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Bis(hydroxymethyl)phenylphosphine, also known as bis(hydroxymethyl)phenylphosphane, is an organophosphorus compound with the chemical formula C8H11O2P. It is a colorless liquid at room temperature and is soluble in common organic solvents. BIS(HYDROXYMETHYL)PHENYLPHOSPHINE is characterized by a phenyl group (C6H5) bonded to a phosphorus atom, which in turn is connected to two hydroxymethyl groups (CH2OH). It is used as a reagent in organic synthesis, particularly in the formation of phosphine ligands for transition metal complexes, and as a precursor in the production of various phosphorus-containing compounds. Due to its reactivity, it is important to handle bis(hydroxymethyl)phenylphosphine with care, typically under an inert atmosphere to prevent unwanted side reactions.

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  • 3127-08-0 Structure
  • Basic information

    1. Product Name: BIS(HYDROXYMETHYL)PHENYLPHOSPHINE
    2. Synonyms: (phenylphosphinidene)bismethanol;(phenylphosphinidene)di-methano;(phenylphosphinidene)dimethanol;BIS(HYDROXYMETHYL)PHENYLPHOSPHINE
    3. CAS NO:3127-08-0
    4. Molecular Formula: C8H11O2P
    5. Molecular Weight: 170.15
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 3127-08-0.mol
  • Chemical Properties

    1. Melting Point: 56-58°C
    2. Boiling Point: 305.1°Cat760mmHg
    3. Flash Point: 138.3°C
    4. Appearance: /
    5. Density: g/cm3
    6. Vapor Pressure: 0.000367mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: BIS(HYDROXYMETHYL)PHENYLPHOSPHINE(CAS DataBase Reference)
    11. NIST Chemistry Reference: BIS(HYDROXYMETHYL)PHENYLPHOSPHINE(3127-08-0)
    12. EPA Substance Registry System: BIS(HYDROXYMETHYL)PHENYLPHOSPHINE(3127-08-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. RIDADR: UN2811
    5. WGK Germany:
    6. RTECS:
    7. HazardClass: 6.1
    8. PackingGroup: III
    9. Hazardous Substances Data: 3127-08-0(Hazardous Substances Data)

3127-08-0 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 3127-08-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,2 and 7 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 3127-08:
(6*3)+(5*1)+(4*2)+(3*7)+(2*0)+(1*8)=60
60 % 10 = 0
So 3127-08-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H11O2P/c9-6-11(7-10)8-4-2-1-3-5-8/h1-5,9-10H,6-7H2

3127-08-0 Well-known Company Product Price

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  • Alfa Aesar

  • (H27733)  Bis(hydroxymethyl)phenylphosphine   

  • 3127-08-0

  • 100mg

  • 539.0CNY

  • Detail
  • Alfa Aesar

  • (H27733)  Bis(hydroxymethyl)phenylphosphine   

  • 3127-08-0

  • 500mg

  • 1656.0CNY

  • Detail

3127-08-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name [hydroxymethyl(phenyl)phosphanyl]methanol

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3127-08-0 SDS

3127-08-0Relevant articles and documents

Synthesis of first representatives of 46-membered P,N,O-containing cyclophanes and their transition metal complexes

Nikolaeva, Yu. A.,Balueva,Ignat'eva,Musina,Karasik

, p. 1319 - 1324 (2016)

A condensation of phenyl- or l-menthylphosphine with formaldehyde and 4,4′-bis-(4′-aminophenoxy)biphenyl proceeding as a covalent self-assembly gave rise to the first representatives of 46-membered P,N,O-containing cyclophanes, namely, 13,17,83,87-tetra-R-3,6,10,13-tetraoxa-1,8(1,5)-di(1,5-diaza-3,7-diphosphacyclooctana)-2,4,5,7,9,11,12,14(1,4)-octabenzenacyclotetradecaphanes (R = Ph (1), l-Ment (2)). The cage macrocyclic tetraphosphine 2 reacted with (cyclooctadiene)dichloroplatinum(ii) and -palladium(ii), as well as with (tetrahydrofuran)pentacarbonyltungsten(0) with the formation of binuclear complexes, in which the metal atoms are coordinated to 1,5-diaza-3,7-diphosphacyclooctane fragments by the P,P-chelate mode.

New aminomethylphosphines with cyanophenyl substituents at the nitrogen atoms

Spiridonova,Balueva,Krivolapov,Litvinov,Musina,Karasik,Sinyashin

, p. 2487 - 2494 (2013)

A condensation of bis(hydroxymethyl)arylphosphines with 3- and 4-aminobenzonitriles leads to the corresponding 3,7-diaryl-1,5-bis(cyanophenyl)- 1,5-diaza-3,7-diphosphacyclooctanes. Acyclic (aryl)bis[N-(2-cyanophenyl) aminomethyl]phosphines are formed in the case of 2-aminobenzonitrile. Molecular and crystalline structure of the compounds obtained was studied by X-ray diffraction analysis.

Synthesis of aminomethylphosphines with triazaadamantane fragments

Kuznetsov,Balueva,Serova,Nikonov

, p. 899 - 902 (2001)

The reaction of (hydroxymethyl)diphenylphosphine with 7-amino-1,3,5-triazaadamantane, followed by ready oxidation of the initially formed aminomethylphosphine gave diphenyl[(1,3,5-triazaadamantan-7-yl)aminomethyl]phosphine oxide. The reactions of bis(hydr

Process for preparation of phosphorane and phosphonyl compounds

-

, (2021/06/06)

The invention relates to the field of new materials of fine chemicals, in particular to a new safe, convenient, mild, efficient, environment-friendly and economical preparation process technology of phosphorane and phosphonyl compounds.

