1671-75-6

Basic information

• Product Name: HEPTANOPHENONE
• Synonyms: N-HEPTANOPHENONE;N-HEXYL PHENYL KETONE;1-Heptanone, 1-phenyl-;1-phenyl-1-heptanon;1-phenyl-heptan-1-one;Heptanophenone, 98+%;Hexyl Phenyl Ketone;Heptanophenone, 98+% 25GR
• CAS NO: 1671-75-6
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.28
• EINECS: 216-802-0
• Product Categories: C13 to C14;Carbonyl Compounds;Ketones;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 1671-75-6.mol
• Article Data: 94

Chemical Properties

• Melting Point: 17 °C(lit.)
• Boiling Point: 155 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow to yellow/Liquid
• Density: 0.946 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5077(lit.)
• BRN: 1865692
• CAS DataBase Reference: HEPTANOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: HEPTANOPHENONE(1671-75-6)
• EPA Substance Registry System: HEPTANOPHENONE(1671-75-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1671-75-6(Hazardous Substances Data)

Usage

Description

HEPTANOPHENONE, also known as 1-Phenyl-1-heptanone, is an alkyl phenyl ketone characterized by its clear slightly yellow to yellow liquid appearance. It has been studied for its inhibitory effect on carbonyl reductase activity in pig heart, showcasing its potential in various applications.

Uses

Used in Organic Synthesis:
HEPTANOPHENONE is used as a building block for organic synthesis, contributing to the creation of various complex organic compounds due to its versatile chemical structure.
Used in Chromatography:
HEPTANOPHENONE is used as a test compound for comparing the kinetic performance of monolithic and fused-core capillary C(18) columns in isocratic-elution liquid chromatography, helping to evaluate and improve the efficiency of separation techniques in analytical chemistry.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 6229, 1987 DOI: 10.1016/S0040-4039(00)61854-3

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 63035-40-5 1-lithio-1,1-bis(1,3,2-dioxaborin-2-yl)hexane 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 1116-73-0 trihexylaluminium 
• 2082-21-5 1-phenylcycloheptanol 
• 626-27-7 n-heptanoic anhydride 
• 143-66-8 sodium tetraphenyl borate 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 592-41-6 1-hexene 
• 100-52-7 benzaldehyde 
• 695-34-1 2-Amino-4-methylpyridine 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 201230-82-2 carbon monoxide 
• 638-45-9 1-Iodohexane 

Downstream Products

• 94763-03-8 7-Phenyl-n-tetradecanol-⁽⁷⁾ 
• 167476-86-0 Hexyl-[1-phenyl-hept-(E)-ylidene]-amine 
• 106560-96-7 1-phenyl-heptylamine 
• 872884-24-7 (Z)-allyl 1-phenyl-1-heptenyl carbonate 
• 1530-20-7 1,1-diphenyl-1-heptene 
• 1530-05-8 1,1-diphenylheptane 
• 6005-98-7 7-hydroxy-7-phenyl-tridecane 
• 614-54-0 (R)-1-phenylheptanol 
• 614-54-0 (S)-(-)-1-phenyl-1-heptanol 
• 169601-59-6 5,6-dihydro-6-hexyl-4-hydroxy-6-phenyl-2H-pyran-2-one 
• 187800-62-0 2-Phenyl-2-trimethylsilanyloxy-octanenitrile 
• 445235-87-0 (Z)-1-phenyl-1-trimethylsilyloxy-1-heptene 

Relevant articles and documents

Direct formation of alkylzinc chlorides using a new active zinc

The reduction of zinc cyanide by lithium napthalenide yields an active form of zinc which undergoes direct oxidative addition to alkylchlorides with the tolerance of some functionality.

Polymeric reagents with propane-1,3-dithiol functions and their precursors for supported organic syntheses

Reliable completely odorless syntheses of soluble copolymeric reagents of styrene type containing propane-1,3-dithiol functions able to convert carbonyl compounds into 1,3-dithiane derivatives and to support other useful transformations are reported together with their progenitor copolymers containing benzenesulfonate or thioacetate groups perfectly stable in open air and suitable for unlimited storage. The effectiveness of the prepared reagents as tools for polymer-supported syntheses to produce ketones by aldehyde umpolung and alkylation is tested in the conversion of benzaldehyde to phenyl n-hexyl ketone starting from copolymers with different contents of active units and molecular weights. To facilitate the adaptation of the prepared soluble copolymeric reagents to other possible applications, a table of solvents and nonsolvents is presented.

Dual functionalities of hydrogen-bonding self-assembled catalysts in chelation-assisted hydroacylation

(Figure Presented) A recyclable catalyst for chelation-assisted hydroacylation of an olefin with primary alcohol was developed using hydrogen-bonding self-assembled catalysts consisting of 2,6-diaminopyridine and barbiturate phosphine - rhodium(I) complex. Upon heating, these two catalysts act as homogeneous catalysts due to cleavage of the hydrogen bond, and these associate to form supramolecular assemblies via hydrogen bonding that can be separated from immiscible product phase upon cooling after the reaction.

Direct conversion of benzyl alcohol to ketone by polymer-supported Rh catalyst

Benzyl alcohol reacted with 1-alkene to give the corresponding ketone by in situ generated polystyrene-based rhodium catalyst. The catalytic activity of this polymer-supported rhodium catalyst has not been reduced after reusing it four times.

Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols

An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage is developed through photocatalysis, to produce ketones or aldehydes as the products. Tertiary, secondary, and primary alcohols bearing a wide range of substituents are suitable substrates. Complex natural alcohols can also perform the transformation selectively. A investigation of the mechanism reveals a procedure that involves chlorine radical improved O-H homolysis, with the assistance of 2,4,6-collidine.

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.