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Dimethylphosphine oxide, an organophosphorus compound, is a versatile chemical with various applications in the field of organic chemistry. It is primarily used for the preparation of triacrylphosphine oxide, acting as an asymmetric catalyst, and in the synthesis of alkenyldiphenylphosphine oxides and Horner-Witting reagents. Furthermore, it serves as a capping ligand in organic chemistry.

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  • 7211-39-4 Structure
  • Basic information

    1. Product Name: DIMETHYLPHOSPHINE OXIDE
    2. Synonyms: Methylphosphinoylmethane;DIMETHYLPHOSPHINOUS ACID;DIMETHYLPHOSPHINE OXIDE;Einecs 230-591-2;Phosphine oxide, diMethyl-;Keto-Dimethyl-Phosphonium;Dimethylphosphine Oxide Dimethyl-Oxo-Phosphonium;Dimethyl-Oxophosphonium
    3. CAS NO:7211-39-4
    4. Molecular Formula: C2H7OP
    5. Molecular Weight: 78.050141
    6. EINECS: 230-591-2
    7. Product Categories: N/A
    8. Mol File: 7211-39-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 84.5 °C at 760 mmHg
    3. Flash Point: 4.906 °C
    4. Appearance: white solid to light yellow/liquid
    5. Density: N/A
    6. Vapor Pressure: 80.598mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
    9. Solubility: N/A
    10. Sensitive: air sensitive
    11. CAS DataBase Reference: DIMETHYLPHOSPHINE OXIDE(CAS DataBase Reference)
    12. NIST Chemistry Reference: DIMETHYLPHOSPHINE OXIDE(7211-39-4)
    13. EPA Substance Registry System: DIMETHYLPHOSPHINE OXIDE(7211-39-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 7211-39-4(Hazardous Substances Data)

7211-39-4 Usage

Uses

Used in Pharmaceutical Industry:
Dimethylphosphine oxide is used as a key intermediate in the preparation of substituted piperazine derivatives, which are DGKα/DGKζ inhibitors. These inhibitors have potential applications in the treatment of viral infections and cancer, making dimethylphosphine oxide an essential component in the development of new therapeutic agents.
Used in Organic Chemistry:
Dimethylphosphine oxide is utilized as an asymmetric catalyst in various organic reactions, facilitating the synthesis of enantiomerically pure compounds. This application is crucial in the production of pharmaceuticals, agrochemicals, and other specialty chemicals that require high levels of stereoselectivity.
Used in Synthesis of Reagents:
In the synthesis of alkenyldiphenylphosphine oxides and Horner-Witting reagents, dimethylphosphine oxide plays a significant role. These reagents are widely used in organic synthesis for the preparation of various organic compounds, including pharmaceuticals, agrochemicals, and materials.
Used in Capping Ligand Applications:
As a capping ligand in organic chemistry, dimethylphosphine oxide is employed to modify the properties of metal complexes, enhancing their stability, solubility, and reactivity. This application is particularly relevant in homogeneous catalysis and the development of new catalytic systems.

References

https://en.wikipedia.org/wiki/Dimethylphosphine_oxide http://www.sigmaaldrich.com/catalog/product/aldrich/287881?lang=en®ion=US Ganesan, Paramasivam, and S. Lakshmipathi. "Impact of heterogeneous passivation of trimethylphosphine oxide and di-methylphosphine oxide surface ligands on the electronic structure of Cd n Se n, (n =6, 15) quantum dots: A DFT study." Physica E: Low-dimensional Systems and Nanostructures 83(2016):284-296.

