methanesulfinylmethane

• ChemBase ID: 964
• Molecular Formular: C2H6OS
• Molecular Mass: 78.13344
• Monoisotopic Mass: 78.01393581
• SMILES: S(=O)(C)C
• Canonical SMILES: CS(=O)C
• InChI: InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
• InChIKey: IAZDPXIOMUYVGZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methanesulfinylmethane
• IUPAC Systematic name: Methanesulfinylmethane (substitutive); Dimethyl(oxido)sulfur (additive)
• IUPAC Traditional name: dimethyl sulfoxide; methanesulfinylmethane
• Brand Name: Decap; Deltan; Demasorb; Demavet; Demeso; Demsodrox; Dermasorb; Dimexide; Dipirartril-tropico; Dolicur; Doligur; Domoso; Dromisol; Durasorb; Gamasol 90; Hyadur; Infiltrina; Kemsol; Rimso 50; Sclerosol; Somipront; Syntexan; Topsym
• Synonyms: Diemthyl sulfoxide; Dimethyl sulfoxide BP; Dimethyl sulfur oxide; Dimethyl sulphoxide; Dimethyl sulpoxide; Dimexidum; Methylsulfinylmethane; Methyl sulfoxide; Sulfinylbis-methane; Sulfinylbismethane; Sulfinyldimethane; Dimethyl sulfoxide; DMSO, 80% aqueous solution; Dimethyl sulphoxide, 80% aqueous solution; DMSO; Dimethyl sulphoxide 99.7+%; Dimethyl sulfoxide; Methyl sulfoxide; Dimethyl sulfoxide, anhydrous; Dimethyl sulfoxide, ACS; Dimethyl sulfoxide, HPLC Grade; Dimethyl sulfoxide, Spectrophotometric Grade; Dimethyl sulfoxide; Methyl Sulfoxide: DMSO; DIMETHYL SULFOXIDE ACS REAGENT GRADE; DIMETHYL SULFOXIDE, BIO GRADE; DIMETHYL SULFOXIDE, ANHYDROSOLV GRADE; Dimethyl sulfoxide solution; Dimethylis sulfoxidum; 二甲基亚砜; 二甲基亚砜, 无水; 二甲基亚砜, ACS; 二甲基亚砜, HPLC级; 二甲基亚砜, 光谱级; 甲基亚砜; 二甲基亚砜; 二甲基亚砜 溶液

Database IDs

• CAS Number: 67-68-5
• EC Number: 200-664-3
• MDL Number: MFCD00002089
• Beilstein Number: 506008
• Merck Index: 143259
• PubChem SID: 24893977; 24885165; 46505009; 24894214; 160964427; 24856722; 24870796; 24865906; 24890014; 24894173; 24893438; 24861602; 24866071; 24872902; 24849315; 24864495; 24893881; 24865908; 24866070; 24894271; 24866073; 24893703; 24893688; 24861675; 24901911
• PubChem CID: 679
• CHEBI ID: 28262
• ATC CODE: M02AX03; G04BX13
• CHEMBL: 504
• Chemspider ID: 659
• DrugBank ID: DB01093
• FEMA ID: 3875
• Gmelin ID: 1556
• KEGG ID: D01043
• MeSH Name: Dimethyl+sulfoxide
• Unique Ingredient Identifier: YOW8V9698H
• Wikipedia Title: Dimethyl_sulfoxide
• Flavis Number: 12.175

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -1.4078656
• LogD (pH = 7.4): -1.4078656
• Log P: -1.4078656
• Molar Refractivity: 20.7254 cm^3
• Polarizability: 8.039938 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.09
• LOG S: -0.08
• Solubility (Water): 6.57e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1E+006 mg/L; Miscible in water; very soluble in diethyl ether
• Apperance: clear, colorless; Clear, colorless Liquid; Colourless liquid; Liquid
• Melting Point: 16-19 °C(lit.); 16-19°C; 18.4°C; 18.5 °C; 18.5°C; 18-20 °C; 19°C
• Boiling Point: 189 °C at 1013 hPa; 189 °C; 189 °C(lit.); 189°C; 189°C
• Flash Point: >110 °C; >230 °F; 188.6 °F; 87 °C (closed cup); 87 °C; 87°C; 87°C(189°F); 89 °C
• Auto Ignition Point: 573 °F
• Density: 1.069 g/mL at 25 °C; 1.10; 1.10 g/mL(lit.); 1.100 g/mL at 20 °C; 1.100-1.104 g/mL at 25 °C (relative density (EP)); 1.1004 g cm^-3; 1.101; 1.104 g/cm^3 at 20 °C; 1.104 g/ml
• Refractive Index: 1.479; 1.479; ε_r = 48; 1.4790; n20/D 1.478-1.479; n20/D 1.479; n20/D 1.479(lit.)
• Vapor Pressure: .55 hPa at 20 °C; 0.42 mmHg ( 20 °C)
• Vapor Density: 2.7 (vs air)
• Absorption Wavelength: UV absorption/ passes test; λ: 265 nm Amax: 0.8; λ: 270 nm Amax: 0.4; λ: 270 nm Amax: 0.40; λ: 270 nm Amax: 1.00; λ: 280 nm Amax: 0.22; λ: 280 nm Amax: 0.30; λ: 285 nm Amax: ≤0.20; λ: 290 nm Amax: 0.16; λ: 290 nm Amax: 0.18; λ: 295 nm Amax: ≤0.20; λ: 295 nm Amax: 0.10; λ: 300 nm Amax: 0.10; λ: 310 nm Amax: 0.06; λ: 320 nm Amax: 0.04; λ: 330 nm Amax: 0.02; λ: 340 nm Amax: 0.01; λ: 350-400 nm Amax: 0.01; λ: 360 nm Amax: 0.003
• Hydrophobicity(logP): -0.7
• pKa: 35
• Viscosity: 1.996 cP at 20 °C
• Organoleptic: butter; alliaceous (onion, garlic)
• Transmittance: 270 nm, ≥20%; 280 nm, ≥50%; 300 nm, ≥80%; 350 nm, ≥98%

