Your Location:Home >Products >1009-14-9

1009-14-9

  • Product NameValerophenone
  • Molecular FormulaC11H14O
  • Purity99%
  • Appearancecolourless liquid
Inquiry

Product Details

Quick Details

  • CasNo: 1009-14-9
  • Molecular Formula: C11H14O
  • Appearance: colourless liquid
  • Purity: 99%

Pharmaceutical Intermediates Valerophenone 1009-14-9 In Stock

  • Molecular Formula:C11H14O
  • Molecular Weight:162.232
  • Appearance/Colour:colourless liquid 
  • Melting Point:-9 °C 
  • Refractive Index:n20/D 1.5143(lit.)  
  • Boiling Point:248.5 °C at 760 mmHg 
  • Flash Point:99.7 °C 
  • PSA:17.07000 
  • Density:0.951 g/cm3 
  • LogP:3.05950 

Valerophenone(Cas 1009-14-9) Usage

Chemical Properties

Valerophenone is a colorless to Light yellow to Light orange clear liquid that is soluble in organic solvents.

Uses

Valerophenone is a prochiral ketone which can undergo Norrish Type II reaction and hence can be used as a UV actinometer in photochemical experiments.

Definition

ChEBI: Valerophenone is an aromatic ketone that consists of benzene substituted by a pentanoyl group. It has a role as a volatile oil component and a plant metabolite.

Synthesis

Valerophenone can be synthesized through several different routes. One possible route involves reacting 4-pentenoic acid with thionyl chloride to produce 4-pentenoyl chloride, which is then reacted with dimethyl malonate to produce 4-pentenoyl dimethyl malonate. This intermediate is then treated with diethyl oxalate to produce ethyl 4-pentenoyl oxalate, which is finally hydrolyzed to produce valerophenone.

Properties and Applications

1-Phenyl-1-pentanone, also known as butyl phenyl ketone or pentanophenone, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 1-Phenyl-1-pentanone is a balsam and valerian tasting compound. 1-Phenyl-1-pentanone has been detected, but not quantified in, a few different foods, such as celery stalks (Apium graveolens var. dulce), green vegetables, and wild celeries (Apium graveolens). This could make 1-phenyl-1-pentanone a potential biomarker for the consumption of these foods.

InChI:InChI=1/C11H14O/c1-2-3-9-11(12)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3

1009-14-9 Relevant articles

Palladium on carbon-catalyzed Α-alkylation of ketones with alcohols as electrophiles: Scope and mechanism

Bennedsen, Niklas R.,Mortensen, Rasmus L.,Kramer, S?ren,Kegn?s, S?ren

, p. 153 - 160 (2019)

The α-alkylation of ketones with alcohol...

A simple synthesis of ketone from carboxylic acid using tosyl chloride as an activator

Jana, Samaresh,Sahoo, Debasis,Sarkar, Sohini

, (2019)

An effective process for the conversion ...

Reaction of Lithium Dialkylcuprates with S-2-Pyridiyl Thioates in the Presence of Oxygen. A Carboxylic Ester Synthesis

Kim, Sunggak,Lee, Jae In,Chung, Bong Young

, p. 1231 - 1232 (1981)

Reaction of lithium dialkylcuprates with...

Toxicity and death following recreational use of 2-pyrrolidino valerophenone

Celine Eiden,Olivier Mathieu,Philippe Cathala,Daniele Debruyne,Eric Baccino,Pierre Petit &Helene Peyriere

, Clinical Toxicology Volume 51, 2013 - Issue 9

We present, here, the first documented cases of recreational use of 2-pyrrolidino valerophenone (PVP) associated with death for one patient, with post-mortem toxicological analysis. Case reports.

Ready Coupling of Acid Chlorides with Tetra-alkyl-lead Derivatives Catalysed by Palladium

Yamada, Jun-ichi,Yamamoto, Yoshinori

, p. 1302 - 1303 (1987)

Palladium-catalysed coupling of acid chl...

