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1067-12-5 Usage

General Description

Phosphinylidynetrimethanol, also known as trimethylphosphine oxide, is a chemical compound with the molecular formula C3H9OP. It is a colorless liquid that is highly flammable and has a strong odor. phosphinylidynetrimethanol is commonly used as a solvent and stabilizer in various chemical reactions and industrial processes. It is also used as a flame retardant in some materials. Phosphinylidynetrimethanol has a wide range of applications in the production of pharmaceuticals, agricultural chemicals, and other organic compounds. However, it is important to handle this compound with caution due to its flammable nature and potential health hazards if not properly handled.

Check Digit Verification of cas no

The CAS Registry Mumber 1067-12-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,6 and 7 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1067-12:
(6*1)+(5*0)+(4*6)+(3*7)+(2*1)+(1*2)=55
55 % 10 = 5
So 1067-12-5 is a valid CAS Registry Number.
InChI:InChI=1/C3H9O4P/c4-1-8(7,2-5)3-6/h4-6H,1-3H2

1067-12-5SDS

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 bis(hydroxymethyl)phosphorylmethanol

1.2 Other means of identification

Product number -
Other names phosphoryltrimethanol

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:1067-12-5 SDS

1067-12-5Synthetic route

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;
tris(hydroxymethyl)phosphine
2767-80-8

tris(hydroxymethyl)phosphine

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With air at 80℃; for 5h; Reagent/catalyst; Temperature;95%
With dihydrogen peroxide
With oxygen at 50 - 60℃; for 5h; Green chemistry;220 g
With dihydrogen peroxide In water at 20℃;
With air In water; toluene at 90℃; for 16h;
formaldehyd
50-00-0

formaldehyd

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
Stage #1: formaldehyd With phosphan In 5,5-dimethyl-1,3-cyclohexadiene at 68℃; under 30003 Torr; for 3h; Inert atmosphere; Autoclave; Large scale;
Stage #2: With dihydrogen peroxide In 5,5-dimethyl-1,3-cyclohexadiene at 55℃; for 5h; Solvent; Pressure; Temperature; Inert atmosphere; Large scale;
95%
tetrakis(hydroxymethyl)phosphonium sulfate
77350-08-4

tetrakis(hydroxymethyl)phosphonium sulfate

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium sulfate With barium(II) hydroxide In water at 60℃;
Stage #2: With dihydrogen peroxide In water at 20℃;
94%
diiodotris<(trimethylsiloxy)methyl>phosphorane
74858-13-2

diiodotris<(trimethylsiloxy)methyl>phosphorane

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With methanol93%
1-iodo-butane
542-69-8

1-iodo-butane

tris(hydroxymethyl)phosphine
2767-80-8

tris(hydroxymethyl)phosphine

A

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

B

butyl bis(hydroxymethyl)phosphineoxide
17919-46-9

butyl bis(hydroxymethyl)phosphineoxide

Conditions
ConditionsYield
Stage #1: 1-iodo-butane; tris(hydroxymethyl)phosphine In methanol at 0 - 70℃; for 4.5h; Inert atmosphere; Schlenk technique;
Stage #2: With triethylamine at 60℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #3: With dihydrogen peroxide In methanol for 2h;
A 12%
B 45%
tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

A

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

B

tris(hydroxymethyl)phosphine
2767-80-8

tris(hydroxymethyl)phosphine

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium chloride With sodium hydroxide In ethanol at 20℃; for 1.25h;
Stage #2: With 4 A molecular sieve; potassium carbonate for 6h;
A 20%
B n/a
tetrakis(hydroxymethyl)phosphonium sulphate

tetrakis(hydroxymethyl)phosphonium sulphate

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
Stage #1: tetrakis(hydroxymethyl)phosphonium sulphate With sodium hydroxide
Stage #2:
0.1%
chlorure de tetrakis(hydroxymethyl)phosphonium
16980-25-9

chlorure de tetrakis(hydroxymethyl)phosphonium

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With sodium hydroxide
tris(acetoxymethyl)phosphine oxide
4851-97-2

tris(acetoxymethyl)phosphine oxide

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With hydrogenchloride In methanol
chlorure de tetrakis(hydroxymethyl)phosphonium
16980-25-9

