16523-54-9 Usage
Description
Dicyclohexylchlorophosphine, also known as Chlorodicyclohexylphosphine, is a clear colorless liquid that serves as a versatile chemical intermediate and reactant in the synthesis of various phosphines and ligands. It is widely utilized in the pharmaceutical industry and in Pd-catalyzed cross-coupling reactions.
Uses
1. Pharmaceutical Industry:
Dicyclohexylchlorophosphine is used as a pharmaceutical intermediate for the synthesis of various compounds with potential therapeutic applications.
2. Chemical Synthesis:
Dicyclohexylchlorophosphine is used as a reactant in the synthesis of several ligands, which are essential in Pd-catalyzed cross-coupling reactions. These ligands include:
a. 1,2-Bis(dicyclohexylphosphinoxy)ethane ligand, which is synthesized by reacting Dicyclohexylchlorophosphine with ethylene glycol in the presence of triethylamine via Michaelis-Arbuzov type rearrangements.
b. 1,1,2,2-tetracyclohexyldiphosphine monosulfide ligand, which is obtained by treating Dicyclohexylchlorophosphine with LiS.
c. Dicyclohexylphosphine oxide, which is a starting material for the preparation of other ligands.
d. Phosphino substituted N-aryl pyrroles, which are used in various chemical reactions.
e. Di-tert-butyl((dicyclohexylphosphino)methyl)phosphine, a ligand with specific applications in catalysis.
f. Dicyclohexylcyclopentylphosphine, another ligand used in Pd-catalyzed cross-coupling reactions.
Precautions
Store in cool, dry conditions in well sealed containers. Protect from humidity and water. Store under dry inert gas. It is sensitive to air and moisture. Incompatible with strong oxidizing agents.
Check Digit Verification of cas no
The CAS Registry Mumber 16523-54-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,5,2 and 3 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 16523-54:
(7*1)+(6*6)+(5*5)+(4*2)+(3*3)+(2*5)+(1*4)=99
99 % 10 = 9
So 16523-54-9 is a valid CAS Registry Number.
InChI:InChI=1/C12H22ClP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2
16523-54-9Relevant articles and documents
The Use of Catalytic Amounts of CuCl and Other Improvements in the Benzyne Route to Biphenyl-Based Phosphine Ligands
Kaye, Steven,Fox, Joseph M.,Hicks, Frederick A.,Buchwald, Stephen L.
, p. 789 - 794 (2001)
Biphenyl-based phosphine ligands can be prepared on a significantly larger scale than previously possible as a result of the following discoveries and improvements to the original experimental procedure: the finding that CuCl catalyzes the coupling of hindered dialkylchlorophosphines with Grignard reagents; the development of conditions that permit ClPCy2 to be prepared and utilized in situ; the development of a more reliable large-scale preparation of 2-dimethylaminophenylmagnesium halide.
Zheda-phos for general α-monoarylation of acetone with aryl chlorides
Li, Pengbin,Lue, Bo,Fu, Chunling,Ma, Shengming
supporting information, p. 1255 - 1259 (2013/06/27)
A new, readily available, and air-stable monophosphine ligand, i.e., Zheda-Phos, has been developed for the general and highly effective palladium-catalyzed monoarylation of acetone with aryl chlorides. The reaction rate is of first-order dependence with the aryl chloride. Copyright
2,6-diisopropoxyphenyl(dicyclohexyl)phosphine: A new ligand for palladium-catalyzed amination reactions of aryl chlorides with potassium hydroxide as the base
Lue, Bo,Li, Pengbin,Fu, Chunling,Xue, Liqin,Lin, Zhenyang,Ma, Shengming
experimental part, p. 100 - 112 (2011/04/12)
A new, readily available monophosphine tetrafluoroborate salt [L2·HBF4] was developed for the palladium-catalyzed amination reaction of aryl chlorides in moderate to high yields with the cheap and easily available potassium hydroxide as the base. The reaction enjoys a wide scope, lower reaction temperatures, shorter reaction times, high yields, and low catalyst loading when compared to some of same amination reactions reported in the literature. Based on a kinetic study, 31P NMR measurements, and DFT calculations, a mechanism involving a 1:1 Pd/L species is proposed.