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Trimethylsulfonium iodide is a white to yellowish crystalline solid that is soluble in water, alcohol, tetrahydrofuran, and dimethyl sulfoxide. It is a sulfoxonium salt with potential applications in various industries due to its unique chemical properties.

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  • 2181-42-2 Structure
  • Basic information

    1. Product Name: Trimethylsulfonium iodide
    2. Synonyms: Trimethylsulfonium iodide,98%;Trimethylsulfonium iodide ,99.5%;Trimethylsulphonium Iodide 99%;triMethylsulfaniuM iodide;TriMethylsulfoniuM iodide, 98% 100GR;TriMethylsulfoniuM iodide, 98% 25GR;TRIMETHYLSULFONIUM IODIDE FOR SYNTHESIS;TriMethylsulfoniuM Iodide, 97+%
    3. CAS NO:2181-42-2
    4. Molecular Formula: C3H9IS
    5. Molecular Weight: 204.07
    6. EINECS: 218-555-4
    7. Product Categories: Iodonium Sulfonium & Oxonium Compounds;Sulfonium Compounds;C-C Bond Formation;OthersOrganic Building Blocks;Sulfonium/Sulfoxonium Compounds;Sulfur Compounds;Synthetic Reagents;Isoquinolines ,Furans ,Quinolines ,Quinaldines
    8. Mol File: 2181-42-2.mol
  • Chemical Properties

    1. Melting Point: 215-220 °C(lit.)
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: White to yellow/Crystalline Powder, Crystals and/or Chunks
    5. Density: 1.6554 (estimate)
    6. Refractive Index: N/A
    7. Storage Temp.: Store below +30°C.
    8. Solubility: 400g/l
    9. Water Solubility: soluble
    10. Sensitive: Light Sensitive
    11. BRN: 3555192
    12. CAS DataBase Reference: Trimethylsulfonium iodide(CAS DataBase Reference)
    13. NIST Chemistry Reference: Trimethylsulfonium iodide(2181-42-2)
    14. EPA Substance Registry System: Trimethylsulfonium iodide(2181-42-2)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS: WR8750000
    6. F: 8
    7. TSCA: Yes
    8. HazardClass: IRRITANT
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 2181-42-2(Hazardous Substances Data)

2181-42-2 Usage

Uses

1. Used in Chemical Synthesis:
Trimethylsulfonium iodide is used as a reagent for the synthesis of epoxides and allylic alcohols. Treatment with a strong base yields the dimethylsulfonium methylide, which reacts in-situ with the carbonyl group of ketones to form these compounds.
2. Used in Pharmaceutical Applications:
Trimethylsulfonium iodide has the potential to inhibit human placental diamine oxidase, which may have implications in the development of new drugs or therapies.
3. Used in Organic Chemistry:
As a sulfoxonium salt, trimethylsulfonium iodide can be utilized in various organic chemistry reactions, particularly those involving the formation of epoxides, which are important intermediates in the synthesis of various pharmaceuticals and other organic compounds.

Preparation

Trimethylsulfoxonium iodide may be prepared by the reaction of dimethyl sulfoxide and iodomethane:(CH3)2SO + CH3I → (CH3)3SO+IAfter standing overnight, the resulting solid white cake is crushed and recrystallized from absolute ethanol to give pure trimethylsulfonium iodide.

Purification Methods

Crystallise the iodide from EtOH. [Emeleus & Heal J Chem Soc 1126 1946, Swain & Kaiser J Am Chem Soc 80 4089 1958, Borredon et al. J Org Chem 55 501 1990, Bouda et al. Synth Commun 17 503 1987.]

