2694-78-2

Basic information

• Product Name: BENZOPHENONE-2,3,4,5,6-D5
• Synonyms: BENZOPHENONE-2,3,4,5,6-D5;BENZOPHENONE-2,3,4,5,6-D5, 98 ATOM % D;Methanone, phenylphenyl-d5-;Benzophenone--d5
• CAS NO: 2694-78-2
• Molecular Formula: C₁₃H₁₀O
• Molecular Weight: 187.25
• Product Categories: Alphabetical Listings;B;Stable Isotopes
• Mol File: 2694-78-2.mol

Chemical Properties

• Melting Point: 47-51 °C(lit.)
• Boiling Point: 305 °C(lit.)
• Flash Point: 123.7°C
• Appearance: /
• Density: 1.117g/cm³
• Vapor Pressure: 0.000823mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: BENZOPHENONE-2,3,4,5,6-D5(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOPHENONE-2,3,4,5,6-D5(2694-78-2)
• EPA Substance Registry System: BENZOPHENONE-2,3,4,5,6-D5(2694-78-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2694-78-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
BENZOPHENONE-2,3,4,5,6-D5 is used as a synthetic building block for the creation of various organic compounds. Its deuterated nature provides unique properties that can be advantageous in specific chemical reactions, leading to improved yields or selectivity.
Used in Analytical Chemistry:
In the field of analytical chemistry, BENZOPHENONE-2,3,4,5,6-D5 serves as an internal standard or a reference compound for mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. Its deuterated atoms help in the accurate determination of molecular weights and structural elucidation of other compounds.
Used in Pharmaceutical Research:
BENZOPHENONE-2,3,4,5,6-D5 is utilized in the development and optimization of pharmaceutical compounds. Its deuterated form can enhance the stability and solubility of drug candidates, potentially improving their pharmacokinetic and pharmacodynamic properties.
Used in Material Science:
In material science, BENZOPHENONE-2,3,4,5,6-D5 can be employed as a component in the synthesis of advanced materials with specific properties, such as improved thermal stability or enhanced conductivity.
Used in Environmental Studies:
BENZOPHENONE-2,3,4,5,6-D5 can be used as a tracer compound in environmental studies, helping researchers to track the fate and transport of pollutants or contaminants in various ecosystems.
Used in the Cosmetics Industry:
In the cosmetics industry, BENZOPHENONE-2,3,4,5,6-D5 may be used as a component in the formulation of various products, such as sunscreens, due to its ability to absorb ultraviolet (UV) radiation, providing protection against harmful UV rays.

InChI:InChI=1/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H/i1D,3D,4D,7D,8D

Upstream product

• 501-65-5 diphenyl acetylene 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 1076-43-3 benzene-d6 
• 3393-96-2 p-nitrobenzanilide 
• 17901-93-8 benzaldehyde-d6 
• 38111-44-3 phenylzinc(II) bromide 
• 100-52-7 benzaldehyde 
• 4165-57-5 bromobenzene-d5 
• 95450-78-5 pentadeuterophenyl-phenyl-methanol 
• 31919-47-8 1-benzoyladamantane 
• 98-88-4 benzoyl chloride 

Downstream Products

• 877203-67-3 C₁₅H₉⁽²⁾H₅ 
• 1099592-06-9 C₁₉H₁₀⁽²⁾H₅N 
• 22526-25-6 2,2,2-trimethyl-1-(2-hydroxyphenyl)ethan-1-one 
• 1446017-31-7 C₁₁H₁₀⁽²⁾H₄O₂ 
• 1428245-14-0 C₁₃H₅⁽²⁾H₅O₂ 
• 1428245-15-1 C₁₃H₆⁽²⁾H₄O₂ 
• 85649-65-6 benzophenone oxime-d₅ 
• 103730-93-4 1-benzylbenzene-2,3,4,5,6-d₅ 
• 1189954-07-1 C₃₂H₃₄⁽²⁾H₅NO₃ 
• 1316815-11-8 C₃₄H₃₆⁽²⁾H₅NO₄ 
• 1316815-02-7 C₄H₄O₄*C₃₂H₃₄⁽²⁾H₅NO₂ 
• 1216953-13-7 C₃₂H₃₄⁽²⁾H₅NO₂ 

