53772-42-2

Basic information

• Product Name: Benzenemethanol, a-(diphenylphosphino)-
• CAS NO: 53772-42-2
• Molecular Formula: C19H17OP
• Molecular Weight: 292.317
• Mol File: 53772-42-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-(diphenylphosphino)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(diphenylphosphino)-(53772-42-2)
• EPA Substance Registry System: Benzenemethanol, a-(diphenylphosphino)-(53772-42-2)

Safety Data

• Hazardous Substances Data: 53772-42-2(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 829-85-6 diphenylphosphane 
• 65567-06-8 lithium diphenylphosphide 
• 140-88-5 ethyl acrylate 

Downstream Products

• 1159262-05-1 Ph₂PCH(Ph)CH₂CH(PPh₂)OH 
• 100-52-7 benzaldehyde 
• 1159262-04-0 C₂₃H₂₃O₄P 
• 1159262-06-2 C₃₅H₃₄O₄P₂ 
• 1159262-07-3 C₂₂H₂₃O₂P 
• 18108-28-6 Methyldiphenyl-<α-hydroxybenzyl>-phosphoniumiodid 
• 1017-88-5 dimethyldiphenylphosphonium iodide 
• 20684-82-6 (diphenylphosphinoyl)(phenyl)methanol 
• 26086-02-2 (α-Methoxy-benzyl)-diphenyl-phosphinoxid 
• 95697-76-0 α-Ethoxybenzyl-diphenylphosphinoxid 

Relevant articles and documents

Synthesis of monohydroxy -methyl- and -ethyl-phosphines PPh2CHROH

The preparation of α-hydroxyphosphines PPh2CHROH with R = H (a), Ph (b) and Et (c), and β-hydroxyphosphines PPh2CHR'HROH (e-i) has been achieved in high yield by reaction of HPPh2 or LiPPh2 with RCHO or the oxides of cyclohexene (e), limonene (f), styrene

Reversible decomposition of mono(α-hydroxy)-phosphines and their reaction with α,β-unsaturated aldehydes

The mono(α-hydroxy)phosphines R2PCH(OH)R' (R = Ph, R' = H, Et, CH2Ph, Ph, p-X-C6H4 R = cyclohexyl, R' = Ph) are prepared under solvent-free conditions by a 1:1 reaction of Ph2PH with the appropriate aldehyde, and their stabilities (with respect to reversible dissociation into reactants), studied in DMSO, Et2O, and MeOH, increase with decreased basicity of the hydroxyphosphine; for example, for the Ph2PCH(OH)C6H4-p-X phosphines, stability decreases in the order: X = CN > Cl > F > H > Me > OMe. A 1:1 room-temperature reaction of the (α-hydroxy)phosphines (except for R' = H) with cinnamaldehyde in DMSO slowly yields the known mono- and di-phosphines Ph2PCH(Ph)CH2CHO (4a) and Ph2PCH(Ph)CH 2CH(PPh2)OH (10a), and the corresponding R'CHO aldehyde. In MeOH, the sequentially formed intermediates, PhCH=CHCH(OH)PPh2, PhCH(OH)C H=CHPPh2, and Ph2PCH(Ph)CH=CHOH, were detected en route to 4a and 10a. Reaction of cinnamaldehyde with Ph2PCH 2OH gives 4a and the hemiacetal Ph2PCH2OCH 2OH formed from the reactant hydroxyphosphine with the co-product formaldehyde. Reactions carried out in MeOH are faster because of the formation of hemiacetals from the phosphine-containing aldehyde products; thus, 4a is seen as Ph2PCH(Ph)CH2CH(OMe)(OH), which on dissolution in Et2O, reverts to the aldehyde. The reaction rates and equilibrium concentrations of the various species depend on the R' group of the reactant phosphine; the rates of consumption of the hydroxyphosphines in the reactions with cinnamaldehyde decrease in the order: Ph2PCH(OH)Ph > Ph 2PCH(OH)Et > Ph2PCH(OH)CH2Ph ? Ph 2PCH2OH. The reactivity pattern of Ph2PCH(OH)Ph with sinapaldehyde [3,5-(OMe)2-4-OH-cinnamaldehyde] in DMSO follows that seen for cinnamaldehyde. Reaction of Ph2PH with cinnamaldehyde in DMSO affords 4a and 10a via the same intermediates seen with the Ph 2PCH(OH)R' reagents, but these latter reactions are thought to occur via direct attack on cinnamaldehyde by the hydroxyphosphine rather than via Ph2PH.