Hexamethyldisiloxane
trimethylsilyl iodide
Conditions | Yield |
---|---|
With phosphorus; iodine at 80℃; for 10h; Temperature; Inert atmosphere; | 99% |
With iodine; aluminium at 55 - 130℃; for 2h; Concentration; Temperature; Inert atmosphere; | 93.9% |
With iodine; aluminium | 66% |
chloro-trimethyl-silane
trimethylsilyl iodide
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; lithium iodide at 60℃; for 10h; Temperature; Reagent/catalyst; Inert atmosphere; | 98.56% |
With lithium iodide for 4h; Ambient temperature; | 88% |
With magnesium iodide In xylene Heating; |
phenyl trimethylsilyl selenide
A
trimethylsilyl iodide
B
diphenyl diselenide
Conditions | Yield |
---|---|
With iodine | A 98% B 96% |
1,1,1,2,2,2-hexamethyldisilane
trimethylsilyl iodide
Conditions | Yield |
---|---|
With iodine at 65 - 130℃; for 2h; | 96.1% |
With iodine In dichloromethane Thermodynamic data; Kinetics; ΔS(excit.), ΔG(excit.), ΔE(excit.); | |
With iodine |
pentamethylcyclopentadienyltrimethylsilane
titanium(IV) iodide
B
trimethylsilyl iodide
Conditions | Yield |
---|---|
In toluene Dropwise addn. of TiI4 in toluene to soln. of C(CH3)5Si(CH3)3 in toluene, stirring (2 h, color change from red to dark-red), reflux (1 h); Evapn. of solvent and byproduct (vacuum), washing of crystals (pentane), dried (vacuum), elem. anal.; | A 95.2% B n/a |
bis(trimethylsilyl)selenide
trimethylsilyl iodide
Conditions | Yield |
---|---|
With iodine In m-xylene | 94% |
trimethylphenylsilane
trimethylsilyl iodide
Conditions | Yield |
---|---|
With I2; AlI3 | 93% |
With I2 | 56% |
With aluminium(III) iodide; iodine | |
With iodine |
potassium ethyl xanthogenate
methyl iodide
A
trimethylsilyl iodide
B
O-ethyl S-methyl dithiocarbonate
Conditions | Yield |
---|---|
In acetone | A n/a B 90% |
tetrakis(trimethylsiloxy)phosphonium iodide
A
trimethylsilyl iodide
B
Tris(trimethylsilyl) phosphate
Conditions | Yield |
---|---|
In benzene Heating; during 5 h the solvent was distilled off, the temp. rose to 110 deg C; | A n/a B 85% |
N,N-diethyl-1,1,1-trimethylsilanamine
trimethylsilyl iodide
Conditions | Yield |
---|---|
With iodine In neat (no solvent) for 15h; Ambient temperature; | 85% |
octamethylcyclotetrasiloxane
A
trimethylsilyl iodide
B
Hexamethyldisiloxane
C
methyl iodide
Conditions | Yield |
---|---|
With aluminium(III) iodide at 140 - 170℃; for 5h; | A n/a B 83.5% C n/a |
1,1,3,3-Tetramethyldisiloxane
Hexamethyldisiloxane
trimethylsilyl iodide
Conditions | Yield |
---|---|
With iodine for 0.166667h; Heating; | 80% |
Conditions | Yield |
---|---|
76% |
acetyl iodide
tris(trimethylsilyl)amine
A
trimethylsilyl iodide
B
N,N-bis(trimethylsilyl)acetamide
Conditions | Yield |
---|---|
at 60 - 70℃; for 6h; | A 65% B 53% |
octamethylcyclotetrasiloxane
A
tetramethylsilane
B
trimethylsilyl iodide
C
Hexamethyldisiloxane
D
tetradecamethylhexasiloxane
Conditions | Yield |
---|---|
With gallium(III) iodide at 140 - 170℃; for 5h; Yields of byproduct given; | A 61% B n/a C n/a D n/a |
With gallium(III) iodide at 140 - 170℃; for 5h; Title compound not separated from byproducts; | A 61% B n/a C n/a D n/a |
With gallium(III) iodide at 140 - 170℃; for 5h; Yield given; Title compound not separated from byproducts; | A 61% B n/a C n/a D n/a |
octamethylcyclotetrasiloxane
A
tetramethylsilane
B
trimethylsilyl iodide
C
Hexamethyldisiloxane
D
dodecamethyl-cyclohexasiloxane
Conditions | Yield |
---|---|
With gallium(III) iodide at 140 - 170℃; for 5h; Yield given; Title compound not separated from byproducts; | A 61% B n/a C n/a D n/a |
octamethylcyclotetrasiloxane
A
tetramethylsilane
B
trimethylsilyl iodide
C