chlorure de tetrakis(hydroxymethyl)phosphonium

A

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

B

tris(hydroxymethyl)phosphine
2767-80-8

tris(hydroxymethyl)phosphine

Conditions
ConditionsYield
With sodium hydroxide
tris<(trimethylsiloxy)methyl>phosphine
63245-87-4

tris<(trimethylsiloxy)methyl>phosphine

A

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

B

tris(chloromethyl)phosphine oxide
4851-89-2

tris(chloromethyl)phosphine oxide

C

bis(chloromethyl)(hydroxymethyl)phosphine oxide
35449-79-7

bis(chloromethyl)(hydroxymethyl)phosphine oxide

D

(chloromethyl)bis(hydroxymethyl)phosphine oxide

(chloromethyl)bis(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With methanol; chlorine 1) CH2Cl2, 20 deg C, 1 h, 2) 20 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;
tris<(trimethylsiloxy)methyl>phosphine oxide
63245-88-5

tris<(trimethylsiloxy)methyl>phosphine oxide

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With hydrogenchloride; methanol 1) C6H6; Yield given. Multistep reaction;
dichlorotris<(trimethylsiloxy)methyl>phosphorane
74858-10-9

dichlorotris<(trimethylsiloxy)methyl>phosphorane

A

methylene chloride
74-87-3

methylene chloride

B

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

C

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With methanol In dichloromethane at -70℃; Yield given;
dibromotris<(trimethylsiloxy)methyl>phosphorane
74872-34-7

dibromotris<(trimethylsiloxy)methyl>phosphorane

A

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

B

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With methanol In dichloromethane at -70℃; Yield given;
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

1,4-dioxo-2,6,7-trioxa-1,4-diphosphabicyclo[2.2.2]octane
4726-80-1

1,4-dioxo-2,6,7-trioxa-1,4-diphosphabicyclo[2.2.2]octane

Conditions
ConditionsYield
With sodium methylate; phosphorous acid trimethyl ester at 150℃; for 5h; Temperature; Reagent/catalyst; Inert atmosphere;96.2%
With trimethyl phosphite; sodium methylate at 150℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere;95.5%
With trichlorophosphate In 1,4-dioxane; water at 10 - 100℃; for 6h; Solvent; Temperature;95.3%
With phosphoric acid triphenyl ester; sodium methylate at 150℃; for 8h; Reagent/catalyst; Temperature; Inert atmosphere;93.2%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

tris-O, O-2-hydroxymethylphosphonophosphoryl phosphonitrile

tris-O, O-2-hydroxymethylphosphonophosphoryl phosphonitrile

Conditions
ConditionsYield
With pyridine; 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine at 130℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere;96.1%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

C4H10O5P2

C4H10O5P2

Conditions
ConditionsYield
With sodium methylate; methoxybenzene at 150℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere;95.9%
P,P-dichlorophenylphosphine oxide
824-72-6

P,P-dichlorophenylphosphine oxide

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

C9H12O5P2

C9H12O5P2

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 140℃; for 6h; Solvent; Temperature;95.3%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

1,1-dimethyl-1-sila-2,6-dioxa-4-oxy-4-phospha-4-hydroxymethylcyclohexane

1,1-dimethyl-1-sila-2,6-dioxa-4-oxy-4-phospha-4-hydroxymethylcyclohexane

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 40 - 130℃; for 13h; Solvent; Temperature;95.3%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

4-oxo-2,6,7-trioxa-1,4-diphosphabicyclo[2.2.2]octane

4-oxo-2,6,7-trioxa-1,4-diphosphabicyclo[2.2.2]octane

Conditions
ConditionsYield
With phosphorus trichloride In acetonitrile at 0 - 80℃; for 4h; Reagent/catalyst; Temperature;94.4%
With triphenyl phosphite; sodium methylate at 150℃; for 7h; Temperature; Reagent/catalyst; Inert atmosphere;94.7%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

phenylthiophosphonic acid dichloride
3497-00-5

phenylthiophosphonic acid dichloride

C9H12O4P2S

C9H12O4P2S

Conditions
ConditionsYield
at 20 - 160℃; for 7h; Temperature; Inert atmosphere;94.2%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

