N-(3-Bromopropyl)phthalimide

Base Information

• Chemical Name: N-(3-Bromopropyl)phthalimide
• CAS No.: 5460-29-7
• Molecular Formula: C11H10BrNO2
• Molecular Weight: 268.11
• Hs Code.: 29251900
• European Community (EC) Number: 226-738-5
• NSC Number: 25170,24937
• UNII: VQG2G776PS
• DSSTox Substance ID: DTXSID40203033
• Nikkaji Number: J37.060F
• Mol file: 5460-29-7.mol

Synonyms:N-(3-BROMOPROPYL)PHTHALIMIDE;5460-29-7;2-(3-Bromopropyl)isoindoline-1,3-dione;N-3-Bromopropylphthalimide;1-Phthalimido-3-bromopropane;3-Bromopropylphthalimide;MFCD00005904;n-(3-bromopropyl)-phthalimide;Phthalimide, N-(3-bromopropyl)-;gamma-Bromopropylphthalimide;1H-Isoindole-1,3(2H)-dione, 2-(3-bromopropyl)-;2-(3-bromopropyl)isoindole-1,3-dione;2-(Bromopropyl)-1,3-dihydro-1,3-dioxoisoindole;2-(3-Bromopropyl)-1H-isoindole-1,3(2H)-dione;2-(3-Bromopropyl)-2,3-Dihydro-1H-Isoindole-1,3-Dione;NSC 24937;VQG2G776PS;.gamma.-Bromopropylphthalimide;EINECS 226-738-5;NSC 25170;NSC-24937;NSC-25170;2-(3-bromo-propyl)-isoindole-1,3-dione;1H-Isoindole-1, 2-(3-bromopropyl)-;N-bromopropylphthalimide;N-Bromopropyl phthalimide;3phthalimidopropyl bromide;N-(bromopropyl)phthalimide;3-phthalimidopropyl bromide;UNII-VQG2G776PS;N-(3bromopropyl)phthalimide;N-3-bromopropyl phthalimide;N-3-bromopropyl-phthalimide;N-(3-bromopropyl)phtalimide;SCHEMBL56978;N-(3-bromopropyl) pthalimide;N-(3-bromopropyl) phthalimide;N-(3-bromo-propyl)-phthalimide;N-[3-(bromo)propyl]phthalimide;DTXSID40203033;N-(3-Bromo-1-propyl)phthalimide;N-(3-Bromoprop-1-yl)phthalimide;NSC24937;NSC25170;STR02619;BBL011920;N-(3-Bromopropyl)phthalimide, 98%;STK802617;AKOS000277232;AM87054;CS-W020520;SB64119;2-(3-bromo-propyl)isoindole-1,3-dione;2-(3-bromopropyl)-isoindole-1,3-dione;(S)-(-)-1-{(RP)-2-[Bis(4-trifluoromethylphenyl)phosphino]ferrocenyl}ethyldi-tert-butylphosphine;BP-12618;SY011981;B1328;FT-0629061;EN300-22940;2-(3-bromopropyl)-1H-isoindole-1,3 (2H)-dione;A830260;2-(3-Bromopropyl)-1H-isoindole-1,3(2H)-dione #;Q-201421;2-(3-bromopropyl)isoindoline-1,3-dione?hydrochloride;F0001-1438

Chemical Property of N-(3-Bromopropyl)phthalimide

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.07E-05mmHg at 25°C
• Melting Point: 72-74 °C(lit.)
• Refractive Index: 1.615
• Boiling Point: 361.4 °C at 760 mmHg
• PKA: -2.21±0.20(Predicted)
• Flash Point: 172.4 °C
• PSA: 37.38000
• Density: 1.578 g/cm³
• LogP: 2.00550
• Storage Temp.: Store below +30°C.
• Solubility.: <1g/l
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 266.98949
• Heavy Atom Count: 15
• Complexity: 256

Purity/Quality:

99% ^*data from raw suppliers

N-(3-Bromopropyl)phthalimide ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CCCBr
• Uses: N-(3-Bromopropyl)phthalimide is used in synthesis of several organic compounds including that of flavonoid derivatives which act as selective ABCC1 modulators with potential use as pharmacological tools for investigation of the role of ABCC1. It is also used in the synthesis of Hederagenin which is a triterpene template for the development of new antitumor compounds.

Technology Process of N-(3-Bromopropyl)phthalimide

There total 18 articles about N-(3-Bromopropyl)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: 92.0%

phthalimide (136918-14-4,85-41-6) + 1,3-dibromo-propane (109-64-8) → 2-(3-bromopropyl)isoindole-1,3-dione (5460-29-7)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; at 20 ℃; for 1h; Neat (no solvent);

DOI:10.1002/jhet.5570450519

Reference yield: 89.0%

N-(3-hydroxypropyl)phthalimide (883-44-3) → 2-(3-bromopropyl)isoindole-1,3-dione (5460-29-7)

Guidance literature:

N-(3-hydroxypropyl)phthalimide; With diisopropyl-carbodiimide; copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; at 100 ℃; for 0.0833333h; microwave irradiation;

With Acetyl bromide; In tetrahydrofuran; at 150 ℃; for 0.0833333h; Further stages.; microwave irradiation;

DOI:10.1039/b211424k

Reference yield: 88.3%

potassium phtalimide (1074-82-4) + 1,3-dibromo-propane (109-64-8) → 2-(3-bromopropyl)isoindole-1,3-dione (5460-29-7)

Guidance literature:

With tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 70 ℃; for 2h;

upstream raw materials:

phthalic anhydride

propan-1-ol-3-amine

N-(3-bromo-propyl)-phthalamic acid

potassium phtalimide

Downstream raw materials:

3-(1-pyrrolidinyl)propylamine

1-(3-aminopropyl)piperidine

4-(3-Aminopropyl)morpholine

N-(3-[1,2,4]triazol-1-yl-propyl)-phthalimide

Refernces

• 1、 Azimi, Sara,Zonouzi, Afsaneh,Firuzi, Omidreza,Iraji, Aida,Saeedi, Mina,Mahdavi, Mohammad,Edraki, Najmeh. "Discovery of imidazopyridines containing isoindoline-1,3-dione framework as a new class of BACE1 inhibitors: Design, synthesis and SAR analysis". . p. 729 - 737. Retrieved 2017.
• 2、 Singh, Ved Prakash,Dowarah, Jayanta,Marak, Brilliant N.,Sran, Balkaran Singh,Tewari, Ashish Kumar. "Study of the structure-bioactivity of fleximers: synthesis, crystal structure, Hirshfeld surface analysis, and anti-inflammatory assays". . . Retrieved 2021/05/05.
• 3、 Yu, Lintao,Shi, Jian,Cheng, Xinfeng,Wang, Keren,Liu, Shuang,Liu, Wenmin,Sang, Zhipei. "Development of phthalimide-donepezil hybrids as potent multitargetdirected ligands for the treatment of alzheimer’s disease". . p. 1155 - 1163. Retrieved 2020/09/15.