Product Name

  • Name

    Trimethylsulfonium iodide

  • EINECS 218-555-4
  • CAS No. 2181-42-2
  • Article Data69
  • CAS DataBase
  • Density 1.6554 (estimate)
  • Solubility Soluble in water
  • Melting Point 215-220 °C(lit.)
  • Formula C3H9S.I
  • Boiling Point
  • Molecular Weight 204.075
  • Flash Point
  • Transport Information
  • Appearance white to yellowish crystalline solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2181-42-2 (Trimethylsulfonium iodide)
  • Hazard Symbols IrritantXi
  • Synonyms Trimethylsulfonium iodide (6CI,7CI);Sulfonium,trimethyl-, iodide (8CI,9CI);
  • PSA 25.30000
  • LogP -2.50190

Synthetic route

methylthiol
74-93-1

methylthiol

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
In chloroform for 5h; Ambient temperature;100%
dimethylsulfide
75-18-3

dimethylsulfide

diiodomethane
75-11-6

diiodomethane

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
In acetonitrile at 50℃; for 168h; Methylation;96%
dimethylsulfide
75-18-3

dimethylsulfide

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
In ethanol for 24h; Ambient temperature;90%
at 20℃; for 16h; Inert atmosphere;78%
at 25℃; for 15h;66%
methyl iodide
74-88-4

methyl iodide

/PCATD358--130/

/PCATD358--130/

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
In tetrahydrofuran 1.) -78 deg C, 6 h, 2.) r.t., 48 h;72%
dimethylsulfide
75-18-3

dimethylsulfide

acetyl iodide
507-02-8

acetyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

dimethylsulfide
75-18-3

dimethylsulfide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
With iodine at 110 - 120℃;
ethanol
64-17-5

ethanol

dimethyl-ethylsulphonium iodide
38263-90-0

dimethyl-ethylsulphonium iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

(4-bromo-phenyl)-phenyl-[2]pyridyl-phosphine sulfide
858242-68-9

(4-bromo-phenyl)-phenyl-[2]pyridyl-phosphine sulfide

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 100℃;
propylene sulphide
1072-43-1

propylene sulphide

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

diethylmethylsulfonium iodide
17459-59-5

diethylmethylsulfonium iodide

A

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

B

triethylsulfonium iodide
1829-92-1

triethylsulfonium iodide

Conditions
ConditionsYield
durch Destillation oder bei mehrstuendigem Kochen;
methanol
67-56-1

methanol

dithiooxamide
79-40-3

dithiooxamide

methyl iodide
74-88-4

methyl iodide

A

Oxalamide
471-46-5

Oxalamide

B

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 150℃;
phenylmethanethiol
100-53-8

phenylmethanethiol

methyl iodide
74-88-4

methyl iodide

A

dibenzyl disulphide
150-60-7

dibenzyl disulphide

B

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 100℃; unter Druck;
benzenecarbothioamide
2227-79-4

benzenecarbothioamide

methyl iodide
74-88-4

methyl iodide

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 130℃; im geschlossenen Rohr;
6-(methylthio)-2(Z)-hexene
1086240-66-5

6-(methylthio)-2(Z)-hexene

acetone
67-64-1

acetone

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 120℃;
methanol
67-56-1

methanol

[1,3,5]trithiane
291-21-4

[1,3,5]trithiane

methyl iodide
74-88-4

methyl iodide

A

Dimethoxymethane
109-87-5

Dimethoxymethane

B

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 80 - 100℃; im Rohr;
[1,3,5]trithiane
291-21-4

[1,3,5]trithiane

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

trithioacetaldehyde
1226972-19-5, 1226972-27-5

trithioacetaldehyde

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
β-trithioacetaldehyde;
methanol
67-56-1

methanol

carbamoylsulfanyl-acetic acid methyl ester
859918-72-2

carbamoylsulfanyl-acetic acid methyl ester

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 110℃;
methyl thiocyanate
556-64-9

methyl thiocyanate

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 100℃; im geschlossenen Rohr;
(S,S)-dimethyl trithiocarbonate
2314-48-9

