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67-68-5

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67-68-5 Usage

Description

Dimethyl sulfoxide (DMSO) is a highly polar and aprotic organic compound, characterized by its colorless and odorless liquid form. It is widely recognized for its exceptional solvent properties and its capacity to penetrate biological membranes, which makes it a versatile substance in various industrial, pharmaceutical, and laboratory applications.

Uses

Used in Pharmaceutical and Laboratory Settings:
Dimethyl sulfoxide is used as a solvent for a variety of substances, including drugs and other chemicals, due to its ability to dissolve both polar and nonpolar compounds.
Used in Drug Delivery:
Dimethyl sulfoxide is used as a vehicle for drug delivery, facilitating the transport of pharmaceutical agents across biological barriers and enhancing their bioavailability.
Used in Tissue and Stem Cell Preservation:
Dimethyl sulfoxide is used as a cryoprotective agent in the preservation of stem cells and tissues, leveraging its capacity to prevent ice crystal formation during cryopreservation.
Used in Topical Pain Relief and Anti-Inflammatory Treatments:
Dimethyl sulfoxide is used as an anti-inflammatory and analgesic agent, providing relief for various conditions due to its ability to reduce inflammation and alleviate pain when applied topically.
Used in Industrial Applications:
Although not explicitly mentioned in the provided materials, DMSO's solvent properties also make it useful in industrial processes where a powerful, polar aprotic solvent is required for dissolving certain substances or facilitating chemical reactions.
It is important to handle DMSO with care, as its ability to penetrate the skin and transport substances into the body necessitates cautious use to avoid unwanted effects from carried substances.

Check Digit Verification of cas no

The CAS Registry Mumber 67-68-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 7 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 67-68:
(4*6)+(3*7)+(2*6)+(1*8)=65
65 % 10 = 5
So 67-68-5 is a valid CAS Registry Number.
InChI:InChI=1/C2H6OS/c1-4(2)3/h1-2H3

67-68-5 Well-known Company Product Price

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  • TCI America

  • (D0798)  Dimethyl Sulfoxide  >99.0%(GC)

  • 67-68-5

  • 25g

  • 100.00CNY

  • Detail
  • TCI America

  • (D0798)  Dimethyl Sulfoxide  >99.0%(GC)

  • 67-68-5

  • 500g

  • 140.00CNY

  • Detail
  • Alfa Aesar

  • (36480)  Dimethyl sulfoxide, ACS, 99.9% min   

  • 67-68-5

  • 500ml

  • 261.0CNY

  • Detail
  • Alfa Aesar

  • (36480)  Dimethyl sulfoxide, ACS, 99.9% min   

  • 67-68-5

  • 1L

  • 419.0CNY

  • Detail
  • Alfa Aesar

  • (36480)  Dimethyl sulfoxide, ACS, 99.9% min   

  • 67-68-5

  • 4L

  • 1431.0CNY

  • Detail
  • Alfa Aesar

  • (36480)  Dimethyl sulfoxide, ACS, 99.9% min   

  • 67-68-5

  • *4x1L

  • 1528.0CNY

  • Detail
  • Alfa Aesar

  • (36480)  Dimethyl sulfoxide, ACS, 99.9% min   

  • 67-68-5

  • *4x4L

  • 5197.0CNY

  • Detail
  • Alfa Aesar

  • (43998)  Dimethyl sulfoxide, anhydrous, 99.8+%, packaged under Argon in resealable ChemSeal? bottles   

  • 67-68-5

  • 100ml

  • 299.0CNY

  • Detail
  • Alfa Aesar

  • (43998)  Dimethyl sulfoxide, anhydrous, 99.8+%, packaged under Argon in resealable ChemSeal? bottles   

  • 67-68-5

  • *4x100ml

  • 964.0CNY

  • Detail
  • Alfa Aesar

  • (43998)  Dimethyl sulfoxide, anhydrous, 99.8+%, packaged under Argon in resealable ChemSeal? bottles   

  • 67-68-5

  • 1L

  • 1002.0CNY

  • Detail
  • Alfa Aesar

  • (43998)  Dimethyl sulfoxide, anhydrous, 99.8+%, packaged under Argon in resealable ChemSeal? bottles   

  • 67-68-5

  • *4x1L

  • 2725.0CNY

  • Detail
  • Alfa Aesar

  • (22914)  Dimethyl sulfoxide, HPLC Grade, 99.9+%   

  • 67-68-5

  • 1L

  • 565.0CNY

  • Detail

67-68-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Dimethyl sulfoxide

1.2 Other means of identification

Product number -
Other names Methane, sulfinylbis-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:67-68-5 SDS

