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3-Hydroxypropionitrile has been used as polar solvent to investigate the orientation of the phospholipid at the surface of the polar solvents by neutral impact collision ion scattering spectroscopy and as a reagent for carboxyl protection in peptide synthesis. It has been used also in solid state composite electrolyte for dye-sensitized solar cells.
Hartwig Pohl; Thomas Krebs; Harald Morgner. Orientation of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine at the surface of formamide and hydroxypropionitrile. Langmuir. 2010, 26,(4), 2473-2476.
Hongxia Wang; Xizhe Liu; Zhaoxiang Wang; Hong Li; Dongmei Li; Qingbo Meng; Liquan Chen. Effect of iodine addition on solid-state electrolyte LiI/3-hydroxypropionitrile (1:4) for dye-sensitized solar cells. Journal of Physical Chemistry B. 2006, 110,(12), 5970-5974.
Protection of carboxylic acids as 2-cyanoethyl esters can be accomplished by DCC-DMAP coupling. The esters can be cleaved with TBAF in DMF-THF: Chem. Pharm. Bull., 42, 147 (1994), or Na2S in methanol: Chem. Pharm. Bull., 42, 1579 (1994).
Can also be used to protect the phosphate group, by condensation with 2,4,6-Triisopropylbenzenesulfonyl chloride, A11458: Chem. Pharm. Bull., 25, 2844 (1977), or DCC: J. Am. Chem. Soc., 83, 159 (1961). Cleavage can be effected with an amine: Tetrahedron Lett., 23, 5119 (1982), ammonia: J. Org. Chem., 59, 2482 (1994); Tetrahedron Lett., 35, 4311 (1994), or TBAF: Tetrahedron Lett., 1255 (1976).
Precursor of 2-cyanoethyl 2,2,2-trichloroethyl phosphorochloridate, a reagent for the phosphorylation of nucleosides: Synthesis, 831 (1980); see 2,2,2-Trichloroethanol, L08163.
Hazard Statements: H303-H315-H319-H335
May be harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.