tris(chloromethyl)phosphine oxide
4851-89-2

tris(chloromethyl)phosphine oxide

Conditions
ConditionsYield
With phosphorus pentachloride In chloroform at 60℃; Chlorination;86%
With pyridine; thionyl chloride
With hydrogenchloride at 180 - 200℃; for 8h; Yield given;
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

tris(allyloxymethyl)phosphine oxide

tris(allyloxymethyl)phosphine oxide

Conditions
ConditionsYield
Stage #1: tri(hydroxymethyl)phosphine oxide With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 35℃; Green chemistry;
Stage #2: 3-chloroprop-1-ene In water at 0 - 50℃; for 12h; Green chemistry;
80%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 0 - 45℃; for 12h;75%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

propargyl bromide
106-96-7

propargyl bromide

tris(prop-2-yn-1-yloxymethyl)phosphane oxide

tris(prop-2-yn-1-yloxymethyl)phosphane oxide

Conditions
ConditionsYield
Stage #1: tri(hydroxymethyl)phosphine oxide With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 35℃; Williamson Ether Synthesis;
Stage #2: propargyl bromide In water; toluene at 0 - 50℃; for 12h; Williamson Ether Synthesis;
62.9%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

4,4'-dimethoxytrityl chloride
40615-36-9

4,4'-dimethoxytrityl chloride

C24H27O6P

C24H27O6P

Conditions
ConditionsYield
With pyridine at 20℃; for 20h;51%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

4,4'-dimethoxytrityl chloride
40615-36-9

4,4'-dimethoxytrityl chloride

(bis-(DMT-oxymethyl))(hydroxymethyl)phosphine oxide

(bis-(DMT-oxymethyl))(hydroxymethyl)phosphine oxide

Conditions
ConditionsYield
With pyridine at 20℃; for 20h;50%
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

sirolimus
53123-88-9

sirolimus

(21E,23E,25E,26E,31R,32S,33R,34R,36S,38S,41S,42R,43R,52R)-40-[bis(hydroxymethyl)phosphorylmethoxy]-42,52-dihydroxy-41-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl]-1-methyl-ethyl]-43-methoxy-31,32,33,34,44,45-hexamethyl-65,66-dioxa-53-azatricyclohexatriaconta-21,23,25(44),26(45)-tetraene-46,47,48,49,50-pentone

(21E,23E,25E,26E,31R,32S,33R,34R,36S,38S,41S,42R,43R,52R)-40-[bis(hydroxymethyl)phosphorylmethoxy]-42,52-dihydroxy-41-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl]-1-methyl-ethyl]-43-methoxy-31,32,33,34,44,45-hexamethyl-65,66-dioxa-53-azatricyclohexatriaconta-21,23,25(44),26(45)-tetraene-46,47,48,49,50-pentone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran; water at 25℃; for 4h;9%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

tris-lauroyloxymethyl-phosphine oxide
4851-93-8

tris-lauroyloxymethyl-phosphine oxide

Conditions
ConditionsYield
With water
tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

bis(hydroxymethyl)phosphinic acid
2074-67-1

bis(hydroxymethyl)phosphinic acid

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

bis(hydroxymethyl)phosphinic acid
2074-67-1

bis(hydroxymethyl)phosphinic acid

Conditions
ConditionsYield
With sodium hydroxide
1-bromo-butane
109-65-9

1-bromo-butane

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

tris-butoxymethyl-phosphane oxide
53695-03-7

tris-butoxymethyl-phosphane oxide

Conditions
ConditionsYield
(i) NaOMe, benzene, (ii) /BRN= 1098260/; Multistep reaction;
methyl bromide
74-83-9

methyl bromide

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

tris-methoxymethyl-phosphane oxide
41528-71-6

tris-methoxymethyl-phosphane oxide

Conditions
ConditionsYield
(i) NaOMe, benzene, (ii) /BRN= 1209223/, toluene; Multistep reaction;
ethyl bromide
74-96-4

ethyl bromide

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

tris(ethoxymethyl)phosphine oxide
13830-01-8

tris(ethoxymethyl)phosphine oxide

Conditions
ConditionsYield
(i) NaOMe, benzene, (ii) /BRN= 1209224/, toluene; Multistep reaction;
formaldehyd
50-00-0