Hexamethyldisiloxane
D
hexadecamethylheptasiloxane
Conditions | Yield |
---|---|
With gallium(III) iodide at 140 - 170℃; for 5h; Yield given; Title compound not separated from byproducts; | A 61% B n/a C n/a D n/a |
acetyl iodide
N,N-bis(trimethylsilyl)ethanamine
A
trimethylsilyl iodide
B
N-trimethylsilyle du N-ethylacetamide
Conditions | Yield |
---|---|
at 60 - 70℃; for 8h; | A 23% B 61% |
phenyltrimethylsilyl ether
A
tetramethylsilane
B
trimethylsilyl iodide
C
Hexamethyldisiloxane
D
methyl iodide
Conditions | Yield |
---|---|
With gallium(III) iodide at 175 - 180℃; for 3h; | A 60% B n/a C n/a D n/a |
With gallium(III) iodide at 175 - 180℃; for 3h; Title compound not separated from byproducts; | A 60% B n/a C n/a D n/a |
tris(trimethylsilyl)amine
benzoyl iodide
A
trimethylsilyl iodide
B
N,N-bis(trimethylsilyl)benzamide
Conditions | Yield |
---|---|
at 120 - 130℃; for 8h; | A 59% B 32% |
1-Iodonaphthalene
ethenyltrimethylsilane
A
1-vinylnaphthalene
B
propene
C
ethene
D
trimethylsilyl iodide
E
Hexamethyldisiloxane
F
buta-1,3-diene
Conditions | Yield |
---|---|
bis(η3-allyl-μ-chloropalladium(II)) In water; N,N-dimethyl-formamide at 100℃; for 5h; Product distribution; other aromatic halides: α-bromonaphthalene, α-halopyridines, iodobenzene, p-substituted iodobenzenes; 9-iodo-m-carborane; other catalysts: (Ph3P)4Pd, LiPdCl3, (PhCN)2PdCl2, (MeCN)2PdCl2, Pd/C; Et3N presence; other solvent: hexametapol; | A 55% B n/a C n/a D n/a E n/a F n/a |
Conditions | Yield |
---|---|
Heating; | A 53% B 13% |
Conditions | Yield |
---|---|
at 116℃; for 12h; | 48% |
N,N-bis(trimethylsilyl)ethanamine
benzoyl iodide
A
trimethylsilyl iodide
B
N-ethyl-N-trimethylsilylbenzamide
Conditions | Yield |
---|---|
at 80 - 104℃; for 13h; | A 36% B 25% C 9.86 g |
S-trimethylsilyl O-ethyldithiocarbonate
methyl iodide
A
trimethylsilyl iodide
B
O-ethyl S-methyl dithiocarbonate
Conditions | Yield |
---|---|
In chloroform-d1 for 24h; | A n/a B 30% |
1-chloro-1,1,3,3,3-pentamethyldisiloxane
A
trimethylsilyl iodide
B
octamethylcyclotetrasiloxane
C
1-chloroheptamethyltrisiloxane
D
1-chloro-1,1,3,3,5,5,7,7,7-nonamethyltetrasiloxane
Conditions | Yield |
---|---|
With sodium iodide In acetonitrile for 18h; Mechanism; Ambient temperature; other siloxanes; other reagent, var. temp.; | A 14% B 10% C n/a D n/a |
Conditions | Yield |
---|---|
at 80℃; | |
at 80℃; |
hexamethyldisilathiane
trimethylsilyl iodide
Conditions | Yield |
---|---|
With 1-Iodoheptane at 160℃; | |
With dibutyl-iodo-borane In carbon disulfide |
n-butylthiotrimethylsilane
trimethylsilyl iodide
Conditions | Yield |
---|---|
With diiodomethane |
Conditions | Yield |
---|---|
at 80℃; | 100% |
4-methyl-1,3-dioxane
trimethylsilyl iodide
A
Hexamethyldisiloxane
B
3-Iodo-1-iodomethoxy-butane
C
1-Iodo-3-iodomethoxy-butane
Conditions | Yield |
---|---|
at 70℃; for 3.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | A 100% B n/a C n/a |
Conditions | Yield |
---|---|
at 100℃; | 100% |
cis,trans-2,5-dimethoxytetrahydrofuran
trimethylsilyl iodide
1,4-Diiodo-1,4-dimethoxy-butane
Conditions | Yield |
---|---|
100% |
cis- and trans-2,6-Dimethoxytetrahydropyran
trimethylsilyl iodide
1,5-Diiodo-1,5-dimethoxy-pentane
Conditions | Yield |
---|---|
100% |
trimethylsilyl iodide
trimethylsiloxydiethylphosphinate
bis(trimethylsilyloxy)diethylphosphonium iodide
Conditions | Yield |
---|---|
In benzene | 100% |
trimethylsilyl iodide
trimethylsiloxydipropylphosphinate
bis(trimethylsilyloxy)dipropylphosphonium iodide
Conditions | Yield |
---|---|
In benzene | 100% |
trimethylsilyl iodide
(methoxyethynyl)bis(pentafluorophenyl)phosphine
(trimethylsilyl)ketene
