tert-Butyl(phenyl)phosphine oxide

Base Information

• Chemical Name: tert-Butyl(phenyl)phosphine oxide
• CAS No.: 6057-79-0
• Molecular Formula: C₁₀H₁₅OP
• Molecular Weight: 182.202
• DSSTox Substance ID: DTXSID80422605
• Mol file: 6057-79-0.mol

Synonyms:tert-Butyl(phenyl)phosphine oxide;6057-79-0;Phosphine oxide, (1,1-dimethylethyl)phenyl-;t-butylphenylphosphine oxide;SCHEMBL1683358;DTXSID80422605;BJQBKYYLWCDABM-UHFFFAOYSA-N;tert-Butyl(phenyl)phosphine oxide #;CS-0203250

Chemical Property of tert-Butyl(phenyl)phosphine oxide

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 181.078227064
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[P+](=O)C1=CC=CC=C1

Technology Process of tert-Butyl(phenyl)phosphine oxide

There total 117 articles about tert-Butyl(phenyl)phosphine oxide 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: 93.0%

tert-Butylphenylphosphine oxide (98976-30-8,57956-51-1,6057-79-0,82945-11-7) + Diethyl (2-methylphenyl)methyl phosphate → (S)-(-)-t-butyl(phenyl)phosphine oxide (6057-79-0,57956-51-1,82945-11-7) + (R)-tert-butyl(2-methylbenzyl)(phenyl)phosphine oxide

Guidance literature:

With rubidium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; C₃₉H₅₀NOPS; In acetonitrile; at 55 ℃; for 114h; Inert atmosphere;

Reference yield: 87.0%

(Rp)-(+)-tert-Butylphenylphosphinothioic acid (54100-47-9) → (S)-(-)-t-butyl(phenyl)phosphine oxide (6057-79-0,57956-51-1,82945-11-7)

Guidance literature:

With nickel; In ethanol; at 15 ℃; for 3h; ultrasonic irradiation;

DOI:10.1002/1099-0690(200009)2000:18<3205::AID-EJOC3205>3.0.CO;2-D

Reference yield: 72.0%

tert-Butylphenylphosphine oxide (98976-30-8,57956-51-1,6057-79-0,82945-11-7) + 1,3-phenylenebis(methylene) tetraethyl bis(phosphate) → (S)-(-)-t-butyl(phenyl)phosphine oxide (6057-79-0,57956-51-1,82945-11-7) + (Rp)-t-butyl(phenyl)phosphine oxide (82945-11-7,6057-79-0,57956-51-1) + (1R,1'R)-(1,3-phenylenebis(methylene))bis(tert-butyl(phenyl)phosphine oxide)

Guidance literature:

With rubidium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; C₃₆H₄₄NOPS; In acetonitrile; at 55 ℃; for 90h; enantioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.202111957

upstream raw materials:

P,P-dichlorophenylphosphine oxide

tert-butylmagnesium chloride

tert-butylchlorophenylphosphane

C₁₇H₁₅OSi^(1-)*K⁽¹⁺⁾

Downstream raw materials:

1,2-di-t-butyl-1,2-diphenyldiphosphane monoxide

(R_p)-(E)-But-2-enyl-tert-butylphenylphosphine oxide

(S)-((S)-tert-Butyl-phenyl-phosphinoyl)-phenyl-methanol

Refernces

• 1、 Dai, Qiang,Liu, Lu,Zhang, Junliang. "Palladium/Xiao-Phos-Catalyzed Kinetic Resolution of sec-Phosphine Oxides by P-Benzylation". supporting information. p. 27247 - 27252. Retrieved 2021/11/17.
• 2、 Trost, Barry M.,Spohr, Simon M.,Rolka, Alessa B.,Kalnmals, Christopher A.. "Desymmetrization of Phosphinic Acids via Pd-Catalyzed Asymmetric Allylic Alkylation: Rapid Access to P-Chiral Phosphinates". . p. 14098 - 14103. Retrieved 2019/10/11.