methanesulfinylmethane

• ChemBase编号: 964
• 分子式: C2H6OS
• 平均质量: 78.13344
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: methanesulfinylmethane
• IUPAC系统名: Methanesulfinylmethane (substitutive); Dimethyl(oxido)sulfur (additive)
• IUPAC传统名: dimethyl sulfoxide; methanesulfinylmethane
• 商标名: 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
• 别名: 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; 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

登记号

• CAS号: 67-68-5
• EC号: 200-664-3
• MDL号: MFCD00002089
• Beilstein号: 506008
• 默克索引号: 143259
• PubChem SID: 24893977; 24894173; 24885165; 24893438; 24861602; 24866070; 24894271; 24866073; 24890014; 46505009; 24894214; 24866071; 24872902; 24849315; 24864495; 160964427; 24893881; 24865908; 24856722; 24870796; 24865906; 24893703; 24893688; 24861675; 24901911
• PubChem CID: 679
• CHEBI ID: 28262
• ATC码: M02AX03; G04BX13
• CHEMBL: 504
• Chemspider ID: 659
• DrugBank ID: DB01093
• FEMA编号: 3875
• Gmelin ID: 1556
• KEGG ID: D01043
• 医学主题词(MeSH): Dimethyl+sulfoxide
• 美国药典/FDA物质标识码: YOW8V9698H
• 维基百科标题: Dimethyl_sulfoxide
• Flavis Number: 12.175

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): -1.4078656
• LogD (pH = 7.4): -1.4078656
• Log P: -1.4078656
• 摩尔折射率: 20.7254 cm^3
• 极化性: 8.039938 Å^3
• 极化表面积: 17.07 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.09
• LOG S: -0.08
• 溶解度: 6.57e+01 g/l

分子性质

理化性质

• 溶解度: 1E+006 mg/L; Miscible in water; very soluble in diethyl ether
• 外观: clear, colorless; Clear, colorless Liquid; Colourless liquid; Liquid
• 熔点: 16-19 °C(lit.); 16-19°C; 18.4°C; 18.5 °C; 18.5°C; 18-20 °C; 19°C
• 沸点: 189 °C at 1013 hPa; 189 °C; 189 °C(lit.); 189°C; 189°C
• 闪点: >110 °C; >230 °F; 188.6 °F; 87 °C (closed cup); 87 °C; 87°C; 87°C(189°F); 89 °C
• 自燃点: 573 °F
• 密度: 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
• 折射率: 1.479; 1.479; ε_r = 48; 1.4790; n20/D 1.478-1.479; n20/D 1.479; n20/D 1.479(lit.)
• 蒸汽压: .55 hPa at 20 °C; 0.42 mmHg ( 20 °C)
• 蒸汽密度: 2.7 (vs air)
• 紫外吸收波长: 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
• 疏水性(logP): -0.7
• pKa: 35
• 粘度: 1.996 cP at 20 °C
• 感官: butter; alliaceous (onion, garlic)
• 透光率: 270 nm, ≥20%; 280 nm, ≥50%; 300 nm, ≥80%; 350 nm, ≥98%

安全信息

• 保存条件: Room Temperature (15-30°C); Room Temperature (15-30°C), Desiccate; Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• 保存注意事项: Hygroscopic; Irritant; Irritant/Hygroscopic/Store under Argon
• RTECS编号: PV6210000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: R:36/37/38; R36/37/38
• 安全公开号: S:20-25-26-37/39; S26, S37/39
• TSCA收录: 是
• 主要危害: Irritant and flammable
• NFPA704:
  

  1

  1

  0
• 爆炸极限: 42 %, 63 °F
• GHS危险声明: H227
• GHS警示性声明: P210-P280-P370+P378A-P403+P235-P501A
• 个人保护装置: 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)