Check Digit Verification of cas no

The CAS Registry Mumber 7211-39-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,2,1 and 1 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 7211-39:
(6*7)+(5*2)+(4*1)+(3*1)+(2*3)+(1*9)=74
74 % 10 = 4
So 7211-39-4 is a valid CAS Registry Number.
InChI:InChI=1/C2H7OP/c1-4(2)3/h4H,1-2H3

7211-39-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name dimethyl(oxo)phosphanium

1.2 Other means of identification

Product number -
Other names dimethyl-oxo-phosphanium

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:7211-39-4 SDS

7211-39-4Synthetic route

methylmagnesium bromide
75-16-1

methylmagnesium bromide

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;88.79%
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 0.5h; Inert atmosphere;63.66%
In tetrahydrofuran at 0 - 20℃; for 5h;
methylmagnesium chloride
676-58-4

methylmagnesium chloride

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 0℃; for 4h;81.39%
In tetrahydrofuran Ambient temperature;80%
In tetrahydrofuran at 30℃; for 1h; Cooling with ice;70.8%
In tetrahydrofuran at 20 - 30℃; for 1h; Cooling with ice;70.8%
(i) THF, (ii) aq. K2CO3; Multistep reaction;
methylene chloride
74-87-3

methylene chloride

A

dimethylphosphinic acid sodium salt
16394-14-2

dimethylphosphinic acid sodium salt

B

methylphosphonic acid disodium salt
2914-38-7, 20677-21-8, 20677-23-0

methylphosphonic acid disodium salt

C

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

D

methylphosphonous acid sodium salt
87930-22-1

methylphosphonous acid sodium salt

Conditions
ConditionsYield
With sodium hydroxide; phase transfer catalyst; phosphorous Further byproducts given;A 0.5%
B 3.5%
C 5%
D 72%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
Stage #1: methylmagnesium chloride With phosphonic acid diethyl ester In tetrahydrofuran at 20 - 30℃; for 1h;
Stage #2: With potassium carbonate In tetrahydrofuran; water
70.8%
With phosphonic acid diethyl ester In tetrahydrofuran at 0 - 20℃; for 5h;
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With Bromotrichloromethane In neat (no solvent) at 25℃; for 0.5h;A 4%
B 50%
dimethyl sulfate
77-78-1

dimethyl sulfate

A

Trimethylphosphine oxide
676-96-0

Trimethylphosphine oxide

B

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With phosphorus; potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In 1,4-dioxane at 60 - 62℃;A 7%
B n/a
(dimethylamino)dimethylphosphine
683-84-1

(dimethylamino)dimethylphosphine

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With water
dimethylmethoxyphosphines-d0
20502-88-9

dimethylmethoxyphosphines-d0

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With water at -10℃;
dimethyl methylthiophosphinite
35449-60-6

dimethyl methylthiophosphinite

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With water
N,N-diethylamino-P,P-dimethylphosphine
685-93-8

N,N-diethylamino-P,P-dimethylphosphine

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With water
(diisopropylamino)(dimethyl)phosphine
53314-20-8

(diisopropylamino)(dimethyl)phosphine

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With sulfuric acid
C10H24O4P2
53723-04-9

C10H24O4P2

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With water In benzene
chlorodimethylphosphine
811-62-1

chlorodimethylphosphine

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
With methanol
With hydrogenchloride
dimethylphosphinic acid
3283-12-3

dimethylphosphinic acid

triphenylphosphine
603-35-0

triphenylphosphine

A

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

B

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
In chloroform-d1 for 96h;A n/a
B 23 %Spectr.
isoquinoline N-oxide
1532-72-5

isoquinoline N-oxide

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

tetramethyl pyrophosphate
690-49-3

tetramethyl pyrophosphate

C

dimethyl trichloromethylphosphonate
29238-81-1

dimethyl trichloromethylphosphonate

D

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

E

dimethyl isoquinolin-1-ylphosphonate
78133-52-5

dimethyl isoquinolin-1-ylphosphonate

Conditions
ConditionsYield
With Bromotrichloromethane In chloroform-d1 at 20℃; for 0.333333h;
methyl bromide
74-83-9

methyl bromide

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Conditions
ConditionsYield
Stage #1: methyl bromide With magnesium In tetrahydrofuran for 2h; Reflux;
Stage #2: With phosphonic acid diethyl ester at 0 - 20℃; for 18h;
5-bromo-3-picoline
3430-16-8

