Sulfonium, trimethyl-, chloride, S-oxide supplier

Name
TRIMETHYLSULFOXONIUM CHLORIDE
EINECS 225-724-6
CAS No. 5034-06-0
Article Data5
CAS DataBase
Density
Solubility
Melting Point 226-229 °C(lit.)
Formula C₃H₉ClOS
Boiling Point
Molecular Weight 128.623
Flash Point
Transport Information
Appearance White powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Trimethylsulfoniumchloride, oxide (6CI,7CI);NSC 221182;Trimethyloxosulfonium chloride;Trimethylsulfoxonium chloride;
PSA 36.28000
LogP -2.62070

Synthetic route

: 1774-47-6
trimethylsulfoxonium iodide

: 5034-06-0
trimethyl sulfoxonium chloride

Conditions

Conditions	Yield
With benzyltri(n-butyl)ammonium chloride In dichloromethane; water for 17h;	98.4%
With benzyltri(n-butyl)ammonium chloride In dichloromethane; water for 24h; Darkness;	84%
With water; chlorine at 50℃;

: 35155-66-9
3-chloro-2-methoxycyclohex-2-en-1-one

: 70775-39-2, 5367-24-8
dimethylsulfoxonium methylide

A: 5034-06-0
trimethyl sulfoxonium chloride

B: 73801-71-5
dimethyloxosulphonium (2-methyl-3-oxocyclohex-1-en-1-yl)methylide

Conditions

Conditions	Yield
In tetrahydrofuran for 18h; Heating;	A 61% B 38%

...Expand

: ruthenium(IV) oxide hydrate

: 3086-29-1
trimethylsulfonium chloride

: 5034-06-0
trimethyl sulfoxonium chloride

Conditions

Conditions	Yield
In water
With sodium hypochlorite In water

: C13H19NOS

: 5034-06-0
trimethyl sulfoxonium chloride

A: 1207754-79-7
C14H21NOS

B: C14H21NOS

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.416667h; Stage #2: C13H19NOS In tetrahydrofuran; hexane at 0 - 20℃;	A 100% B n/a

...Expand

: 24210-19-3
methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate

: 5034-06-0
trimethyl sulfoxonium chloride

: 850796-29-1
dimethylsulfoxonium (3S)-2-oxo-3-(benzyloxycarbonylamino)-4-methylpentylide

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Heating / reflux; Stage #2: methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate In tetrahydrofuran at 0℃; for 4h;	98%
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran for 2h; Heating; Stage #2: methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate In tetrahydrofuran at 0℃; for 4h;

: 28819-05-8
(S)-2-benzyloxycarbonylamino-propionic acid methyl ester

: 5034-06-0
trimethyl sulfoxonium chloride

: 676486-18-3
benzyl (S)-(4-(dimethyl(oxo)-λ6-sulfaneylidene)-3-oxobutan-2-yl)carbamate

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Heating / reflux; Stage #2: (S)-2-benzyloxycarbonylamino-propionic acid methyl ester In tetrahydrofuran at 0℃; for 4h;	97%
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at 60℃; for 2h; Stage #2: With Monomethyl terephthalate In tetrahydrofuran at 0℃; for 5h; Stage #3: (S)-2-benzyloxycarbonylamino-propionic acid methyl ester In tetrahydrofuran at 0℃; for 4h;	77%
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran for 2h; Heating; Stage #2: (S)-2-benzyloxycarbonylamino-propionic acid methyl ester In tetrahydrofuran at 0℃; for 4h;

: 5034-06-0
trimethyl sulfoxonium chloride

: 39511-12-1
(E)-3-(furan-2-yl)-1-phenyl-2-propen-1-one

: 959936-93-7
[(1S,2S)-2-(2-furyl)cyclopropyl]phenylmethanone

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In tetrahydrofuran for 5.5h; Heating; Stage #2: (E)-3-(furan-2-yl)-1-phenyl-2-propen-1-one With 4 A molecular sieve In tetrahydrofuran; toluene for 18h; Corey-Chaykovsky cyclopropanation; Further stages.;	96%

: 22966-19-4
trans-4'-methoxychalcone

: 5034-06-0
trimethyl sulfoxonium chloride

: 959936-90-4
(4-methoxyphenyl)[(1S,2S)-2-phenylcyclopropyl]methanone

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In tetrahydrofuran for 5.5h; Heating; Stage #2: trans-4'-methoxychalcone With 4 A molecular sieve In tetrahydrofuran; toluene for 18h; Corey-Chaykovsky cyclopropanation; Further stages.;	95%

