Diethyl 4-methoxybenzylphosphonate

Base Information

• Chemical Name: Diethyl 4-methoxybenzylphosphonate
• CAS No.: 1145-93-3
• Molecular Formula: C12H19 O4 P
• Molecular Weight: 258.254
• Hs Code.: 2931900090
• European Community (EC) Number: 214-548-5
• DSSTox Substance ID: DTXSID101249159
• Nikkaji Number: J93.740A
• Mol file: 1145-93-3.mol

Synonyms:1145-93-3;Diethyl 4-methoxybenzylphosphonate;Diethyl (4-Methoxybenzyl)phosphonate;1-(diethoxyphosphorylmethyl)-4-methoxybenzene;ethoxy-ethylperoxy-[(4-methoxyphenyl)methyl]phosphane;Phosphonic acid, [(4-methoxyphenyl)methyl]-, diethyl ester;4-methoxybenzylphosphonic acid diethyl ester;1-(diethoxyphosphorylmethyl)-4-methoxy-benzene;Phosphonic acid, ((4-methoxyphenyl)methyl)-, diethyl ester;Phosphonic acid, P-[(4-methoxyphenyl)methyl]-, diethyl ester;SCHEMBL914036;C12H19O4P;4-(Diethylphosphonomethyl)anisole;DTXSID101249159;diethyl-(4-methoxybenzyl)phosphonate;MFCD00015662;diethyl (4-methoxybenzyl)-phosphonate;diethyl-(4-methoxybenzyl)-phosphonate;AKOS015852089;AS-70983;Diethyl 4-methoxybenzylphosphonate, >=98%;CS-0108718;D4000;diethyl [(4-methoxyphenyl)methyl]phosphonate;FT-0618929;(4-Methoxybenzyl)phosphonic Acid Diethyl Ester;Diethyl P-[(4-methoxyphenyl)methyl]phosphonate;A803203;J-003106;[(4-Methoxyphenyl)methyl]phosphonic acid diethyl ester;Phosphonic acid,p-[(4-methoxyphenyl)methyl]-,diethyl ester

Chemical Property of Diethyl 4-methoxybenzylphosphonate

Chemical Property:

• Vapor Pressure: 3.68E-05mmHg at 25°C
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 155 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 54.57000
• Density: 1.5 g/mL at 25 °C(lit.)
• LogP: 3.46130
• Water Solubility.: Not miscible in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 258.10209608
• Heavy Atom Count: 17
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

Diethyl 4-methoxybenzylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CC1=CC=C(C=C1)OC)OCC
• Uses: Diethyl 4-methoxybenzylphosphonate is used in synthesis of C-aryl glycosides. It acts as a reactant for synthesis of γ -Monofluorinated goniothalamin analogs via ring-opening hydrofluorination, stilbenoid derivatives with neuroprotective activity, resveratrol-chroman hybrids with antioxidant activity, Oligostilbenoids using regioselective cyclodehydration and arylation.

Technology Process of Diethyl 4-methoxybenzylphosphonate

There total 28 articles about Diethyl 4-methoxybenzylphosphonate 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%

p-Methoxybenzyl bromide (2746-25-0) + triethyl phosphite (122-52-1) → diethyl 4-methoxybenzylphosphonate (1145-93-3)

Guidance literature:

In water; at 80 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.joc.6b03037

Reference yield: 96.0%

triethyl phosphite (122-52-1) → diethyl 4-methoxybenzylphosphonate (1145-93-3)

Guidance literature:

at 130 ℃; for 24h;

DOI:10.1016/j.bmc.2004.08.008

Reference yield: 94.0%

p-Methoxybenzyl bromide (2746-25-0) + phosphonic acid diethyl ester (762-04-9) → diethyl 4-methoxybenzylphosphonate (1145-93-3)

Guidance literature:

With water; palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;

DOI:10.1055/s-0028-1087522

upstream raw materials:

triethyl phosphate

p-methoxybenzyl chloride

1-(4-Methoxy-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide

triethyl phosphite

Downstream raw materials:

1-methoxy-4-(4-styrylstyryl)benzene

trans-4-butyl-4′-methoxystilbene

3,5,4'-trimethoxy-trans-stilbene

(E)-1-methoxymethyloxy-2-(4-methoxy)styrylbenzene

Refernces

• 1、 Krzyzanowski, Adrian,Saleeb, Michael,Elofsson, Mikael. "Synthesis of Indole-, Benzo[ b]thiophene-, and Benzo[ b]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B". . p. 6650 - 6654. Retrieved 2018.
• 2、 Bag, Sukdev,Jayarajan, Ramasamy,Dutta, Uttam,Chowdhury, Rajdip,Mondal, Rahul,Maiti, Debabrata. "Remote meta-C–H Cyanation of Arenes Enabled by a Pyrimidine-Based Auxiliary". . p. 12538 - 12542. Retrieved 2017.
• 3、 Ash, Jeffrey,Cordero, Paula,Huang, Hai,Kang, Jun Yong. "Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids". . p. 6007 - 6014. Retrieved 2021/07/21.