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

• ChemBase ID: 75042
• Molecular Formular: C9H6BrNO2
• Molecular Mass: 240.05344
• Monoisotopic Mass: 238.95819044
• SMILES: N1(C(=O)c2c(cccc2)C1=O)CBr
• Canonical SMILES: BrCN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C9H6BrNO2/c10-5-11-8(12)6-3-1-2-4-7(6)9(11)13/h1-4H,5H2
• InChIKey: UUSLLECLCKTJQF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(bromomethyl)-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-(bromomethyl)isoindole-1,3-dione
• Synonyms: 2-(Bromomethyl)-1H-isoindole-1,3(2H)-dione; N-(Bromomethyl)phthalimide; N-BROMOMETHYLPHTHALIMIDE; Phthalimidomethyl bromide; N-(Bromomethyl)phthalimide; 2-(Bromomethyl)isoindoline-1,3-dione; 2-(bromomethyl)-1H-isoindole-1,3(2H)-dione; N-溴甲基酞酰亚胺; N-(溴甲基)邻苯二甲酰亚胺

Database IDs

• CAS Number: 5332-26-3
• EC Number: 226-239-2
• MDL Number: MFCD00005897
• Beilstein Number: 140943
• PubChem SID: 24855225; 162039960; 24850569
• PubChem CID: 79244

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3113048
• LogD (pH = 7.4): 1.3113048
• Log P: 1.3113048
• Molar Refractivity: 51.6675 cm^3
• Polarizability: 18.871626 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 144-150°C; 152-155 °C; 152-155 °C(lit.); 152-155°C; 153 - 155°C
• Hydrophobicity(logP): 1.767

Safety Information

• Storage Warning: Irritant/Light Sensitive/Moisture Sensitive; Moisture & Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280G-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (AT); 95%; 95+%; 97%
• Grade: purum
• Empirical Formula (Hill Notation): C9H6BrNO2

DETAILS

Sigma Aldrich - 252611

Packaging
5, 25 g in glass bottle

REFERENCES

• Arbuzov reaction with triethyl phosphite followed by cleavage with hydrazine hydrate provides a route to diethyl (aminomethyl)phosphonate. Protection as the benzylidene derivative permits the use of this phosphonate in the Wadsworth-Emmons reaction: Org. Synth. Coll., 8, 451 (1993) and references therein.