N-(Hydroxymethyl)phthalimide

Base Information

• Chemical Name: N-(Hydroxymethyl)phthalimide
• CAS No.: 118-29-6
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.159
• Hs Code.: 2925.19
• European Community (EC) Number: 204-241-4
• NSC Number: 39723,27471,27350
• UNII: G8L8BA278J
• DSSTox Substance ID: DTXSID1026954
• Nikkaji Number: J16G
• Wikidata: Q27117985
• Metabolomics Workbench ID: 56016
• ChEMBL ID: CHEMBL3183835
• Mol file: 118-29-6.mol

Synonyms:N-(hydroxymethyl)phthalimide;N-hydroxymethylphthalimide

Chemical Property of N-(Hydroxymethyl)phthalimide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 5.96E-05mmHg at 25°C
• Melting Point: 147-149 °C
• Refractive Index: 1.644
• Boiling Point: 332 °C at 760 mmHg
• PKA: 13.17±0.10(Predicted)
• Flash Point: 154.6 °C
• PSA: 57.61000
• Density: 1.462 g/cm³
• LogP: 0.17030
• Storage Temp.: Store below +30°C.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 227

Purity/Quality:

98% ^*data from raw suppliers

N-(Hydroxymethyl)phthalimide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CO
• Uses: N-(Hydroxymethyl)phthalimide is used as a reactant in the synthesis of 5-[(3-aralkyl amido/imidoalkyl)phenyl]-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines as antiviral agents. For amidomethylation of aromatics in triflic acid.

Technology Process of N-(Hydroxymethyl)phthalimide

There total 21 articles about N-(Hydroxymethyl)phthalimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

phthalimide (136918-14-4,85-41-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione (118-29-6)

Guidance literature:

In water; at 100 ℃; for 4h;

DOI:10.1002/chem.201102366

Reference yield: 95.0%

N-(bromomethyl)phtalimide (5332-26-3) → 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione (118-29-6)

Guidance literature:

With cesium formate; In methanol; for 18h; Reflux; Inert atmosphere;

DOI:10.1016/j.jorganchem.2009.06.031

Reference yield: 84.0%

phthalimide (136918-14-4,85-41-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + phosphonic acid diethyl ester (762-04-9) → 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione (118-29-6)

Guidance literature:

In 1,1,2,2-tetrachloroethylene; at 110 ℃; for 8h;

DOI:10.1016/j.tet.2011.01.061

upstream raw materials:

phthalimide

formaldehyd

N-(bromomethyl)phtalimide

diisopropylamine

Downstream raw materials:

(3-phthalimidomethyl-phenyl)-acetic acid

(4-phthalimidomethyl-phenyl)-acetic acid

N-(2-hydroxy-5-nitro-benzyl)-phthalimide

N-(2-hydroxy-9,10-dioxo-9,10-dihydro-[1]anthrylmethyl)-phthalamic acid