Catalyst Pendent-Base Effects on Cyclization of Alkynyl Amines

Stubbs, James M.,Chapple, Devon E.,Boyle, Paul D.,Blacquiere, Johanna M.

, p. 3694 - 3702 (2018/08/06)

A family of [CpRu(PP)(MeCN)]PF6 complexes (2 a–e and 4) were prepared in which the bis-phosphine ligand contains a pendent tertiary amine in the second-coordination sphere. 2 a–e contain PPh2NR′2 ligands with two amine groups as the pendent base. Complex 4 has the PPh2NPh1 ligand with only one pendent amine. The catalytic performance of 2 a–e and 4 were assessed in the cyclization of 2-ethynyl aniline and 2-ethynylbenzyl alcohol. It was revealed that the positioning of the pendent amine near the metal active site is essential for high catalyst performance. A comparison of PPh2NR′2 catalysts (2 a–e) showed minimal difference in performance as a function of pendent amine basicity. Rather, only a threshold basicity – in which the pendent amine was more basic than the substrate – was required for high performance.

Synthesis and Structure of N-Pyridyl-Containing Cyclic Aminomethylphosphines

Spiridonova, Yu. S.,Musina,Dayanova,Naumova,Litvinov,Karasik

, p. 2257 - 2262 (2019/01/04)

N-pyridyl-containing cyclic aminomethylphosphines have been prepared via condensation of the corresponding bis(hydroxymethyl)arylphosphines with p-aminopyridine and m-aminomethylpyridine.

Light-driven hydrogen production from aqueous solutions based on a new Dubois-type nickel catalyst

Zhou,Yang,Huang

, p. 7471 - 7475 (2017/04/04)

In this work, we report a new photocatalytic system that links multifunctional semiconductor nanocrystals with emerging water-soluble molecular catalysts made of earth-abundant elements for H2 generation [Ni(P2RN2R′)2(BF4)2]4-, R = Ph, R′ = [PhSO3]- (NiS). This noble metal free hybrid exhibits remarkable catalytic activity with a turnover number of 511 for H2 production and a photon-to-H2 conversion efficiency of 12.5%. The mechanistic insight into such high efficiency in this photocatalytic system was examined using a combination of steady-state emission and time-resolved absorption spectroscopy.

Coordination and conformational isomers in mononuclear iron complexes with pertinence to the [FeFe] hydrogenase active site

Orthaber, Andreas,Karnahl, Michael,Tschierlei, Stefanie,Streich, Daniel,Stein, Matthias,Ott, Sascha

, p. 4537 - 4549 (2014/03/21)

A series of six mononuclear iron complexes of the type [Fe(X-bdt)(P R2NPh2)(CO)] (PR 2NPh2 = 1,5-diaza-3,7-diphosphaoctane, bdt = benzenedithiolate with X = H, Cl2 or Me and R = Ph, Bn, Cyc or tert-Bu) was prepared. This new class of penta-coordinate iron complexes contains a free coordination site and a pendant base as essential structural features of the [FeFe]-hydrogenase active site. The bidentate nature of the PR2NPh2 ligands was found to be crucial for the preferential formation of coordinatively unsaturated penta-coordinate complexes, which is supported by first principle calculations. IR-spectroscopic data suggest the presence of coordination isomers around the metal center, as well as multiple possible conformers of the PR 2NPh2 ligand. This finding is further corroborated by X-ray crystallographic and computational studies. 31P{1H}-NMR- and IR-spectroscopic as well as electrochemical measurements show that the electronic properties of the complexes are strongly, and independently, influenced by the P-substituents at the PR2NPh2 ligand as well as by modifications of the bdt bridge. These results illustrate the advantages of this modular platform, which allows independent and selective tuning through site specific modifications. Potential catalytic intermediates, namely singly reduced and protonated complexes, have been further investigated by spectroscopic methods and exhibit remarkable stability. Finally, their general capacity for electro-catalytic reduction of protons to molecular hydrogen was verified.

Electrocatalytic oxidation of formate by [Ni(PR 2NR′2)2(CH3CN)] 2+ complexes

Galan, Brandon R.,Schoeffel, Julia,Linehan, John C.,Seu, Candace,Appel, Aaron M.,Roberts, John A. S.,Helm, Monte L.,Kilgore, Uriah J.,Yang, Jenny Y.,Dubois, Daniel L.,Kubiak, Clifford P.

experimental part, p. 12767 - 12779 (2011/10/05)

[Ni(PR2NR′2) 2(CH3CN)]2+ complexes with R = Ph, R′ = 4-MeOPh or R = Cy, R′ = Ph, and a mixed-ligand [Ni(PR 2NR′2)(PR′′ 2NR′

Synthesis of novel paracyclophanes with linear P,N-containing spacers

Ignat'eva,Balueva,Karasik,Kulikov,Kozlov,Latypov,Loennecke,Hey-Hawkins,Sinyashin

, p. 1828 - 1837 (2008/09/20)

Condensation of bis(hydroxymethyl)mesityl-and bis(hydroxymethyl) phenylphosphines with N,N′-disubstituted bis(4-aminophenyl)methanes and bis(4-amino-3-carboxyphenyl)methane occurred as covalent self-assembly spontaneously giving a mixture of trans-and cis-diastereomers of 1,5,19,23-tetra-R′-3,21-di-R-1,5,19,23-tetraaza-3,21-diphospha[5.1.5.1] paracyclophanes as the major products. The trans-isomer (R is mesityl; R′ is methyl) was isolated in the individual state and structurally characterized by X-ray diffraction analysis. Sulfurization of macrocyclic diphosphines (R = Ph; R′ is 3-pyridylmethyl or 4-pyridylmethyl) gave the corresponding diphosphine disulfides, the trans-stereoisomer being isolated in the individual state.

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