Tetramethylphosphonium iodide supplier

Name
TETRAMETHYLPHOSPHONIUM IODIDE
EINECS
CAS No. 993-11-3
Article Data14
CAS DataBase
Density
Solubility
Melting Point 312-322°C
Formula C4H12 P . I
Boiling Point
Molecular Weight 218.018
Flash Point
Transport Information
Appearance
Safety Poison by subcutaneous and intravenous routes. When heated to decomposition it emits very toxic fumes of PO_x and I⁻. See also IODIDES.
Risk Codes R36/37/38;
Molecular Structure
Hazard Symbols R36/37/38:Irritating to eyes, respiratory system and skin.;
Synonyms Tetramethylphosphoniumiodide (6CI,7CI); NSC 617058
PSA 13.59000
LogP -1.47280

Synthetic route

: 14580-91-7, 29218-61-9
trimethyl(methylene)phosphorane

: 77812-56-7
dicarbonyl(η5-cyclopentadienyl)[η1-(2-trimethylphosphonio)propionyl]iron(II) iodide

A: 84083-95-4
C5H5(CO)2FeC(O)C(CH3)P(CH3)3

B: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
In diethyl ether to suspn. of Fe complex in ether Me3PCH2 dissolved in ether added dropwise at room temp., allowed to react for 45 h; filtered, concd. in vac., treated with pentane, ppt. washed with pentane, dried in vac.; elem. anal.;	A 90% B 98%

...Expand

: 74-88-4
methyl iodide

A: 993-11-3
tetramethylphosphonium iodide

B: Methyl-bis(trimethylphosphinomethyl)-phosphan-diiodid

C: (Dimethyl-phosphinoylmethyl)-trimethyl-phosphonium; iodide

D: Dimethyl-bis(trimethylphosphoniomethyl)phosphiumtriiodid

Conditions

Conditions	Yield
In methanol Further byproducts given;	A n/a B n/a C n/a D 58%

...Expand

: 74-88-4
methyl iodide

: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
With calcium phosphide; water In methanol at 0℃; for 51h; Reflux;	53%

: 67-56-1
methanol

A: 993-11-3
tetramethylphosphonium iodide

B: 594-09-2
trimethylphosphane

Conditions

Conditions	Yield
With phosphonium iodide at 160 - 180℃; das Hydrojodid bildet sich;

: 917-64-6
methyl magnesium iodide

: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
With diethyl ether; phosphorus diiodide Einw. das Reaktionsprodukts von Wasser;

: 115-10-6
Dimethyl ether

A: 993-11-3
tetramethylphosphonium iodide

B: 594-09-2
trimethylphosphane

Conditions

Conditions	Yield
With phosphonium iodide at 120 - 140℃;

: 74-88-4
methyl iodide

: 594-09-2
trimethylphosphane

: 993-11-3
tetramethylphosphonium iodide

: 2314-97-8
iodotrifluoromethane

: 594-09-2
trimethylphosphane

A: 75-46-7
trifluoromethan

B: 421-57-8
dimethyl(trifluoromethyl)phosphine

C: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
analoge Reaktionen mit Trimethylarsin und mit Trimethylstibin;

...Expand

: 3676-91-3
tetramethyldiphosphane

: 74-88-4
methyl iodide

: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
at 200℃;

: Dimethyl-bis(trimethylphosphoniomethyl)phosphiumtriiodid

A: 993-11-3
tetramethylphosphonium iodide

B: C7H20P2(2+)*2I(1-)

C: (Dimethyl-phosphinoylmethyl)-trimethyl-phosphonium; iodide

Conditions

Conditions	Yield
In water-d2 at 25℃; Product distribution; other solvents: CD3OD, CD3OD/D2O, CD3OD/H2O; influence of solvent on rate of hydrolysis, solvent isotope effect;

...Expand

: 2314-97-8
iodotrifluoromethane

: 594-09-2
trimethylphosphane

A: 421-57-8
dimethyl(trifluoromethyl)phosphine

B: 98026-25-6
diiodotrimethylphosphorane

C: 57539-05-6
Bis-trifluormethyl-trimethyl-phosphoran

D: 354-46-1
trifluormethyltrimethylphosphoniumiodid

E: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
In neat (no solvent) Product distribution; trifluoromethylating of phosphorus compounds;

