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67-68-5 - Dimethyl sulfoxide, 99+% - DMSO - Methyl sulfoxide - A13280 - Alfa Aesar

A13280 Dimethyl sulfoxide, 99+%

CAS 번호
67-68-5
동의어
DMSO
Methyl sulfoxide

사이즈 가격 ($) 수량 재고 여부
500g 28.80
2500g 69.50
10000g 230.00
장바구니에 추가 대량 견적에 추가 항목 보기

Dimethyl sulfoxide, 99+%

MDL
MFCD00002089
EINECS
200-664-3

화학적 특성

화학식
C2H6OS
화학 식량
78.13
융점
18.4°
비등점
189°
인화점
87°(189°F)
밀도
1.101
굴절률
1.4790
감도
Hygroscopic
용해도
Miscible with water, ethanol, ether, benzene, chloroform and acetone.

용도

Dimethyl Sulfoxide (DMSO) is used as a solvent for chemical reactions involving salts, most notably in Finkelstein reactions and in other nucleophilic substitutions. DMSO is an effective pain relieving agent. It is also used in antifreeze or hydraulic fluids and utilized in the oxidation of thiols and disulfides to sulfonic acids. It is used to enhance dermal absorption of many chemicals. It is also used as a cryoprotectant and is added to cell media to reduce ice formation and thereby prevent cell death during the freezing process.

참고

Hygroscopic. Incompatible with acid chlorides, phosphorus halides, strong acids, strong oxidizing agents and strong reducing agents.

참조 문헌

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 ß-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.

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 150oC, 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).

DMSO is a very weak acid (pKa= 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).

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.

Mozhzhukhina, N.; Longinotti, M. P.; Corti, H. R.; Calvo, E. J. A conductivity study of preferential solvation of lithium ion in acetonitrile-dimethyl sulfoxide mixtures. Electrochim. Acta 2015, 154, 456-461.

Song, S.; Huang, X.; Liang, Y. F.; Tang, C.; Li, X.; Jiao, N. From simple organobromides or olefins to highly value-added bromohydrins: a versatile performance of dimethyl sulfoxide. Green Chem. 2015, 17 (5), 2727-2731.

GHS 해저드 및 주의 설명서

해저드 설명서 (EU): H227

Combustible liquid.

주의 설명서: P210u-P280a-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

기타 참조

Merck
14,3259
바일슈타인
506008
통합 관세 코드
2930.90
TSCA(독성물질규제법)"
Yes
RTECS(화학물질 독성 등록)
PV6210000

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