Relevant articles and documents

Gas phase carbon and deuterium isotope effects on electron affinity of benzophenone: A combined experimental and theoretical study

Carbonyl-13C, 17O, and C6D5 isotope effects (IEs) on the electron transfer equilibrium between benzophenone and benzophenone radical anion were determined by means of fourier transfer ion cyclotron resonance (FT-ICR) measurements and the ab initio MO calculations (UHF/6-31G*). The experimental and theoretical IEs are in excellent agreement with each other (K12/K13 = 1.03 (50°C, ICR), 1.026 (50°C, MO) and KD5/KH5 = 1.35 (50°C, ICR), 1.325 (50°C, MO)). The carbonyl-13C, 17O, ring 13C12, and D10 IEs were calculated as 1.044, 1.025, 1.206, and 2.812, respectively, at -75°C. The carbonyl-13C and 17O IEs disagree with the reported IEs in liquid NH3 (K12/K13 = 2.0, K16//K17 = 0.26, at -75°C, Stevenson et al. J. Phys. Chem. 1988, 92, 3687) and are close to unity as generally expected. The present results do not support the explanation in terms of an ion association effect in the liquid phase.

Redox-Divergent Hydrogen-Retentive or Hydrogen-Releasing Synthesis of 3,4-Dihydroisoquinolines or Isoquinolines

A rare Ru-catalyzed highly selective synthesis of 3,4-dihydroisoquinolines or isoquinolines is accomplished via a redox-divergent hydrogen-retentive or hydrogen-releasing fashion. Notably, high cis-selectivity of 3,4-dihydroisoquinolines is achieved. Potential applications are shown by gram-scale reactions and very concise synthesis of N-containing polycyclic aromatic compounds. Primary mechanistic investigations indicate that the sequence of the major pathway involves Ru-catalyzed C-H activation, alkyne insertion, and subsequent 6π-electrocyclization.

Iron-Carbonyl-Catalyzed Redox-Neutral [4+2] Annulation of N-H Imines and Internal Alkynes by C-H Bond Activation

Stoichiometric C-H bond activation of arenes mediated by iron carbonyls was reported by Pauson as early as in 1965, yet the catalytic C-H transformations have not been developed. Herein, an iron-catalyzed annulation of N-H imines and internal alkynes to furnish cis-3,4-dihydroisoquinolines is described, and represents the first iron-carbonyl-catalyzed C-H activation reaction of arenes. Remarkablely, this is also the first redox-neutral [4+2] annulation of imines and alkynes proceeding by C-H activation. The reaction also features only cis stereoselectivity and excellent atom economy as neither base, nor external ligand, nor additive is required. Experimental and theoretical studies reveal an oxidative addition mechanism for C-H bond activation to afford a dinuclear ferracycle and a synergetic diiron-promoted H-transfer to the alkyne as the turnover-determining step. Double dose of iron: The titled redox-neutral [4+2] annulations to furnish cis-3,4-dihydroisoquinolines were achieved by using iron catalysis. Mechanistic studies show the synergy of dinuclear iron in the C-H bond activation and turnover-limiting hydrogen-transfer steps. The reaction demonstrates excellent atom economy and exclusive cis stereoselectivity.

Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of N-Sulfinylimines and Benzimidates

C-H activation of arenes has been established as an important strategy for heterocycle synthesis via annulations between arenes and unsaturated coupling partners. However, nitriles failed to act as such a coupling partner. Dioxazolones have been employed as a synthon of nitriles, and subsequent coupling with arenes such as N-sulfinylimines and benzimidates bearing a functionalizable directing group provided facile access to two classes of quinazolines under Co(III)-catalysis.