5-bromo-3-picoline

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

3-dimethylphosphoryl-5-methylpyridine

3-dimethylphosphoryl-5-methylpyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile for 20h; Reflux;100%
dichloro( 1,5-cyclooctadiene)platinum(ll)
12080-32-9

dichloro( 1,5-cyclooctadiene)platinum(ll)

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

dichlorobis[dimethylphosphinous acid]platinum(II)

dichlorobis[dimethylphosphinous acid]platinum(II)

Conditions
ConditionsYield
In tetrahydrofuran soln. of Pt complex and ligand (2 equiv.) in THF was stirred under reflufor 22 h; filtered over Celite; concd. (vac.);99%
n-octyne
629-05-0

n-octyne

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

C10H21OP
1278596-93-2

C10H21OP

Conditions
ConditionsYield
With palladium(II)(diphenylphosphinic acid(-2H)); 1,3-bis-(diphenylphosphino)propane In toluene at 110℃; for 5h; Inert atmosphere; regioselective reaction;99%
Iododecane
2050-77-3

Iododecane

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

decyldimethylphosphine oxide
2190-95-6

decyldimethylphosphine oxide

Conditions
ConditionsYield
Stage #1: dimethyl phosphine oxide With sodium hexamethyldisilazane In tetrahydrofuran at 22℃; for 0.25h; Inert atmosphere; Darkness;
Stage #2: Iododecane In tetrahydrofuran at 22℃; for 16h; Inert atmosphere; Darkness; chemoselective reaction;
99%
4-iodo-2-(trifluoromethoxy)aniline

4-iodo-2-(trifluoromethoxy)aniline

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

4-(dimethylphosphoryl)-2-(trifluoromethoxy)aniline hydrochloride

4-(dimethylphosphoryl)-2-(trifluoromethoxy)aniline hydrochloride

Conditions
ConditionsYield
Stage #1: 4-iodo-2-(trifluoromethoxy)aniline; dimethyl phosphine oxide With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 150℃; for 0.333333h; Inert atmosphere; Microwave irradiation;
Stage #2: With hydrogenchloride In methanol
98%
dichloro(benzene)ruthenium(II) dimer
37366-09-9

dichloro(benzene)ruthenium(II) dimer

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

C8H13Cl2OPRu

C8H13Cl2OPRu

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 14h; Inert atmosphere; Schlenk technique;97%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

C8H17OP
1278596-94-3

C8H17OP

Conditions
ConditionsYield
With palladium(II)(diphenylphosphinic acid(-2H)); 1,2-bis-(diphenylphosphino)ethane In toluene at 110℃; for 25h; Inert atmosphere; regioselective reaction;96%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

(Trifluoracetyl)dimethylphosphinoxid

(Trifluoracetyl)dimethylphosphinoxid

Conditions
ConditionsYield
for 1h; -196 deg C to RT;95.7%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone
58905-19-4

1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

1-(4-Chlorphenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)ethyl-dimethyloxophosphoran

1-(4-Chlorphenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)ethyl-dimethyloxophosphoran

Conditions
ConditionsYield
at 80 - 100℃;95%
(2-formylphenyl)(diphenyl)phosphine
50777-76-9

(2-formylphenyl)(diphenyl)phosphine

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

(dimethyl-phosphinoyl)-(2-diphenylphosphanyl-phenyl)-methanol

(dimethyl-phosphinoyl)-(2-diphenylphosphanyl-phenyl)-methanol

Conditions
ConditionsYield
With ammonia In 1,2-dimethoxyethane Addition;95%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

1-dodecylbromide
143-15-7

1-dodecylbromide

dodecyl(dimethyl)phosphine oxide
871-95-4

dodecyl(dimethyl)phosphine oxide

Conditions
ConditionsYield
Stage #1: dimethyl phosphine oxide With sodium hexamethyldisilazane In tetrahydrofuran at 22℃; for 0.25h; Inert atmosphere;
Stage #2: 1-dodecylbromide In tetrahydrofuran at 22℃; for 16h; Inert atmosphere; chemoselective reaction;
93%
3-fluoro-5-((7-iodo-1-oxo-2,3-dihydro-1H-inden-4-yl)oxy)benzonitrile