67-68-5Synthetic route

dimethylsulfide
75-18-3

dimethylsulfide

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With Fe(AAEMA)3; oxygen; isovaleraldehyde In 1,2-dichloro-ethane under 760 Torr; for 20h; Ambient temperature;100%
With lithium perchlorate; Re(O)(2-(2'-hydroxyphenyl)-2-oxazoline)2Cl In [D3]acetonitrile; water-d2 at 20℃; for 4h;100%
With C12H11Cl3N2O3 In chloroform for 7h; Reflux;100%
dimethylsulfoximine
1520-31-6

dimethylsulfoximine

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With tert.-butylnitrite In chloroform at 25℃; for 0.166667h;100%
With p-TolSO2NO In acetonitrile at 35℃; further solvents, reagents, sulfoximides;
Sodium trans-Bis(dimethhyl sulfoxide) tetrachlororuthenate(III)
131759-88-1, 61779-28-0

Sodium trans-Bis(dimethhyl sulfoxide) tetrachlororuthenate(III)

mer,cis-{RuCl3(2O)2(DMSO)}
131759-93-8

mer,cis-{RuCl3(2O)2(DMSO)}

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With HClO4; H2O In water Kinetics; byproducts: chlorode ion; Reaction was performed at pH=1 and temp. 35°C.;A 100%
B 100%
triars
40169-66-2

triars

A

RuCl2(OS(CH3)2)(CH3C(CH2As(C6H5)2)3)
112220-32-3

RuCl2(OS(CH3)2)(CH3C(CH2As(C6H5)2)3)

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In toluene Ar atmosphere, heating (80°C, 10 min, 90°C, overnight), pptn.; washing of ppt. (toluene, Et2O), drying; elem. anal.;A 96%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

3,4,5-trimethoxybenzaldehyde oxime
39201-89-3

3,4,5-trimethoxybenzaldehyde oxime

A

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

B

3,4,5-trimethoxybenzonitrile
1885-35-4

3,4,5-trimethoxybenzonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h;A n/a
B 96%
trifluoroacetic acid
76-05-1

trifluoroacetic acid

S,S-dimethyl-4-methylanilinosulfonium picrate

S,S-dimethyl-4-methylanilinosulfonium picrate

A

2,2,2-trifluoro-N-(4-methylphenyl)acetamide
350-96-9

2,2,2-trifluoro-N-(4-methylphenyl)acetamide

B

p-toluidine
106-49-0

p-toluidine

C

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
at 50℃; for 5h; Elimination; acylation; retro-Pummerer reaction;A 3%
B 95%
C 67%
dimethylsulfide
75-18-3

dimethylsulfide

A

dimethylsulfone
67-71-0

dimethylsulfone

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With C30H24N2O7W; dihydrogen peroxide In dichloromethane; water for 1h; Reflux;A 94%
B 6%
With dihydrogen peroxide In ethanol; hexane; water at 60℃; for 0.0833333h;A 92%
B 6%
With dihydrogen peroxide In water at 30 - 35℃; for 24h; Sealed tube; Green chemistry;A 62%
B 68%
veratramide
1521-41-1

veratramide

dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

A

veratronitrile
2024-83-1

veratronitrile

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile for 2h; Reflux;A 94%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

Benzaldoxime
932-90-1

Benzaldoxime

A

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

B

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 5.5h;A n/a
B 94%
Benzoyl(4-chlorbenzoyl)(dimethylsulfonio)methanid

Benzoyl(4-chlorbenzoyl)(dimethylsulfonio)methanid

A

1-(4-chlorophenyl)-3-phenylpropane-1,2,3-trione
54458-32-1

1-(4-chlorophenyl)-3-phenylpropane-1,2,3-trione

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With ozone 1) CH2Cl2, -78 deg C, 2) Et2O, H2O;A 93%
B n/a
(η5-pentamethylcyclopentadienyl)(CPhCHCOO)(Me2SO)rhodium

(η5-pentamethylcyclopentadienyl)(CPhCHCOO)(Me2SO)rhodium

A

(η5-pentamethylcyclopentadienyl)(CPhCHCOOMe)Irhodium

(η5-pentamethylcyclopentadienyl)(CPhCHCOOMe)Irhodium

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With methyl iodide In toluene N2 atmosphere; stirring (2-15 h, 60°C); elem. anal.;A 92%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

4-nitrobenzaldehyde oxime
1129-37-9

4-nitrobenzaldehyde oxime

A

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

B

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 6h;A n/a
B 92%
Bis(4-chlorbenzoyl)(dimethylsulfonio)methanid

