Diethyl (3,3-dimethyl-2-oxobutyl)phosphonate

Base Information

• Chemical Name: Diethyl (3,3-dimethyl-2-oxobutyl)phosphonate
• CAS No.: 814-16-4
• Molecular Formula: C10H21 O4 P
• Molecular Weight: 236.248
• European Community (EC) Number: 212-393-8
• DSSTox Substance ID: DTXSID40231078
• Nikkaji Number: J193.196B
• Wikidata: Q83111895
• Mol file: 814-16-4.mol

Synonyms:814-16-4;Diethyl (3,3-dimethyl-2-oxobutyl)phosphonate;EINECS 212-393-8;diethyl(3,3-dimethyl-2-oxobutyl)phosphonate;SCHEMBL12446811;C10H21O4P;DTXSID40231078;AKOS004907025;1-(Diethoxyphosphinyl)-3,3-dimethyl-2-butanone

Chemical Property of Diethyl (3,3-dimethyl-2-oxobutyl)phosphonate

Chemical Property:

• Vapor Pressure: 0.000951mmHg at 25°C
• Boiling Point: 303.1°C at 760 mmHg
• Flash Point: 151°C
• PSA: 62.41000
• Density: 1.037g/cm³
• LogP: 2.86770
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 236.11774614
• Heavy Atom Count: 15
• Complexity: 245

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CC(=O)C(C)(C)C)OCC

Technology Process of Diethyl (3,3-dimethyl-2-oxobutyl)phosphonate

There total 13 articles about Diethyl (3,3-dimethyl-2-oxobutyl)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: 85.0%

Diethyl methylphosphonate (683-08-9) → diethyl (3,3-dimethyl-2-oxobutyl)phosphonate (814-16-4)

Guidance literature:

With n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -60 ℃;

Reference yield: 68.0%

phosphonic acid diethyl ester (762-04-9) + acetylpinacolin (7307-04-2) → diethyl (3,3-dimethyl-2-oxobutyl)phosphonate (814-16-4)

Guidance literature:

With dipotassium peroxodisulfate; silver(I) acetate; In water; N,N-dimethyl-formamide; at 85 ℃; for 24h; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201704910

Reference yield: 53.0%

Methyl pivalate (598-98-1) + diethyl iodomethanephosphonate (10419-77-9) → diethyl (3,3-dimethyl-2-oxobutyl)phosphonate (814-16-4)

Guidance literature:

With magnesium; trimethylphosphane; CoCl₂; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-2002-33653

upstream raw materials:

Diethyl methylphosphonate

pivaloyl chloride

1-Bromopinacolon

triethyl phosphite

Downstream raw materials:

(E)-2,2-dimethyl-6-phenylhex-5-en-3-one

(4E,6RS)-2,2-dimethyl-6-phenylhept-4-en-3-one

(Z)-2,2-dimethyl-6-phenylhept-5-en-3-one

(E)-2,2-dimethyl-6-phenylhept-5-en-3-one

Refernces

• 1、 Qi, Danyang,Dong, Wanrong,Peng, Zhihong,Zhang, Yingjun,An. "Mukaiyama reagent-promoted metal-free preparation of alkynyl sulfones and phosphonates under mild conditions". . . Retrieved 2019/08/01.
• 2、 Zhang, Yang,Zhang, Yanqin,Xiao, Jing,Peng, Zhihong,Dong, Wanrong,An, Delie. "Base-induced one-pot preparation of N- or P-substituted alkynes". supporting information. p. 7806 - 7815. Retrieved 2015/12/31.