: ethyl 2-(6-(tritylamino)pyridin-3-yl)acrylate

: 5034-06-0
trimethyl sulfoxonium chloride

: ethyl 1-(6-(tritylamino)pyridin-3-yl)cyclopropane-1-carboxylate

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: ethyl 2-(6-(tritylamino)pyridin-3-yl)acrylate In tetrahydrofuran at 20℃; for 0.5h;	95%
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: ethyl 2-(6-(tritylamino)pyridin-3-yl)acrylate In tetrahydrofuran at 2℃; for 0.5h;	95%

: 5034-06-0
trimethyl sulfoxonium chloride

: 39511-11-0
(E)-1-phenyl-3-(thiophen-2-yl)-2-propen-1-one

: [(1S,2S)-2-(2-thiophenyl)cyclopropyl]phenylmethanone

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In tetrahydrofuran for 5.5h; Heating; Stage #2: (E)-1-phenyl-3-(thiophen-2-yl)-2-propen-1-one With 4 A molecular sieve In tetrahydrofuran; toluene for 18h; Corey-Chaykovsky cyclopropanation; Further stages.;	94%

: (R)-N-{3-[4-(4-oxo-piperidin-1-yl)-3,5-difluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-methanesulfonate

: 5034-06-0
trimethyl sulfoxonium chloride

: (5S)-N-{3-[4-(1-oxa-6-azaspiro[2.5]oct-6-yl)-3,5-difluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran Reflux; Stage #2: (R)-N-{3-[4-(4-oxo-piperidin-1-yl)-3,5-difluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-methanesulfonate In tetrahydrofuran for 2h; Reflux;	94%

: 868612-22-0
(E)-1-(4-Allyloxy-phenyl)-3-phenyl-propenone

: 5034-06-0
trimethyl sulfoxonium chloride

: 959936-98-2
[4-allyloxyphenyl][(1S,2S)-2-phenylcyclopropyl]methanone

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In tetrahydrofuran for 5.5h; Heating; Stage #2: (E)-1-(4-Allyloxy-phenyl)-3-phenyl-propenone With 4 A molecular sieve In tetrahydrofuran; toluene for 18h; Corey-Chaykovsky cyclopropanation; Further stages.;	92%

: 24721-26-4, 956-04-7, 22252-16-0
4-chlorochalcone

: 5034-06-0
trimethyl sulfoxonium chloride

: 959936-91-5
[(1S,2S)-2-(4-chlorophenyl)cyclopropyl]phenylmethanone

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In tetrahydrofuran for 5.5h; Heating; Stage #2: 4-chlorochalcone With 4 A molecular sieve In tetrahydrofuran; toluene for 18h; Corey-Chaykovsky cyclopropanation; Further stages.;	92%

: 5034-06-0
trimethyl sulfoxonium chloride

: (1S,6R)-8-Oxo-7-aza-bicyclo[4.2.0]octane-7-carboxylic acid tert-butyl ester

: C15H27NO4S

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: (1S,6R)-8-Oxo-7-aza-bicyclo[4.2.0]octane-7-carboxylic acid tert-butyl ester In tetrahydrofuran for 2h; Inert atmosphere;	92%

: 5034-06-0
trimethyl sulfoxonium chloride

: 207616-49-7
C25H28O4

: 207616-64-6
C26H30O4

Conditions

Conditions	Yield
With sodium hydride In dimethyl sulfoxide for 2h; Ambient temperature;	89%

: 84828-97-7
1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione

: 5034-06-0
trimethyl sulfoxonium chloride

: 102789-10-6
3′,5′-O-(tetraisopropyldisiloxane-1,3-diyl)uridine 2′(S)-spiroepoxide

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In dimethyl sulfoxide; mineral oil; Petroleum ether at 0 - 5℃; for 0.5h; Inert atmosphere; Stage #2: 1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 0 - 5℃; for 0.5h;	89%

: 5034-06-0
trimethyl sulfoxonium chloride

: 70775-39-2, 5367-24-8
dimethylsulfoxonium methylide

Conditions

Conditions	Yield
With sodium hydride In toluene Heating;	88%
With sodium hydride In tetrahydrofuran for 2h; Heating;
With sodium hydride In tetrahydrofuran for 4h; Heating;

