90-90-4

Basic information

• Product Name: 4-BROMOBENZOPHENONE
• Synonyms: P-BROMOBENZOPHENONE;LABOTEST-BB LT00053402;4-BROMOBENZOPHENONE;(4-Bromophenyl)(phenyl)methanone;(4-bromophenyl)phenyl-methanon;4-bromo-benzophenon;4-bromophenylphenylketone;Benzophenone, 4-bromo-
• CAS NO: 90-90-4
• Molecular Formula: C₁₃H₉BrO
• Molecular Weight: 261.11
• EINECS: 202-024-9
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 90-90-4.mol
• Article Data: 194

Chemical Properties

• Melting Point: 79-84 °C(lit.)
• Boiling Point: 350 °C(lit.)
• Flash Point: 350°C
• Appearance: White to light beige/Crystalline Powder
• Density: 1.4245 (rough estimate)
• Vapor Pressure: 5.62E-05mmHg at 25°C
• Refractive Index: 1.5130 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water but slightly soluble in other solvents such as ethanol, ether and benzene.
• BRN: 1910182
• CAS DataBase Reference: 4-BROMOBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOBENZOPHENONE(90-90-4)
• EPA Substance Registry System: 4-BROMOBENZOPHENONE(90-90-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• RTECS: DJ0350000
• Hazardous Substances Data: 90-90-4(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO LIGHT BEIGE CRYSTALLINE POWDER

Uses

4-Bromobenzophenone is used in analytical applications such as HPLC and GC. It is also used as a chemical reagent and pharmaceutical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 2708, 1966 DOI: 10.1021/jo01346a526Tetrahedron Letters, 27, p. 929, 1986 DOI: 10.1016/S0040-4039(00)84140-4

Purification Methods

Crystallise the phenone from EtOH. The 2,4-dinitrophenylhydrazone forms orange-red leaflets from dioxane/EtOH with m 207-209o. [Allen & Van Allan J Am Chem Soc 66 7 1944, Beilstein 7 H 422, 7 III 2079, 7 IV 1378.]

InChI:InChI=1/C13H9BrO/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9H

Upstream product

• 40292-19-1 (4-aminophenyl)(4-bromophenyl)methanone 
• 108-86-1 bromobenzene 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 5472-32-2 1,2-bis-(4-bromo-phenyl)-1,2-diphenyl-ethane-1,2-diol 
• 103-73-1 Phenetole 
• 29334-16-5 phenyl(4-bromophenyl)methanol 
• 35861-34-8 C₁₃H₁₀BrO 
• 18066-89-2 1-bromo-4-<(bromophenyl)methyl>benzene 
• 1137-43-5 (4-bromophenyl)(phenyl)methanethione 
• 98-07-7 Benzotrichlorid 
• 586-75-4 4-chlorobenzoyl chloride 
• 587-85-9 diphenylmercury(II) 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 101606-21-7 (4-bromo-phenyl)-phenyl-[2]pyridyl-methanol 
• 132568-80-0 4-(4-bromo-phenyl)-4-hydroxy-4-phenyl-but-2-ynoic acid amide 
• 127568-31-4 N-(4-bromo-benzhydryl)-formamide 
• 861622-36-8 (4-bromo-phenyl)-[1]naphthyl-phenyl-methanol 
• 29334-16-5 phenyl(4-bromophenyl)methanol 
• 56311-15-0 (4-[1,3,6,2]dioxazaborocan-2-yl-phenyl)-phenyl-methanol 
• 130820-18-7 1-(4-bromophenyl)-1-(1-methyl-4-piperidinyl)-1-phenylmethanol 
• 119-61-9 benzophenone 
• 134-84-9 4-Methylbenzophenone 
• 20428-67-5 3,3-diphenyl-3-hydroxy-N,N-dimethylpropanamide 
• 76385-38-1 (4-allylphenyl)(phenyl)methanone 
• 23405-48-3 4-methylthiobenzophenone 
• 1503-49-7 p-cyanobenzophenone 
• 77120-71-9 phenyl-1, p-bromophenyl-1 ethoxy-5 hydroxy-1 hexene-4 yne-2 

Relevant articles and documents

Self-Assembled 2,3-Dicyanopyrazino Phenanthrene Aggregates as a Visible-Light Photocatalyst

In this study, 2,3-dicyanopyrazino phenanthrene (DCPP), a commodity chemical that can be prepared at an industrial scale, was used as a photocatalyst in lieu of Ru or Ir complexes in C-X (X = C, N, and O) bond-forming reactions under visible-light irradiation. In these reactions, [DCPP]n aggregates were formed in situ through physical π-πstacking of DCPP monomers in organic solvents. These aggregates exhibited excellent photo- and electrochemical properties, including a visible light response (430 nm), long excited-state lifetime (19.3 μs), high excited-state reduction potential (Ered([DCPP]n*/[DCPP]n·-) = +2.10 V vs SCE), and good reduction stability. The applications of [DCPP]n aggregates as a versatile visible-light photocatalyst were demonstrated in decarboxylative C-C cross-coupling, amidation, and esterification reactions.

Photo-induced oxidative cleavage of C-C double bonds of olefins in water

The carbonyl compounds, synthesized by the oxidative cleavage of their corresponding olefins, are of great significance in organic synthesis, especially aryl ketones. We have developed a gentle and effective protocol, using acid red 94 as the organic metal-free photocatalyst, O2 as the oxidant, and water as the solvent. Under visible light irradiation, aryl ketone derivatives were obtained in moderate to excellent yields, showing good economic and environmental advantages.

AIBN initiated functionalization of the benzylic sp3 C[sbnd]H and C[sbnd]C bonds in the presence of dioxygen

A sp3 C[sbnd]H bond functionalization and C[sbnd]C bond cleavage were realized by AIBN/O2 catalyst system, providing a series of benzophenones under mild reaction conditions. The mechanistic study shows that a peroxide intermediate is involved in this transformation, and in the case of diphenylmethanes, the sp3 C[sbnd]C bond is cleaved through the peroxide rearrangement, which might provides a new way to cleave relatively strong C[sbnd]C bond and be applied to more general C[sbnd]C bond activation.