Check Digit Verification of cas no

The CAS Registry Mumber 2181-42-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,8 and 1 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2181-42:
(6*2)+(5*1)+(4*8)+(3*1)+(2*4)+(1*2)=62
62 % 10 = 2
So 2181-42-2 is a valid CAS Registry Number.
InChI:InChI=1/C3H9S.HI/c1-4(2)3;/h1-3H3;1H/q+1;/p-1

2181-42-2 Well-known Company Product Price

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  • TCI America

  • (T1056)  Trimethylsulfonium Iodide  >98.0%(T)

  • 2181-42-2

  • 25g

  • 360.00CNY

  • Detail
  • TCI America

  • (T1056)  Trimethylsulfonium Iodide  >98.0%(T)

  • 2181-42-2

  • 500g

  • 2,750.00CNY

  • Detail
  • Alfa Aesar

  • (A12639)  Trimethylsulfonium iodide, 99%   

  • 2181-42-2

  • 50g

  • 424.0CNY

  • Detail
  • Alfa Aesar

  • (A12639)  Trimethylsulfonium iodide, 99%   

  • 2181-42-2

  • 250g

  • 1976.0CNY

  • Detail
  • Alfa Aesar

  • (A12639)  Trimethylsulfonium iodide, 99%   

  • 2181-42-2

  • 1000g

  • 7252.0CNY

  • Detail
  • Aldrich

  • (T80489)  Trimethylsulfoniumiodide  98%

  • 2181-42-2

  • T80489-25G

  • 377.91CNY

  • Detail
  • Aldrich

  • (T80489)  Trimethylsulfoniumiodide  98%

  • 2181-42-2

  • T80489-100G

  • 1,177.02CNY

  • Detail

2181-42-2SDS

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 trimethylsulfanium,iodide

1.2 Other means of identification

Product number -
Other names trimethylsulfanium 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:2181-42-2 SDS

2181-42-2Synthetic 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%

2181-42-2Relevant articles and documents

Trimethylsulfonium Lead Triiodide: An Air-Stable Hybrid Halide Perovskite

Kaltzoglou, Andreas,Stoumpos, Constantinos C.,Kontos, Athanassios G.,Manolis, Georgios K.,Papadopoulos, Kyriakos,Papadokostaki, Kyriaki G.,Psycharis, Vasilis,Tang, Chiu C.,Jung, Young-Kwang,Walsh, Aron,Kanatzidis, Mercouri G.,Falaras, Polycarpos

, p. 6302 - 6309 (2017)

We report on the synthesis, characterization, and optoelectronic properties of the novel trimethylsulfonium lead triiodide perovskite, (CH3)3SPbI3. At room temperature, the air-stable compound adopts a hexagonal crystal structure with a 1D network of face-sharing [PbI6] octahedra along the c axis. UV-vis reflectance spectroscopy on a pressed pellet revealed a band gap of 3.1 eV, in agreement with first-principles calculations, which show a small separation between direct and indirect band gaps. Electrical resistivity measurements on single crystals indicated that the compound behaves as a semiconductor. According to multi-temperature single-crystal X-ray diffraction, synchrotron powder X-ray diffraction, Raman spectroscopy, and differential scanning calorimetry, two fully reversible structural phase transitions occur at ?5 and ca. ?100 °C with reduction of the unit cell symmetry to monoclinic as temperature decreases. The role of the trimethylsulfonium cation regarding the chemical stability and optoelectronic properties of the new compound is discussed in comparison with APbI3 (A = Cs, methylammonium, and formamidinium cation), which are most commonly used in perovskite solar cells.

A Novel Synthesis of Methyltin Tri-iodide with Environmental Implications

Manders, William F.,Olson, Gregory J.,Brinckman, Frederick E.,Bellama, Jon M.

, p. 538 - 540 (1984)

Methyltin tri-iodide and methylsulphur species are produced by an unusual heterogeneous reaction between MeI and SnS in water at room temperature which may bear on ubiquitous occurrence of methylstannanes in the environment.

Synthesis and Biological Evaluation of Bromo- and Fluorodanicalipin A

Fischer, Stefan,Huwyler, Nikolas,Wolfrum, Susanne,Carreira, Erick M.

, p. 2555 - 2558 (2016)

We disclose the syntheses of (+)-bromodanicalipin A as well as (±)-fluorodanicalipin A. The relative configuration and ground-state conformation in solution of both molecules was secured by J-based configuration analysis which revealed that these are identical to natural danicalipin A. Furthermore, preliminary toxicological investigations suggest that the adverse effect of danicalipin A may be due to the lipophilicity of the halogens. Halologs: The syntheses of bromo- and fluorodanicalipin A are reported and the ground-state conformation was determined by J-based configuration analysis (see scheme, R=H). A preliminary comparative study of their toxicology suggests that the adverse effect arises from the lipophilicity of the halogens which counterbalance the polar C14 sulfate.

Reactions of (triethylstannylthioalkyl)trialkoxysilanes and (triethylstannylthioalkyl)trialkoxysilatranes with methyl iodide

Sorokin,Voronkov

, p. 2056 - 2060 (2008)

Reactions of (triethylstannylthioalkyl)trimethoxysilanes Et 3SnS(CH2)nSi(OMe)3 (n = 1, 2) and (triethylstannylthioalkyl)trialkoxysilatranes Et3Sn(CH2) n Sa [hereinafter Sa = Si(O

Synthesis, characterization and optoelectronic properties of chemically stable (CH3)3SPbI3?xBrx and (CH3)3SPbI3?xClx (x?=?0, 1, 2, 3) perovskites

Kaltzoglou, Andreas,Elsenety, Mohamed M.,Koutselas, Ioannis,Kontos, Athanassios G.,Papadopoulos, Kyriakos,Psycharis, Vassilis,Raptopoulou, Catherine P.,Perganti, Dorothea,Stergiopoulos, Thomas,Falaras, Polycarpos

, p. 67 - 73 (2018)

We report on the novel series of (CH3)3SPbI3?xBrx and (CH3)3SPbI3?xClx (x = 0, 1, 2, 3) perovskite compounds. X-ray diffraction analysis shows that the solid solutions of (CH3)3SPbI3?xBrx (x = 0, 1, 2, 3) and (CH3)3SPbI3?xClx (x = 0, 1, 2) crystallize in hexagonal symmetry (space group P63mc, No. 186) with 1D columns of face-sharing [PbX6] octahedra. (CH3)3SPbCl3 crystallizes in orthorhombic symmetry (space group Pnma, No. 62) forming 3D network of vertex- and face-sharing [PbCl6] octahedra. Optical and vibrational properties were investigated using UV–vis reflectance, photoluminescence and Raman spectroscopy at room temperature. The compounds show high chemical stability in ambient air at temperatures up to 80 °C and under solar simulator, in contrast to the hygroscopic CH3NH3PbI3 or CH(NH2)2PbI3 that are commonly used in perovskite solar cells. First principles theoretical ab initio and efficient semiempirical extended Hückel calculations were performed to evaluate the energy band gap values, whose results are in good agreement with the experimentally determined values.

Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials

Wang, Yumei,Zhang, Ziwu,Deng, Lichan,Lao, Tianfeng,Su, Zhengquan,Yu, Yue,Cao, Hua

supporting information, p. 7171 - 7176 (2021/09/14)

A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as the piezoelectric material in this transformation. This method features no usage of solvent, simple experimental operation, scalable potential, and high conversion efficiency, which make it attractive and practical.

Method for preparing naproxen intermediate

-

Paragraph 0095-0100, (2020/12/08)

A technical scheme of the invention provides a method for preparing a naproxen intermediate represented by a chemical structural formula I. Preparation reactions are as follows: 6-methoxy-2-acetonaphthone and trimethyl sulfonium hydrogen sulfate are subjected to an epoxidation reaction in the presence of alkali so as to prepare 2-(6-methoxynaphthyl)-1,2-epoxypropane, the 2-(6-methoxynaphthyl)-1,2-epoxypropane is subjected to catalyzed rearrangement through silica gel or FeCl3 and then reacts with hydroxylamine hydrochloride, thereby preparing an intermediate, i.e., 2-(6-methoxy-2-naphthyl)propyl oxime (I) in one step. Naproxen is prepared by employing a one-pot method through a key intermediate, i.e., 2-(6-methoxy-2-naphthyl)propyl oxime.

