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

• ChemBase ID: 71767
• Molecular Formular: C9H7NO3
• Molecular Mass: 177.15678
• Monoisotopic Mass: 177.04259309
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)CO
• Canonical SMILES: OCN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C9H7NO3/c11-5-10-8(12)6-3-1-2-4-7(6)9(10)13/h1-4,11H,5H2
• InChIKey: MNSGOOCAMMSKGI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(hydroxymethyl)-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: N-(hydroxymethyl)phthalimide
• Synonyms: 2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione; 2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione; (Phthalimid-1-yl)methanol; N-(Hydroxymethyl)phthalimide; Phthalimidomethanol; N-(Hydroxymethyl)phthalimide; 2-(Hydroxymethyl)isoindoline-1,3-dione; 2-(hydroxymethyl)-2,3-dihydro-1H-isoindole-1,3-dione; N-羟甲基酞酰亚胺; N-羟甲基邻苯二甲酰亚胺; N-(羟甲基)邻苯二甲酰亚胺

Database IDs

• CAS Number: 118-29-6
• EC Number: 204-241-4
• MDL Number: MFCD00005899
• Beilstein Number: 140946
• PubChem SID: 162037160; 24895627
• PubChem CID: 8354

CALCULATED PROPERTIES

• Acid pKa: 13.904436
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.33709803
• LogD (pH = 7.4): 0.3370979
• Log P: 0.33709803
• Molar Refractivity: 45.3133 cm^3
• Polarizability: 16.660858 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 140-145 °C; 140-147°C; 147 - 149°C; 147-149 °C(lit.); 147-149°C°C
• Hydrophobicity(logP): 0.522

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: TI5270000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 95%; 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C9H7NO3

DETAILS

Sigma Aldrich - H41803

Packaging
100 g in poly bottle
Safe reagent for the in situ generation of anhydrous formaldehyde in organic solvents.2
Application
For amidomethylation of aromatics in triflic acid.1

REFERENCES

• Used for the introduction of the phthalimidomethyl group by electrophilic substitution of aromatic compounds. For reviews on this amidomethylation reaction, see: Org. React., 14, 52 (1965); Synthesis, 49, (1970); 85, 181 (1984).
• In the presence of diethylamine, protection of carboxylic acids as phthalimidomethyl esters has been reported. The group can be cleaved with hydrazine in MeOH, by a variety of basic or acidic conditions: Rec. Trav. Chim., 82, 941 (1963), or with Zn in AcOH: Chem. Ind. (London), 1204 (1970).