5460-29-7

Basic information

• Product Name: N-(3-BROMOPROPYL)PHTHALIMIDE
• Synonyms: AURORA KA-570;GAMMA-BROMOPROPYLPHTHALIMIDE;LABOTEST-BB LT00455358;2-(3-BROMO-PROPYL)-ISOINDOLE-1,3-DIONE;2-(3-BROMOPROPYL)-1H-ISOINDOLE-1,3(2H)-DIONE;AKOS 226-47;TIMTEC-BB SBB003049;N-(3-BROMOPROPYL)PHTHALIMIDE
• CAS NO: 5460-29-7
• Molecular Formula: C₁₁H₁₀BrNO₂
• Molecular Weight: 268.11
• EINECS: 226-738-5
• Product Categories: N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Bifunctional CrosslinkersOrganic Building Blocks;Carbonyl Compounds;Cyclic Imides;Linkers;Peptide Synthesis;alkyl bromide
• Mol File: 5460-29-7.mol
• Article Data: 62

Chemical Properties

• Melting Point: 72-74 °C(lit.)
• Boiling Point: 361℃
• Flash Point: 172℃
• Appearance: White to light beige/Crystalline Powder or Crystals
• Density: 1.578
• Vapor Pressure: 2.07E-05mmHg at 25°C
• Refractive Index: 1.6320 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: <1g/l
• PKA: -2.21±0.20(Predicted)
• BRN: 157547
• CAS DataBase Reference: N-(3-BROMOPROPYL)PHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-BROMOPROPYL)PHTHALIMIDE(5460-29-7)
• EPA Substance Registry System: N-(3-BROMOPROPYL)PHTHALIMIDE(5460-29-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 5460-29-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

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.

Purification Methods

Place it in a Soxhlet and extract it with Et2O, whereby the bis-phthalimido impurity is not extracted. Evaporate the Et2O and recrystallise the residue from EtOH, aqueous EtOH or pet ether. [Gabriel & Weiner Chem Ber 21 2669 1888, Gaudry Can J Chem 31 1060 1953, Beilstein 21/10 V 1277.]

InChI:InChI=1/C11H10BrNO2/c12-6-3-7-13-10(14)8-4-1-2-5-9(8)11(13)15/h1-2,4-5H,3,6-7H2

Upstream product

• 1074-82-4 potassium phtalimide 
• 109-64-8 1,3-dibromo-propane 
• 136918-14-4 phthalimide 
• 883-44-3 N-(3-hydroxypropyl)phthalimide 
• 1198089-20-1 1-bromo-3-(trifluoromethoxy)propane 
• 85-44-9 phthalic anhydride 
• 33081-78-6 sodium phthalimide 
• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 598-17-4 1,1-dibromopropane 
• 121776-77-0 N-(3-bromo-propyl)-phthalamic acid 
• 10035-10-6 hydrogen bromide 
• 506-68-3 bromocyane 
• 156-87-6 propan-1-ol-3-amine 

Downstream Products

• 23159-07-1 3-(1-pyrrolidinyl)propylamine 
• 3529-08-6 1-(3-aminopropyl)piperidine 
• 123-00-2 4-(3-Aminopropyl)morpholine 
• 101225-88-1 N-(3-[1,2,4]triazol-1-yl-propyl)-phthalimide 
• 904-10-9 N-[3-(4-Nitrophenoxy)propyl]phthalimide 
• 101243-52-1 N-[3-(4-acetylamino-phenoxy)-propyl]-phthalimide 
• 55747-45-0 ethyl 2-acetyl-5-(1,3-dioxo-1,3-dihydro-2-isoindolyl)pentanoate 
• 856827-99-1 2-(3-((4-methoxyphenyl)amino)propyl)isoindoline-1,3-dione 
• 6345-82-0 N,N-dipropyl-1,3-propanediamine 
• 102-83-0 3-dibutylaminopropylamine 
• 26342-06-3 6-amino-hexan-2-one 
• 71510-41-3 2-(5-oxohexyl)-1H-isoindole-1,3(2H)-dione 
• 104-78-9 diethylaminopropylamine 
• 63868-77-9 N-[3-(2-diethylamino-ethylmercapto)-propyl]-phthalimide 

Relevant articles and documents

Microwave assisted synthesis of melatonin

Melatonin was prepared from phthalimide by N- and C-alkylation, cyclization, hydrolytic, decarboxylation, and acetylation. The four-pot reactions were carried out on microwave irradiation in good yield with short time.

Study of the structure-bioactivity of fleximers: synthesis, crystal structure, Hirshfeld surface analysis, and anti-inflammatory assays

Synthesized and natural pyridones/pyridines derivatives exhibiting diverse biological activities. 2-pyridone has lactam-lactim tautomerization like thymine and uracil bases. In this study, COX-2 target based series of pyridone/pyridine linked fleximers were designed, synthesized and studied. All analogues binding affinity with COX-2 active site were studied through molecular docking, and anti-inflammatory activity studied by in vivo analysis. Weak interactions were studied to find binding sites among analogues through crystal packing, Hirshfeld surface analysis and in silico analysis. All the analogues exhibited anti-inflammatory activity, while compound (3) is the most active analogue among the series. In contrast, since compound (3) is a pyridine-phthalimide ring-containing analogue, the presence of a phthalimide group probably favors anti-inflammatory activity over other types of rings. The results suggested further investigations on compounds as anti-inflammatory prodrugs.

Niraparib intermediate, preparation method and application thereof, and synthesis method of niraparib

The invention relates to a compound alpha-(3-aminopropyl)-p-bromophenylacetic acid, a preparation method and application thereof, (S)-3-(4-bromophenyl)-piperidine-2-one, a preparation method and application thereof, and synthesis methods of (S)-3-(4-bromophenyl)-piperidine) p-toluenesulfonate, N-Boc-(3S)-(4-bromophenyl)piperidine and niraparib. 4-bromophenylacetate 5 is used as a raw material, a nucleophilic reaction is carried out on the raw material and a nitrogen source reagent 4 under the action of an alkali to generate a compound 6; the compound 6 is subjected to deprotection and hydrolysis to obtain an amino acid compound 7; and the amino acid compound 7 is subjected to chiral column separation or chemical resolution to obtain compounds 8 and 9; and the separated enantiomer 8 can besubjected to racemization and resolution conversion (or chiral column separation) to obtain a compound 9, and the process material cost is greatly reduced. After the compound 9 is obtained, a compound1 can be obtained through conventional condensation reaction ring closing, reduction and BOC loading. Splitting operation is advanced, and the enantiomer 8 is subjected to racemization recovery treatment and is repeatedly applied to different splitting batches to continuously obtain the product 9, so the process material cost is lower.

Synthesis, physico-chemical properties and microsomal stability of compounds bearing aliphatic trifluoromethoxy group

Effects of the trifluoromethoxy substituent on physico-chemical properties of compounds, such as kinetic solubility, lipophilicity and microsomal clearance, was studied in a series of aliphatic derivatives. It was found that kinetic solubility of the CF3O-containing compounds was comparable to that of analogs, i.e. compounds bearing CH3O and CF3 moieties. The CF3O-substituted compounds had higher lipophilicity as compared to methoxy analogues, and nearly the same like CF3-bearing compounds. Microsomal stability studies indicated that the trifluoromethoxy group typically decreased metabolic stability of the corresponding derivatives as compared to either CH3O- or CF3-substituted counterparts, except for N-alkoxy(sulfon)amide series.