Stereoselective Cyclopropanation of (-)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides

Ledingham, Edward T.,Merritt, Christopher J.,Sumby, Christopher J.,Taylor, Michelle K.,Greatrex, Ben W.

supporting information, p. 2652 - 2662 (2017/06/13)

The synthesis of tri- and tetrasubstituted cyclopropanes from 3-aryl-substituted levoglucosenones (LGO) has been developed. In contrast to the unstabilised ylide dimethylsulfonium methylide which gives epoxides from LGO via 1,2-addition, we have found that the soft nucleophile dimethylsulfoxonium methylide affords cyclopropanes in moderate yields from LGO and in excellent yields and stereoselectivity with 3-aryl LGO derivatives. The use of 1,1,3,3-tetramethylguanidine as base in DMSO to generate the ylide provided the best yields and shortest reaction times. Ester stabilised sulfonium ylides could also be used to generate tetrasubstituted cyclopropane derivatives. One of the products was converted into a cyclopropyl lactone via Baeyer-Villiger oxidation to demonstrate the utility of applying cyclopropanation chemistry to LGO. Georg Thieme Verlag Stuttgart.New York.

Preparation method of medetomidine and intermediate thereof

-

Paragraph 0076; 0077; 0078; 0079, (2017/08/28)

The invention relates to a preparation method of 2-(2, 3-xylyl)-2-methyloxirane. The method is characterized in that the preparation process includes the following reaction shown as the specification, wherein Y is selected from Cl, Br, I, CH3SO4 or HSO4; alkali is selected from KOH, NaOH, LiOH, CsOH, K2CO3, Li2CO3, Cs2CO3, Na2CO3, EtONa, EtOK, (CH3)2CHONa, (CH3)2CHOK, (CH3)3CONa, (CH3)3COK, NH2Na or NH2K. The invention adopts the synthesis method using the 2-(2, 3-xylyl)-2-methyloxirane critical intermediate to prepare medetomidine.

ARYL-ALKYLAMINES AND HETEROARYL-ALKYLAMINES AS PROTEIN KINASE INHIBITORS

-

Page/Page column 209-210, (2010/11/25)

The invention provides a compound of the formula (II): or a salt, solvate, tautomer or N-oxide thereof; wherein n is 0 or 1; one of Y1 and Y2 is CH and the other is selected from CH, CR8 and N; q is 0, 1 or 2 provided that q is 0 or 1 when Y1 or Y2 is CR8; R1 is an aryl or heteroaryl group of 5 to 10 ring members; R2a and R3a each are hydrogen, C1-4 hydrocarbyl or C1-4 acyl wherein the hydrocarbyl and acyl moieties are optionally substituted by fluorine, hydroxy, amino, methylamino, dimethylamino or methoxy; or NR2aR3a forms an imidazole group or a saturated monocyclic 4-7 membered heterocyclic group optionally containing a second heteroatom ring member selected from O and N; R18 is hydrogen or methyl; R19 is hydrogen or methyl; R24 is hydrogen or R24, R2a and the intervening nitrogen atom and carbon atoms together form an azetidine, pyrrolidine or piperidine ring; R25 is hydrogen or a C1-4 alkyl group wherein the C1-4 alkyl group is optionally substituted by hydroxy or amino provided that there are at least two carbon atoms between the hydroxy or amino group and the oxygen atom to which R25 is attached; and R4 and R5 each are hydrogen or a substituent as defined in the claims

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