...Expand

: 2314-97-8
iodotrifluoromethane

: 594-09-2
trimethylphosphane

A: 421-57-8
dimethyl(trifluoromethyl)phosphine

B: 57539-05-6
Bis-trifluormethyl-trimethyl-phosphoran

C: 354-46-1
trifluormethyltrimethylphosphoniumiodid

D: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
In neat (no solvent) Further byproducts given;

...Expand

: 55272-61-2
dimesitylbis(trimethylphosphine)chromium(II)

A: chromium(II) iodide

B: 527-53-7
1,2,3,5-Tetramethylbenzene

C: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
With CH3I In diethyl ether; toluene soln. of CH3I in toluene is added to stirred room-temp. soln. of Cr(C6H2Me3)2(PMe3)2 in diethyl ether, stirring for 3 h; elem. anal.;

...Expand

: 38707-70-9
8-formylquinoline

: 993-11-3
tetramethylphosphonium iodide

: 96911-08-9
8-ethenylquinoline

Conditions

Conditions	Yield
Stage #1: tetramethylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -70 - 20℃; for 2h; Inert atmosphere; Stage #2: 8-formylquinoline In tetrahydrofuran; hexane at -20℃; for 5h; Inert atmosphere; Reflux;	84%

: 91-02-1
phenyl(pyridin-2-yl)methanone

: 993-11-3
tetramethylphosphonium iodide

: 15260-65-8
2-(1-phenylvinyl)pyridine

Conditions

Conditions	Yield
Stage #1: tetramethylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -70 - 20℃; for 2h; Inert atmosphere; Stage #2: phenyl(pyridin-2-yl)methanone In tetrahydrofuran; hexane at -20℃; for 5h; Inert atmosphere; Reflux;	84%

: 993-11-3
tetramethylphosphonium iodide

: 181591-24-2
chloroditetradecyl phosphate

: ditetradecyl (trimethylphosphonio)methylphosphonate iodide

Conditions

Conditions	Yield
Stage #1: tetramethylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -10℃; Stage #2: chloroditetradecyl phosphate In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.;	76%

: 993-11-3
tetramethylphosphonium iodide

: Phosphorochloridic acid bis-((Z)-octadec-9-enyl) ester

: dioleyl (trimethylphosphonio)methylphosphonate iodide

Conditions

Conditions	Yield
Stage #1: tetramethylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -10℃; Stage #2: Phosphorochloridic acid bis-((Z)-octadec-9-enyl) ester In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.;	68%

: 51905-34-1
pentamethylcyclopentadienyllithium

: 10361-82-7
samarium(III) chloride

: 993-11-3
tetramethylphosphonium iodide

: (C5(CH3)5)2Sm{(CH2)(CH2)P(CH3)2}*2LiCl

Conditions

Conditions	Yield
With methyllithium In tetrahydrofuran suspn. of Cp'Li and anhydrous SmCl3 refluxed overnight, filtered, addn. of a soln. of Li(THF)2Cp'2SmCl2 to a soln. of LiCH2CH2PMe2 (from MeLi and Me4PI in Et2O prepd.) at -78°C under N2, warming to room temp., stirring (4 h); filtered, extd. (THF), evapn. (vac.), extd. (CH2Cl2), concd., cooling (-20°C), filtered, dried (vacuo), elem. anal.;	63%
With methyllithium In toluene suspn. of Cp'Li and anhydrous SmCl3 refluxed overnight, filtered, addn. of a soln. of Li(THF)2Cp'2SmCl2 to a soln. of LiCH2CH2PMe2 (from MeLi and Me4PI in Et2O prepd.) at -78°C under N2, warming to room temp., stirring (4 h); filtered, extd. (THF), evapn. (vac.), extd. (CH2Cl2), concd., cooling (-20°C), filtered, dried (vacuo), elem. anal.;	63%

...Expand

: 993-11-3
tetramethylphosphonium iodide

: 14580-91-7, 29218-61-9
trimethyl(methylene)phosphorane

Conditions

Conditions	Yield
With diethyl ether; phenyllithium
With diethyl ether; methyllithium
With n-butyllithium In hexane at -78℃; Inert atmosphere;

: 993-11-3
tetramethylphosphonium iodide

: 14814-27-8
tetramethylphosphonium hydroxide

Conditions

Conditions	Yield
With silver(l) oxide

: 60-29-7
diethyl ether

: 993-11-3
tetramethylphosphonium iodide

: 591-51-5
phenyllithium

: 14580-91-7, 29218-61-9
trimethyl(methylene)phosphorane

Conditions

Conditions	Yield
je nach dem Mengenverhaeltnis;

