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Properties of substance:

(RS)-2-chloropropan-1-ol

Group of substances:

organic

Physical appearance:

colorless liquid

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

C3H7ClO

Structural formula as text:

CH3CHClCH2OH

Molar/atomic mass: 94.538

Boiling point (°C):

133.5

CAS №: 78-89-7


Solubility (g/100 g of solvent):

diethyl ether: very soluble [Ref.]
ethanol: very soluble [Ref.]
water: very soluble [Ref.]

Density:

1.1092 (20°C, d4)

Synthesis 1:

Reference: Fickett, W., Garner, H.K., Lucas, H.J. The Configuration of Optically Active 1,2-Dichloropropane / Journal of the American Chemical Society. - 1951. - Vol. 73, No. 11 pp. 5067 [doi: 10.1021/ja01155a012]

In a 1-liter flask fitted with reflux condenser with a Dry Ice trap at the condenser outlet were placed 400 ml. (445 g., 4.2 moles) of diethylene glycol and 50 g. (0.25 mole) of p-toluenesulfonic acid (with 1,56H2O —Note). The system was evacuated to 3 mm. and the mixture was refluxed to remove water. To the cooled mixture was then added 100 g. (0.35 mole) of 2-chloropropyl 3,5-dinitrobenzoate (m.p. 78.0—78.3°) [and reflux continued]. When 55 g. of liquid had been collected in the trap the material coming over was apparently largely dioxane, although it gave a positive chlorine test. Calcium chloride was added and the mixture was extracted with ether. The ether extracts were dried with calcium chloride and fractionated. The first fraction, 17.2 g., had b.p. 40—68° at 75 mm. The final fraction, 14.1 g., had b.p. 70.4—70.5° at 75 mm., n(25, D) 1.4363. The final and intermediate fractions were then refractionated, giving 13.5 g., 38% yield on the recovery from the ester and 23% yield for the over-all purification starting with the impure 2-chloropropane-1-ol. The main fraction, b.p. 70.3°/75 mm., had n(25 C, D) 1.4360, d(25/4) 1.1020.

Refractive index (nD):

1.439 (20°C)

Vapour pressure (Torr):

29 (53°C)
75 (70.3°C)

References:

  1. CRC Handbook of Chemistry and Physics. - 95ed. - CRC Press, 2014. - pp. 3-118
  2. Fickett, W., Garner, H.K., Lucas, H.J. The Configuration of Optically Active 1,2-Dichloropropane / Journal of the American Chemical Society. - 1951. - Vol. 73, No. 11. - pp. 5064 [DOI: 10.1021/ja01155a012]
  3. Промышленные хлорорганические продукты: Справочник. - М.: Химия, 1978. - pp. 242 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru