4885-19-2

Basic information

• Product Name: 4-(DIETHYLAMINOMETHYL)-BROMOBENZENE
• Synonyms: 4-(DIETHYLAMINOMETHYL)-BROMOBENZENE;N-(4-broMobenzyl)-N-ethylethanaMine
• CAS NO: 4885-19-2
• Molecular Formula: C₁₁H₁₆BrN
• Molecular Weight: 242.16
• Product Categories: alkyl bromide
• Mol File: 4885-19-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 264.837 °C at 760 mmHg
• Flash Point: 113.97 °C
• Appearance: /
• Density: 1.241 g/cm³
• CAS DataBase Reference: 4-(DIETHYLAMINOMETHYL)-BROMOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(DIETHYLAMINOMETHYL)-BROMOBENZENE(4885-19-2)
• EPA Substance Registry System: 4-(DIETHYLAMINOMETHYL)-BROMOBENZENE(4885-19-2)

Safety Data

• Hazardous Substances Data: 4885-19-2(Hazardous Substances Data)

Usage

General Description

4-(Diethylaminomethyl)-bromobenzene, also known as N,N-diethyl-4-bromobenzylamine, is an organic compound with the chemical formula C12H18BrN. It is a pale yellow liquid with a molecular weight of 263.18 g/mol. 4-(Diethylaminomethyl)-bromobenzene is commonly used as a reagent in organic synthesis and is known for its use as a precursor in the synthesis of various pharmaceutical and agrochemical products. It is also utilized in the production of dyes and pigments, as well as in research and development for the synthesis of new chemical compounds. 4-(Diethylaminomethyl)-bromobenzene is considered to be a potentially hazardous substance and should be handled with care, following proper safety measures and guidelines.

Upstream product

• 5892-99-9 4-bromo-N,N-diethylbenzamide 
• 109-89-7 diethylamine 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 106-38-7 para-bromotoluene 

Downstream Products

• 578724-70-6 4-(but-3-enyl)-N,N-diethylbenzylamine 
• 856795-95-4 N-ethyl-p-bromobenzylamine 
• 1329705-04-5 1,2-bis(bis{p-[(diethylamino)methyl]phenyl}phosphino)ethane 
• 1329705-07-8 2,2'-bis(bis{p-[(diethylamino)methyl]phenyl}phosphino)-4,4'-dimethyldiphenyl ether 
• 927690-09-3 (+/-)-(2-chlorophenyl)[4-(N,N-diethylaminomethyl)phenyl]methanol 
• 1012785-44-2 N-ethyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)ethanamine 
• 1384460-90-5 1-(4-(cyclopenta-2,4-dienyldimethylsilyl)phenyl)-N,N-diethylmethanamine 
• 305801-81-4 C₂₉H₃₁N₄O⁽¹⁺⁾*I^(1-) 

Relevant articles and documents

Consecutive β,β′-Selective C(sp3)?H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C6F5)3

Tris(pentafluorophenyl)borane has been found to catalyze the two-fold C(sp3)?H silylation of various trialkylamine derivatives with dihydrosilanes, furnishing the corresponding 4-silapiperidines in decent yields. The multi-step reaction cascade involves amine-to-enamine dehydrogenation at two alkyl residues and two electrophilic silylation reactions of those enamines, one inter- and one intramolecular.

A BEt3-Base catalyst for amide reduction with silane

Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si-H···B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.

Aqueous Suzuki Coupling Reactions of Basic Nitrogen-Containing Substrates in the Absence of Added Base and Ligand: Observation of High Yields under Acidic Conditions

A series of aqueous heterogeneous Suzuki coupling reactions of substrates containing basic nitrogen centers with phenylboronic acid in the absence of added base and ligand is presented. High yields of products were obtained by employing aryl bromides containing aliphatic 1°, 2°, and 3° amine substituents, and good to high yields were obtained by employing a variety of substituted bromopyridines. In the former series, the pH of the aqueous phase changed from basic to acidic during the course of the reaction, while in the latter series the aqueous phase was on the acidic side of the pH scale throughout the entire course of reaction. A mechanistic interpretation for these observations, which generally preserves the oxo palladium catalytic cycle widely accepted in the literature, is presented.