Bis(4-chlorbenzoyl)(dimethylsulfonio)methanid

A

1,3-bis(4-chlorophenyl)propane-1,2,3-trione
29574-62-7

1,3-bis(4-chlorophenyl)propane-1,2,3-trione

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With ozone 1) CH2Cl2, -78 deg C, 2) Et2O, H2O;A 91%
B n/a
dimethylsulfide
75-18-3

dimethylsulfide

cis-[Ru(1,4,7-trimethyl-1,4,7-triazacyclononane)O2(trifluoroacetate)]ClO4

cis-[Ru(1,4,7-trimethyl-1,4,7-triazacyclononane)O2(trifluoroacetate)]ClO4

acetonitrile
75-05-8

acetonitrile

A

[(1,4,7-trimethyl-1,4,7-triazacyclononane)(CF3CO2)Ru(II)(CH3CN)2]ClO4

[(1,4,7-trimethyl-1,4,7-triazacyclononane)(CF3CO2)Ru(II)(CH3CN)2]ClO4

B

dimethylsulfone
67-71-0

dimethylsulfone

C

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile Me2S reacted with Ru-compound in degassed acetonitrile;A n/a
B 9%
C 91%
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

A

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

B

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 4h;A n/a
B 91%
benzamide
55-21-0

benzamide

dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

A

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

B

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
In acetonitrile for 2h; Reflux;A n/a
B 91%
[bis(dimethylsulfoxide-O)(triphos)aquaruthenium(II)] triflate
112220-39-0

[bis(dimethylsulfoxide-O)(triphos)aquaruthenium(II)] triflate

A

Ru(CF3SO3)(CO)2(CH3C(CH2P(C6H5)2)3)(1+)*CF3SO3(1-)={Ru(CF3SO3)(CO)2(CH3C(CH2P(C6H5)2)3)}(CF3SO3)
112220-44-7

Ru(CF3SO3)(CO)2(CH3C(CH2P(C6H5)2)3)(1+)*CF3SO3(1-)={Ru(CF3SO3)(CO)2(CH3C(CH2P(C6H5)2)3)}(CF3SO3)

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With CO In dichloromethane byproducts: H2O; stirring of soln. under CO atmosphere (15 min); pptn. (Et2O addn.), washing (Et2O), drying; elem. anal.;A 90%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

cinnamaldehyde oxime
59336-59-3

cinnamaldehyde oxime

A

cinnamic nitrile
1885-38-7

cinnamic nitrile

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h;A 90%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

4-nitrobenzamide
619-80-7

4-nitrobenzamide

A

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

B

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
In acetonitrile for 4h; Reflux;A n/a
B 90%
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

4-chlorobenzaldoxime
3848-36-0

4-chlorobenzaldoxime

A

4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 5h;A 89%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

4-chlorobenzamide
619-56-7

4-chlorobenzamide

A

4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile for 3h; Reflux;A 89%
B n/a
2-(dimethyl-λ4-sulfaneylidene)-1,3-diphenylpropane-1,3-dione
34025-26-8

2-(dimethyl-λ4-sulfaneylidene)-1,3-diphenylpropane-1,3-dione

A

1,3-diphenyl-propane-1,2,3-trione
643-75-4

1,3-diphenyl-propane-1,2,3-trione

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With ozone 1) CH2Cl2, -78 deg C, 2) Et2O, H2O;A 88%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

A

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

B

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 4h;A n/a
B 88%
dimethylsulfide
75-18-3

dimethylsulfide

C96H104MnN7O(1+)*Cl6Sb(1-)

C96H104MnN7O(1+)*Cl6Sb(1-)

A

C96H104MnN7(1+)*Cl6Sb(1-)

C96H104MnN7(1+)*Cl6Sb(1-)

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In dichloromethane at 25℃; Inert atmosphere;A n/a
B 88%
Ru(OS(CH3)2)3(CH3C(CH2As(C6H5)2)3)(2+)*2CF3SO3(1-)={Ru(OS(CH3)2)3(CH3C(CH2As(C6H5)2)3)}(CF3SO3)2
112220-37-8

Ru(OS(CH3)2)3(CH3C(CH2As(C6H5)2)3)(2+)*2CF3SO3(1-)={Ru(OS(CH3)2)3(CH3C(CH2As(C6H5)2)3)}(CF3SO3)2

A

Ru(CF3SO3)(CO)2(CH3C(CH2As(C6H5)2)3)(1+)*CF3SO3(1-)={Ru(CF3SO3)(CO)2(CH3C(CH2As(C6H5)2)3)}(CF3SO3)
112220-46-9

Ru(CF3SO3)(CO)2(CH3C(CH2As(C6H5)2)3)(1+)*CF3SO3(1-)={Ru(CF3SO3)(CO)2(CH3C(CH2As(C6H5)2)3)}(CF3SO3)

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With CO In dichloromethane stirring of soln. under CO atmosphere (3 h); pptn. (Et2O addn.), washing (Et2O), drying; elem. anal.;A 87%
B n/a
(η5-pentamethylcyclopentadienyl)(CPhCHCOO)(Me2SO)iridium

(η5-pentamethylcyclopentadienyl)(CPhCHCOO)(Me2SO)iridium

A

(η5-pentamethylcyclopentadienyl)(CHCMeCOOMe)Iiridium

(η5-pentamethylcyclopentadienyl)(CHCMeCOOMe)Iiridium

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With methyl iodide In toluene N2 atmosphere; stirring (2-15 h, 60°C); elem. anal.;A 87%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

thiophene-2-carbaldehyde oxime
29683-84-9

thiophene-2-carbaldehyde oxime

A

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h;A 87%
B n/a
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

n-octanamide
629-01-6

n-octanamide

A

caprylnitrile
124-12-9

caprylnitrile

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile for 4h; Reflux;A 87%
B n/a
4-methoxyphenylacetamide
3424-93-9

4-methoxyphenylacetamide

dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

A

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

B

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

Conditions
ConditionsYield
In acetonitrile for 2h; Reflux;A n/a
B 86%
acetic anhydride
108-24-7

acetic anhydride

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

(methylthio)methyl acetate
16437-69-7

(methylthio)methyl acetate

Conditions
ConditionsYield
at 100℃; for 7h;100%
84%
With chloroform
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

dimethylsulfone
67-71-0

dimethylsulfone

Conditions
ConditionsYield
With sodium molybdate dihydrate; dihydrogen peroxide In methanol; water at 25℃; for 0.5h; Kinetics; Concentration;100%
With iron(II) perchlorate monohydrate; ozone; acetonitrile100%
With dihydrogen peroxide; [(η5-C5Me5)Mo(CO)3Cl] In acetonitrile at 35℃; for 2h;99%
4-nitro-phenol
100-02-7

4-nitro-phenol

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

1-<(methylthio)methoxy>-4-nitrobenzene
4527-37-1

1-<(methylthio)methoxy>-4-nitrobenzene

Conditions
ConditionsYield
With t-butyl bromide; triethylamine at 35℃; for 24h;100%
6,6-Diphenylfulvene
2175-90-8

6,6-Diphenylfulvene

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

<5-(Diphenylmethylen)-1,3-cyclopentadien-1-yl>dimethylsulfonium-perchlorat

<5-(Diphenylmethylen)-1,3-cyclopentadien-1-yl>dimethylsulfonium-perchlorat

Conditions
ConditionsYield
With lithium perchlorate; trifluoroacetic anhydride In dichloromethane -10 deg C to r.t.;100%
With monoperchlorate; trifluoroacetic anhydride 1.) -10 deg C; Yield given. Multistep reaction;
UC1023
17182-23-9

UC1023

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

(20R)-20-(Methylthiomethoxy)-5α-pregnan-3β-ylacetat
82055-16-1

(20R)-20-(Methylthiomethoxy)-5α-pregnan-3β-ylacetat

Conditions
ConditionsYield
With acetic anhydride In acetic acid for 96h; Ambient temperature;100%
(bis(diisopropylamino)phosphanyl)(trimethylsilyl)diazomethane
97135-48-3

(bis(diisopropylamino)phosphanyl)(trimethylsilyl)diazomethane

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

C18H43N2OPSSi
97135-52-9

C18H43N2OPSSi

Conditions
ConditionsYield
In benzene Irradiation;100%
In benzene for 8h; Ambient temperature; Irradiation; Yield given;
In benzene for 8h; Irradiation; Yield given;
7-Nitro-anthra[1,9-cd]isoxazol-6-one
85192-92-3

7-Nitro-anthra[1,9-cd]isoxazol-6-one

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

1-S,S-dimethyl-N-(5-nitroanthraquinon-1-yl)sulfoximide
85193-01-7

1-S,S-dimethyl-N-(5-nitroanthraquinon-1-yl)sulfoximide

Conditions
ConditionsYield
100%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

dimethylsulfide
75-18-3

dimethylsulfide

Conditions
ConditionsYield
With benzo[1,3,2]dioxaborole In benzene-d6 at 20℃; for 48h;100%
With phenylsilane; dimanganese decacarbonyl In neat (no solvent) at 100℃;96%
With sodium tetrahydroborate; iron(III) chloride In ethanol; water 1.) room temperature, 2 h, 2.) reflux, 5 - 10 min;94%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

