Title: Benzathine
CAS Registry Number: 140-28-3
CAS Name: N,N¢-Bis(phenylmethyl)-1,2-ethanediamine
Additional Names: N,N¢-dibenzylethylenediamine; 1,2-bis(benzylamino)ethane; DBED
Molecular Formula: C16H20N2
Molecular Weight: 240.34
Percent Composition: C 79.96%, H 8.39%, N 11.66%
Literature References: Prepd from N,N¢-dibenzenesulfonyl-N,N¢-dibenzylethylenediamine by heating with concd HCl in bomb tube at 170-180°: Bleier, Ber. 32, 1829 (1899); from ethylene chloride and benzylamine: Frost et al., J. Am. Chem. Soc. 71, 3842 (1949); by reduction of N,N¢-dibenzylideneethylenediamine: DE 98031 (1898 to Schering); Chem. Zentralbl. 1898, II, 743; Van Alphen, Rec. Trav. Chim. 54, 93 (1935); Lob, ibid. 55, 859 (1936); Szabo et al., Antibiot. Chemother. 1, 499 (1951); Rebenstorf, US 2773098 (1956 to Upjohn).
Properties: Oily liquid, mp 26°. d420 1.024. bp12 212-213°; bp4 195°. nD20 1.5624. Insol in water. Freely sol in the usual organic solvents except CS2, with which it gives a solid addition product.
Melting point: mp 26°
Boiling point: bp12 212-213°; bp4 195°
Index of refraction: nD20 1.5624
Density: d420 1.024
Derivative Type: Diacetate
Molecular Formula: C20H28N2O4
Molecular Weight: 360.45
Percent Composition: C 66.64%, H 7.83%, N 7.77%, O 17.75%
Properties: Needles, mp 111°. Soly in water: 253 mg/ml.
Melting point: mp 111°
Derivative Type: Dihydrobromide
Molecular Formula: C16H22Br2N2
Molecular Weight: 402.17
Percent Composition: C 47.78%, H 5.51%, Br 39.74%, N 6.97%
Properties: Shiny leaflets, dec 300°. Soly in water: 30 mg/ml.
Derivative Type: Dihydrochloride
Molecular Formula: C16H22Cl2N2
Molecular Weight: 313.27
Percent Composition: C 61.34%, H 7.08%, Cl 22.63%, N 8.94%
Properties: Shiny leaflets, dec 298°. Soly in water: 23.9 mg/ml.
Derivative Type: Sulfate
Molecular Formula: C16H22N2O4S
Molecular Weight: 338.42
Percent Composition: C 56.78%, H 6.55%, N 8.28%, O 18.91%, S 9.47%
Properties: Crystals, dec 247-250°. Soly in water: 15.8 mg/ml.
Derivative Type: Disalicylate
Molecular Formula: C30H34N2O6
Molecular Weight: 518.60
Percent Composition: C 69.48%, H 6.61%, N 5.40%, O 18.51%
Properties: Crystals, mp 85°. Soly in water: 2.43 mg/ml.
Melting point: mp 85°
Use: Manuf of a repository form of penicillins G and V, q.q.v. |