: 139297-65-7
1-(1-chlorocyclopropyl)-2-(2-chlorophenyl)ethanone

: 5034-06-0
trimethyl sulfoxonium chloride

: 2-(1-chloro-cycloprop-1-yl)-2-(2'-chloro-benzyl)-oxirane

Conditions

Conditions	Yield
With sodium hydroxide In water; toluene	87.3%

: 3674-18-8
Boc-D-pheO-succinyl

: 5034-06-0
trimethyl sulfoxonium chloride

: 923601-68-7
(R)-dimethylsulfoxonium 2-oxo-3-(tert-butoxycarbonylamino)-4-phenylbutylide

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at 90℃; for 2h; Stage #2: Boc-D-pheO-succinyl In tetrahydrofuran at -20℃;	87%

: C19H17NO2

: 5034-06-0
trimethyl sulfoxonium chloride

: C20H19NO2

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In tetrahydrofuran for 2.5h; Heating / reflux; Stage #2: C19H17NO2 In tetrahydrofuran at 50℃; for 3h; Stage #3: With water; ammonium chloride In tetrahydrofuran at 0℃;	87%

: 1179348-77-6
(S)-2-benzylcarbamoyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester

: 5034-06-0
trimethyl sulfoxonium chloride

: 1179348-69-6
C20H30N2O5S

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: (S)-2-benzylcarbamoyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran for 1h; Inert atmosphere;	87%

: 52595-94-5
dichloro(bis(diphenylphosphino)methane)platinum(II)

: 5034-06-0
trimethyl sulfoxonium chloride

: {Pt(P(C6H5)2CH3)(P(C6H5)2(OH))((CH2)2S(O)(CH3))}(1+)*Cl(1-)={Pt(P2(C6H5)4CH3(OH))((CH2)2S(O)(CH3))}Cl

Conditions

Conditions	Yield
With Bu4NCl or 15-crown-5 or n-C16H33N(CH3)3Br In sodium hydroxide; dichloromethane aq. NaOH; phase-transfer-catalysis; room temp., <2 N NaOH; elem. anal.;	85%

: 28819-05-8
(S)-2-benzyloxycarbonylamino-propionic acid methyl ester

: 5034-06-0
trimethyl sulfoxonium chloride

A: 1142-20-7
N-Cbz-Ala

B: 676486-18-3
benzyl (S)-(4-(dimethyl(oxo)-λ6-sulfaneylidene)-3-oxobutan-2-yl)carbamate

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at 60℃; for 2h; Stage #2: With water In tetrahydrofuran at 0℃; for 5h; Stage #3: (S)-2-benzyloxycarbonylamino-propionic acid methyl ester In tetrahydrofuran at 0℃; for 4h; Reagent/catalyst;	A 4% B 84%
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at 60℃; for 2h; Stage #2: With water In tetrahydrofuran at 0℃; for 5h; Stage #3: (S)-2-benzyloxycarbonylamino-propionic acid methyl ester In tetrahydrofuran at 0℃; for 4h;	A 73% B 22%

...Expand

: 5034-06-0
trimethyl sulfoxonium chloride

: 1-phenyl-6,6-dimethylspiro[2.5]octane-4,8-dione

: 7,7-dimethyl-3-phenyl-2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-one

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 6,6-dimethyl-1-phenylspiro[2.5]octane-4,8-dione In dimethyl sulfoxide at 20℃; for 12h; regioselective reaction;	83%

: 619-42-1
4-methoxycarbonylphenyl bromide

: 5034-06-0
trimethyl sulfoxonium chloride

: 1179348-62-9
1-(4-bromophenyl)-2-(2-dimethyl(oxo)-λ6-sulfanylidene)ethan-1-one

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: 4-methoxycarbonylphenyl bromide In tetrahydrofuran for 2h; Inert atmosphere;	82%

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylate

: 5034-06-0
trimethyl sulfoxonium chloride

: dimethylsulfoxonium 2-((3R,4S)-1-benzyloxycarbonyl-4-ethylpyrrolidin-3-yl)-2-oxo-ethylide

Conditions

Conditions	Yield
Stage #1: (R)-1-(1-Naphthyl)ethylamine; (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylate With phosphoric acid In tert-butyl methyl ether for 0.5h; Stage #2: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1.5h; Stage #3: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at -5 - -1℃; for 2.25h; Concentration; Reagent/catalyst; Solvent; Temperature; Reflux;	82%