(3S)-2-(N-benzylamino)-3-(chloromethyl)valeronitrile

(3S)-2-(N-benzylamino)-3-(chloromethyl)valeronitrile

(S)-2-(Benzyl-methylsulfanylmethyl-amino)-3-chloromethyl-pentanenitrile

(S)-2-(Benzyl-methylsulfanylmethyl-amino)-3-chloromethyl-pentanenitrile

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane at -60℃; for 0.333333h;100%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

(methylthio)methyl cyclohexanecarboxylate
16437-72-2

(methylthio)methyl cyclohexanecarboxylate

Conditions
ConditionsYield
With t-butyl bromide; sodium hydrogencarbonate at 35 - 45℃; for 13h; Esterification;100%
With oxalyl dichloride; triethylamine In dichloromethane at -60 - 20℃; for 0.5h; Swern oxidation;97%
With triethylamine at 160℃; for 20h; Schlenk technique; Inert atmosphere;70%
With triethylamine at 160℃; under 760.051 Torr; for 20h; Pummerer Sulfoxide Rearrangement; Schlenk technique; Inert atmosphere; Green chemistry;70%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

C32H50O7Si
223547-75-9

C32H50O7Si

C34H54O7SSi
170510-29-9

C34H54O7SSi

Conditions
ConditionsYield
With acetic anhydride at 25℃; for 19h;100%
(S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester
109721-08-6

(S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

(3R)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid
205647-16-1

(3R)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid

Conditions
ConditionsYield
Stage #1: dimethyl sulfoxide With n-butyllithium In tetrahydrofuran; hexane at -30 - 2℃; for 0.666667h; Metallation;
Stage #2: (S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester In tetrahydrofuran; hexane at -66 - -30℃; for 0.916667h; Acylation;
100%
Acetic acid (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyloxy)-5-acetoxymethyl-4-((2S,3S,4S,5S,6R)-4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

Acetic acid (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyloxy)-5-acetoxymethyl-4-((2S,3S,4S,5S,6R)-4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Acetic acid (2R,3R,4R,5R)-2-((1S,2R,3R,4S,6R)-2-acetoxy-4,6-diazido-3-methylsulfanylmethoxy-cyclohexyloxy)-5-acetoxymethyl-4-((2S,3S,4S,5S,6R)-4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

Acetic acid (2R,3R,4R,5R)-2-((1S,2R,3R,4S,6R)-2-acetoxy-4,6-diazido-3-methylsulfanylmethoxy-cyclohexyloxy)-5-acetoxymethyl-4-((2S,3S,4S,5S,6R)-4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
With acetic anhydride; acetic acid at 20℃; for 48h; Pummerer rearrangement;100%
2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin-ruthenium(II)-carbonyl-dimethylsulfoxide
112374-62-6

2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin-ruthenium(II)-carbonyl-dimethylsulfoxide

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin-ruthenium(II)-bis(dimethylsulfoxide)

2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin-ruthenium(II)-bis(dimethylsulfoxide)

Conditions
ConditionsYield
In dimethyl sulfoxide Irradiation (UV/VIS); photolysis of a degassed or argon-bubbled DMSO soln. of the Ru complex;100%
5,10,15,20-tetraphenyl-21H,23H-porphyrin-ruthenium(II)-carbonyl-dimethylsulfoxide
866596-13-6, 82621-20-3

5,10,15,20-tetraphenyl-21H,23H-porphyrin-ruthenium(II)-carbonyl-dimethylsulfoxide

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

5,10,15,20-tetraphenyl-21H,23H-porphyrin-ruthenium(II)-bis-dimethylsulfoxide

5,10,15,20-tetraphenyl-21H,23H-porphyrin-ruthenium(II)-bis-dimethylsulfoxide

Conditions
ConditionsYield
In dimethyl sulfoxide Irradiation (UV/VIS); photolyzing the Ru complex in a sealed degassed or argon-bubbled DMSO soln.;100%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

dichlorobis(dimethyl sulfoxide)platinum(II)

dichlorobis(dimethyl sulfoxide)platinum(II)

