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124-64-1

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124-64-1 Usage

Chemical Properties

Clear light pink or yellow-green solution

Uses

Different sources of media describe the Uses of 124-64-1 differently. You can refer to the following data:
1. Flame-retarding agent for cotton fabrics. May be used in combination with triethylolamine and urea (Roxel process) or with triethanolamine and tris(1-aziridinyl) phosphine oxide.
2. Tetrakis(hydroxymethyl)phosphonium chloride solution (80% in H2O) has been used as a reducing agent and stabilizing ligand for the synthesis of gold nanoparticles (AuNPs) from gold(III) chloride trihydrate (HAuCl4.3H2O). It is a tetra-functional, amine-reactive, aqueous crosslinker that can be used for tuning the properties of protein-based hydrogels for 3D cell encapsulation applications.

Definition

A crystalline compound made by the reaction of phosphine, formaldehyde, and hydrochloric acid.

General Description

Clear slightly viscous,colorless to yellow liquid (20% H2O solution).

Air & Water Reactions

Hygroscopic. Water soluble.

Reactivity Profile

Tetrakis(hydroxymethyl)phosphonium chloride reacts vigorously with oxidizers and alkalis. Reacts with cellulose.

Health Hazard

ACUTE/CHRONIC HAZARDS: Tetrakis(hydroxymethyl)phosphonium chloride may be corrosive. When heated to decomposition, it may emit very toxic fumes of POx, hydrogen chloride and bis(chloromethyl)ether. Decomposition of Tetrakis(hydroxymethyl)phosphonium chloride in an aqueous environment may produce phosphine, formaldehyde and hydrogen chloride.

Fire Hazard

Tetrakis(hydroxymethyl)phosphonium chloride is probably combustible.

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise it from AcOH and dry it at 100o in a vacuum. An 80% w/v aqueous solution has d4 1.33 [Reeves J Am Chem Soc 77 3923 1955]. [Beilstein 1 IV 3062.]

Check Digit Verification of cas no

The CAS Registry Mumber 124-64-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 4 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 124-64:
(5*1)+(4*2)+(3*4)+(2*6)+(1*4)=41
41 % 10 = 1
So 124-64-1 is a valid CAS Registry Number.
InChI:InChI=1/2C4H12O4P.C2H2O4/c2*5-1-9(2-6,3-7)4-8;3-1(4)2(5)6/h2*5-8H,1-4H2;(H,3,4)(H,5,6)/q2*+1;/p-2

124-64-1 Well-known Company Product Price

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  • Aldrich

  • (404861)  Tetrakis(hydroxymethyl)phosphoniumchloridesolution  80% in H2O

  • 124-64-1

  • 404861-100ML

  • 724.23CNY

  • Detail
  • Aldrich

  • (404861)  Tetrakis(hydroxymethyl)phosphoniumchloridesolution  80% in H2O

  • 124-64-1

  • 404861-500ML

  • 2,372.76CNY

  • Detail

124-64-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetrakis(hydroxymethyl)phosphonium chloride

1.2 Other means of identification

Product number -
Other names Phosphonium, tetrakis(hydroxymethyl)-, chloride

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:124-64-1 SDS

124-64-1Synthetic route

formaldehyd
50-00-0

formaldehyd

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Conditions
ConditionsYield
Stage #1: formaldehyd With phosphorus; bis(tri-n-butyltin)oxide; 1,1'-azobis(1-cyanocyclohexanenitrile) In ethanol at 20℃; for 16h;
Stage #2: With hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; Cooling with liquid nitrogen;
80%
With hydrogenchloride; phosphorus hydrogen; water at 80℃;
With hydrogenchloride; phosphan
hydrogenchloride
7647-01-0

hydrogenchloride

formaldehyd
50-00-0

formaldehyd

phosphorus

phosphorus

tri-n-butyl-tin hydride
688-73-3

tri-n-butyl-tin hydride

A

tributyltin chloride
1461-22-9

tributyltin chloride

B

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Conditions
ConditionsYield
Stage #1: phosphorus; tri-n-butyl-tin hydride In toluene at 20℃; for 16h; Schlenk technique; Irradiation;
Stage #2: formaldehyd In ethanol at 20℃; for 16h;
Stage #3: hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 2h; Cooling with liquid nitrogen;
A 96%
B 75%
formaldehyd
50-00-0