(S,S)-dimethyl trithiocarbonate

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 80 - 90℃;
3 Monate lang im Dunkel stehenlaesst und die Krystalle mit Alkohol und schwefliger Saeure erwaermt;
at 80 - 90℃;
im Dunkeln bei monatelanger Einw. und Behandeln des entstandenen Polyjodids mit waessrig-alkoholischer schwefliger Saeure;
ethyl isoamyl sulfide
66481-77-4

ethyl isoamyl sulfide

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 100℃;
O,O,S-trimethyl phosphorothioate
152-20-5

O,O,S-trimethyl phosphorothioate

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 100℃;
O,O,O-trimethylthiophosphate
152-18-1

O,O,O-trimethylthiophosphate

methyl iodide
74-88-4

methyl iodide

A

O,O,S-trimethyl phosphorothioate
152-20-5

O,O,S-trimethyl phosphorothioate

B

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 100℃;
ethanol
64-17-5

ethanol

diallyl sulphide
592-88-1

diallyl sulphide

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Dimethyldisulphide
624-92-0

Dimethyldisulphide

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 100℃;
dimethyltrisulfane
3658-80-8

dimethyltrisulfane

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 100℃;
allylmethyl sulfide
10152-76-8

allylmethyl sulfide

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

diallyl sulphide
592-88-1

diallyl sulphide

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 24℃; Geschwindigkeit dieser Reaktion;
ethyl isothiocyanate
542-90-5

ethyl isothiocyanate

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

Conditions
ConditionsYield
at 105 - 108℃; im zugeschmolzenen Rohr;
ethyl thioacetate
625-60-5

ethyl thioacetate

methyl iodide
74-88-4

methyl iodide

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

3-chloro-4-methoxy-benzaldehyde
4903-09-7

3-chloro-4-methoxy-benzaldehyde

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2-(3-chloro-4-methoxyphenyl)oxirane

2-(3-chloro-4-methoxyphenyl)oxirane

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 7h; Corey-Tschaikosky Epoxidation; Inert atmosphere;100%
With sodium hydride; dimethyl sulfoxide 1.) THF, 0 deg C, 5 min, 2.) a) 0 deg C, 15 min, b) 25 deg C, 2h; Multistep reaction;
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

benzaldehyde
100-52-7

benzaldehyde

styrene oxide
96-09-3

styrene oxide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 38℃; for 48h;100%
Stage #1: trimethylsulphonium iodide With sodium hydroxide In water for 0.166667h; Corey-Chaykovsky reaction;
Stage #2: benzaldehyde With 1,3-bis[3,5-bis(trifluoromethyl)phenyl]urea In dichloromethane; water at 20℃; for 24h; Inert atmosphere;
93%
With potassium hydroxide In acetonitrile at 60℃; for 3h;87%
benzophenone
119-61-9

benzophenone

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

1,1-diphenyloxirane
882-59-7

1,1-diphenyloxirane

Conditions
ConditionsYield
Stage #1: trimethylsulphonium iodide With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 20℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: benzophenone In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 0 - 20℃; Inert atmosphere; Schlenk technique;
100%
With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 0 - 25℃; for 16h; Corey-Chaykovsky reaction;98%
With potassium hydroxide In tert-butyl alcohol at 40 - 50℃; for 12h; Corey-Chaykovsky epoxidation;97%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

5-methoxy-2-(naphthalen-1-yl)benzaldehyde
199117-07-2

5-methoxy-2-(naphthalen-1-yl)benzaldehyde

1-(2-(epoxyethyl)-4-methoxyphenyl)naphthalene
199117-08-3

1-(2-(epoxyethyl)-4-methoxyphenyl)naphthalene

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane for 96h; Cycloaddition; Heating;100%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2-(9-phenanthryl)-5-methoxybenzaldehyde
199117-10-7

2-(9-phenanthryl)-5-methoxybenzaldehyde

9-(2-(epoxyethyl)-4-methoxyphenyl)phenanthrene
199117-11-8

9-(2-(epoxyethyl)-4-methoxyphenyl)phenanthrene

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane for 96h; Cycloaddition; Heating;100%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene
354529-43-4

3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene

2-(2-dibenzothiophen-3-yl-5-methoxy-phenyl)-oxirane

2-(2-dibenzothiophen-3-yl-5-methoxy-phenyl)-oxirane

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 60 - 65℃; for 20h;100%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

