N-(Chloromethyl)phthalimide

• Catalog No.: A12018
• CAS Number: 17564-64-6
• M. F.: C9H6ClNO2
• M. W.: 195.60244
• Purity: 97%

SYNONYMS

• Title: N-(氯甲基)邻苯二甲酰亚胺
• IUPAC name: 2-(chloromethyl)-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-(chloromethyl)isoindole-1,3-dione

DATABASE IDS

• MDL Number: MFCD00005898
• Beilstein Number: 140942
• EC Number: 241-541-4
• CAS Number: 17564-64-6

PROPERTIES

• Purity: 97%
• Melting Point: 131-135°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是

REFERENCES

• Reagent for carboxyl protection, e.g. in peptide synthesis, by reaction in the presence of an amine: Rec. Trav. Chim., 82, 941 (1963); or with KF in DMF: Synth. Commun., 8, 515 (1978). The phthalimidomethyl ester can be cleaved in various ways including hydrazinolysis, HBr in acetic acid or Zn/AcOH. See also N-(Hydroxymethyl)phthalimide, B21292 and Appendix 6.
• Reagent for the amidomethylation of aromatic systems. For reviews of amidomethylation, see: Org. React., 14, 52 (1965); Synthesis, 49 (1970); 85, 181 (1984).
• Also reported for the protection of thiols as the S-phthalimidomethyl (Pim) derivative. Cleavage is by hydrazinolysis, followed by Hg(II), Cu(II) or I₂: Chem. Lett., 2139 (1994).