formaldehyd

phosphan
7803-51-2

phosphan

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Conditions
ConditionsYield
With hydrogenchloride In water passing PH3 in aq. formaldehyde soln. containing HCl at ambient temp.;;
With hydrogenchloride In water passing PH3 in aq. formaldehyde soln. containing HCl at 80 °C;;
With HCl In water passing PH3 in aq. formaldehyde soln. containing HCl at 80 °C;;
With HCl In water passing PH3 in aq. formaldehyde soln. containing HCl at ambient temp.;;
formaldehyd
50-00-0

formaldehyd

phosphine

phosphine

hydrochloric acid

hydrochloric acid

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Conditions
ConditionsYield
With water
formaldehyd
50-00-0

formaldehyd

tris(hydroxymethyl)phosphine
2767-80-8

tris(hydroxymethyl)phosphine

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Conditions
ConditionsYield
With hydrogenchloride
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

tris(hydroxymethyl)phosphine
2767-80-8

tris(hydroxymethyl)phosphine

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With potassium hydroxide In methanol; water at 15 - 20℃; for 0.166667h;
Stage #2: With zinc(II) chloride; sodium sulfite In methanol; water at 25℃; Reagent/catalyst; Solvent;
98.3%
With triethylamine at 60℃; for 4h; Elimination;95%
With sodium hydroxide
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

p-toluidine
106-49-0

p-toluidine

Tetrakis-(p-tolylamino-methyl)-phosphonium; chloride

Tetrakis-(p-tolylamino-methyl)-phosphonium; chloride

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;95%
In ethanol for 2h;
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

1-amino-naphthalene
134-32-7

1-amino-naphthalene

C44H40N4P(1+)*Cl(1-)

C44H40N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;100%
1-amino-4-chloronaphthalene
4684-12-2

1-amino-4-chloronaphthalene

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

C44H36Cl4N4P(1+)*Cl(1-)

C44H36Cl4N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;91%
4-Bromo-1-naphthylamine
2298-07-9

4-Bromo-1-naphthylamine

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

C44H36Br4N4P(1+)*Cl(1-)

C44H36Br4N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;85%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

4-methoxy-aniline
104-94-9

4-methoxy-aniline

C32H40N4O4P(1+)*Cl(1-)

C32H40N4O4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;97%
2-Fluoroaniline
348-54-9

2-Fluoroaniline

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

C28H28F4N4P(1+)*Cl(1-)

C28H28F4N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;97%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

C32H28N8P(1+)*Cl(1-)

C32H28N8P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;94%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

m-cyanoaniline
2237-30-1

m-cyanoaniline

C32H28N8P(1+)*Cl(1-)

C32H28N8P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;92%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

C32H28N8P(1+)*Cl(1-)

C32H28N8P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;91%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

4-chloro-aniline
106-47-8

4-chloro-aniline

C28H28Cl4N4P(1+)*Cl(1-)

C28H28Cl4N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;90%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

C28H28I4N4P(1+)*Cl(1-)

C28H28I4N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;97%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

C36H48N4P(1+)*Cl(1-)

C36H48N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;93%
4-propylaniline
2696-84-6

4-propylaniline

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

C40H56N4P(1+)*Cl(1-)

C40H56N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;85%
4-Isopropylaniline
99-88-7

4-Isopropylaniline

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

C40H56N4P(1+)*Cl(1-)

C40H56N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;87%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

4-fluoroaniline
371-40-4

4-fluoroaniline

C28H28F4N4P(1+)*Cl(1-)

C28H28F4N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;83%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

4-bromo-aniline
106-40-1

4-bromo-aniline

C28H28Br4N4P(1+)*Cl(1-)

C28H28Br4N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;83%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

methyl iodide
74-88-4

methyl iodide

[hydroxymethyl(methyl)phosphanyl]methanol
5958-52-1

[hydroxymethyl(methyl)phosphanyl]methanol

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With triethylamine at 20℃; for 18h;
Stage #2: methyl iodide In tetrahydrofuran at -40 - 20℃;
33%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

2-(trifluoromethyl)benzenamine
88-17-5

2-(trifluoromethyl)benzenamine

C32H28F12N4P(1+)*Cl(1-)

C32H28F12N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In methanol at 20℃; for 2h;72%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

tris(hydroxymethyl)phosphine sulfide
1067-13-6

tris(hydroxymethyl)phosphine sulfide

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With triethylamine In N,N-dimethyl-formamide; toluene at 60℃; for 1h; Inert atmosphere;
Stage #2: With octasulfur In N,N-dimethyl-formamide; toluene Inert atmosphere;
94%
potassium tetrachloropalladate(II)

potassium tetrachloropalladate(II)

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

C3H9Cl3O3PPd(1-)*K(1+)

C3H9Cl3O3PPd(1-)*K(1+)

