2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetyl chloride

• ChemBase ID: 60225
• Molecular Formular: C10H6ClNO3
• Molecular Mass: 223.61254
• Monoisotopic Mass: 223.00362074
• SMILES: c1cccc2c1C(=O)N(C2=O)CC(=O)Cl
• Canonical SMILES: ClC(=O)CN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C10H6ClNO3/c11-8(13)5-12-9(14)6-3-1-2-4-7(6)10(12)15/h1-4H,5H2
• InChIKey: RHZBRCQIKQUQHQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetyl chloride
• IUPAC Traditional name: 2-(1,3-dioxoisoindol-2-yl)acetyl chloride
• Synonyms: (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl chloride; (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-acetyl chloride; 1,3-Dioxo-2-isoindolineacetyl chloride; NSC 401729; Phthalylglycine acid chloride; Phthalylglycyl chloride; N-邻苯二甲酰甘氨酰氯

Database IDs

• CAS Number: 6780-38-7
• EC Number: 229-840-8
• MDL Number: MFCD00192872
• PubChem SID: 24882779; 162025966
• PubChem CID: 81242

CALCULATED PROPERTIES

• Acid pKa: 19.912136
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.9284121
• LogD (pH = 7.4): 0.9284121
• Log P: 0.9284121
• Molar Refractivity: 54.1546 cm^3
• Polarizability: 19.889076 Å^3
• Polar Surface Area: 54.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Partition Coefficient: 1.476

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Toxic (T)
• UN Number: 2923
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 25-34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2923 8/PG 3

Product Information

• Purity: 95+%; 96%
• Empirical Formula (Hill Notation): C10H6ClNO3

DETAILS

Sigma Aldrich - 636401

Packaging
1 g in glass bottle
Application
Reactant involved in:
• Synthesis of selenium-containing amino acid analogs with bactericidal and antifungal activity1
• Photoinduced single electron transfer cyclization for preparation of cyclic peptides2
• Arndt-Eistert synthesis3
• Mitsunobu and arbuzov-type multicomponent pathway4
• Remote C-H bond functionalization5
• Amido-alkylation for synthesis of benzofuran derivatives6