Product Name

  • Name

    Iodotrimethylsilane

  • EINECS 240-171-0
  • CAS No. 16029-98-4
  • Article Data120
  • CAS DataBase
  • Density 1.508 g/cm3
  • Solubility reacts with water
  • Melting Point <0°C
  • Formula C3H9ISi
  • Boiling Point 101.5 °C at 760 mmHg
  • Molecular Weight 200.094
  • Flash Point 15.2 °C
  • Transport Information UN 2924 3/PG 2
  • Appearance Straw liquid
  • Safety 16-26-36/37/39-43-45-25
  • Risk Codes 11-14-34
  • Molecular Structure Molecular Structure of 16029-98-4 (Iodotrimethylsilane)
  • Hazard Symbols FlammableF,CorrosiveC
  • Synonyms trimethyliodosilane;iodo-trimethyl-silane;Silane, iodotrimethyl-;Trimethyl Iodo Silane;(Iodo)-trimethylsilane;Trimethylsilyl iodide;Trimethyliodosilane(TMIS);trimethyliodo silane;
  • PSA 0.00000
  • LogP 2.25630

Synthetic route

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
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; aluminium66%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
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
33861-17-5

phenyl trimethylsilyl selenide

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
With iodineA 98%
B 96%
1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
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
136990-69-7

pentamethylcyclopentadienyltrimethylsilane

titanium(IV) iodide
7720-83-4

titanium(IV) iodide

A

pentamethylcyclopentadienyltitanium triiodide

pentamethylcyclopentadienyltitanium triiodide

B

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
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
4099-46-1

bis(trimethylsilyl)selenide

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
With iodine In m-xylene94%
trimethylphenylsilane
768-32-1

trimethylphenylsilane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
With I2; AlI393%
With I256%
With aluminium(III) iodide; iodine
With iodine
potassium ethyl xanthogenate
140-89-6

potassium ethyl xanthogenate

methyl iodide
74-88-4

methyl iodide

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

O-ethyl S-methyl dithiocarbonate
623-54-1

O-ethyl S-methyl dithiocarbonate

Conditions
ConditionsYield
In acetoneA n/a
B 90%
tetrakis(trimethylsiloxy)phosphonium iodide
53380-41-9

tetrakis(trimethylsiloxy)phosphonium iodide

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

Tris(trimethylsilyl) phosphate
10497-05-9

Tris(trimethylsilyl) phosphate

Conditions
ConditionsYield
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
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
With iodine In neat (no solvent) for 15h; Ambient temperature;85%
octamethylcyclotetrasiloxane
556-67-2

octamethylcyclotetrasiloxane

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

C

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With aluminium(III) iodide at 140 - 170℃; for 5h;A n/a
B 83.5%
C n/a
1,1,3,3-Tetramethyldisiloxane
3277-26-7

1,1,3,3-Tetramethyldisiloxane

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
With iodine for 0.166667h; Heating;80%
Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

aluminium(III) iodide
7784-23-8

aluminium(III) iodide

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
76%
acetyl iodide
507-02-8

acetyl iodide

tris(trimethylsilyl)amine
1586-73-8

tris(trimethylsilyl)amine

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

N,N-bis(trimethylsilyl)acetamide
10416-58-7

N,N-bis(trimethylsilyl)acetamide

Conditions
ConditionsYield
at 60 - 70℃; for 6h;A 65%
B 53%
octamethylcyclotetrasiloxane
556-67-2

octamethylcyclotetrasiloxane

A

tetramethylsilane
75-76-3

tetramethylsilane

B

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

C

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

D

tetradecamethylhexasiloxane
107-52-8

tetradecamethylhexasiloxane

Conditions
ConditionsYield
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
556-67-2

octamethylcyclotetrasiloxane

A

tetramethylsilane
75-76-3

tetramethylsilane

B

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

C

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

D

dodecamethyl-cyclohexasiloxane
540-97-6

dodecamethyl-cyclohexasiloxane

Conditions
ConditionsYield
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
556-67-2

octamethylcyclotetrasiloxane

A

tetramethylsilane
75-76-3

tetramethylsilane

B

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

C

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

D

hexadecamethylheptasiloxane
541-01-5

hexadecamethylheptasiloxane

Conditions
ConditionsYield
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
507-02-8

acetyl iodide

N,N-bis(trimethylsilyl)ethanamine
2477-39-6

N,N-bis(trimethylsilyl)ethanamine

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

N-trimethylsilyle du N-ethylacetamide
23138-72-9

N-trimethylsilyle du N-ethylacetamide

Conditions
ConditionsYield
at 60 - 70℃; for 8h;A 23%
B 61%
phenyltrimethylsilyl ether
1529-17-5

phenyltrimethylsilyl ether

A

tetramethylsilane
75-76-3

tetramethylsilane

B

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

C

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

D

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
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
1586-73-8

tris(trimethylsilyl)amine

benzoyl iodide
618-38-2

benzoyl iodide

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

N,N-bis(trimethylsilyl)benzamide
38850-27-0

N,N-bis(trimethylsilyl)benzamide

Conditions
ConditionsYield
at 120 - 130℃; for 8h;A 59%
B 32%
1-Iodonaphthalene
90-14-2

1-Iodonaphthalene

ethenyltrimethylsilane
754-05-2

ethenyltrimethylsilane

A

1-vinylnaphthalene
826-74-4

1-vinylnaphthalene

B

propene
187737-37-7

propene

C

ethene
74-85-1

ethene

D

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

E

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

F

buta-1,3-diene
106-99-0

buta-1,3-diene

Conditions
ConditionsYield
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
C11H17NOSi*HI