Conditions
ConditionsYield
In water for 2h;100%
In water91%
In water at 20℃;90%
oxalyl dichloride
79-37-8

oxalyl dichloride

3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanol
268234-15-7

3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanol

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanone
268234-16-8

3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanone

Conditions
ConditionsYield
Stage #1: oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.25h;
Stage #2: 3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanol With triethylamine In dichloromethane at 20℃; for 1.33333h;
100%
bismuth trifluoride

bismuth trifluoride

trimethylsilylazide
4648-54-8

trimethylsilylazide

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

bismuth triazide dimethylsulfoxide adduct

bismuth triazide dimethylsulfoxide adduct

Conditions
ConditionsYield
at 20℃; for 24h; Inert atmosphere;100%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

PNU-91325

PNU-91325

Conditions
ConditionsYield
With phosphorus pentoxide In dichloromethane at 20℃; for 24h;100%
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Ritter's trifluoroiodomethane-DMSO complex

Ritter's trifluoroiodomethane-DMSO complex

Conditions
ConditionsYield
at -78 - 23℃; Schlenk technique; Inert atmosphere;100%
at -78 - 23℃; Inert atmosphere;100%
at -78℃;
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

([1-benzyl-3-methyl]imidazolyl-2-ene)silver(I) bromide

([1-benzyl-3-methyl]imidazolyl-2-ene)silver(I) bromide

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

cis-(1-methyl-3-benzylimidazol-2-ylidene)PtBr2(DMSO)

cis-(1-methyl-3-benzylimidazol-2-ylidene)PtBr2(DMSO)

Conditions
ConditionsYield
at 60℃; for 24h;100%
2-(3′,4′-dihydroxyphenyl)-2,3-dihydro-4,6-dihydroxy-2-(methoxy)-3-benzo furanone

2-(3′,4′-dihydroxyphenyl)-2,3-dihydro-4,6-dihydroxy-2-(methoxy)-3-benzo furanone

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

2-(3′,4′-dimethoxyphenyl)-2,3-dihydro-4,6-dimethoxy-2-(methoxy)-3-benzofuranone

2-(3′,4′-dimethoxyphenyl)-2,3-dihydro-4,6-dimethoxy-2-(methoxy)-3-benzofuranone

Conditions
ConditionsYield
Stage #1: 2-(3′,4′-dihydroxyphenyl)-2,3-dihydro-4,6-dihydroxy-2-(methoxy)-3-benzo furanone With potassium carbonate In acetone at 58℃; for 0.5h;
Stage #2: dimethyl sulfoxide at 58℃; for 60h;
99.6%
[magnesium(2,6-di-tert-butyl-4-methylphenolate)2(tetrahydrofuran)2]
67825-24-5

[magnesium(2,6-di-tert-butyl-4-methylphenolate)2(tetrahydrofuran)2]

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

[magnesium(2,6-di-tert-butyl-4-methylphenolate)2(dimethylsulfoxide)2]

[magnesium(2,6-di-tert-butyl-4-methylphenolate)2(dimethylsulfoxide)2]

Conditions
ConditionsYield
In toluene for 0.05h; Inert atmosphere; Glovebox;99.5%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

(-)-mutilone
14431-67-5

(-)-mutilone

(3aS,4R,6S,8R,9R,9aR,10R)-hexahydro-4,6,9,10-tetramethyl-<(methylthio)methoxy>-6-vinyl-3a,9-propano-3aH-cyclopentacyclooctene-1,5(4H,6H)-dione
113323-23-2

(3aS,4R,6S,8R,9R,9aR,10R)-hexahydro-4,6,9,10-tetramethyl-<(methylthio)methoxy>-6-vinyl-3a,9-propano-3aH-cyclopentacyclooctene-1,5(4H,6H)-dione

Conditions
ConditionsYield
With acetic anhydride In acetic acid Ambient temperature;99%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Veratric acid
93-07-2

Veratric acid

(methylthio)methyl 3,4-dimethoxybenzoate
33838-03-8

(methylthio)methyl 3,4-dimethoxybenzoate

Conditions
ConditionsYield
With oxalyl dichloride; triethylamine In dichloromethane at -60 - 20℃; for 0.5h; Swern oxidation;99%
for 0.166667h; Microwave irradiation; Sealed vessel;94%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-hydroxyethyl 4-methoxycarbonylphenyl sulfide
13458-01-0

2-hydroxyethyl 4-methoxycarbonylphenyl sulfide

Conditions
ConditionsYield
With caesium carbonate at 25℃; for 0.75h;99%
(4E,8E)-(R)-2-Hydroxy-2,5,9-trimethyl-11-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-undeca-4,8-dienoic acid methyl ester
868784-06-9

(4E,8E)-(R)-2-Hydroxy-2,5,9-trimethyl-11-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-undeca-4,8-dienoic acid methyl ester

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

(4E,8E)-(R)-2,5,9-Trimethyl-2-methylsulfanylmethoxy-11-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-undeca-4,8-dienoic acid methyl ester
868784-07-0

(4E,8E)-(R)-2,5,9-Trimethyl-2-methylsulfanylmethoxy-11-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-undeca-4,8-dienoic acid methyl ester

Conditions
ConditionsYield
With acetic anhydride at 23℃; for 24h;99%

67-68-5Relevant articles and documents

Cotton, F. A.,Francis, R.

