Formic acid

• Catalog No.: A13285
• CAS Number: 64-18-6
• M. F.: CH2O2
• M. W.: 46.02538
• Purity: 97%

SYNONYMS

• Title: 甲酸
• IUPAC name: formic acid
• IUPAC Traditional name: formic acid

DATABASE IDS

• MDL Number: MFCD00003297
• Merck Index: 144241
• EC Number: 200-579-1
• Beilstein Number: 1209246
• CAS Number: 64-18-6

PROPERTIES

• Purity: 97%
• Boiling Point: 100-101°C
• Density: 1.220
• Flash Point: 50°C(156°F)
• Melting Point: 7-9°C
• Refractive Index: 1.3710
• GHS Hazard statements: H331-H302-H314-H318-H226
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 35
• RTECS: LQ4900000
• Safety Statements: 23-26-45
• Storage Warning: Hygroscopic
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN1779
• Packing Group: II

REFERENCES

• Dehydration with sulfuric acid can be used to generate CO in situ. Subsequent reaction with tertiary carbocations gives the corresponding carboxylic acid (the Koch-Haaf carboxylation). For examples, see: Org. Synth. Coll., 5, 20, 739 (1973); improved procedure: Synth. Commun., 19, 1945 (1989). 1,4-Diols in which one alcohol is tertiary give -lactones: Chem. Lett., 1187 (1982).
• Used in combination with formaldehyde in the Eschweiler-Clarke reductive methylation of amines, the formic acid acting as a hydride donor. Review: Org. React., 5, 290 (1949). For an example, see: Org. Synth. Coll., 3, 723 (1955).
• In the presence of Raney nickel alloy, reduces aromatic nitriles to aldehydes in high yield: J. Chem. Soc., 5775 (1965); for list of examples, see: Org. Synth. Coll., 6, 631 (1988).
• Hydrogen donor, in combination with Pd on carbon, in catalytic transfer hydrogenations; see, e.g.: Selective reduction of dinitroarenes to nitroanilines: J. Org. Chem., 45, 4992 (1980). Dehalogenation of aryl halides: Synthesis, 876 (1982). Hydrogenation of aromatic rings: Tetrahedron Lett., 33, 7477 (1992). See also Palladium, A12012, Cyclohexene, A11359, and Ammonium formate, A10699. For a comparative mechanistic study of formic acid and formate salts in hydrogenolysis of aryl chlorides, see: J. Org. Chem., 60, 1347 (1995).
• In combination with Selenium(IV) oxide, 12358, improved results have been obtained in the allylic oxidation of sterically-hindered olefins: Synth. Commun., 24, 29213 (1994).
• Cleaves trityl groups selectively in the presence of benzylidene acetals or TBDMS ethers: Tetrahedron Lett., 27, 579 (1986).
• Instead of the unstable formic anhydride, formylations may be carried out with formic acid and acetic anhydride to generate the mixed acetic formic anhydride in situ. For a review, see: Tetrahedron, 46, 1081 (1990). This reagent has been used for the deoxygenation of tertiary amine oxides: Chem. Lett., 1517 (1985).