3-fluoro-5-((7-iodo-1-oxo-2,3-dihydro-1H-inden-4-yl)oxy)benzonitrile

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

3-[(7-(dimethyloxophosphine)-1-oxo-indan-4-yl)oxy]-5-fluorobenzonitrile

3-[(7-(dimethyloxophosphine)-1-oxo-indan-4-yl)oxy]-5-fluorobenzonitrile

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 150℃; for 10h; Inert atmosphere;93%
formaldehyd
50-00-0

formaldehyd

phenylmethyl 1-piperazinecarboxylate
31166-44-6

phenylmethyl 1-piperazinecarboxylate

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

benzyl 4-((dimethylphosphoryl)methyl)piperazine-1-carboxylate
1260402-40-1

benzyl 4-((dimethylphosphoryl)methyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Stage #1: formaldehyd; phenylmethyl 1-piperazinecarboxylate With toluene-4-sulfonic acid In tetrahydrofuran at 60℃; for 1h;
Stage #2: dimethyl phosphine oxide In tetrahydrofuran at 60℃;
93%
1-chloroundecane
2473-03-2

1-chloroundecane

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

undecyldimethylphosphine oxide

undecyldimethylphosphine oxide

Conditions
ConditionsYield
Stage #1: dimethyl phosphine oxide With sodium hexamethyldisilazane In tetrahydrofuran at 22℃; for 0.25h; Inert atmosphere;
Stage #2: 1-chloroundecane In tetrahydrofuran at 22℃; for 16h; Inert atmosphere; chemoselective reaction;
92%
salicylaldehyde
90-02-8

salicylaldehyde

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Dimethyl-(hydroxy(o-hydroxyphenyl)methyl)phosphinoxid

Dimethyl-(hydroxy(o-hydroxyphenyl)methyl)phosphinoxid

Conditions
ConditionsYield
In dichloromethane for 120h; Ambient temperature;91.8%
2-(1H-imidazol-1-yl)-1-phenylethanone
24155-34-8

2-(1H-imidazol-1-yl)-1-phenylethanone

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

1-Hydroxy-2-(imidazol-1-yl)-1-phenylethyl-dimethyloxophosphoran

1-Hydroxy-2-(imidazol-1-yl)-1-phenylethyl-dimethyloxophosphoran

Conditions
ConditionsYield
In diethyl ether at 25℃; for 4h;91%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Dimethyl-(hydroxy(3,4,5-trimethoxyphenyl)methyl)phosphinoxid

Dimethyl-(hydroxy(3,4,5-trimethoxyphenyl)methyl)phosphinoxid

Conditions
ConditionsYield
In dichloromethane for 120h; Ambient temperature;90.6%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone
58905-26-3

1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone

1-Hydroxy-1-phenyl-2-(1,2,4-triazol-1-yl)ethyl-dimethyloxophosphoran

1-Hydroxy-1-phenyl-2-(1,2,4-triazol-1-yl)ethyl-dimethyloxophosphoran

Conditions
ConditionsYield
In diethyl ether at 25℃; for 4h;90%
C9H10BrNO4

C9H10BrNO4

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

C11H16NO5P

C11H16NO5P

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 130℃; for 3h; Sealed tube; Inert atmosphere;90%
(R)-7-(benzyloxy)-9-bromo-12-((S)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl)-3,4,12,12a-tetrahydro-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazine-6,8-dione

(R)-7-(benzyloxy)-9-bromo-12-((S)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl)-3,4,12,12a-tetrahydro-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazine-6,8-dione

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

(R)-7-(benzyloxy)-12-((S)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl)-9-(dimethylphosphoryl)-3,4,12,12a-tetrahydro-1H-[1,4] oxazino [3,4-c]pyrido[2,1-f] [1,2,4] triazine-6,8-dione