, p. 2986 - 2991 (1960)

Synthesis and reactivity of two new trichloromethyl substituted dihydroisoquinoline-derived oxaziridines

Aydi, Rihab,Kammoun, Majed

, p. 134 - 144 (2016)

N-Alkyl oxaziridines may be used as reagents for the oxidation of sulfides in acid-promoted reactions. This article reports on a simple and efficient synthesis of two new trichloromethyl substituted dihydroisoquinoline oxaziridines, a new family of organi

Magnetic nanoparticles supported Cu2+ and Ce3+ complexes: toward the chemical and electrochemical oxidation of alcohol and sulfide derivatives

Tamoradi, Taiebeh,Navaee, Aso,Salimi, Abdollah,Mousavi, Seyedeh Masoumeh,Ghadermazi, Mohammad,Veisi, Hojat

, p. 4517 - 4530 (2019)

Abstract: Heterogeneous catalysts are more prominent rather than homogenous catalysts since they are simply separated from products. To improve and develop heterogeneous catalysts, two core–shell magnetic nanocatalysts are prepared by anchoring of Cu and Ce complexes on the surface of Fe3O4, then the efficiency of the obtained catalysts are tested toward both chemical and electrochemical oxidation of sulfide and alcohol derivatives. Characterization of mentioned catalysts was performed by using FT-IR, XRD, EDX and SEM. The obtained results confirm that the reported method has outstanding advantages such as short reaction time, high yield, easy operation, easy separation, inexpensive and non-toxic material and chemical and thermal stability. Graphical abstract: [Figure not available: see fulltext.].

Kinetics and mechanism of the oxidation of dimethyl sulfide by hydroperoxides in aqueous medium: Study on the potential contribution of liquid-phase oxidation of dimethyl sulfide in the atmosphere

Amels, Peter,Elias, Horst,Wannowius, Klaus-Juergen

, p. 2537 - 2544 (1997)

Conventional and multi-wavelength stopped-flow spectrophotometry has been used to study the kinetics of the oxidation of dimethyl sulfide (DMS) by hydroperoxides, ROOH = hydrogen peroxide (H2O2), peroxo formic acid (HCO3H), peroxo acetic acid (CH3CO3H), peroxo nitrous acid (ONOOH), peroxo monosulfuric acid anion (PMS = HSO5-), and the H2O2 analogue hypochlorous acid (HOCl), in aqueous solution in the pH range 0-14 at 293 K and I = 1.0 M. The reaction between DMS and ROOH and between dimethyl sulfoxide (DMSO) and ROOH is a second-order process, leading to DMSO and dimethyl sulfone (DMSO2), respectively. It was shown by gas chromatography that, except for the oxidant ONOOH, DMSO and DMSO2 are the only oxidation products. It follows from the pH dependence of the second-order rate constant k2 that both the hydroperoxide ROOH, rate constant kROOH, and its anion ROO-, rate constant kROO, oxidize DMS and DMSO, respectively. The data for kROOH (dm3 mol-1 s-1) and for kROO (dm3 mol-1 s-1) at 293 K for the formation of DMSO and DMSO2 are presented. For the oxidation of DMS kROOH > kROO; for the step DMS → DMSO, kROOH ranges from 4780 (PMS) to 0.018 (H2O2), whereas kROO lies in the range 88 (PMS) to 0.0018 (H2O2); for the step DMSO → DMSO2, kROOH ranges from 349 (HOCl) to 2.7 × 10-6 (H2O2), whereas kROO lies in the range 18 (PMS) to 8.4 × 10-5 (H2O2). A mechanistic interpretation of the oxidation reactions, based on the ambifunctional character of both ROOH and DMSO, is presented. The relevance of in-cloud oxidation of DMS by atmospheric hydroperoxides such as CH3CO3H and HCO3H is discussed and substantiated.