Safety Information

• Storage Condition: Room Temperature (15-30°C); Room Temperature (15-30°C), Desiccate; Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• Storage Warning: Hygroscopic; Irritant; Irritant/Hygroscopic/Store under Argon
• RTECS: PV6210000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: R:36/37/38; R36/37/38
• Safety Statements: S:20-25-26-37/39; S26, S37/39
• TSCA Listed: 是
• Main Hazard: Irritant and flammable
• NFPA704:
  

  1

  1

  0
• Explode Limits: 42 %, 63 °F
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥99%; (USP XXIV); ≥99%; ≥99.0%; ≥99.0% (GC); ≥99.5%; ≥99.5% (GC); ≥99.6%; ≥99.7%; ≥99.7% (GC); ≥99.8% (GC); ≥99.9%; ≥99.9% (GC); ≥99.95% (GC); 99.8%; 99.8+%; 99.9%; 99.9% min; 99.9+%; 99+%
• Concentration: 50 wt. % in H2O
• Grade: absolute; ACS; ACS reagent; ACS spectrophotometric grade; analytical standard; anhydrous; B&J Brand (product of Burdick & Jackson); biotech. grade; Biotechnology Performance Certified; CHROMASOLV® Plus; for HPLC; for molecular biology; for residue analysis; for UV-spectroscopy; Halal; HPLC grade; JIS special grade; PCR Reagent; Ph Eur; puriss.; puriss. p.a.; purum; REAGENT; ReagentPlus®; SAJ first grade
• Packaging: packaged under Argon in resealable ChemSeal? bottles; vial of 1 mL
• Suitability: complies for IR spectroscopy; GC-Headspace tested; meets EP testing specifications; meets EP, USP testing specifications; meets USP testing specifications; plant cell culture tested; suitable for absorption spectrum analysis; suitable for hybridoma; suitable for plant cell culture
• Evaporation Residue: <0.0005%; ≤0.002%; ≤0.005%; ≤0.01%; ≤0.0100%
• Impurities: <0.005% water; <0.050% water; <0.1% water (Karl Fischer); ≤0.0001% heavy metals (as Pb); ≤0.001 meq/g Titr. acid; ≤0.001 meq/g Titratable acid; ≤0.001% free acid (as CH3COOH); ≤0.001% free acid (as H2SO4); ≤0.002% non-volatile matter; ≤0.03% water; ≤0.03% water (Karl Fischer); ≤0.1% water; ≤0.1% water (Karl Fischer); ≤0.1% water (Karl Fischer, USP); ≤0.100% water; ≤0.2% water; ≤0.2% water (Karl Fischer); ≤0.2% water (Karl Fischer, EP); ≤0.3% water; ≤1 ppm higher-boiling impurities; Dnases, none detected; insoluble matter, passes filter test; phosphatases, none detected; proteases, none detected; RNases, none detected
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.5 mg/kg; Fe: ≤1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤1 mg/kg; Ni: ≤0.5 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg
• Foreign Activity: DNase and RNase, none detected
• Sterility: sterile-filtered
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality Level: GMP; PREMIUM
• Quality: dried; over molecular sieve (H2O ≤0.005%); over molecular sieve (H2O ≤0.01%)
• λ: 1 cm path, H2O reference; H2O reference; neat
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioUltra
• Linear Formula: (CH3)2SO
• Empirical Formula (Hill Notation): C2H6OS

DETAILS

MP Biomedicals - 02194819

Molecular Biology Reagent
Purity: =99%
Meets ACS specifications.

