596-43-0

Basic information

• Product Name: Triphenylmethyl bromide
• Synonyms: Triphenylbromomethane, Trityl bromide;Bromidetriphenylmethane ,98%;Triphenylmethyl bromide,98%;Bromotriphenylmethane,Triphenylbromomethane, Trityl bromide;Triphenylbromomethane Triphenylmethyl Bromide Bromotriphenylmethane;(broMoMethanetriyl)tribenzene;Bromidetriphenylmethane;Triphenylmethylebromide
• CAS NO: 596-43-0
• Molecular Formula: C₁₉H₁₅Br
• Molecular Weight: 323.23
• EINECS: 209-884-4
• Product Categories: Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Aryl;Building Blocks;C13 to C37+;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents
• Mol File: 596-43-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 152-154 °C(lit.)
• Boiling Point: 230 °C15 mm Hg(lit.)
• Flash Point: 230°C/15mm
• Appearance: Light yellow/Crystalline Powder
• Density: 1,55 g/cm3
• Refractive Index: 1.6411 (estimate)
• Storage Temp.: 0-6°C
• Solubility: dioxane: 0.1 g/mL, clear
• Sensitive: Moisture Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• BRN: 1878494
• CAS DataBase Reference: Triphenylmethyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Triphenylmethyl bromide(596-43-0)
• EPA Substance Registry System: Triphenylmethyl bromide(596-43-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: PA5550000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 596-43-0(Hazardous Substances Data)

Usage

Chemical Properties

light yellow powder

Uses

Different sources of media describe the Uses of 596-43-0 differently. You can refer to the following data:
1. Reagent for the preparation of trityl esters.
2. It is considered as a more reactive reagent than Chlorotriphenyl-methane, for the preparation of trityl esters. It is also used in one-pot conversion of amino acids to their N-trityl derivatives involving N,O-ditritylation and selective methanolysis of the trityl ester.

InChI:InChI=1/C20H17Br/c21-16-20(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-15H,16H2

Upstream product

• 596-30-5 ditrityl peroxide 
• 97924-47-5 2-methoxy-1,3-bis-trityloxy-propane 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 71-43-2 benzene 
• 506-96-7 Acetyl bromide 
• 968-39-8 Triphenylmethylethylether 
• 596-31-6 methoxytriphenylmethane 
• 18909-18-7 1-diphenylmethylene-4-trityl-2,5-cyclohexadiene 
• 98-07-7 Benzotrichlorid 
• 86296-07-3 1-O-trityl-2.3.4.5-tetra-O-acetyl-L-fucitol 
• 50611-24-0 1.6-di-O-trityl-2.3.4.5-tetra-O-acetyl-galactitol 
• 519-73-3 triphenylmethane 
• 7726-95-6 bromine 

Downstream Products

• 1801-42-9 2,3-diphenyl-1H-inden-1-one 
• 63019-13-6 but-1-ene-1,1,2-triyltribenzene 
• 95435-84-0 ethyl 2,3,3-triphenyl-prop-2-enoate 
• 19672-33-4 trityl-malonic acid diethyl ester 
• 1101-55-9 7,7-Diphenyl-p-mentha-1⁽⁷⁾,2,5-trien-8-carbonsaere-methylester 
• 854843-91-7 4-methyl-2-trityl-[1,3,2]dioxaphosphinin-2-oxide 
• 166660-56-6 triphenylmethylphosphinic acid 
• 860253-09-4 N-p-tolyl-N'-trityl-hydrazine 
• 113752-93-5 N-(3-nitro-phenyl)-N'-trityl-hydrazine 
• 519-73-3 triphenylmethane 
• 2216-49-1 triphenylmethyl radical 
• 971-85-7 triphenylmethyl acetate 
• 52418-74-3 3-((triphenylmethyl)oxy)-1-octyne 
• 119039-42-8 Ditritylchimylalkohol 

Relevant articles and documents

C(sp3)-H Fluorination with a Copper(II)/(III) Redox Couple

Despite the growing interest in the synthesis of fluorinated organic compounds, few reactions are able to incorporate fluoride ions directly into alkyl C-H bonds. Here, we report the C(sp3)-H fluorination reactivity of a formally copper(III) fluoride complex. The C-H fluorination intermediate, LCuF, along with its chloride and bromide analogues, LCuCl and LCuBr, were prepared directly from halide sources with a chemical oxidant and fully characterized with single-crystal X-ray diffraction, X-ray absorption spectroscopy, UV-vis spectroscopy, and 1H nuclear magnetic resonance spectroscopy. Quantum chemical calculations reveal significant halide radical character for all complexes, suggesting their ability to initiate and terminate a C(sp3)-H halogenation sequence by sequential hydrogen atom abstraction (HAA) and radical capture. The capability of HAA by the formally copper(III) halide complexes was explored with 9,10-dihydroanthracene, revealing that LCuF exhibits rates 2 orders of magnitude higher than LCuCl and LCuBr. In contrast, all three complexes efficiently capture carbon radicals to afford C(sp3)-halogen bonds. Mechanistic investigation of radical capture with a triphenylmethyl radical revealed that LCuF proceeds through a concerted mechanism, while LCuCl and LCuBr follow a stepwise electron transfer-halide transfer pathway. The capability of LCuF to perform both hydrogen atom abstraction and radical capture was leveraged to enable fluorination of allylic and benzylic C-H bonds and α-C-H bonds of ethers at room temperature.

Reaction of acyl halides with alkyl diphenylmethyl or alkyl triphenylmethyl ethers

-

'Redox-switch' catalysis of C-C bond formation with H2: One-electron reduction of the trityl cation

Different products are formed from the electron transfer reaction between the ruthenium hydride 1 and the trityl cation when 1 is employed as a 'redox-switch' catalyst or as stoichiometric reducing agent. In the first case 1 converts H2 into a one-electron reducing agent for C-C bond formation, thus yielding the product known as Gomberg's dimer. In contrast, only triphenylmethane is produced in the stoichiometric reactions, by an electron-transfer/hydride-transfer mechanism.