Description

N-Hydroxymethylphthalimide (CAS 118-29-6) is a high-purity organic compound with the molecular formula C₉H₇NO₃. This white to off-white crystalline solid is widely utilized in synthetic organic chemistry and pharmaceutical research. As a derivative of phthalimide, it features a hydroxymethyl group (-CH₂OH) attached to the nitrogen atom, enhancing its reactivity in nucleophilic substitutions and polymer applications. With a molecular weight of 177.16 g/mol, it is soluble in polar organic solvents such as DMSO, DMF, and acetone, but exhibits limited solubility in water. Ideal for researchers developing bioactive compounds, crosslinking agents, or polymer modifiers, this reagent is rigorously tested for consistency (≥98% purity by HPLC) and supplied in secure, light-resistant packaging to ensure stability.

Properties

• CAS Number: 118-29-6
• Complexity: 227
• IUPAC Name: 2-(hydroxymethyl)isoindoline-1,3-dione
• InChI: InChI=1S/C9H7NO3/c11-5-10-8(12)6-3-1-2-4-7(6)9(10)13/h1-4,11H,5H2
• InChI Key: MNSGOOCAMMSKGI-UHFFFAOYSA-N
• Exact Mass: 177.042593085
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.16
• SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CO
• Topological: 57.6
• Monoisotopic Mass: 177.042593085
• Synonyms: N-(Hydroxymethyl)phthalimide, 118-29-6, N-Hydroxymethylphthalimide, Phthalimidomethyl alcohol, N-Methylolphthalimide, Phthalimidomethanol, Oxymethyl phthalimide, Hydroxymethylphthalimide, 2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione, 1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-, Methanol, phthalimido-, 2-(hydroxymethyl)isoindole-1,3-dione, Oxymethylphthalimide, PHTHALIMIDE, N-(HYDROXYMETHYL)-, NSC 27350, EINECS 204-241-4, BRN 0140946, G8L8BA278J, DTXSID1026954, CHEBI:38816, AI3-28943, NSC-27350, DTXCID506954, 5-21-10-00366 (Beilstein Handbook Reference), 204-241-4, inchi=1/c9h7no3/c11-5-10-8(12)6-3-1-2-4-7(6)9(10)13/h1-4,11h,5h, 2-(hydroxymethyl)isoindoline-1,3-dione, N-hydroxymethyl phthalimide, MFCD00005899, 2-(hydroxymethyl)-2,3-dihydro-1H-isoindole-1,3-dione, 1H-Isoindole-1, 2-(hydroxymethyl)-, UNII-G8L8BA278J, (Hydroxymethyl)phthalimide, N-hydroxy methylphthalimide, N-hydroxymethyl-phthalimide, N-(Hydroxymethyl)phtalimide, N-(hydroxymethy) phthalimide, N-(hydroxymethyl)-phthalimide, SCHEMBL101555, N–(hydroxymethyl)-phthalimide, SCHEMBL6330619, SCHEMBL7287742, CHEMBL3183835, ALBB-017986, BCP27127, HY-Y0895, N-(Hydroxymethyl)phthalimide, 97%, NSC27350, NSC27471, NSC39723, STR02558, Tox21_200859, 2-Hydroxymethyl-isoindole-1,3-dione, NSC-27471, NSC-39723, SBB041136, STK028674, AKOS000269457, FH33638, SB66110, 2-(hydroxymethyl)-1,3-isoindolinedione, 2-(hydroxymethyl)-isoindole-1,3-dione, NCGC00248852-01, NCGC00258413-01, PIMOH (N-Hydroxymethyl phthalimide acid, AC-19446, CAS-118-29-6, 2-(hydroxymethyl)benzo[c]azoline-1,3-dione, CS-0015898, H0648, NS00023806, ST45038203, 2-(hydroxymethyl)benzo[c]azolidine-1,3-dione, EN300-17143, D70499, 2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione #, Q27117985, F0777-0575

Application

N-Hydroxymethylphthalimide serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals and agrochemicals. It is employed in the development of crosslinking agents for resins and polymers due to its reactive hydroxymethyl group. Researchers also utilize it to synthesize N-substituted phthalimide derivatives for antimicrobial or anticancer studies. Its stability and functional group compatibility make it valuable in peptide coupling and protecting group strategies.

Safety and Hazards

GHS Hazard Statements

• H315 (11.9%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (11.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (11.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (11.9%)
• Eye Irrit. 2A (11.9%)
• STOT SE 3 (11.9%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.