C11H17NOSi*HI

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

N-phenyl-N-trimethylsilylacetamide
10557-63-8

N-phenyl-N-trimethylsilylacetamide

Conditions
ConditionsYield
Heating;A 53%
B 13%
diiododimethylsilane
15576-81-5

diiododimethylsilane

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
at 116℃; for 12h;48%
N,N-bis(trimethylsilyl)ethanamine
2477-39-6

N,N-bis(trimethylsilyl)ethanamine

benzoyl iodide
618-38-2

benzoyl iodide

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

N-ethyl-N-trimethylsilylbenzamide
23728-69-0

N-ethyl-N-trimethylsilylbenzamide

C

C15H28NOSi2(1+)*I(1-)

C15H28NOSi2(1+)*I(1-)

Conditions
ConditionsYield
at 80 - 104℃; for 13h;A 36%
B 25%
C 9.86 g
S-trimethylsilyl O-ethyldithiocarbonate
136490-79-4

S-trimethylsilyl O-ethyldithiocarbonate

methyl iodide
74-88-4

methyl iodide

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

O-ethyl S-methyl dithiocarbonate
623-54-1

O-ethyl S-methyl dithiocarbonate

Conditions
ConditionsYield
In chloroform-d1 for 24h;A n/a
B 30%
1-chloro-1,1,3,3,3-pentamethyldisiloxane
2943-62-6

1-chloro-1,1,3,3,3-pentamethyldisiloxane

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

octamethylcyclotetrasiloxane
556-67-2

octamethylcyclotetrasiloxane

C

1-chloroheptamethyltrisiloxane
18297-87-5

1-chloroheptamethyltrisiloxane

D

1-chloro-1,1,3,3,5,5,7,7,7-nonamethyltetrasiloxane
14415-31-7

1-chloro-1,1,3,3,5,5,7,7,7-nonamethyltetrasiloxane

Conditions
ConditionsYield
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
me3Si(pr-2-J)
18140-04-0

me3Si(pr-2-J)

A

propene
187737-37-7

propene

B

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
at 80℃;
at 80℃;
hexamethyldisilathiane
3385-94-2

hexamethyldisilathiane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
With 1-Iodoheptane at 160℃;
With dibutyl-iodo-borane In carbon disulfide
n-butylthiotrimethylsilane
3553-78-4

n-butylthiotrimethylsilane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Conditions
ConditionsYield
With diiodomethane
1,3-dioxane
505-22-6

1,3-dioxane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

iodomethyl 3-iodopropyl ether
112539-38-5

iodomethyl 3-iodopropyl ether

Conditions
ConditionsYield
at 80℃;100%
4-methyl-1,3-dioxane
1120-97-4

4-methyl-1,3-dioxane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

A

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

B

3-Iodo-1-iodomethoxy-butane
130824-89-4

3-Iodo-1-iodomethoxy-butane

C

1-Iodo-3-iodomethoxy-butane
130824-88-3

1-Iodo-3-iodomethoxy-butane

Conditions
ConditionsYield
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
1,3-dioxepane
505-65-7

1,3-dioxepane

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

4-iodobutyl iodomethyl ether
112539-39-6

4-iodobutyl iodomethyl ether

Conditions
ConditionsYield
at 100℃;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

1,4-Diiodo-1,4-dimethoxy-butane
86428-40-2

1,4-Diiodo-1,4-dimethoxy-butane

Conditions
ConditionsYield
100%
cis- and trans-2,6-Dimethoxytetrahydropyran
6581-57-3

cis- and trans-2,6-Dimethoxytetrahydropyran

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

1,5-Diiodo-1,5-dimethoxy-pentane
86428-42-4

1,5-Diiodo-1,5-dimethoxy-pentane

Conditions
ConditionsYield
100%
trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

trimethylsiloxydiethylphosphinate
42346-39-4

trimethylsiloxydiethylphosphinate

bis(trimethylsilyloxy)diethylphosphonium iodide
140846-35-1

bis(trimethylsilyloxy)diethylphosphonium iodide

Conditions
ConditionsYield
In benzene100%
trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

trimethylsiloxydipropylphosphinate
53483-29-7

trimethylsiloxydipropylphosphinate

bis(trimethylsilyloxy)dipropylphosphonium iodide
140846-36-2

bis(trimethylsilyloxy)dipropylphosphonium iodide

Conditions
ConditionsYield
In benzene100%
trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

(methoxyethynyl)bis(pentafluorophenyl)phosphine
95112-05-3

(methoxyethynyl)bis(pentafluorophenyl)phosphine

(trimethylsilyl)ketene
131981-61-8

(trimethylsilyl)ketene

Conditions
ConditionsYield
In nitromethane at 20℃; for 2h;100%
trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

Ethoxyethynyl-bis-pentafluorophenyl-phosphane
119099-30-8

Ethoxyethynyl-bis-pentafluorophenyl-phosphane

(trimethylsilyl)ketene
131981-61-8

(trimethylsilyl)ketene

Conditions
ConditionsYield
In nitromethane at 20℃; for 2h;100%
trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

ethyl P-(diethoxymethyl)phosphonite
65600-72-8

ethyl P-(diethoxymethyl)phosphonite

(diethoxymethyl)tris(trimethylsiloxy)phosphonium iodide

(diethoxymethyl)tris(trimethylsiloxy)phosphonium iodide

Conditions
ConditionsYield
In dichloromethane for 1.5h;100%

Iodotrimethylsilane Specification

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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