Conditions | Yield |
---|---|
In nitromethane at 20℃; for 2h; | 100% |
trimethylsilyl iodide
Ethoxyethynyl-bis-pentafluorophenyl-phosphane
(trimethylsilyl)ketene
Conditions | Yield |
---|---|
In nitromethane at 20℃; for 2h; | 100% |
trimethylsilyl iodide
ethyl P-(diethoxymethyl)phosphonite
Conditions | Yield |
---|---|
In dichloromethane for 1.5h; | 100% |
The Trimethyliodosilane, with the CAS register number 16029-98-4, has other names as iodotrimethylsilane; iodotrimethylsilyl iodide; tmis; ct3610;iodotrimethyl-silan; silane, iodotrimethyl-; trimethyliodosilane(tmis); trimethyliodosilane.
The characteristics of this chemical could be summarized as: (1)ACD/LogP: 2.83; (2)ACD/LogD(pH5.5): 2.83; (3)ACD/LogD(pH7.4): 2.83; (4)ACD/BCF(pH5.5): 83.47; (5)ACD/BCF(pH7.4): 83.47; (6)ACD/KOC(pH5.5): 826.1; (7)ACD/KOC(pH7.4): 826.1; (8)IndexofRefraction: 1.479; (9)MolarRefractivity: 37.63cm3; (10)MolarVolume: 132.6cm3; (11)Polarizability: 14.91×10-24 cm3; (12)SurfaceTension: 21.2dyne/cm; (13)Density: 1.508g/cm3; (14)FlashPoint: 15.2°C; (15)EnthalpyofVaporization: 32.66kJ/mol; (16)BoilingPoint: 101.5°Cat760mmHg; (17)VapourPressure: 40.5mmHgat25°C.
This is a kind of flammable liquid and is sensitive to light and moisture, so it should be kept with the storage temp. of -20°C. Being among the highly flammable chemicals, it may catch fire in contact with air, only needing brief contact with an ignition source, and it has a very low flash point or evolve highly flammable gases in contact with water. Besides, it is corrosive for it may destroy living tissue on contact. What's more, it may reacts violently with water and then causes burns.
As for so many dangerous possibilities, you should be very careful while dealing with this chemical. First, wear suitable protective clothing, gloves and eye/face protection and then keep away from sources of ignition - No smoking. But if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; If in case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water); And if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Except all these, remember to avoid contacting with eyes, for it is very irritant to our eyes. And you could also go to WGK Germany 3 to obtain more safety information.
As for its product categories, there are various, including silane compounds; si (classes of silicon compounds); silicon compounds (for synthesis); si-x (f, br, i) compounds; synthetic organic chemistry; alkyl silanes; blocking agents; protective agents; silylating agents, while its preparation products are including 1-fluoro-4-(trifluoromethylthio)benzene, 4-fluorothiophenol, eschenmoser's salt, (2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid, 5-methyl-l-tryptophan. Besides, its raw materials are the aluminium and hexamethyldisiloxane.
When comes to its usage, we should say it is widely used in many ways, such as the organic synthesis and other synthsis of medicines. And you could also get this kind of chemical by the below method.
Firstly, react 5.6g(0.21mol) aluminite powder and 16.2g (0.10mol) HMDSO in the reactor and then replace the air with nitrogen; Secondly, heat to 60℃, add 50.8g(0.2mol) iodine while stiring and then
heat up to 140℃ and have the backflow for 1.5h; Thirdly, go through the atmospheric distillation and finally you could get 32.6-35.3g TMSI, with the productivity of 82-88%.
Additionally, you could convert the following data information into the molecular structure:
SMILES:I[Si](C)(C)C
InChI:InChI=1/C3H9ISi/c1-5(2,3)4/h1-3H3
InChIKey:CSRZQMIRAZTJOY-UHFFFAOYAB
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