(R)-7-(benzyloxy)-12-((S)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl)-9-(dimethylphosphoryl)-3,4,12,12a-tetrahydro-1H-[1,4] oxazino [3,4-c]pyrido[2,1-f] [1,2,4] triazine-6,8-dione

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In acetonitrile at 90℃; for 20h; Inert atmosphere;90%
m-iodonitrobenzene
645-00-1

m-iodonitrobenzene

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

dimethyl(3-nitrophenyl)phosphine oxide
26786-59-4

dimethyl(3-nitrophenyl)phosphine oxide

Conditions
ConditionsYield
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 90℃; for 4h; Sealed tube;89%
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 20 - 90℃; for 3.16667h; Inert atmosphere;79%
3,5-di-tert-butyl-o-benzoquinone
3383-21-9

3,5-di-tert-butyl-o-benzoquinone

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

Dimethylphosphinsaeure-2-hydroxy-3,5-di-tert-butylphenylester
131028-82-5

Dimethylphosphinsaeure-2-hydroxy-3,5-di-tert-butylphenylester

Conditions
ConditionsYield
In dichloromethane for 1h; Heating;88.4%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethanone
24155-33-7

1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethanone

1-(4-Fluorphenyl)-1-hydroxy-2-(imidazol-1-yl)ethyl-dimethyloxophosphoran

1-(4-Fluorphenyl)-1-hydroxy-2-(imidazol-1-yl)ethyl-dimethyloxophosphoran

Conditions
ConditionsYield
at 80 - 100℃;88%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

4'-fluoro-2-(1H-1,2,4-triazol-1-yl)acetophenone
58905-21-8

4'-fluoro-2-(1H-1,2,4-triazol-1-yl)acetophenone

1-(4-Fluorphenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)ethyl-dimethyloxophosphoran

1-(4-Fluorphenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)ethyl-dimethyloxophosphoran

Conditions
ConditionsYield
at 80 - 100℃;87%
[RuCl2(hexamethylbenzene)]2

[RuCl2(hexamethylbenzene)]2

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

C14H25Cl2OPRu

C14H25Cl2OPRu

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 14h; Inert atmosphere; Schlenk technique;87%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

α,α'-dibromo-o-xylene
91-13-4

α,α'-dibromo-o-xylene

(1,2-phenylenebis(methylene))bis(dimethylphosphine oxide)

(1,2-phenylenebis(methylene))bis(dimethylphosphine oxide)

Conditions
ConditionsYield
Stage #1: dimethyl phosphine oxide With sodium hexamethyldisilazane In tetrahydrofuran at 22℃; for 0.25h; Inert atmosphere;
Stage #2: α,α'-dibromo-o-xylene In tetrahydrofuran at 22℃; Inert atmosphere; chemoselective reaction;
87%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

1,3-bis-(bromomethyl)benzene
626-15-3

1,3-bis-(bromomethyl)benzene

(1,3-phenylenebis(methylene))bis(dimethylphosphine oxide)

(1,3-phenylenebis(methylene))bis(dimethylphosphine oxide)

Conditions
ConditionsYield
Stage #1: dimethyl phosphine oxide With sodium hexamethyldisilazane In tetrahydrofuran at 22℃; for 0.25h; Inert atmosphere;
Stage #2: 1,3-bis-(bromomethyl)benzene In tetrahydrofuran at 22℃; Inert atmosphere; chemoselective reaction;
87%
dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

diazepam
439-14-5

diazepam

7-chloro-1,3-dihydro-5-(2-(dimethylphosphoryl)phenyl)-1-methyl-2H-benzo[e][1,4]diaze pin-2-one

7-chloro-1,3-dihydro-5-(2-(dimethylphosphoryl)phenyl)-1-methyl-2H-benzo[e][1,4]diaze pin-2-one