formaldehyd

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

(5-oxo-5λ5-[1,3,5]dioxaphosphinan-5-yl)-methanol
69805-21-6

(5-oxo-5λ5-[1,3,5]dioxaphosphinan-5-yl)-methanol

Conditions
ConditionsYield
at 180 - 200℃;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

tris<(trimethylsiloxy)methyl>phosphine oxide
63245-88-5

tris<(trimethylsiloxy)methyl>phosphine oxide

1-Bromopentane
110-53-2

1-Bromopentane

tri(hydroxymethyl)phosphine oxide
1067-12-5

tri(hydroxymethyl)phosphine oxide

tris-pentyloxymethyl-phosphane oxide
18982-80-4

tris-pentyloxymethyl-phosphane oxide

Conditions
ConditionsYield
(i) NaOMe, benzene, (ii) /BRN= 1730981/; Multistep reaction;

1067-12-5Relevant articles and documents

Filipescu et al.

, p. 821 (1963)

Study on thermal degradation and combustion behavior of flame retardant unsaturated polyester resin modified with a reactive phosphorus containing monomer

Lin, Ying,Yu, Bin,Jin, Xin,Song, Lei,Hu, Yuan

, p. 49633 - 49642 (2016)

A halogen-free phosphorus-containing monomer (TAOPO) with a P-C bond was successfully synthesized and used as a co-curing agent to prepare intrinsic flame-retardant unsaturated polyester resin (FR-UPR) by radical bulk polymerization with different TAOPO content. The thermal degradation and flame retardancy of pure UPR and FR-UPR were investigated by thermogravimetric analysis (TGA), cone calorimetry tests and limiting oxygen index (LOI). As the phosphorus content increased to 3%, FR-UPR (URP-3) showed a lower peak heat release rate (PHRR) and total heat release (THR), reducing by 45.7% and 45.5% those of pure UPR, while the LOI value and char residue increased markedly. Besides, thermal-oxidative degradation behaviors of different UPR samples were characterized by real-time infrared spectrometry (RT-IR) and thermogravimetry-Fourier transform infrared (TG-FTIR) spectroscopy, revealing the degradation mechanism. Furthermore, the residual char of UPRs was investigated by scanning electron microscopy (SEM) and Raman spectroscopy. The results indicated that the incorporation of TAOPO into UPR could effectively prompt the UP matrix to form a more compact char layer which acted as a protective barrier to reduce heat release during combustion.

-

Grayson,M.

, p. 79 - 83 (1963)

-

Phosphorus-containing polymers from tetrakis-(hydroxymethyl)phosphonium sulfate iii. A new hydrolysis-resistant tris(allyloxymethyl)phosphine oxide and its thiol-ene reaction under ultraviolet irradiation

Tan, Zhiwei,Wu, Chengyan,Zhang, Min,Lv, Wenzhong,Qiu, Jinjun,Liu, Chengmei

, p. 41705 - 41713 (2014)

Two kinds of new phosphorus-containing crosslinked polymer materials were prepared via thiol-ene photopolymerization and their properties were studied. In order to prepare these crosslinked polymer materials, multifunctional monomer tris(allyloxymethyl)phosphine oxide (TAOPO) was synthesized from an eco-friendly raw material, tetrakis(hydroxymethyl) phosphonium sulfate (THPS). Crosslinked poly(phosphine oxide) networks were then produced by a thiol-ene reaction in which TAOPO reacts with the two kinds of polythiol under ultraviolet (UV) irradiation. The new crosslinked polymers possess long-term hydrolysis-resistance property because the monomer TAOPO contains a phosphorus-carbon bond. The crosslinked polymers have a high gel content, high dielectric constant, low dielectric loss, and excellent transparency with a high refractive index and high Abbe number. DMA and TGA results indicated that all cured poly(phosphine oxide) were uniform networks and exhibited a high thermal stability. This journal is

STABLE MODIFIED POLYMER POLYOL DISPERSIONS

-

Paragraph 0340-0341; 0352-0353, (2021/06/26)

The present invention relates to new stable modified polymer polyol dispersions. The modified polymer polyols of the present invention comprise at least one polyol and a stable dispersion of polymeric particles in the at least one polyol. There are also disclosed processes for the preparation of the herein described modified polymer polyols, and processes for preparing polyurethane materials containing them.

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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