MP Biomedicals - 02191418

ACS Reagent Grade
Purity: >99.9
Specific gravity: 1.10 gm/ml
clear, colorless liquid.

MP Biomedicals - 02190186

Purity: 99+%
1 ml = approx. 1.10 g
NOT FOR HUMAN USE!

DrugBank - DB01093

• Drug Groups: approved
• Description: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during cryopreservation. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation. [PubChem]
• Indication: For the symptomatic relief of patients with interstitial cystitis.
• Pharmacology: Dimethyl Sulfoxide may have anti-inflammatory, antioxidant and analgesic activities. Dimethyl Sulfoxide also readily penetrates cellular membranes. The membrane-penetrating ability of dimethyl sulfoxide may enhance diffusion of other substances through the skin. For this reason, mixtures of idoxuridine and dimethyl sulfoxide have been used for topical treatment of herpes zoster in the United Kingdom.
• Toxicity: The oral LD₅₀ of dimethyl sulfoxide in the dog is greater than 10 gm/kg. It is improbable that this dosage level could be obtained with intravesical instillation of dimethyl sulfoxide in the patient.
• Affected Organisms: Humans and other mammals
• Biotransformation: Dimethyl sulfoxide is metabolized in man by oxidation to dimethyl sulfone or by reduction in dimethyl sulfide. Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.
• Absorption: Readily and rapidly absorbed following administration by all routes and distributed throughout the body.
• Elimination: Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Apollo Scientific Ltd - OR61029

Hybri-Max grade, sterile-filtered, hybridoma tested

Sigma Aldrich - D8418

Frequently Asked Questions
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Caution
容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。
包装
1 L in glass bottle
5.5, 7.5, 50, 100, 250, 500 mL in glass bottle
1, 1.5 mL in poly bottle

Sigma Aldrich - 41639

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Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Other Notes
Polybrene / DMSO-assisted gene transfer1

Sigma Aldrich - D2438

Frequently Asked Questions
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Application
Human and animal cell lines grown in culture are generally stored frozen. Freezing protects the cell line from changes due to genetic drift and minimizes risk of contamination. Liquid nitrogen used in conjunction with a cryoprotective agent such as DMSO is a widely used method for preserving cells. Without the presence of a cryoprotective agent, freezing is lethal to most mammalian cells. Damage is caused by mechanical injury by ice crystals, concentration of electrolytes, pH changes, and denaturation of proteins. These lethal effects are minimized by adding a cryoprotective agent which lowers the freezing point and allows for a slower cooling rate. BPC-tested DMSO also meets the requirements of biotechnology and tissue engineering applications.
Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Features and Benefits
Ready-to-use sterile filtered product conveniently packaged septum screw-capped amber bottles. Meets USP and EP testing requirements

Sigma Aldrich - D4540

Frequently Asked Questions
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Caution
容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。
包装
1 L in glass bottle
100, 500 mL in glass bottle

Sigma Aldrich - 41650

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Other Notes
Sales restrictions may apply

Sigma Aldrich - 673439

Packaging
200 L in poly drum

Sigma Aldrich - 471267

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Packaging
1, 4 L in poly bottle
18 L in VerSA-Flow™
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ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 154938

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Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Packaging
1, 2, 4×2, 4×4 L in glass bottle
100 mL in glass bottle

Sigma Aldrich - D1435

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Application
一种用于聚合酶链式反应 (PCR) 的极性非质子溶剂，并可用作保存细胞、组织和器官的玻璃化抗冻剂。
Caution
容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。
包装
1 L in poly bottle
500 mL in poly bottle

Sigma Aldrich - 07-4871

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 07-4875

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Suitability
for biological purposes

Sigma Aldrich - 07-4860

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 276855

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Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Other Notes
Pure-Pac® II containers require the Micromatic MacroValve coupler for dispensing solvents, Z560723.
Packaging
1, 6×1, 2 L in Sure/Seal™
18 L in Pure-Pac™ 1
20 L in Pure-Pac™ 2
View returnable container options.
100, 12×100 mL in Sure/Seal™
200 L in Pure-Pac™ 1
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Pure-Pac is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 51779

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
General description
Watch a 6-minute presentation that demonstrates the effective use of our High Purity Solvents for GC Headspace Analysis
Suitability
tested for GC-HS
Protocols & Applications
The Utility of Headspace Grade Solvents for the Analysis of Organic Volatile Impurities

Sigma Aldrich - 94563

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Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - D5879

Frequently Asked Questions
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Caution
容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。
包装
1 gal in glass bottle
1, 6×1, 4 L in poly bottle
100, 500 mL in poly bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 270431

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Packaging
2 L in glass bottle

Sigma Aldrich - 41638

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 41645

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Other Notes
Sales restrictions may apply

