9772. Tromethamine

Nomenclature

CAS number: 77-86-1
2-Amino-2-(hydroxymethyl)-1,3-propanediol; trimethylol aminomethane; tris(hydroxymethyl)aminomethane; trisamine; tris buffer; trometamol; tromethane; TRIS; THAM (Fisher Sci.); Trizma (Sigma-Aldrich).
C4H11NO3; mol wt 121.14.
C 39.66%, H 9.15%, N 11.56%, O 39.62%.

Description and references

May be prepd by reduction or catalytic hydrogenation of the corresp nitro compd. Prepn of similar compds: Hass, Vanderbilt, US 2174242 (1940); Johnson, Degering, J. Org. Chem. 8, 7 (1943); Boileau, Mem. Poudres 35, Annexe 7-76 (1953). Prepn by electrolytic reduction: McMillan, US 2485982 (1949 to Comm. Solvents Corp.). Titrimetric standard: Whitehead, J. Chem. Educ. 36, 297 (1959). Monograph: Ann. N.Y. Acad. Sci. 92, Art. 2, pp 333-812 (June 17, 1961). Crystal structure: R. Rudman et al., Science 200, 531 (1978). GC determn in plasma: H. Hulshoff, H. B. Kostenbauder, J. Chromatogr. 145, 155 (1978). Pharmacokinetics in rabbits: H. Brasch, H. Iven, Arch. Int. Pharmacodyn. 254, 4 (1981). Use as a biological buffer: R. A. Durst, B. R. Staples, Clin. Chem. 18 206 (1972); S. P. Fling, D. S. Gregerson, Anal. Biochem. 155, 83 (1986); T. Higa, D. M. Desiderio, ibid. 173, 463 (1988). Interaction with hydroxyl radicals: M. Hicks, J. M. Gebicki, FEBS Lett. 199, 92 (1986). Review of clinical experience in treatment of acidemia: G. G. Nahas et al., Drugs 55, 191-224 (1998).

Chemical structure

Properties

Crystalline mass, mp 171-172°. bp10 219-220°. Weak, monoacidic base: pKb (25°): 5.91. pKa (20°): 8.3. pKa (37°): 7.82. pH of 0.1 molar aq soln 10.4. Aq solns do not absorb CO2 from the air. Soly at 25° (mg/ml) in water: 550; ethylene glycol: 79.1; methanol: 26; anhydr ethanol: 14.6; 95% ethanol: 22.0; DMF: 14; acetone: 2.0; ethyl acetate: 0.5; olive oil: 0.4; cyclohexane: 0.1; chloroform: 0.05; carbon tetrachloride: <0.05.

Use

In the synthesis of surface-active agents, vulcanization accelerators, pharmaceuticals. As emulsifying agent for cosmetic creams and lotions, mineral oil and paraffin wax emulsions, leather dressings, textile specialties, polishes, cleaning compds, so-called soluble oils. Absorbent for acidic gases. Biological buffer. Acidimetric standard.

Therapeutic Category

Alkalinizing agent.

Keywords

Alkalinizing Agent