药理学性质

• 过敏源: no known allergens

产品相关信息

• 纯度: ≥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+%
• 浓度: 50 wt. % in H2O
• 级别: 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
• 包装: packaged under Argon in resealable ChemSeal? bottles; vial of 1 mL
• 适用性: 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
• 蒸发残渣: <0.0005%; ≤0.002%; ≤0.005%; ≤0.01%; ≤0.0100%
• 杂质: <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
• 痕量阳离子: 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
• 无菌消毒: sterile-filtered
• 有效期: (limited shelf life, expiry date on the label)
• 产品质量级别: GMP; PREMIUM
• 品质说明: dried; over molecular sieve (H2O ≤0.005%); over molecular sieve (H2O ≤0.01%)
• λ: 1 cm path, H2O reference; H2O reference; neat
• 药典: testing & handling conforms to Pharmacopeia
• 产品线: BioUltra
• 线性分子式: (CH3)2SO
• Empirical Formula (Hill Notation): C2H6OS

详细说明

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

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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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Polybrene / DMSO-assisted gene transfer1

Sigma Aldrich - D2438

Frequently Asked Questions
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培养基中生长的人和动物细胞系通常采用冷冻保存。冷冻可以避免细胞系因遗传漂变而发生改变，并且可以最大限度降低被污染的风险。液氮与冷冻保护剂（诸如 DMSO）结合使用，是广泛采用的细胞保存方法。如果不使用冷冻保护剂，大多数哺乳动物细胞都会冷冻致死。冰晶将对细胞产生机械性损伤，此外电解液浓度、pH 值变化以及蛋白质变性，都将对细胞产生损害。冷冻保护剂将降低凝固点并保持更低的冷却速率，可最大限度减小这些致命影响。经生物技术性能认证 (BPC) 测试的 DMSO 还符合生物技术和组织工程应用的要求。
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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。
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产品经过消毒和过滤，包装在带隔垫的螺纹盖棕色瓶中，可立即使用。符合·USP 和·EP 测试要求

Sigma Aldrich - D4540

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Sigma Aldrich - 41650

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可能实行销售限制

Sigma Aldrich - 673439

包装
200 L in poly drum

Sigma Aldrich - 471267

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Sigma Aldrich - 154938

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包装
1, 2, 4×2, 4×4 L in glass bottle
100 mL in glass bottle

Sigma Aldrich - D1435

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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。
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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
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。

Sigma Aldrich - 07-4875

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。
Suitability
for biological purposes

Sigma Aldrich - 07-4860

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。

Sigma Aldrich - 276855

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Pure-Pac® II 容器需要 Micromatic MacroValve 连接器以分配溶剂 (Z560723)。
包装
1, 6×1, 2 L in Sure/Seal™
18 L in Pure-Pac™ 1
20 L in Pure-Pac™ 2
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100, 12×100 mL in Sure/Seal™
200 L in Pure-Pac™ 1
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Pure-Pac 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 51779

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General description
Watch a 6-minute presentation that demonstrates the effective use of our High Purity Solvents for GC Headspace Analysis
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针对 GC-HS 进行了测试
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The Utility of Headspace Grade Solvents for the Analysis of Organic Volatile Impurities

Sigma Aldrich - 94563

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Sigma Aldrich - D5879

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1 gal in glass bottle
1, 6×1, 4 L in poly bottle
100, 500 mL in poly bottle
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ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 270431

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
2 L in glass bottle

Sigma Aldrich - 41638

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。

Sigma Aldrich - 41645

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。
Other Notes
可能实行销售限制

Sigma Aldrich - M81802

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Sigma Aldrich - 34869

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Application
适用于高效液相色谱法、分光光度法、环境检测
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1, 6×1, 2, 4×2, 2.5, 4×4 L in glass bottle
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Sigma Aldrich - 472301

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1, 6×1, 2, 2.5, 4, 4×4 L in glass bottle
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200 L in poly drum
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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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Sigma Aldrich - 527963

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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
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Sigma Aldrich - W387509

Caution
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包装
1 kg in glass bottle
1 sample in glass bottle
10, 25 kg in poly drum

Sigma Aldrich - 39291

Caution
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Sigma Aldrich - 41640

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Other Notes
用于合成1

Sigma Aldrich - 41641

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Sigma Aldrich - 07-4870

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Sigma Aldrich - 41644

Caution
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Sigma Aldrich - 34943

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。

Sigma Aldrich - D7941

Caution
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包装
500 mL in glass bottle

Sigma Aldrich - 41648

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。

Sigma Aldrich - 41647

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。

Sigma Aldrich - 60153

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。

参考文献

• 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).