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16029-98-4 Usage

Chemical Properties

Straw liquid

Uses

Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.

Preparation

Iodotrimethylsilane is prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes. Other have been reported for the preparation of Trimethylsilyl Iodide(TMS-I): chlorotrimethylsilane undergoes halogen exchange with either lithium iodide in CHCl3 or sodium iodide in MeCN, which allows in situ reagent formation. Alternatively, hexamethyldisilane reacts with iodine at 25–61°C to afford TMS-I with no byproducts.

Application

Iodotrimethylsilane can be used as a versatile reagent for the mild dealkylation of ethers, carboxylic esters, lactones, carbamates, acetals, phosphonate and phosphate esters; cleavage of epoxides, cyclopropyl ketones; conversion of vinyl phosphates to vinyl iodides; neutral nucleophilic reagent for halogen exchange reactions, carbonyl and conjugate addition reactions; use as a trimethylsilylating agent for formation of enol ethers, silyl imino esters, and N-silylenamines, alkyl, alkenyl and alkynyl silanes; Lewis acid catalyst for acetal formation, α- alkoxymethylation of ketones, for reactions of acetals with silyl enol ethers and allylsilanes; reducing agent for epoxides, enediones, α-ketols, sulfoxides, and sulfonyl halides; dehydrating agent for oximes.

Reactions

Trimethylsilyl iodide reacts under mild conditions in the absence of a catalyst with alkyl fluorides as well as with benzyl and tertiary alkyl chlorides and bromides to give good yields of alkyl iodides and the corresponding trimethylsilyl halides.

General Description

Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.

Synthesis

This procedure describes a convenient method for the preparation of Iodotrimethylsilane: A 250-ml., two-necked, round-bottomed flask equipped with a magnetic stirring bar, an addition funnel for solids, and a reflux condenser bearing a nitrogen inlet is charged with 5.6 g. (0.21 mole) of aluminum powder and 16.2 g. (0.100 mole) of hexamethyldisiloxane and purged with nitrogen. The mixture is stirred and heated with an oil bath at 60°C as 50.8 g. (0.200 mole) of iodine is added slowly through the addition funnel over 55 minutes. The bath temperature is raised to ca. 140°C, and the mixture is heated under reflux for 1.5 hours. The reflux condenser is removed, and the flask is equipped for distillation at atmospheric pressure. The bath temperature is gradually raised from 140°C to 210°C, and the clear, colorless distillate is collected, yielding 32.6–35.3 g. (82–88%) of iodotrimethylsilane, b.p. 106–109°C.

Purification Methods

Add a little antimony powder and fractionate with this powder in the still. 20 1.470. Stabilise the distillate with 1% wt of Cu powder. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4009.]

Check Digit Verification of cas no

The CAS Registry Mumber 16029-98-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,0,2 and 9 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 16029-98:
(7*1)+(6*6)+(5*0)+(4*2)+(3*9)+(2*9)+(1*8)=104
104 % 10 = 4
So 16029-98-4 is a valid CAS Registry Number.
InChI:InChI=1/C3H9ISi/c1-5(2,3)4/h1-3H3

16029-98-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (I0308)  Trimethylsilyl Iodide (stabilized with Aluminum)  >95.0%(T)

  • 16029-98-4

  • 5g

  • 210.00CNY

  • Detail
  • TCI America

  • (I0308)  Trimethylsilyl Iodide (stabilized with Aluminum)  >95.0%(T)

  • 16029-98-4

  • 25g

  • 600.00CNY

  • Detail
  • Alfa Aesar

  • (A12902)  Iodotrimethylsilane, 97%, stab. with copper   

  • 16029-98-4

  • 5g

  • 209.0CNY

  • Detail
  • Alfa Aesar

  • (A12902)  Iodotrimethylsilane, 97%, stab. with copper   

  • 16029-98-4

  • 25g

  • 633.0CNY

  • Detail
  • Alfa Aesar

  • (A12902)  Iodotrimethylsilane, 97%, stab. with copper   

  • 16029-98-4

  • 100g

  • 2042.0CNY

  • Detail
  • Alfa Aesar

  • (A12902)  Iodotrimethylsilane, 97%, stab. with copper   

  • 16029-98-4

  • 250g

  • 4495.0CNY

  • Detail
  • Aldrich

  • (195529)  Iodotrimethylsilane  97%

  • 16029-98-4

  • 195529-5G

  • 243.36CNY

  • Detail
  • Aldrich

  • (195529)  Iodotrimethylsilane  97%

  • 16029-98-4

  • 195529-25G

  • 737.10CNY

  • Detail
  • Aldrich

  • (195529)  Iodotrimethylsilane  97%

  • 16029-98-4

  • 195529-100G

  • 2,253.42CNY

  • Detail

16029-98-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Iodotrimethylsilane

1.2 Other means of identification

Product number -
Other names TriMethylsilyl Iodide

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:16029-98-4 SDS

16029-98-4Synthetic 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%

16029-98-4Relevant articles and documents

Evidence for an oxygen anthracene sandwich complex

Klaper, Matthias,Linker, Torsten

, p. 11896 - 11899 (2013)