...Expand

: 60-29-7
diethyl ether

: 993-11-3
tetramethylphosphonium iodide

: 591-51-5
phenyllithium

: 21752-68-1
(dimethyl-methylene-phosphoranyl)-methyl lithium

Conditions

Conditions	Yield
je nach dem Mengenverhaeltnis;

...Expand

: 14580-91-7, 29218-61-9
trimethyl(methylene)phosphorane

: 77812-56-7
dicarbonyl(η5-cyclopentadienyl)[η1-(2-trimethylphosphonio)propionyl]iron(II) iodide

A: 84083-95-4
C5H5(CO)2FeC(O)C(CH3)P(CH3)3

B: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
In diethyl ether to suspn. of Fe complex in ether Me3PCH2 dissolved in ether added dropwise at room temp., allowed to react for 45 h; filtered, concd. in vac., treated with pentane, ppt. washed with pentane, dried in vac.; elem. anal.;	A 90% B 98%

...Expand

: 74-88-4
methyl iodide

A: 993-11-3
tetramethylphosphonium iodide

B: Methyl-bis(trimethylphosphinomethyl)-phosphan-diiodid

C: (Dimethyl-phosphinoylmethyl)-trimethyl-phosphonium; iodide

D: Dimethyl-bis(trimethylphosphoniomethyl)phosphiumtriiodid

Conditions

Conditions	Yield
In methanol Further byproducts given;	A n/a B n/a C n/a D 58%

...Expand

: 74-88-4
methyl iodide

: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
With calcium phosphide; water In methanol at 0℃; for 51h; Reflux;	53%

: 67-56-1
methanol

A: 993-11-3
tetramethylphosphonium iodide

B: 594-09-2
trimethylphosphane

Conditions

Conditions	Yield
With phosphonium iodide at 160 - 180℃; das Hydrojodid bildet sich;

: 917-64-6
methyl magnesium iodide

: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
With diethyl ether; phosphorus diiodide Einw. das Reaktionsprodukts von Wasser;

: 115-10-6
Dimethyl ether

A: 993-11-3
tetramethylphosphonium iodide

B: 594-09-2
trimethylphosphane

Conditions

Conditions	Yield
With phosphonium iodide at 120 - 140℃;

: 74-88-4
methyl iodide

: 594-09-2
trimethylphosphane

: 993-11-3
tetramethylphosphonium iodide

: 2314-97-8
iodotrifluoromethane

: 594-09-2
trimethylphosphane

A: 75-46-7
trifluoromethan

B: 421-57-8
dimethyl(trifluoromethyl)phosphine

C: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
analoge Reaktionen mit Trimethylarsin und mit Trimethylstibin;

...Expand

: 3676-91-3
tetramethyldiphosphane

: 74-88-4
methyl iodide

: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
at 200℃;

: Dimethyl-bis(trimethylphosphoniomethyl)phosphiumtriiodid

A: 993-11-3
tetramethylphosphonium iodide

B: C7H20P2(2+)*2I(1-)

C: (Dimethyl-phosphinoylmethyl)-trimethyl-phosphonium; iodide

Conditions

Conditions	Yield
In water-d2 at 25℃; Product distribution; other solvents: CD3OD, CD3OD/D2O, CD3OD/H2O; influence of solvent on rate of hydrolysis, solvent isotope effect;

...Expand

: 2314-97-8
iodotrifluoromethane

: 594-09-2
trimethylphosphane

A: 421-57-8
dimethyl(trifluoromethyl)phosphine

B: 98026-25-6
diiodotrimethylphosphorane

C: 57539-05-6
Bis-trifluormethyl-trimethyl-phosphoran

D: 354-46-1
trifluormethyltrimethylphosphoniumiodid

E: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
In neat (no solvent) Product distribution; trifluoromethylating of phosphorus compounds;

...Expand

: 2314-97-8
iodotrifluoromethane

: 594-09-2
trimethylphosphane

A: 421-57-8
dimethyl(trifluoromethyl)phosphine

B: 57539-05-6
Bis-trifluormethyl-trimethyl-phosphoran

C: 354-46-1
trifluormethyltrimethylphosphoniumiodid

D: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
In neat (no solvent) Further byproducts given;

...Expand

: methylmagnesium iodide

P2I4: P2I4

: 993-11-3
tetramethylphosphonium iodide

: 67-56-1
methanol

A: 993-11-3
tetramethylphosphonium iodide

B trimethylphosphonium iodide: trimethylphosphonium iodide

Conditions

Conditions	Yield
With phosphonium iodide at 160 - 180℃;

: 115-10-6
Dimethyl ether

A: 993-11-3
tetramethylphosphonium iodide

B trimethylphosphonium iodide: trimethylphosphonium iodide

Conditions

Conditions	Yield
With phosphonium iodide at 120 - 140℃;

: 55272-61-2
dimesitylbis(trimethylphosphine)chromium(II)

A: chromium(II) iodide

B: 527-53-7
1,2,3,5-Tetramethylbenzene

C: 993-11-3
tetramethylphosphonium iodide

Conditions

Conditions	Yield
With CH3I In diethyl ether; toluene soln. of CH3I in toluene is added to stirred room-temp. soln. of Cr(C6H2Me3)2(PMe3)2 in diethyl ether, stirring for 3 h; elem. anal.;

...Expand

: 38707-70-9
8-formylquinoline

: 993-11-3
tetramethylphosphonium iodide

: 96911-08-9
8-ethenylquinoline

Conditions

Conditions	Yield
Stage #1: tetramethylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -70 - 20℃; for 2h; Inert atmosphere; Stage #2: 8-formylquinoline In tetrahydrofuran; hexane at -20℃; for 5h; Inert atmosphere; Reflux;	84%

: 91-02-1
phenyl(pyridin-2-yl)methanone

: 993-11-3
tetramethylphosphonium iodide

: 15260-65-8
2-(1-phenylvinyl)pyridine

Conditions

Conditions	Yield
Stage #1: tetramethylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -70 - 20℃; for 2h; Inert atmosphere; Stage #2: phenyl(pyridin-2-yl)methanone In tetrahydrofuran; hexane at -20℃; for 5h; Inert atmosphere; Reflux;	84%

: 993-11-3
tetramethylphosphonium iodide

: 181591-24-2
chloroditetradecyl phosphate

: ditetradecyl (trimethylphosphonio)methylphosphonate iodide

Conditions

Conditions	Yield
Stage #1: tetramethylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -10℃; Stage #2: chloroditetradecyl phosphate In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.;	76%

: 993-11-3
tetramethylphosphonium iodide

: Phosphorochloridic acid bis-((Z)-octadec-9-enyl) ester

: dioleyl (trimethylphosphonio)methylphosphonate iodide

Conditions

Conditions	Yield
Stage #1: tetramethylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -10℃; Stage #2: Phosphorochloridic acid bis-((Z)-octadec-9-enyl) ester In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.;	68%

: 51905-34-1
pentamethylcyclopentadienyllithium

: 10361-82-7
samarium(III) chloride

: 993-11-3
tetramethylphosphonium iodide

: (C5(CH3)5)2Sm{(CH2)(CH2)P(CH3)2}*2LiCl

Conditions

Conditions	Yield
With methyllithium In tetrahydrofuran suspn. of Cp'Li and anhydrous SmCl3 refluxed overnight, filtered, addn. of a soln. of Li(THF)2Cp'2SmCl2 to a soln. of LiCH2CH2PMe2 (from MeLi and Me4PI in Et2O prepd.) at -78°C under N2, warming to room temp., stirring (4 h); filtered, extd. (THF), evapn. (vac.), extd. (CH2Cl2), concd., cooling (-20°C), filtered, dried (vacuo), elem. anal.;	63%
With methyllithium In toluene suspn. of Cp'Li and anhydrous SmCl3 refluxed overnight, filtered, addn. of a soln. of Li(THF)2Cp'2SmCl2 to a soln. of LiCH2CH2PMe2 (from MeLi and Me4PI in Et2O prepd.) at -78°C under N2, warming to room temp., stirring (4 h); filtered, extd. (THF), evapn. (vac.), extd. (CH2Cl2), concd., cooling (-20°C), filtered, dried (vacuo), elem. anal.;	63%

...Expand

: 993-11-3
tetramethylphosphonium iodide

: 14580-91-7, 29218-61-9
trimethyl(methylene)phosphorane

Conditions

Conditions	Yield
With diethyl ether; phenyllithium
With diethyl ether; methyllithium
With n-butyllithium In hexane at -78℃; Inert atmosphere;

: 993-11-3
tetramethylphosphonium iodide

: 14814-27-8
tetramethylphosphonium hydroxide

Conditions

Conditions	Yield
With silver(l) oxide

: 60-29-7
diethyl ether

: 993-11-3
tetramethylphosphonium iodide

: 591-51-5
phenyllithium

: 14580-91-7, 29218-61-9
trimethyl(methylene)phosphorane

Conditions

Conditions	Yield
je nach dem Mengenverhaeltnis;