Sigma Aldrich - M81802

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 34869

Frequently Asked Questions
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Application
Suitable for HPLC, spectrophotometry, environmental testing
Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Packaging
1, 6×1, 2, 4×2, 2.5, 4×4 L in glass bottle
20 L in Nowpak™
100, 12×100, 500 mL in glass bottle
50 L in comp drum
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CHROMASOLV is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 472301

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Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Packaging
1, 6×1, 2, 2.5, 4, 4×4 L in glass bottle
18 L in VerSA-Flow™
200 L in poly drum
50 L in Pure-Pac™ 2
50 L in comp drum
100, 500, 6×500 mL in glass bottle
400 L in Pure-Pac™ 1

Sigma Aldrich - 494429

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Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Packaging
2 L in Sure/Seal™
View returnable container options.
Legal Information
Pure-Pac is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 527963

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Legal Information
Product of Arkema

Sigma Aldrich - D9170

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Application
已发现二甲基亚砜 (1-10%) 可加速链复性，据信，它还可赋予核酸热稳定性而避免发生脱嘌呤作用。作为 PCR 助溶剂，DMSO 可有助于提高产率，尤其是在长 PCR 技术中。
Caution
容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。
包装
1 vial in glass bottle
5 vials in glass bottle

Sigma Aldrich - 07-4872

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - W387509

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Packaging
1 kg in glass bottle
1 sample in glass bottle
10, 25 kg in poly drum

Sigma Aldrich - 39291

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 41640

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Other Notes
Use as reagent in synthesis1

Sigma Aldrich - 41641

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 07-4870

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 41644

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 34943

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - D7941

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.
Packaging
500 mL in glass bottle

Sigma Aldrich - 41648

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 41647

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Sigma Aldrich - 60153

Caution
Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

REFERENCES

• Tosylates or activated halides can be oxidized with DMSO to aldehydes and ketones (Kornblum oxidation). ɑ-Bromo ketones are oxidized at room temperature to ɑ-keto aldehydes: J. Am .Chem. Soc., 79, 6562 (1957). Benzylic halides, on heating in the presence of NaHCO₃, give benzaldehydes: J. Am. Chem. Soc., 114, 6227 (1992). Under similar conditions at 150^oC, primary alkyl iodides: J. Chem. Soc., 520 (1964), and alkyl chlorides and bromides in the presence of NaI: Synth. Commun., 16, 1343 (1986), are oxidized to aldehydes. Unactivated bromides have also been oxidized to aldehydes in the presence of Ag salts: Tetrahedron Lett., 917 (1974). For oxidation of benzyl alcohols to benzaldehydes, catalyzed by HBr, see: Synlett, 2041 (2002). DMSO is more often used in combination with a variety of activating agents for selective oxidation of primary and secondary alcohols to carbonyl compounds under very mild conditions. For examples, see: Oxalyl chloride, A18012, or Trifluoroacetic anhydride, A13614 (Swern oxidation), Acetic anhydride, L04295 (Albright-Goldman), N,N'-Dicyclohexylcarbodiimide, A10973 (Pfitzner-Moffatt), Sulfur trioxide-pyridine complex, A12202 (Parikh-Doering), Triphosgene, A14932 and Phenyl phosphorodichloridate, A10479. Reviews: Synthesis, 70 (1971); 165 (1981); 857 (1990).
• Aromatic amines can be substituted in the para-position by reaction with DMSO in the presence of conc. HCl with or without CuCl to give 4-aminobenzaldehydes: J. Chem. Soc., Perkin 1, 2235 (1992). The intermediate species is thought to be chloromethyl methyl sulfoxide.
• Dipolar aprotic solvent with advantages over e.g. N,N-Dimethylformamide, A13547, 1-Methyl-2-pyrrolidinone, A12260 of lower toxicity and generally higher solvent power for many types of material.
• Powerful solvent for many inorganic ions, primarily due to solvation of the cations with consequent enhanced reactivity of the counter anions both in increased nucleophilicity and base strength. In DMSO, the relative nucleophilicities of the halide ions are reversed (F^- > I^-). The rate of aromatic fluorodenitration in a range of polar aprotic solvents was highest for DMSO: J. Fluorine Chem., 35, 591 (1987); see Potassium fluoride, 14130. For enhanced base strength, see e.g.: cyclization of ω-bromo acids to lactones by K₂CO₃: Org. Synth. Coll., 6, 698 (1988); exhaustive alkylation of ketones with KOH: Tetrahedron Lett., 31, 859 (1990).
• Malonic and ?-keto esters can be conveniently decarboalkoxylated by heating in wet DMSO: J. Org. Chem., 43, 138 (1978), avoiding the need for separate hydrolysis and decarboxylation steps.
• DMSO is a very weak acid (pK_a= 31) but can be deprotonated by NaH, giving "dimsyl sodium", which is a useful strong base e.g. for the Wittig reaction: J. Org. Chem., 28, 1128 (1963).