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With potassium hydroxide In methanol
Stage #2: potassium tetrachloropalladate(II) In methanol for 336h; Inert atmosphere;
37%
4‐bromobutylferrocene
129826-46-6

4‐bromobutylferrocene

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Fc(CH2)4P(CH2OH)2
1599441-98-1

Fc(CH2)4P(CH2OH)2

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With potassium hydroxide In methanol for 1h; Schlenk technique; Inert atmosphere;
Stage #2: 4‐bromobutylferrocene In methanol for 21h; Schlenk technique; Inert atmosphere; Reflux;
Stage #3: With triethylamine In diethyl ether; water for 1h; Schlenk technique; Inert atmosphere;
ω-bromohexane ferrocene
136237-36-0

ω-bromohexane ferrocene

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Fc(CH2)6P(CH2OH)2
1599442-01-9

Fc(CH2)6P(CH2OH)2

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With potassium hydroxide In methanol for 1h; Schlenk technique; Inert atmosphere;
Stage #2: ω-bromohexane ferrocene In methanol; ethanol for 20.5h; Schlenk technique; Inert atmosphere; Reflux;
Stage #3: With triethylamine In diethyl ether; water for 2h; Schlenk technique; Inert atmosphere;
11-bromo-n-undecylferrocene

11-bromo-n-undecylferrocene

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Fc(CH2)11P(CH2OH)2
1599442-03-1

Fc(CH2)11P(CH2OH)2

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With potassium hydroxide In methanol for 1h; Schlenk technique; Inert atmosphere;
Stage #2: 11-bromo-n-undecylferrocene In methanol for 20.5h; Schlenk technique; Inert atmosphere; Reflux;
Stage #3: With triethylamine In diethyl ether; water for 2h; Schlenk technique; Inert atmosphere;
N-trimethyl-N-ruthenocenylammonium iodide

N-trimethyl-N-ruthenocenylammonium iodide

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

RcCH2P(CH2OH)2
1599442-18-8

RcCH2P(CH2OH)2

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With potassium hydroxide In methanol for 1h; Schlenk technique; Inert atmosphere;
Stage #2: N-trimethyl-N-ruthenocenylammonium iodide In methanol for 20h; Schlenk technique; Inert atmosphere; Reflux;
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

A

tri(4-fluorophenyl)phosphine oxide
18437-79-1

tri(4-fluorophenyl)phosphine oxide

B

bis(4-fluorophenyl)methylphosphine oxide

bis(4-fluorophenyl)methylphosphine oxide

Conditions
ConditionsYield
With 3 A molecular sieve; potassium carbonate; [(o-Tol)2PC6H4CH2Pd(OAc)]2 In N,N-dimethyl acetamide at 130℃; for 17h;A 10%
B 40%
With 3 A molecular sieve; potassium carbonate; [(o-Tol)2PC6H4CH2Pd(OAc)]2 In N,N-dimethyl acetamide at 130℃; for 17h;A 23 % Chromat.
B 13 % Chromat.
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 50℃; for 2h; Elimination;100%
With barium carbonate In water
With sodium hydroxide
With sodium hydroxide; dihydrogen peroxide at 70 - 80℃; for 1h;
With sodium hydroxide at 20℃; Rate constant;

124-64-1Relevant articles and documents

Hoffman, A.

, p. 1684 - 1688 (1921)

Synthesis of monophosphines directly from white phosphorus

Scott, Daniel J.,Cammarata, Jose,Schimpf, Maximilian,Wolf, Robert

, p. 458 - 464 (2021/04/09)

Monophosphorus compounds are of enormous industrial importance due to the crucial roles they play in applications such as pharmaceuticals, photoinitiators and ligands for catalysis, among many others. White phosphorus (P4) is the key starting material for the preparation of all such chemicals. However, current production depends on indirect and inefficient, multi-step procedures. Here, we report a simple, effective ‘one-pot’ synthesis of a wide range of organic and inorganic monophosphorus species directly from P4. Reduction of P4 using tri-n-butyltin hydride and subsequent treatment with various electrophiles affords compounds that are of key importance for the chemical industry, and it requires only mild conditions and inexpensive, easily handled reagents. Crucially, we also demonstrate facile and efficient recycling and ultimately catalytic use of the tributyltin reagent, thereby avoiding the formation of substantial Sn-containing waste. Accessible, industrially relevant products include the fumigant PH3, the reducing agent hypophosphorous acid and the flame-retardant precursor tetrakis(hydroxymethyl)phosphonium chloride. [Figure not available: see fulltext.]

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