Thermal analysis, phase transitions and molecular reorientations in [Fe(OS(CH3)2)6](ClO4)2

Szostak, El?bieta,Migda?-Mikuli, Anna

, p. 1151 - 1158 (2017)

Thermogravimetric analysis connected with quadruple mass spectroscopy (TG/MS) for an identification of [Fe(OS(CH3)2)6](ClO4)2 decomposition products, carried out to determine its thermal stability, has indicated that the title compound does not change its mass till ca. 385?K. Above this temperature, it starts slowly to lose a part of (CH3)2SO ligands, which begins to form a liquid phase, in which the title compound partially dissolves. Finally, at ca. 476?K, when two from six coordinated (CH3)2SO were detached from central atom, the [Fe(OS(CH3)2)4](ClO4)2 is formed. At ca. 514?K this sample explodes. Differential scanning calorimetry (DSC) measurements performed in the temperature range of 100–443?K revealed existence of two anomalies on DSC curves. The first, a big one, at Tc?≈?338?K is associated with the phase transition: crystal phase Cr. 1???rotational phase Rot. 1, and the second, a small one, at Tm1?≈?414?K is associated with two parallel processes, which are: decomposition of [Fe(OS(CH3)2)6](ClO4)2 with the DMSO release and dissolution of [Fe(OS(CH3)2)6?x](ClO4)2 in DMSO. The large value of solid–solid phase transition entropy change (?Sc?≈?79.3?J?mol?1?K?1) and small value of the melting process (?Sm?≈?5.8?J?mol?1?K?1) indicate on such large configurational disorder in the high-temperature phase that this phase can be considered as a rotational phase (so called also as “plastic crystals”). The results of the vibrational and reorientational dynamics of (CH3)2SO ligands and ClO4 ? anions in the high- and low-temperature phases of [Fe(OS(CH3)2)6](ClO4)2, investigated by Fourier transform infrared absorption spectroscopy, show that even in the low-temperature phase the CH3 groups in (CH3)2SO ligands and also the ClO4 ? anions perform fast (correlation time τR?≈?10?12?s) reorientational motions. These reorientational motions above Tc temperature became so fast that in the rotational phase they turn into nearly free rotational motions.

Selective oxidation of alcohols and sulfides: Via O2using a Co(ii) salen complex catalyst immobilized on KCC-1: Synthesis and kinetic study

Allahresani, Ali,Hemmat, Kaveh,Naghdi, Elaheh,Nasseri, Mohammad Ali

, p. 37974 - 37981 (2020)

The aim of this study was to immobilize a Co(ii) salen complex on KCC-1 as a catalyst that can be recovered (Co(ii) salen complex?KCC-1). Field-emission transmission electron microscopy, FT-IR spectroscopy, thermogravimetric analysis, elemental analysis,

Synthesis of a Novel μ-Oxo Binuclear Copper(II) Complex Ligated by Hydrotris(3,5-dimethyl-1-pyrazolyl)borate

Kitajima, Nobumasa,Koda, Takayuki,Moro-Oka, Yoshihiko

, p. 347 - 350 (1988)

A novel μ-oxo binuclear copper(II) complex, 2O in which the each of coppers coordinates to three nitrogens, was prepared by the reaction of a copper(I) triphenylphosphine complex with iodosylbenzene.

Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions

Hajjami, Maryam,Sheikhaei, Shiva,Gholamian, Fatemeh,Yousofvand, Zakieh

, p. 2420 - 2435 (2021/01/04)

Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]

Oxovanadium and dioxomolybdenum complexes: synthesis, crystal structure, spectroscopic characterization and applications as homogeneous catalysts in sulfoxidation

Kargar, Hadi,Kaka-Naeini, Azar,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Amiri Rudbari, Hadi,Munawar, Khurram Shahzad

, p. 1563 - 1583 (2021/05/11)

New oxovanadium and dioxomolybdenum Schiff base complexes, [VO(L)(OCH3)] n and [MoO2(L)(CH3OH)], were synthesized by treating an ONO donor Schiff base (H2L) derived by condensation of 3-ethoxysalicylaldehyde and nicotinic hydrazide with oxo and dioxo acetylacetonate salts of vanadium and molybdenum (VO(acac)2 and MoO2(acac)2), respectively. The synthesized ligand and complexes were characterized by FTIR, multinuclear (1H, 13C) NMR, elemental and single crystal X-ray diffraction analysis. In both complexes, the geometry around the central metal ions was distorted octahedral as revealed by diffraction studies. Theoretical calculations of the synthesized compounds were carried out by DFT at B3LYP/Def2-TZVP level of theory, which showed good correlation with the experimental results. Moreover, the catalytic efficiency of both complexes was investigated by oxidizing aryl and alkyl sulfides in the presence of 30% H2O2 in ethanol.

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