Ir(III)-Catalyzed Synthesis of Isoquinoline N-Oxides from Aryloxime and α-Diazocarbonyl Compounds

An efficient Ir(III)-catalyzed C-H activation and annulations of aryloxime with α-diazocarbonyl compounds has been developed for the synthesis of substituted isoquinoline N-oxides. The reaction proceeds under mild atmospheric conditions, without any external oxidants and releases N2 and H2O as the byproducts. In addition, synthetic applications of the N-oxide products have been established by performing further functionalization. An interesting dimeric iridacyclic complex allied through a bis-silver carboxylate bridge has been isolated that efficiently catalyzed the reaction.

Nickel N-heterocyclic carbene-catalyzed cross-coupling reaction of aryl aldehydes with organozinc reagents to produce aryl ketones

The transformation of aromatic aldehydes into aryl ketones by nickel-catalyzed cross-coupling has been developed. This transformation represents an efficient and attractive synthetic utilization of organozinc reagents. The reaction provides a mild, practical method toward the synthesis of aryl ketones which are versatile intermediates and building blocks in organic synthesis.

Synthesis of indazoles and azaindazoles by intramolecular aerobic oxidative C-N coupling under transition-metal-free conditions

A transition-metal-free oxidative C-N coupling method has been developed for the synthesis of 1H-azaindazoles and 1H-indazoles from easily accessible hydrazones. The procedure uses TEMPO, a basic additive, and dioxygen gas as the terminal oxidant. This reaction demonstrates better reactivity, functional group tolerance, and broader scope than comparable metal catalyzed reactions. A transition-metal-free oxidative C-N coupling method has been developed for the synthesis of 1H-azaindazoles and 1H-indazoles from easily accessible hydrazones (see scheme). The procedure uses TEMPO, a basic additive, and dioxygen gas as the terminal oxidant. This reaction demonstrates better reactivity, functional group tolerance, and broader scope than comparable metal catalyzed reactions. TEMPO=2,2,6,6-tetramethyl-1-piperidinyloxy.

Synthesis of ortho-acylphenols through the palladium-catalyzed ketone-directed hydroxylation of arenes

ortho-Acylphenols are an important structural motif found in a diversity of bioactive molecules ranging from natural products to drugs (Figure 1). Moreover, they also serve as versatile building blocks for the synthesis of various pharmaceuticals, such as warfarin, as well as agrichemicals, flavors, and fragrances. Classic approaches to the synthesis of o-acylphenols generally involve a two-step process: acylation of phenols followed by Fries rearrangement of the resulting phenyl esters (Scheme 1a). On the other hand, direct C-acylation of phenols has also been known under more forcing conditions. Although effective, these approaches are often complicated by the formation of undesired p-substituted products when bulky acyl groups need to be introduced, as well as the limited variety of ketones that can be generated.

Synthesis of [2H5]-ebastine fumarate and [ 2H5]-hydroxyebastine

This study describes the synthesis of deuterium-labelled ebastine fumarate and its deuterium-labelled metabolite hydroxyebastine. The synthesis of the two desired compounds both used [2H5]-bromodiphenylmethane as deuterium-labelled reagent, which was synthesized beforehand in three steps. [2H5]-ebastine was synthesized in further three steps with a 27% overall yield and [2H5]-hydroxyebastine was synthesized in further seven steps with a 13% overall yield.

Reactions and mechanistic studies of rhenium-catalyzed insertion of α,β-unsaturated carbonyl compounds into a C-H bond

A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the insertion of α, β-unsaturated carbonyl compounds into a C-H bond of aromatic compounds having nitrogen-containing directing groups. In this reaction, Re2(CO)10 can also be used as a catalyst. When imines are employed as the aromatic substrates, sequential cyclization proceeds and indene derivatives are obtained in good to excellent yields. This reactivity is in contrast to those of ruthenium and rhodium complexes, which are usually used as catalysts in the insertion reactions of unsaturated molecules into a C-H bond. Investigations on the reaction mechanism indicate that the rhenium catalyst promotes C-H bond activation of aromatic compounds, the insertion of α, β-unsaturated carbonyl compounds into a Re-C bond, and intramolecular nucleophilic cyclization followed by reductive elimination and the elimination of an amine.