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Properties of substance:

3,5-dinitrobenzoyl chloride

Group of substances:

organic

Physical appearance:

yellow needles crystals

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

C7H3ClN2O5

Structural formula as text:

(O2N)2C6H3COCl

Molar/atomic mass: 230.562

Melting point (°C):

74

CAS №: 99-33-2

Solubility (g/100 g of solvent):

carbon tetrachloride: soluble [Ref.]
chloroform: soluble [Ref.]
diethyl ether: soluble [Ref.]
petroleum ether: sparingly soluble [Ref.]

Synthesis 1:

Reference: Saunders, B. C., Stacey, G.J., Wilding, I.G.E. The Preparation of 3:5-Dinitrobenzoic Acid and 3:5-Dinitrobenzoyl Chloride / Biochemical Journal. - 1942. - Vol. 36, No. 3-4 pp. 371 [doi: 10.1042/bj0360368]

(NO2)2C6H3COOH + PCl5 → (NO2)2C6H3COCl + POCl3 + HCl

3,5-Dinitrobenzoic acid (30 g., 1 equiv.) was mixed with PCl5 (33 g., 1.1 equiv.) and the mixture was heated under reflux in an oil bath at 120—130° for 1,25 hr. The phosphorus oxychloride was then distilled off at 25° (20 mm.), the temperature of the bath being finally raised to 110° during this process. On cooling, the residue in the flask solidified to a brown mass of crude 3,5-dinitrobenzoyl chloride (yield, theoretical; m.p. 63° to a clear liquid). Carbon tetrachloride proved to be a very suitable solvent for recrystallization, particularly for large quantities. Yield of recrystallized material, 25 g. (77%), m.p. 66—68°. Beautiful long white needles of pure material, with m.p. 69.5°, were obtained by recrystallization from light petroleum (b.p. 40—60°), but a relatively large amount of solvent was required.

Found: N, 12.2; Cl, 15.5. Calc. for C7H3O5N2Cl: N, 12.2; Cl, 15.4%.

Reactions:

  1. [Ref.1aster]
    (O2N)2C6H3COCl + 2C6H5NH2 → (O2N)2C6H3CONHC6H5 + C6H5NH3Cl

Vapour pressure (Torr):

12 (196°C)

References:

  1. CRC Handbook of Chemistry and Physics. - 95ed. - CRC Press, 2014. - pp. 3-224
  2. Химический энциклопедический словарь. - Под ред. Кнунянц И.Л. - М.: Советская энциклопедия, 1983. - pp. 175 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru