Diethyl benzylphosphonate

Base Information

• Chemical Name: Diethyl benzylphosphonate
• CAS No.: 1080-32-6
• Molecular Formula: C11H17 O3 P
• Molecular Weight: 228.228
• Hs Code.: 2931900090
• European Community (EC) Number: 214-097-4
• NSC Number: 62294
• UNII: T6D4QWT656
• DSSTox Substance ID: DTXSID0022145
• Nikkaji Number: J50.272C
• Wikidata: Q27289734
• ChEMBL ID: CHEMBL1476940
• Mol file: 1080-32-6.mol

Synonyms:Diethyl benzylphosphonate;1080-32-6;Benzylphosphonic acid diethyl ester;Phosphonic acid, (phenylmethyl)-, diethyl ester;diethoxyphosphorylmethylbenzene;Diethoxyphosphonomethylbenzene;Diethyl phosphonate, benzyl-;DIethylbenzylPHOSPHONATE;PHOSPHONIC ACID, BENZYL-, DIETHYL ESTER;diethyl (phenylmethyl)phosphonate;C11H17O3P;EINECS 214-097-4;MFCD00009078;NSC 62294;BRN 2580931;UNII-T6D4QWT656;AI3-22859;(Diethoxyphosphonomethyl)benzene;T6D4QWT656;benzyl-phosphonic acid diethyl ester;Phosphonic acid, P-(phenylmethyl)-, diethyl ester;NSC-62294;diethyl benzylphoshonate;benzyl diethyl phosphonate;Diethyl(benzyl)phosphonate;Benzylphosphonic acid diethyl;NCIOpen2_002803;MLS001143942;SCHEMBL366215;WLN: 2OPO&O2&1R;diethyl phenylmethanephosphonate;diethoxyphosphoryl-methyl-benzene;Diethyl benzylphosphonate, 99%;CHEMBL1476940;DTXSID0022145;AIPRAPZUGUTQKX-UHFFFAOYSA-;HMS2204M22;HMS3329C14;NSC62294;STR03726;JC-228;STL570271;AKOS000279045;CS-W012997;NCGC00247627-01;SMR001196012;SY033130;LS-106456;B1795;FT-0624776;EN300-49861;A801796;J-002044;Q27289734

Chemical Property of Diethyl benzylphosphonate

Chemical Property:

• Appearance/Colour: CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID
• Vapor Pressure: 0.00221mmHg at 25°C
• Refractive Index: n20/D 1.497(lit.)
• Boiling Point: 298.8°Cat760mmHg
• Flash Point: >113 ºC
• PSA: 45.34000
• Density: 1.095
• LogP: 3.45270
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 228.09153140
• Heavy Atom Count: 15
• Complexity: 202

Purity/Quality:

98% ^*data from raw suppliers

Diethyl benzylphosphonate ^*data from reagent suppliers

Safty Information:

• Statements: 36/38-36/37/38
• Safety Statements: 24/25-37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organophosphates, Other
• Canonical SMILES: CCOP(=O)(CC1=CC=CC=C1)OCC
• Uses: Reactant for synthesis of: ? 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders ? Natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions ? Stilbenes via on-column oxidation of vicinal diols and Horn Diethyl benzylphosphonate is used as a reactant for synthesis of 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders and natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions. It is also used as reactant for cyclization of aryl ethers, amines and amides & for investigating the effects of functional groups on the performance of clue organic LEDs. Reactant for synthesis of: 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disordersNatural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactionsStilbenes via on-column oxidation of vicinal diols and Horner-Emmons reactionsInhibitors of teh Wnt pathway for colon cancer repression using Wadsworth-Emmons reactionsAntimalarial drug analogs against P. falciparumReactant for:Cyclization of aryl ethers, amines, and amidesInvestigating the effects of functional groups on the performance of clue organic LEDs

Technology Process of Diethyl benzylphosphonate

There total 73 articles about Diethyl benzylphosphonate 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%

benzyl bromide (100-39-0) + triethyl phosphite (122-52-1) → O,O-diethyl benzylphosphonate (1080-32-6)

Guidance literature:

at 130 ℃; for 16h; Sealed tube;

DOI:10.1002/chem.201701204

Reference yield: 98.0%

benzyl bromide (100-39-0) + triethyl phosphite (122-52-1) → ethyl bromide (74-96-4) + ethylphosphonic acid diethyl ester (78-38-6) + O,O-diethyl benzylphosphonate (1080-32-6)

Guidance literature:

at 140 ℃; for 0.25h; microwave irradiation;

DOI:10.1002/chem.200600168

Reference yield: 98.0%

benzylphosphonic acid (6881-57-8) + Triethyl orthoacetate (78-39-7) → O,O-diethyl benzylphosphonate (1080-32-6)

Guidance literature:

at 90 ℃; for 24h; Green chemistry;

DOI:10.3390/molecules26185637

upstream raw materials:

diethyl ether

sodium diethyl phosphite

benzyl chloride

triethyl phosphite

Downstream raw materials:

Triphenylethylene

1-ethoxy-4-methylbenzene

2-ethoxytoluene

1-chloro-2-ethoxybenzene

Refernces

• 1、 Martyanov, Timofey P.,Ushakov, Evgeny N.,Nuriev, Vyacheslav N.,Aleksandrova, Nadezhda A.,Sazonov, Sergey K.,Vedernikov, Artem I.,Kuz'mina, Lyudmila G.,Klimenko, Lubov S.,Martyanova, Elena G.,Gromov, Sergey P.. "Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition". . p. 3164 - 3175. Retrieved 2021.
• 2、 Taniguchi, Yuki,Fujii, Nobuto,Takaki, Ken,Fujiwara, Yuzo. "Lanthanoid-metal-mediated reaction of acylphosphonates: evidence for the formation of an acyllanthanoid complex". . p. 173 - 180. Retrieved 1995.
• 3、 Villemin, Didier,Simeon, Fabrice,Decreus, Hugues,Jaffres, Paul-Alain. "Rapid and efficient Arbuzov reaction under microwave irradiation". . p. 209 - 213. Retrieved 1998.
• 4、 Poindexter, Michael K.,Katz, Thomas J.. "SIMPLE CONVERSION OF ARYL BROMIDES TO ARYLMETHYLPHOSPHONATES". . p. 1513 - 1516. Retrieved 1988.
• 5、 Lukashev,Tarasenko,Beletskaya. "Palladium-catalyzed cross-coupling reactions of organocopper derivatives of methylphosphonic esters and amides with aryl and hetaryl iodides". . p. 172 - 178. Retrieved 2001.
• 6、 Czakler, Matthias,Artner, Christine,Schubert, Ulrich. "Acetic acid mediated synthesis of phosphonate-substituted titanium oxo clusters". . p. 2038 - 2045. Retrieved 2014.
• 7、 Mikolajczyk,M. et al.. "-". . p. 2967 - 2972. Retrieved 1979.
• 8、 Kaboudin,Balakrishna. "Surface-mediated solid phase reactions: Microwave assisted Arbuzov rearrangement on the solid surface". . p. 2773 - 2776. Retrieved 2001.
• 9、 Singh, Anil K.,Kanvah, Sriram. "Photophysical studies of substituted 1,2-diarylethenes: Twisted intramolecular charge transfer fluorescence in dimethoxycyano-substituted 1,2-diarylethene". . p. 395 - 401. Retrieved 2001.
• 10、 Yang, Ling,Tan, Dong-Hang,Fan, Wen-Xin,Liu, Xu-Ge,Wu, Jia-Qiang,Huang, Zhi-Shu,Li, Qingjiang,Wang, Honggen. "Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates". . p. 3454 - 3458. Retrieved 2021.