Yield

Stage #1: (R)-1-(1-Naphthyl)ethylamine; (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylate With phosphoric acid In tert-butyl methyl ether for 0.5h;
Stage #2: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1.5h;
Stage #3: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran at -5 - -1℃; for 2.25h; Concentration; Reagent/catalyst; Solvent; Temperature; Reflux;

82%

...Expand

: 1620143-03-4
1-phenylspiro-[2.5]octane-4,8-dione

: 5034-06-0
trimethyl sulfoxonium chloride

: 3-phenyl-2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-one

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 1-phenylspiro-[2.5]octane-4,8-dione In dimethyl sulfoxide at 20℃; for 12h; Reagent/catalyst; Solvent; regioselective reaction;	82%

: 1-(4-methylphenyl)-spiro[2.5]octane-4,8-dione

: 5034-06-0
trimethyl sulfoxonium chloride

: 3-(4-methylphenyl)-2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-one

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 1-(4-methylphenyl)-spiro[2.5]octane-4,8-dione In dimethyl sulfoxide at 20℃; for 12h; regioselective reaction;	82%

: methoxymethyl gambogate

: 5034-06-0
trimethyl sulfoxonium chloride

: methoxymethyl 9,10-cyclopropanegambogate

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 15℃; for 3h;	81%

: 1-(1-chlorocyclopropyl)-2-(4-chloro-2-fluorophenyl)ethanone

: 5034-06-0
trimethyl sulfoxonium chloride

: 2-(1-chlorocyclopropyl)-2-(4-chloro-2-fluorobenzyl)oxirane

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-(1-chlorocyclopropyl)-2-(4-chloro-2-fluorophenyl)ethanone In tetrahydrofuran; mineral oil at 0 - 20℃; for 22h;	81%

: 611-13-2
2-furoic acid methyl ester

: 5034-06-0
trimethyl sulfoxonium chloride

: 2-(dimethyl(oxo)-λ6-sulfaneylidene)-1-(furan-2-yl)ethan-1-one

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran for 2h; Heating; Stage #2: 2-furoic acid methyl ester In tetrahydrofuran at 20℃;	80%

: 5034-06-0
trimethyl sulfoxonium chloride

: 85909-08-6
tert-butyl 2-oxopyrrolidine-1-carboxylate

: 1179348-67-4
C12H23NO4S

Conditions

Conditions	Yield
Stage #1: trimethyl sulfoxonium chloride With potassium tert-butylate In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: tert-butyl 2-oxopyrrolidine-1-carboxylate In tetrahydrofuran for 1h; Inert atmosphere;	80%

Sulfonium, trimethyl-, chloride, S-oxide Specification

The systematic name of Sulfoxonium,trimethyl-, chloride (8CI,9CI) is Sulfonium, trimethyl-, chloride, S-oxide. With the CAS registry number 5034-06-0, it is also named as Trimethyloxosulfonium chloride. The product's categories are Small Molecule; C-C Bond Formation; Synthetic Reagents; Organic Building Blocks; Sulfonium / Sulfoxonium Compounds; Sulfur Compounds. It is white powder which should be sealed in the container and stored in the cool and dry place. In addition, the container should be filled with inert gas.

The other characteristics of this product can be summarized as: (1)#H bond acceptors: 1; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 0; (4)Polar Surface Area: 17.07 Å²; (5)Exact Mass: 128.006263; (6)MonoIsotopic Mass: 128.006263; (7)Topological Polar Surface Area: 18.1; (8)Heavy Atom Count: 6; (9)Formal Charge: 0; (10)Complexity: 53; (11)Covalently-Bonded Unit Count: 2.

Uses of Sulfoxonium,trimethyl-, chloride (8CI,9CI): It can react with 1-(4-chloro-benzenesulfonyl)-2-phenyl-aziridine to get 1-(4-chloro-benzenesulfonyl)-3-phenyl-azetidine. This reaction needs reagent 50percent aq. NaOH, tetrabutylammonium hydrogen sulphate and solvent CH₂Cl₂. The yield is 45%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:[Cl-].O=[S+](C)(C)C
2. InChI:InChI=1/C3H9OS.ClH/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1
3. InChIKey:KQYWHJICYXXDSQ-REWHXWOFAE

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	180mg/kg (180mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02230,

Product Name

TRIMETHYLSULFOXONIUM CHLORIDE

Synthetic route

Sulfonium, trimethyl-, chloride, S-oxide Specification

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