Conditions
ConditionsYield
With potassium hexafluorophosphate; [Cp*Rh(OAc)2] In methanol at 65℃; Electrochemical reaction;87%
benzyl bromide
100-39-0

benzyl bromide

dimethyl phosphine oxide
7211-39-4

dimethyl phosphine oxide

benzyldimethylphosphine oxide
18629-11-3

benzyldimethylphosphine oxide

Conditions
ConditionsYield
Stage #1: dimethyl phosphine oxide With sodium hexamethyldisilazane In tetrahydrofuran at 22℃; for 0.25h; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; chemoselective reaction;
86.2%

7211-39-4Relevant articles and documents

Dimethylphosphinato and dimethylarsinato complexes of palladium(II), [Pd(Me2PO2)2]3and Pd(Me 2AsO2)2, and their adducts

Ioannou, Panayiotis V.

, p. 1347 - 1353 (2010)

The complexes [Pd(Me2PO2)2]3 and Pd(Me2AsO2)2 were prepared from the corresponding acids and palladium(II) acetate. Their structures were deduced by IR and NMR spectroscopy. Addition of pyridine and 2,2'-bipyridine to [Pd(Me 2PO2)2]3 gave the adducts Pd(Me 2PO2)2py2 and Pd(Me 2PO2)2bipy, which were characterized by 1H NMR spectroscopy. Addition of nicotinic acid and nicotinamide in water gave the adducts Pd(Me2PO2)2L 2, whereas in methanol the adducts Pd(Me2PO 2)2L were obtained. The cacodylate containing complex formed the adducts Pd(Me2AsO2)2py and Pd(Me2AsO2)2bipy1/2, which are unstable in CDCl3. Triphenylphosphine deoxygenated both Pd(Me2MO 2)2 complexes, but the palladium(II) containing products could not be isolated, The expected Pd(Me2P-O)2 reacted further and gave many products, whereas the anticipated Pd(Me 2As-O)2 did not bind triphenylphosphine.

Highly Enantioselective Synthesis of Phosphorus-Containing ?-Benzosultams by Bifunctional Phosphonium Salt-Promoted Hydrophosphonylation

Zhang, Song,Feng, Zhenghuai,Jiang, Chunhui,Yu, Xiaojun,Pan, Jianke,Du, Juan,Jiang, Zhiyu,Chen, Yuan,Wang, Tianli

supporting information, p. 11285 - 11290 (2021/07/02)

?-Benzosultam derivatives are potential drug candidates with diverse biological activities. A series of chiral ?-benzosultams bearing phosphorus functionalities was synthesized by catalytic asymmetric hydrophosphonylation in the presence of a bifunctional phosphonium salt catalyst. The desired hydrophosphonylation products were obtained in good yields with high enantioselectivities, and scale-up reactions and further derivations were successfully accomplished. Some control experiments were also conducted to elucidate the plausible reaction mechanism of this chemical transformation.

DIMETHYLPHOSPHINE OXIDE COMPOUND

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Paragraph 0047, (2021/02/25)

Disclosed is an application of a series of dimethylphosphine oxide compounds in the preparation of an LRRK2 kinase activity inhibitor-related drug, specifically an application of the compound shown in formula (I) or a pharmaceutically acceptable salt thereof in the preparation of an LRRK2 kinase activity inhibitor-related drug.

TYK2 INHIBITORS AND USES THEREOF

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Paragraph 00662; 00663, (2018/04/27)

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

USE OF PHOSPHINE OXIDE COMPOUNDS IN A SEMICONDUCTING LAYER COMPRISED IN AN ELECTRONIC DEVICE

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Page/Page column 49; 50, (2018/12/13)

The present invention relates to the use of a compound represented by the general formula (I) wherein A1 and A2 are independently selected from C1 to C60 carbon-containing groups; A3 to A9 are independently selected from hydrogen, C1 to C60 carbon-containing groups, or halogen; R1 and R2 are independently selected from C1 to C60 carbon-containing groups which are attached to the phosphorous atom by a sp3-hybridized carbon atom; X is a single covalent bond or a spacer group consisting of 1 to 120 covalently bound atoms; in a semiconducting layer comprised in an electronic device, a respective semiconducting layer, a respective electronic device and respective compounds.

