N-(5-BROMOPENTYL)PHTHALIMIDE

Base Information

• Chemical Name: N-(5-BROMOPENTYL)PHTHALIMIDE
• CAS No.: 954-81-4
• Molecular Formula: C13H14BrNO2
• Molecular Weight: 296.164
• Hs Code.: 2925190090
• Mol file: 954-81-4.mol

Synonyms:Phthalimide,N-(5-bromopentyl)- (7CI,8CI);2-(5-Bromopentyl)-1H-isoindole-1,3(2H)-dione;2-(5-Bromopentyl)isoindole-1,3-dione;N-(5-Bromopentyl)phthalamide;N-(5-Bromopentyl)phthalimide;NSC 83526;

Chemical Property of N-(5-BROMOPENTYL)PHTHALIMIDE

Chemical Property:

• Vapor Pressure: 2.18E-06mmHg at 25°C
• Melting Point: 58 °C
• Refractive Index: 1.591
• Boiling Point: 393.1 °C at 760 mmHg
• PKA: -2.13±0.20(Predicted)
• Flash Point: 191.5 °C
• PSA: 37.38000
• Density: 1.459 g/cm³
• LogP: 2.78570
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.

Purity/Quality:

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

N-(5-Bromopentyl)phthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-50/53-43-22
• Safety Statements: 26-36/37/39-61-60-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is a pharmaceutical intermediate and is used in medicine. N-(5-Bromopentyl)phthalimide acts as a reagent in the synthesis of organofluorine isoselenocyanate analogs of sulforaphane with anticancer activity against two breast cancer cell lines. It also functions as a reagent in the preparation of N-[[[[(benzothiazolyl)methyl]thio]pyrimidinyl]hexyl]biotinamide (biotin-BMMP) and determination of its activity toward HIV-1 virus.

Technology Process of N-(5-BROMOPENTYL)PHTHALIMIDE

There total 6 articles about N-(5-BROMOPENTYL)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: 1.0%

2-[2-(5-Bromo-pentyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-butyric acid methyl ester → 2-(pent-4-enyl)-isoindoline-1,3-dione (7736-25-6) + N-(5-bromopentyl)phthalimide (954-81-4) + 2-(1-Hydroxy-3-oxo-2-pent-4-enyl-2,3-dihydro-1H-isoindol-1-yl)-butyric acid methyl ester

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran;

Reference yield:

2-pentyl-1H-isoindole-1,3(2H)-dione (71510-39-9) → N-(3-bromo-pentyl)-phthalimide (859299-26-6) + 4-bromo-1-phthalimidopentane (59353-62-7) + N-(5-bromopentyl)phthalimide (954-81-4)

Guidance literature:

With N-bromo-N-(t-butyl)-3,5-bis(trifluoromethyl)benzamide; In benzene; at 20 ℃; for 4h; Overall yield = 56.4 %Chromat.; Sealed tube; Irradiation; Inert atmosphere;

DOI:10.1021/ja508469u

Reference yield:

amyl iodide (628-17-1) + potassium phtalimide (1074-82-4) → N-(3-bromo-pentyl)-phthalimide (859299-26-6) + 4-bromo-1-phthalimidopentane (59353-62-7) + N-(5-bromopentyl)phthalimide (954-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / 80 °C

2: N-bromo-N-(t-butyl)-3,5-bis(trifluoromethyl)benzamide / benzene / 4 h / 20 °C / Sealed tube; Irradiation; Inert atmosphere

With N-bromo-N-(t-butyl)-3,5-bis(trifluoromethyl)benzamide; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja508469u

upstream raw materials:

phthalic anhydride

5-hydroxypentylamine

phosphorus tribromide

5-phthalimido-1-pentanol

Downstream raw materials:

6-phenyl-2-<2-(phthalimido)pentyl>-3(2H)-pyridazinone

1-(2-methoxyphenyl)-4-<5-(2-phthalimido)pentyl>piperazine

4-amino-5-chloro-N-(1-(5-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)-pentyl)piperidin-4-ylmethyl)-2-methoxybenzamide

2-(2-aminopentylthio)methyl-3,5-dicarboethoxy-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine

Refernces

• 1、 Schmidt, Valerie A.,Quinn, Ryan K.,Brusoe, Andrew T.,Alexanian, Erik J.. "Site-selective aliphatic C-H bromination using N -bromoamides and visible light". . p. 14389 - 14392. Retrieved 2014/12/10.
• 2、 -. "PROCESS FOR PREPARING ALPHA,OMEGA-DIAMINO ACIDS". . . Retrieved 2008/06/13.