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Properties of substance:

DMSO

Synonyms:

dimethylsulfoxide
dimethyl sulfoxide

Group of substances:

organic

Physical appearance:

colorless oily liquid

Empirical formula (Hill's system for organic substances):

C2H6OS

Structural formula as text:

(CH3)2SO

Molar/atomic mass: 78.13

Melting point (°C):

18.45

Boiling point (°C):

189

Decomposition temperature (°C):

150

CAS №: 67-68-5

Solubility (g/100 g of solvent):

1,2-dichloroethane: miscible [Ref.]
acetic acid: miscible [Ref.]
acetone: soluble [Ref.]
aniline: miscible [Ref.]
benzene: soluble [Ref.]
carbon tetrachloride: miscible [Ref.]
chloroform: soluble [Ref.]
diethyl ether: soluble [Ref.]
dimethylformamide: miscible [Ref.]
ethanol: soluble [Ref.]
formamide: miscible [Ref.]
formic acid: miscible [Ref.]
glycerol: miscible [Ref.]
nitrobenzene: miscible [Ref.]
pyridine: miscible [Ref.]
sulfuric acid: miscible [Ref.]
toluene: miscible [Ref.]
water: soluble [Ref.]

Properties of solutions:

18,6% (wt.), solvent - water
  Freezing point (°C) = -8.
32,5% (wt.), solvent - water
  Freezing point (°C) = -17.
43,3% (wt.), solvent - water
  Freezing point (°C) = -45.
52% (wt.), solvent - water
  Freezing point (°C) = -110.
65% (wt.), solvent - water
  Freezing point (°C) = -140.
74,3% (wt.), solvent - water
  Freezing point (°C) = -125.
81,3% (wt.), solvent - water
  Freezing point (°C) = -45.
86,7% (wt.), solvent - water
  Freezing point (°C) = -12.
91% (wt.), solvent - water
  Freezing point (°C) = -3.
94,5% (wt.), solvent - water
  Freezing point (°C) = 7.
97,5% (wt.), solvent - water
  Freezing point (°C) = 12.

Hygroscopic:

yes

Interatomic distances and bond angles:

Interatomic distances (in pm): 109 (C-H)
Interatomic distances (in pm): 181 (C-S)
Interatomic distances (in pm): 148 (S=O)
Bond angles (in degrees): 96,4 (C-S-C)
Bond angles (in degrees): 106,7 (C-S-O)
Bond angles (in degrees): 107,5 (H-C-S)

Density:

1.1 (20°C, g/cm3)
1.1014 (25°C, g/cm3)

Reactions:

  1. Yeild 57%. [Ref.1]
    2C6H5COCl + 2CH3S(O)CH3 + CaC2 → 2C6H5COCH2S(O)CH3 + CaCl2 + C2H2
  2. [Ref.1]
    HOC6H5 + (CH3)2SO + HCl → HOC6H4S(CH3)2Cl + H2O
  3. [Ref.1aster, Ref.2aster, Ref.3aster]
    K2[PtCl4] + 2(CH3)2SO → [Pt((CH3)2SO)2Cl2] + 2KCl

Refractive index (nD):

1.477 (25°C)
1.4783 (20°C)

Vapour pressure (Torr):

0.7 (21°C)
12 (72.5°C)
16 (79.8°C)
17 (83°C)

Dissociation:

pKBH+ (1) = -1.8 (25°C, water)
pKa (1) = 31.3 (20°C, water)

Permittivity (dielectric constant):

45 (25°C)

Dipole moment (D):

3.96 (20°C)

Viscosity (mPa·s):

2.473 (20°C)

Surface tension (mN/m):

42.98 (25°C)

Standard molar enthalpy (heat) of formation ΔfH0 (298.15 K, kJ/mol):

-204.2 (l)

Standard molar Gibbs energy of formation ΔfG0 (298.15 K, kJ/mol):

-99.9 (l)

Standard molar entropy S0 (298.15 K, J/(mol·K)):

188.3 (l)

Molar heat capacity at constant pressure Cp (298.15 K, J/(mol·K)):

153 (l)

Enthalpy (heat) of vaporization ΔvapH (kJ/mol):

57.28

Flash point (°C):

95

Standard molar enthalpy (heat) of formation ΔfH0 (298.15 K, kJ/mol):

-151.3 (g)

LD50 (mg/kg):

20000 (mice, intraperitoneal)
= 63 (1) ( CH3SO)
= 45 (6) ( CHS)
= 61 (2) ( CH3S=CH2)
= 7,38
= 7,5

References:

  1. Xiao-Feng Wua, Kishore Natteb The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis / Advanced Synthesis and Catalysis. - 2016. - Vol. 358, No. 3. - pp. 336-352
  2. Advanced Synthesis and Catalysis. - 2020. - Vol. 362, No. 1. - pp. 65-86 [DOI: 10.1002/adsc.201901021]
  3. Angewandte Chemie International Edition. - 1967. - Vol. 6, No. 4. - pp. 318-334 [DOI: 10.1002/anie.196703181]
  4. CRC Handbook of Chemistry and Physics. - 90ed. - CRC Press, 2010. - pp. 5-22
  5. Flick E.W. Industrial solvent handbook. - 5ed. - 1998. - pp. 223-235
  6. Progress in inorganic chemistry. - Vol. 12. - John Wiley & Sons, 1970. - pp. 1-99
  7. Smallwood I.M. Handbook of organic solvent properties. - 1996. - pp. 253-255
  8. Вредные вещества в промышленности: Справочник для химиков, инженеров и врачей. - 7-е изд., Т.2. - Л.: Химия, 1976. - pp. 396-398 [Russian]
  9. Гордон А., Форд Р. Спутник химика. - М.: Мир, 1976. - pp. 77 [Russian]
  10. Гутман В. Химия координационных соединений в неводных растворах. - М.: Мир, 1971. - pp. 197-202 [Russian]
  11. Некрасов Б.В. Основы общей химии. - Т.1. - М.: Химия, 1973. - pp. 561 [Russian]
  12. Общая органическая химия. - Т. 5, под ред. Бартона Д. и Оллиса В.Д. - М.: Химия, 1983. - pp. 256-293 [Russian]
  13. Рабинович В.А., Хавин З.Я. Краткий химический справочник. - Л.: Химия, 1977. - pp. 144 [Russian]
  14. Реутов О.А., Курц А.Л., Бутин К.П. Органическая химия. - 2-е изд., Ч.1. - М.: Бином. Лаборатория знаний, 2005. - pp. 222 [Russian]
  15. Физер Л., Физер М. Реагенты для органического синтеза. - Т. 1: А-Е. - М., 1970. - pp. 319-335 [Russian]
  16. Физер Л., Физер М. Реагенты для органического синтеза. - Т. 5. - М., 1971. - pp. 124-134 [Russian]
  17. Физер Л., Физер М. Реагенты для органического синтеза. - Т. 6. - М., 1975. - pp. 86-89 [Russian]
  18. Физер Л., Физер М. Реагенты для органического синтеза. - Т. 7. - М.: Мир, 1978. - pp. 160-162 [Russian]
  19. Химическая энциклопедия. - Т. 2. - М.: Советская энциклопедия, 1990. - pp. 64 [Russian]
  20. Химия и жизнь. - 2011. - №6. - pp. 10 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru