132833-51-3

Basic information

• Product Name: 4-(4-Bromobenzyl)morpholine
• Synonyms: Morpholine,4-[(4-broMophenyl)Methyl]-
• CAS NO: 132833-51-3
• Molecular Formula: C₁₁H₁₄BrNO
• Molecular Weight: 256.15
• Product Categories: Amino;Aryl;Organohalides;alkyl bromide
• Mol File: 132833-51-3.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 313.2 °C at 760mmHg
• Flash Point: 143.2 °C
• Appearance: /
• Density: 1.399 g/cm³
• Vapor Pressure: 0.000505mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 4-(4-Bromobenzyl)morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Bromobenzyl)morpholine(132833-51-3)
• EPA Substance Registry System: 4-(4-Bromobenzyl)morpholine(132833-51-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 132833-51-3(Hazardous Substances Data)

Usage

General Description

4-(4-Bromobenzyl)morpholine is a chemical compound with the molecular formula C11H13BrNO. It is a substituted morpholine derivative with a bromo group attached to a benzyl moiety. 4-(4-Bromobenzyl)morpholine is commonly used in organic synthesis and medicinal chemistry as a building block and intermediate for the synthesis of various pharmaceuticals and fine chemicals. It possesses potential biological activities and has been studied for its potential applications in the development of drugs for the treatment of various diseases. Additionally, 4-(4-Bromobenzyl)morpholine has also been investigated for its use as a reagent in organic reactions and as a starting material for the synthesis of complex molecules. Overall, this compound is a versatile and valuable chemical for use in various chemical and pharmaceutical applications.

InChI:InChI=1/C11H14BrNO/c12-11-3-1-10(2-4-11)9-13-5-7-14-8-6-13/h1-4H,5-9H2

Upstream product

• 110-91-8 morpholine 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 873-75-6 4-bromobenzenemethanol 
• 106-38-7 para-bromotoluene 
• 459-49-4 p-bromobenzyl fluoride 
• 1233656-28-4 C₁₆H₁₈BrO₄P 
• 55883-45-9 4-bromobenzyliodide 
• 1122-91-4 4-bromo-benzaldehyde 
• 75382-07-9 (4-bromophenyl)-1-morpholinoacetonitrile 

Downstream Products

• 1093191-20-8 4-[4-(2-(trimethylsilyl)ethynyl)benzyl]morpholine 
• 933986-59-5 4-(morpholinomethyl)phenylacetylene 
• 1395409-50-3 methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate 
• 1395409-38-7 (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(2-(4-(morpholinomethyl)phenyl)ethynyl)phenyl)-tetrahydrofuran-2-carboxamide 
• 1202486-22-3 N-(4-(4-methylpiperazin-1-yl)phenyl)-5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine 
• 1202490-78-5 N-(4-chlorophenyl)-5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine 
• 1093191-13-9 (S)-methyl 3-tert-butoxycarbonylamino-2-(7-((4-(morpholinomethyl)phenyl)ethynyl)-4-oxoquinazolin-3(4H)-yl)propanoate 

Relevant articles and documents

Design and synthesis of benzopyran-based inhibitors of the hypoxia-inducible factor-1 pathway with improved water solubility

While progress has been made in treating cancer, cytotoxic chemotherapeutic agents are still the most widely used drugs and are associated with severe side-effects. Drugs that target unique molecular signalling pathways are needed for treating cancer with low or no intrinsic toxicity to normal cells. Our goal is to target hypoxic tumours and specifically the hypoxia inducible factor (HIF) pathway for the development of new cancer therapies. To this end, we have previously developed benzopyran-based HIF-1 inhibitors such as arylsulfonamide KCN1. However, KCN1 and its earlier analogs have poor water solubility, which hamper their applications. Herein, we describe a series of KCN1 analogs that incorporate a morpholine moiety at various positions. We found that replacing the benzopyran group of KCN1 with a phenyl group with a morpholinomethyl moiety at the para positions had minimal effect on potency and improved the water solubility of two new compounds by more than 10-fold compared to KCN1, the lead compound.

Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides

We describe the first thiourea-catalyzed C?F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

BrCCl3 represents a rarely used benzylic brominating reagent with complementary reactivity to other reagents. Its reactivity has been revisited in continuous flow, revealing compatibility with electron-rich aromatic substrates. This has brought about the development of a p-methoxybenzyl bromide generator for PMB protection, which was successfully demonstrated on a pharmaceutically relevant intermediate on 11 g scale, giving 91% yield and a PMB-Br space-time-yield of 1.27 kg L?1 h?1