4-(2-formyl-4-methoxyphenyl)dibenzothiophene
485824-06-4

4-(2-formyl-4-methoxyphenyl)dibenzothiophene

4-(2-epoxyethyl-4-methoxyphenyl)dibenzothiophene
485824-12-2

4-(2-epoxyethyl-4-methoxyphenyl)dibenzothiophene

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 65 - 70℃; for 20h;100%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

5-benzyloxy-4,7,8-trimethoxy-naphthalene-2-carbaldehyde
828940-60-9

5-benzyloxy-4,7,8-trimethoxy-naphthalene-2-carbaldehyde

2-(5-benzyloxy-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane
828940-42-7

2-(5-benzyloxy-4,7,8-trimethoxy-naphthalen-2-yl)-oxirane

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 0℃;100%
6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde
409346-73-2

6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran
99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Stage #1: trimethylsulphonium iodide With sodium hydride In dimethyl sulfoxide cooling;
Stage #2: 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde In dimethyl sulfoxide at 20℃; for 1h;
100%
7-(2-formyl-4-methoxyphenyl)benzo[b]thiophene
842167-37-7

7-(2-formyl-4-methoxyphenyl)benzo[b]thiophene

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2-(2-benzo[b]thiophen-7-yl-5-methoxy-phenyl)-oxirane
842167-38-8

2-(2-benzo[b]thiophen-7-yl-5-methoxy-phenyl)-oxirane

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 65℃; for 16h;100%
2-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)thiophene-3-carboxaldehyde

2-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)thiophene-3-carboxaldehyde

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2-[2-(4-methoxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-thiophen-3-yl]-oxirane
874143-00-7

2-[2-(4-methoxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-thiophen-3-yl]-oxirane

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 60 - 65℃; for 13h;100%
3-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)thiophene-2-carboxaldehyden
874142-97-9

3-(4-methoxy-5,6,7,8-tetrahydro-1-naphthyl)thiophene-2-carboxaldehyden

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2-[3-(4-methoxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-thiophen-2-yl]-oxirane
874142-98-0

2-[3-(4-methoxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-thiophen-2-yl]-oxirane

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 60 - 65℃; for 15h;100%
N-t-butylcarbonyl-6-(2-isopropoxy-4-formylphenyl)-pyridin-2-ylamine

N-t-butylcarbonyl-6-(2-isopropoxy-4-formylphenyl)-pyridin-2-ylamine

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

N-t-butylcarbonyl-6-(2-isopropoxy-4-oxiranylphenyl)-pyridin-2-ylamine
221111-41-7

N-t-butylcarbonyl-6-(2-isopropoxy-4-oxiranylphenyl)-pyridin-2-ylamine

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile at 60℃; for 2.5h;100%
With potassium hydroxide; N2 In water; acetonitrile
With potassium hydroxide; N2 In water; acetonitrile
2-methoxyestrone
362-08-3, 7683-30-9

2-methoxyestrone

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

3-hydroxy-2-methoxyestra-1,3,5(10)-triene-17β-spiro-1',2'-oxirane
752246-12-1

3-hydroxy-2-methoxyestra-1,3,5(10)-triene-17β-spiro-1',2'-oxirane

Conditions
ConditionsYield
Stage #1: 2-methoxyestrone; trimethylsulphonium iodide With potassium tert-butylate In DMF (N,N-dimethyl-formamide) at 10 - 20℃; for 0.5h;
Stage #2: With water; ammonium chloride In DMF (N,N-dimethyl-formamide) at 0℃;
100%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
29668-44-8

2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde

6-Oxiranyl-2,3-dihydro-benzo[1,4]dioxine
389124-25-8

6-Oxiranyl-2,3-dihydro-benzo[1,4]dioxine

Conditions
ConditionsYield
With potassium hydroxide; water In acetonitrile at 60℃; for 1.5h;100%
aqueous sodium chloride

aqueous sodium chloride

(E)-β-ionone
79-77-6

(E)-β-ionone

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2-Methyl-2-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]oxirane
58689-13-7

2-Methyl-2-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]oxirane

Conditions
ConditionsYield
In tetrahydrofuran; water; dimethyl sulfoxide; mineral oil; pentane100%
(4-bromophenyl)(phenyl)methanone
90-90-4

(4-bromophenyl)(phenyl)methanone

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2-(4-bromophenyl)-2-phenyloxirane
1070671-69-0

2-(4-bromophenyl)-2-phenyloxirane

Conditions
ConditionsYield
Stage #1: trimethylsulphonium iodide With sodium hydride In tetrahydrofuran at 55℃; for 6h;
Stage #2: (4-bromophenyl)(phenyl)methanone In tetrahydrofuran at 55℃; for 16h;
100%
3β-((triisopropylsilyl)oxy)pregn-5-en-20-one
241139-90-2

3β-((triisopropylsilyl)oxy)pregn-5-en-20-one

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

3β-(triisopropylsiloxy)-22-homopregn-5-en-20R,22-epoxide
1038992-96-9

3β-(triisopropylsiloxy)-22-homopregn-5-en-20R,22-epoxide

Conditions
ConditionsYield
Stage #1: trimethylsulphonium iodide With potassium hexamethylsilazane In tetrahydrofuran at -5℃; for 0.25h;
Stage #2: 3β-((triisopropylsilyl)oxy)pregn-5-en-20-one In tetrahydrofuran at -65 - 25℃; for 3.83h;
100%
(4-chlorophenyl)(4-iodophenyl)methanone
99847-42-4

(4-chlorophenyl)(4-iodophenyl)methanone

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

(RS)-2-(4-chloro-phenyl)-2-(4-iodo-phenyl)-oxirane
857532-00-4

(RS)-2-(4-chloro-phenyl)-2-(4-iodo-phenyl)-oxirane

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 3h; Product distribution / selectivity;100%
Stage #1: trimethylsulphonium iodide With sodium hydride In dimethyl sulfoxide for 0.75h;
Stage #2: (4-chlorophenyl)(4-iodophenyl)methanone In dimethyl sulfoxide at 20℃; for 24h;
97%
97%
Stage #1: trimethylsulphonium iodide With sodium hydride In dimethyl sulfoxide for 0.5h;
Stage #2: (4-chlorophenyl)(4-iodophenyl)methanone In dimethyl sulfoxide at 20℃; for 24h; Product distribution / selectivity;
97%
Stage #1: trimethylsulphonium iodide With sodium hydride In dimethyl sulfoxide for 0.5h;
Stage #2: (4-chlorophenyl)(4-iodophenyl)methanone In dimethyl sulfoxide at 20℃; for 24h;
97%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

trimethylsulfonium azide
7364-15-0

trimethylsulfonium azide

Conditions
ConditionsYield
With silver(I) azide In water at 0 - 20℃; for 2.5h;100%
C14H16N2O
741705-66-8

C14H16N2O

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

C15H18N2O

C15H18N2O

Conditions
ConditionsYield
Stage #1: trimethylsulphonium iodide With sodium hydride In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: C14H16N2O In dimethyl sulfoxide for 3h;
100%
C16H10O2S2
1617510-33-4

C16H10O2S2

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

C18H14O2S2
1617510-38-9

C18H14O2S2

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 25 - 60℃; for 3h; Inert atmosphere;100%
(E)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylcyclohex-1-en-1-yl)but-3-en-2-one

(E)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylcyclohex-1-en-1-yl)but-3-en-2-one

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

(E)-tert-butyl((3,3-dimethyl-2-(2-(2-methyloxiran-2-yl)vinyl)cyclohex-1-en-1-yl)methoxy)dimethylsilane

(E)-tert-butyl((3,3-dimethyl-2-(2-(2-methyloxiran-2-yl)vinyl)cyclohex-1-en-1-yl)methoxy)dimethylsilane

Conditions
ConditionsYield
Stage #1: trimethylsulphonium iodide With dimsylsodium In tetrahydrofuran; dimethyl sulfoxide at -5℃; Corey-Tschaikosky Epoxidation; Inert atmosphere;
Stage #2: (E)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylcyclohex-1-en-1-yl)but-3-en-2-one In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 1h; Inert atmosphere;
100%
(3E)-4-(3-isopropyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

(3E)-4-(3-isopropyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

(E)-isopropyldimethyl((2,4,4-trimethyl-3-(2-(2-methyloxiran-2-yl)vinyl)cyclohex-2-en-1-yl)oxy)silane