Oxygen sticks in between acenes: The rate of the photooxygenation of bis(anthryl)alkanes with singlet oxygen shows a maximum for a defined chain length (n=4). In combination with calculations, a bathochromic shift of the UV/Vis absorption for only one endoperoxide and a CT absorption band, this gives considerable evidence for an oxygen anthracene sandwich complex. Copyright

N-aminomethylation vs. C-aminomethylation of indole and pyrrole with an N,O-acetal controlled by the hardness of a counter ion of an iminium compound

Sakai, Norio,Okano, Hidetoshi,Shimamura, Kazuyori,Konakahara, Takeo

, p. 501 - 503 (2014)

Under relatively strong Lewis acidic conditions (a softer counter ion) using TMSOTf and TMSI, the aminomethylation of indole or pyrrole with a typical N,O-acetal preferentially produced the kinetically favored N-aminomethylated indole or pyrrole derivative. Use of a relatively weak Lewis acid (a harder counter ion), such as TMSCl and TMSBr, preferentially produced the thermodynamically favored C-aminomethylated indole and pyrrole derivative.

Evaluation of aroma-active compounds in Pontianak orange peel oil (Citrus nobilis Lour. var. microcarpa Hassk.) by gas chromatography-olfactometry, aroma reconstitution, and omission test

Dharmawan, Jorry,Kasapis, Stefan,Sriramula, Praveena,Lear, Martin J.,Curran, Philip

, p. 239 - 244 (2009)

The aroma-active compounds of Pontianak orange peel oil (Citrus nobilis Lour. var. microcarpa Hassk.) were characterized by using gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA) techniques. Forty-one compounds were found to be aroma-active, which were mainly dominated by saturated and unsaturated aldehydes. The flavor dilution (FD) factor was within the range of 2-2048, and compounds having the highest FD factor were α-pinene, β-pinene, linalool, and 2-methoxy-3-(2- methylpropyl) pyrazine, including a few unknown compounds. On the basis of GC-O results, odor activity value (OAV) and relative flavor activity (RFA) were determined for aroma model reconstitution. These resembled the original aroma of the peel oil for the green, fatty, fresh, peely, floral, and tarry attributes, with the model solution derived from OAV being the closest to Pontianak oil. Omission tests were carried out to verify the significance of (Z)-5-dodecenal and 1-phenylethyl mercaptan as key compounds in the aroma of Pontianak orange peel oil.

Unsupported metal silyl ether coordination

Pahl, Jürgen,Elsen, Holger,Friedrich, Alexander,Harder, Sjoerd

, p. 7846 - 7849 (2018)

Simple silyl ethers like O(SiMe3)2 in contrast to normal ethers are inert to metal bonding; however, a “naked”, highly Lewis-acidic, cationic Mg species enforces complexation. DFT calculations indicate that agostic interactions and van der Waals attraction significantly contribute to the stability of this first example of unsupported metal silyl ether coordination.

Balcombe et al.

, p. 1353,1354-1357 (1975)

The Ring Opening Reaction of Cyclopolysilanes, (R2Si)n (n=3-6), with Iodine. A Kinetic Study

Watanabe, Hamao,Shimoyama, Hiromi,Muraoka, Tsutomu,Kougo, Yuichi,Kato, Motohiko,Nagai, Yoichiro

, p. 769 - 770 (1987)

Reactions of a series of peralkylcyclopolysilanes with iodine were found to proceed via second-order kinetics.Rate constans show that, in general, the smaller rings react faster than larger rings.Values of the activation parameters, Ea and ΔG, decreased with the decreasing ring size and are parallel with those of the oxidation potentials and of the transition energies.

Finkelstein Reaction in Non-polar Organic Solvents: A Streamlined Synthesis of Organic Iodides

Takahashi, Yusuke,Seki, Masahiko

, p. 1974 - 1978 (2021)

The Finkelstein reaction of organic halides was found to proceed smoothly in non-polar organic solvents other than acetone when operated in the presence of a catalytic amount of tetra-n-butylammonium bromide and water. The new protocol was successfully applied to a preparation of ethyl 5-iodopentanoate from the corresponding bromide which was used directly for zinc reagent formation and Fukuyama coupling to enable the formation of the (+)-biotin side chain in a streamlined manner. Rate acceleration by microwave irradiation and an application to the synthesis of trimethylsilyl iodide will be described as well.

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Hundeck

, p. 23,26 (1966)

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METHOD FOR PRODUCING IODOTRIALKYLSILANE COMPOUND

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Paragraph 0059-0064, (2021/06/04)

PROBLEM TO BE SOLVED: To provide a method for producing iodotrialkylsilane compounds that can be produced stably even in various organic solvents. SOLUTION: A method for producing an iodotrialkylsilane compound (2A) includes bringing a halogenated trialkylsilane compound (1A) into contact with an alkali iodide metal salt in an organic solvent for a reaction to occur between them (X is F, Cl, or Br). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

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