2-(chloromethyl)-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 103107
• Molecular Formular: C9H6ClNO2
• Molecular Mass: 195.60244
• Monoisotopic Mass: 195.00870612
• SMILES: ClCN1C(=O)c2c(cccc2)C1=O
• Canonical SMILES: ClCN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C9H6ClNO2/c10-5-11-8(12)6-3-1-2-4-7(6)9(11)13/h1-4H,5H2
• InChIKey: JKGLRGGCGUQNEX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(chloromethyl)-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-(chloromethyl)isoindole-1,3-dione
• Synonyms: N-(Chloromethyl)phthalimide; N-CHLOROMETHYL PHTHALIMIDE; 2-(Chloromethyl)isoindoline-1,3-dione; N-(CHLOROMETHYL)PHTHALIMIDE; N-氯甲基邻苯二甲酰亚胺; N-(氯甲基)邻苯二甲酰亚胺

Database IDs

• CAS Number: 17564-64-6
• EC Number: 241-541-4
• MDL Number: MFCD00005898
• Beilstein Number: 140942
• PubChem SID: 162089816; 24853898
• PubChem CID: 87154

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.530856
• LogD (pH = 7.4): 1.530856
• Log P: 1.530856
• Molar Refractivity: 48.8509 cm^3
• Polarizability: 17.884499 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 131-135 °C; 131-135 °C(lit.); 131-135°C; 133-135°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38-43-52/53; 36/37/38; R:36/37/38
• Safety Statements: 26-36-45-61; 26-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H317-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ~97-98%; ≥97.0% (AT); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C9H6ClNO2

DETAILS

MP Biomedicals - 02150624

Purity: ~97-98%
Used in amino acid synthesis to protect carboxylic acid groups.

MP Biomedicals - 05226185

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 232424

Packaging
10, 50 g in poly bottle

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).