphonic acid, gadolinium (3+) salt (3:2);phenylphosphonic acid, holmium (3+) salt (3:2);phenylphosphonic acid, lanthanum (3+) salt (3:2);phenylphosphonic acid, lutetium (3+) salt (3:2);phenylphosphonic acid, magnesium salt;phenylphosphonic acid, monocalcium salt;phenylphosphonic acid, monolead (2+) salt;phenylphosphonic acid, monomagnesium salt;phenylphosphonic acid, monosodium salt;phenylphosphonic acid, neodymium (3+) salt (3:2);phenylphosphonic acid, neodymium (3+) salt (3:2), monohydrate;phenylphosphonic acid, potassium salt;phenylphosphonic acid, praseodymium (3+) salt (3:2);phenylphosphonic acid, praseodymium (3+) salt (3:2), dihydrate;phenylphosphonic acid, samarium (3+) salt (3:2);phenylphosphonic acid, samarium (3+) salt (3:2), dihydrate;phenylphosphonic acid, sodium salt;phenylphosphonic acid, terbium (3+) salt (3:2);phenylphosphonic acid, thulium (3+) salt (3:2);phenylphosphonic acid, ytterbium (3+) salt (3:2);phenylphosphonic acid, yttrium (3+) salt (3:2);phenylphosphonic acid, zinc salt;phenylphosphonic acid, zirconium (1+) salt (2:1)

Chemical Property of Phenylphosphonic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 1.3E-05mmHg at 25°C
• Melting Point: 162-164 °C(lit.)
• Refractive Index: n20/D 1.523(lit.)
• Boiling Point: 353.661 °C at 760 mmHg
• PKA: pK1:1.83;pK2:7.07 (25°C)
• Flash Point: 167.688 °C
• PSA: 67.34000
• Density: 1.422 g/cm³
• LogP: 0.48960
• Storage Temp.: 2-8°C
• Water Solubility.: 40.4 g/100 mL (25 ºC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 158.01328108
• Heavy Atom Count: 10
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

Phenylphosphonic Acid >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xn
• Hazard Codes: C,Xn
• Statements: 34-37-41-37/38-22-38
• Safety Statements: 26-39-37/39-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(=O)(O)O
• Uses: Intermediate in antifouling paint agents; catalyst in organic reactions. Phenylphosphonic acid additive used with Noyori's catalyst for oxidation of sulfides to sulfones. Used as additive of unsaturated polyester PU resin. It also can be added into nylon to improve its polymerization degree. It can be used as extreme pressure agent of lube; used as catalyst of carboxylic acid & alcohol reaction; it can be used as fire retarding treatment of fiber used asganic materials.

Technology Process of Phenylphosphonic acid

There total 69 articles about Phenylphosphonic 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: 100.0%

diisopropyl phenylphosphonate (7237-16-3) → phenylphosphonate (1571-33-1)

Guidance literature:

With trifluorormethanesulfonic acid; In toluene; at 120 ℃; for 24h; Temperature; Reagent/catalyst; Inert atmosphere;

Reference yield: 100.0%

diethyl phenylphosphonate (1754-49-0) → phenylphosphonate (1571-33-1)

Guidance literature:

With hydrogenchloride; Heating;

DOI:10.1055/s-1990-26813

Reference yield: 99.0%

dibenzyl phenylphosphonate (19236-61-4) → phenylphosphonate (1571-33-1)

Guidance literature:

With Nafion; In toluene; at 80 ℃; for 8h; Solvent; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c00550

upstream raw materials:

phenylphosphinic acid

phenyltetrachlorophosphorane

dibromo-dichloro-phenyl-phosphorane

tetrabromo-phenyl-phosphorane

Downstream raw materials:

P,P-dichlorophenylphosphine oxide

(m-nitrophenyl)phosphonic acid

o-nitrophenylphosphonic acidi13

methylphosphate

Refernces

• 1、 Kikukawa et al.. "". . p. 1493,1496. Retrieved 1979.
• 2、 Li, Naixin,Pratt. "Inhibition of serine β-lactamases by acyl phosph(on)ates: A new source of inert acyl [and phosphyl] enzymes". . p. 4264 - 4268. Retrieved 1998.
• 3、 Br?se, Stefan,Hassan, Zahid,Nieger, Martin,O?wald, Simon,Zippel, Christoph. "C-P bond formation of cyclophanyl-, and aryl halides: Via a UV-induced photo Arbuzov reaction: A versatile portal to phosphonate-grafted scaffolds". . p. 3309 - 3312. Retrieved 2022/02/11.
• 4、 Bolton, Sarah G.,Chouinard, Julie E.,Garcia, Arman C.,Golledge, Stephen L.,Newton, Turner D.,Pluth, Michael D.,Zakharov, Lev N.. "Hydrolysis-Based Small-Molecule Hydrogen Selenide (H2Se) Donors for Intracellular H2Se Delivery". . p. 19542 - 19550. Retrieved 2021/11/23.