(E)-isopropyldimethyl((2,4,4-trimethyl-3-(2-(2-methyloxiran-2-yl)vinyl)cyclohex-2-en-1-yl)oxy)silane

Conditions
ConditionsYield
Stage #1: trimethylsulphonium iodide With dimsylsodium In tetrahydrofuran; dimethyl sulfoxide at -5℃; Corey-Tschaikosky Epoxidation; Inert atmosphere;
Stage #2: (3E)-4-(3-isopropyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one In tetrahydrofuran; dimethyl sulfoxide at -5℃; for 0.75h; Inert atmosphere;
100%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde
29668-43-7

2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde

5-(oxiran-2-yl)-2,3-dihydro-1,4-benzodioxine

5-(oxiran-2-yl)-2,3-dihydro-1,4-benzodioxine

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 7h; Corey-Tschaikosky Epoxidation; Inert atmosphere;100%
6,6'-(thiophene-2,5-diyl)bis(3-octylbenzaldehyde)

6,6'-(thiophene-2,5-diyl)bis(3-octylbenzaldehyde)

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2,5-bis(4-octyl-2-(oxiran-2-yl)phenyl)thiophene

2,5-bis(4-octyl-2-(oxiran-2-yl)phenyl)thiophene

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 60℃; for 4h; Inert atmosphere;100%
With potassium hydroxide In acetonitrile at 60℃; for 4h; Johnson-Corey-Chaykovsky Reaction; Inert atmosphere; Schlenk technique;
2,5-bis(6-octylbenzo[b]thiophen-2-yl)-1,4-phthalaldehyde

2,5-bis(6-octylbenzo[b]thiophen-2-yl)-1,4-phthalaldehyde

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2,2′-(2,5-bis(6-octylbenzo[b]thiophen-2-yl)-1,4-phenylene)bis(oxirane)

2,2′-(2,5-bis(6-octylbenzo[b]thiophen-2-yl)-1,4-phenylene)bis(oxirane)

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 60℃; for 3h; Schlenk technique; Inert atmosphere;100%
2-methylcyclooctanone
10363-27-6

2-methylcyclooctanone

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

4-methyl-1-oxaspiro[2.7]decane

4-methyl-1-oxaspiro[2.7]decane

Conditions
ConditionsYield
With potassium tert-butylate at 20℃;100%
2-benzylcyclooctan-1-one
22442-07-5

2-benzylcyclooctan-1-one

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

4-benzyl-1-oxaspiro[2.7]decane

4-benzyl-1-oxaspiro[2.7]decane

Conditions
ConditionsYield
With potassium tert-butylate at 20℃;100%

TRIMETHYLSULFONIUM IODIDE Chemical Properties

Molecular Formula: C3H9IS
Formula Weight: 204.07
Synonyms: Trimethylsulfonium iodine ; trimethylsulfone iodide ; Sulfonium, trimethyl-, iodide ; Trimethylsulfoniumiodid
Melting Point: 215-220 °C(lit.)
Water Solubility : TRIMETHYLSULFONIUM IODIDE (2181-42-2) is soluble
Sensitive of TRIMETHYLSULFONIUM IODIDE (2181-42-2) : Light Sensitive
Chemical Properties: TRIMETHYLSULFONIUM IODIDE (2181-42-2) is a white to yellowish crystalline solid

TRIMETHYLSULFONIUM IODIDE Toxicity Data With Reference

1.    

ipr-rat LDLo:88 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 20 (1971),135.
2.    

scu-mus LDLo:300 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 25 (1925),315.
3.    

ivn-mus LD50:18 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#02185 .

TRIMETHYLSULFONIUM IODIDE Consensus Reports

Reported in EPA TSCA Inventory.

TRIMETHYLSULFONIUM IODIDE Safety Profile

Safety: CAUTION: May irritate eyes, skin, and respiratory tract
Hazard Codes : Xi: Irritant
Risk Statements : 36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements : 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany : 3
RTECS : WR8750000
F : 8: Photosensitive
HS Code : 29309070
Poison by intraperitoneal, subcutaneous, and intravenous routes. When heated to decomposition it emits very toxic fumes of I and SOx. See also IODIDES.

TRIMETHYLSULFONIUM IODIDE Specification

Storage of TRIMETHYLSULFONIUM IODIDE (2181-42-2): Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep container closed when not in use. 

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