N-Bromophthalimide

Base Information

• Chemical Name: N-Bromophthalimide
• CAS No.: 2439-85-2
• Molecular Formula: C8H4 Br N O2
• Molecular Weight: 226.029
• Hs Code.: 29251900
• European Community (EC) Number: 219-467-9
• NSC Number: 3525
• UNII: 8EC67S8PWW
• DSSTox Substance ID: DTXSID70179136
• Nikkaji Number: J37.031B
• Wikidata: Q83049646
• Mol file: 2439-85-2.mol

Synonyms:N-bromophthalimide

Chemical Property of N-Bromophthalimide

Chemical Property:

• Appearance/Colour: off-white powder.
• Vapor Pressure: 0.000147mmHg at 25°C
• Melting Point: 194-198 °C(lit.)
• Boiling Point: 332.3 °C at 760 mmHg
• PKA: -3.53±0.20(Predicted)
• Flash Point: 154.8 °C
• PSA: 37.38000
• Density: 1.932 g/cm³
• LogP: 1.53040
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture & Light Sensitive
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 224.94254
• Heavy Atom Count: 12
• Complexity: 217

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Bromophthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)Br
• Uses: Brominating agent. N-Bromophthalimide has been used:as reagent in allylic amination reactions of alkenesbrominating reagent in enantioselective synthesis of multisubstituted biaryl derivatives by chiral phosphoric acid catalyzed asymmetric brominationas a titrant in titrimetric determination of isoniazid in pure form or in tablets N-BROMOPHTHALIMIDE (cas# 2439-85-2) is a useful catalyst for reactions such as the Hofmann-?Loffler reactions of sulfonimides under visible Light and the synthesis of naphthols via bromide-mediated intermolecular annulation.

Technology Process of N-Bromophthalimide

There total 10 articles about N-Bromophthalimide 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) → N-bromophthalimide (2439-85-2)

Guidance literature:

With sodium bromate; sulfuric acid; hydrogen bromide; In acetic acid; for 0.333333h; Ambient temperature;

DOI:10.1246/bcsj.66.2426

Reference yield: 90.0%

→ N-bromophthalimide (2439-85-2)

Guidance literature:

With [bis(acetoxy)iodo]benzene; bromine; In acetonitrile; at 20 ℃;

Reference yield: 66.0%

2,2'-(phenyl-λ3-iodanediyl)bis(isoindoline-1,3-dione) (86451-26-5) → N-bromophthalimide (2439-85-2)

Guidance literature:

With bromine; In tetrachloromethane; for 12h;

DOI:10.1055/s-1983-30282

upstream raw materials:

phthalimide

potassium phtalimide

2,2'-(phenyl-λ³-iodanediyl)bis(isoindoline-1,3-dione)

water

Downstream raw materials:

N-(benzylthio)phthalimide

1-O-acetyl-2,5,6-tri-O-benzoyl-4-hydroxy-3,4-O-(α-phthalimidobenzylidene)-β-D-galactofuranose

1-O-acetyl-2,3,5,6-tetra-O-benzoyl-4-bromo-β-D-galactofuranose

(p-bromomethylphenyl)diphenylphosphine oxide

Refernces

• 1、 -. "Preparation method of 3,5-dibromo-2-aminobenzoic acid". Paragraph 0038-0073. . Retrieved 2019/01/16.
• 2、 Kaupang, Asmund,Bonge-Hansen, Tore. "α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions". supporting information. p. 1407 - 1413. Retrieved 2013/08/23.