...Expand

: 60-29-7
diethyl ether

: 993-11-3
tetramethylphosphonium iodide

: 591-51-5
phenyllithium

: 21752-68-1
(dimethyl-methylene-phosphoranyl)-methyl lithium

Conditions

Conditions	Yield
je nach dem Mengenverhaeltnis;

...Expand

: 60-29-7
diethyl ether

: 993-11-3
tetramethylphosphonium iodide

: 591-51-5
phenyllithium

: tris-lithiomethyl-methylene-phosphorane

Conditions

Conditions	Yield
je nach dem Mengenverhaeltnis;

...Expand

: 993-11-3
tetramethylphosphonium iodide

: 591-51-5
phenyllithium

: 21752-68-1
(dimethyl-methylene-phosphoranyl)-methyl lithium

Conditions

Conditions	Yield
With diethyl ether

: 993-11-3
tetramethylphosphonium iodide

: 591-51-5
phenyllithium

: tris-lithiomethyl-methylene-phosphorane

Conditions

Conditions	Yield
With diethyl ether

: 993-11-3
tetramethylphosphonium iodide

: 591-51-5
phenyllithium

: bis-(2-hydroxy-2,2-diphenyl-ethyl)-dimethyl-phosphonium; iodide

Conditions

Conditions	Yield
With diethyl ether beim Behandeln des Reaktionsgemisches mit Benzophenon;

: 993-11-3
tetramethylphosphonium iodide

: 2397-68-4
sodium tetraethylaluminate

: C8H20Al(1-)*C4H12P(1+)

Conditions

Conditions	Yield
With triethylaluminum In toluene

: 993-11-3
tetramethylphosphonium iodide

: sodium aluminum diethyl dihydride

: C4H12Al(1-)*C4H12P(1+)

Conditions

Conditions	Yield
With triethylaluminum In toluene

: 993-11-3
tetramethylphosphonium iodide

: tetramethylphosphonium triiodide

Conditions

Conditions	Yield
With trifluoroacetic acid
With iodine In solid at 40℃;

: 993-11-3
tetramethylphosphonium iodide

: 1518-16-7
7,7',8,8'-tetracyanoquinodimethane

: 94017-56-8
2C12H4N4*C4H12P(1+)*I(1-)

Conditions

Conditions	Yield
In acetonitrile at 35℃;

Tetramethylphosphonium iodide Chemical Properties

Molecule structure of Tetramethylphosphonium iodide (CAS NO.993-11-3) :

IUPAC Name: tetramethylphosphanium iodide
Molecular Weight: 218.016311 g/mol
Molecular Formula: C₄H₁₂IP
Melting Point: 312-322 °C
H-Bond Acceptor: 1
Exact Mass: 217.97213
MonoIsotopic Mass: 217.97213
Heavy Atom Count: 6
Complexity: 19.1
Canonical SMILES: C[P+](C)(C)C.[I-]
InChI: InChI=1S/C4H12P.HI/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1
InChIKey: TVVPMLFGPYQGTG-UHFFFAOYSA-M
EINECS of Tetramethylphosphonium iodide (CAS NO.993-11-3) : 213-605-1

Tetramethylphosphonium iodide Toxicity Data With Reference

1.		scu-mus LDLo:100 mg/kg		JPETAB Journal of Pharmacology and Experimental Therapeutics. 25 (1925),315.
2.		ivn-mus LDLo:12 mg/kg		JPETAB Journal of Pharmacology and Experimental Therapeutics. 25 (1925),315.

Tetramethylphosphonium iodide Safety Profile

Poison by subcutaneous and intravenous routes. When heated to decomposition it emits very toxic fumes of PO_x and I⁻. See also IODIDES.
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.

Tetramethylphosphonium iodide Specification

Tetramethylphosphonium iodide (CAS NO.993-11-3) is also called Tetramethylphosphonium ; NSC 617058 ; Phosphonium, tetramethyl-, iodide .

Product Name

TETRAMETHYLPHOSPHONIUM IODIDE

Synthetic route

Tetramethylphosphonium iodide Chemical Properties

Tetramethylphosphonium iodide Toxicity Data With Reference

Tetramethylphosphonium iodide Safety Profile

Tetramethylphosphonium iodide Specification

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