ORGANIC ELECTRONIC DEVICE COMPRISING AN ORGANIC SEMICONDUCTOR LAYER

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Page/Page column 52, (2018/12/13)

The present invention relates to a compound of formula 1 and an organic electronic device comprising an organic semiconductor layer, wherein at least one organic semiconductor layer comprises a compound of formula (1), wherein L1 has the formula (2) and L2 has the formula (3), wherein L1 and L2 are bonded at "*" via a single bond independently to the same or different arylene groups or heteroarylenes group of Ar1; and wherein X1, X2 are independently selected from O, S and Se; Ar1 is selected from substituted or unsubstituted C20 to C52 arylene or C14 to C64 heteroarylene, wherein the substituent of the substituted C20 to C52 arylene or C14 to C64 heteroarylene are independently selected from C1 to C12 alkyl, C1 to C12 alkoxy, CN, halogen, OH, C6 to C25 aryl and C2 to C21 heteroaryl; R1, R2 are independently selected from substituted or unsubstituted C1 to C16 alkyl, wherein the substituent of substituted C1 to C16 alkyl is selected from C6 to C18 arylene or C2 to C12 heteroarylene; R3, R4 are independently selected from substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C18 arylene, C2 to C20 heteroarylene, wherein the substituent of substituted C1 to C16 alkyl, the substituent of the substituted C6 to C18 arylene, C2 to C20 heteroarylene are independently selected from C6 to C18 arylene or C2 to C12 heteroarylene; n is selected from 1 to 5, wherein n is an integer number.

ORGANIC SEMICONDUCTIVE LAYER COMPRISING PHOSPHINE OXIDE COMPOUNDS

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Page/Page column 80; 81, (2017/06/29)

The present invention relates to an. organic semiconductive layer which is an electron transport layer and/or an electron injection layer and/or an n-type charge generation layer, the organic semiconductive layer comprising at least one compound of formula (1) wherein R1 and R2 are each independently selected from C1 to C16 alkyl; Ar1 is selected from C6 to C14 arylene or C3 to C12 heteroarylene; Ar2 is independently selected from C14 to C40 arylene or C8 to C40 heteroarylene; R3 is independently selected from H, C1 to C12 alkyl or C10 to C20 aryl; wherein each of Ar1, Ar2 and R3 may each independently be uesubstituted or substituted with at least one C1 to C12 alky group; n is 0 or 1; and m is 1 in case of n = 0; and m is 1 or 2 in case of n = 1, phosphine oxide compounds comprised therein and to organic electroluminescent devices comprising such layers and compounds.

Metal-free phosphonation of heteroarene N-oxides with trialkyl phosphite at room temperature

Chen, Ming-Tao,You, Xia,Bai, Li-Gang,Luo, Qun-Li

supporting information, p. 3165 - 3169 (2017/04/21)

A new protocol is described for the conversion of heteroarene N-oxides to heteroarylphosphonates through in situ activation with bromotrichloromethane. The N-oxides of isoquinoline, quinoline, quinoxaline and 1,10-phenanthroline were fast transformed into the corresponding heteroarylphosphonates in up to 92% yield under mild conditions in the absence of solvent and metal catalysts. The good functional group tolerance, low cost, feasibility of scale up, and wide availability of reagents make this method a prominent complement to the Hirao coupling.

Preparation method, intermediate and crystal form of spironolamine arylphosphine oxide

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Paragraph 0092-0096, (2017/08/30)

The invention discloses a preparation method and a crystal form of high-purity spironolamine arylphosphine oxide. The invention further discloses a method for preparing a compound shown as a formula (I) and an intermediate compound.

Spiro aryl phosphorus oxide or sulfide

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Paragraph 0188; 0189; 0190; 0191, (2016/10/08)

The invention discloses a spiro aryl phosphorus oxide or sulfide as ALK inhibitor, and in particular discloses a compound shown in a formula (I) as an ALK inhibitor or a pharmaceutically acceptable salt thereof.

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