Photoreaction of Valerophenone in Aqueous Solution

R. G. Zepp, M. M. Gumz, W. L. Miller, and H. Gao

, The Journal of Physical Chemistry A 1998, 102, 28, 5716–5723

Kinetics and products of the photoreaction of the phenyl ketone valerophenone were investigated as a function of temperature, pH, and wavelength in aqueous solution. The use of valerophenone as a convenient actinometer for studies in water is discussed; its half-lives during midday exposure to summer sunlight in temperate latitudes are <30 min.

Palladium-Catalyzed Cross-Coupling Reactions of Carboxylic Anhydrides with Organozinc Reagents

Wang, Donghui,Zhang, Zhaoguo

, p. 4645 - 4648 (2003)

(Matrix presented) Negishi-type cross-co...

ANWENDUNG NICHTSTABILISIERTER EISEN(II)-ALKYLE ALS HOCHSELEKTIVE NUCLEOPHILE ALKYLIERUNGSREAGENZIEN

Kauffmann, Thomas,Laarmann, Barbara,Menges, Detlef,Voss, Karl-Uwe,Wingbermuehle, Dorothea

, p. 507 - 510 (1990)

Nonstabilized Fe(II) alkyls (RFeCl, R2Fe...

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

Jin, Cheng,Gu, Lijun,Yuan, Minglong

, p. 4341 - 4345 (2015)

The transformation of aromatic aldehydes...

Polystyrene resins containing 1,3-propanedithiol functions for solid-phase organic syntheses

Bertini, Vincenzo,Pocci, Marco,Lucchesini, Francesco,Alfei, Silvana,De Munno, Angela

, p. 864 - 866 (2003)

A completely odourless reliable synthesi...

Alcohols for the α-alkylation of methyl ketones and indirect aza-wittig reaction promoted by nickel nanoparticles

Alonso, Francisco,Riente, Paola,Yus, Miguel

, p. 4908 - 4914 (2008)

Nickel nanoparticles have been found to ...

Chemiluminescence of Imino-1,2-dioxetan Formed from Ketenimine and Singlet Oxygen

Ito, Yoshikatsu,Yokoya, Hiroaki,Kyono, Kazuaki,Yamamura, Soichiro,Yamada, Yutaka,Matsuura, Teruo

, p. 898 - 900 (1980)

The chemiluminescent properties of sever...

A Novel Ru(VII)/Ru(IV) Mediatory System for Electrooxidation of Primary and Secondary Alcohols, Leading to Aldehydes and Ketones

Torii, Sigeru,Yoshida, Akihito

, p. 369 - 370 (1995)

A soluble Ru(VII)/Ru(IV) redox system in...

Suzuki-Miyaura coupling of simple ketones via activation of unstrained carbon-carbon bonds

Xia, Ying,Wang, Jianchun,Dong, Guangbin

, p. 5347 - 5351 (2018)

Here, we describe that simple ketones ca...

A New Oxidizing Reagent: Triethylsilyl Hydrotrioxide

Posner, Gary H.,Webb, Kevin S.,Nelson, William M.,Kishimoto, Takashi,Seliger, Howard H.

, p. 3252 - 3254 (1989)

Triethylsilyl hydrotrioxide (Et3SiOOOH) ...

Nickel catalyzed cross-coupling of modified alkyl and alkenyl Grignard reagents with aryl- and heteroaryl nitriles: Activation of the C-CN bond

Miller, Joseph A.,Dankwardt, John W.

, p. 1907 - 1910 (2003)

The nickel catalyzed cross-coupling of a...

Reactivities of mixed organozinc and mixed organocopper reagents. Part 13 Kinetic study for phosphine-catalyzed acylation of alkylarylzincs and effect of residual group on the transfer rate of alkyl group

?mür Pekel, ?zgen

, p. 190 - 195 (2016)

Kinetics of reactions of di-n-butylzinc,...

Direct and efficient one-pot preparation of ketones from aldehydes using N-tert-butylphenylsulfinimidoyl chloride

Crawford, James J.,Henderson, Kenneth W.,Kerr, William J.

, p. 5073 - 5076 (2006)

(Chemical Equation Presented) A general,...

Nucleophilic properties of butyllithium versus free carboxylic acids

Einhorn,Einhorn,Luche

, p. 2771 - 2774 (1991)

In opposition to the generally accepted ...

Reactivities of mixed organozinc and mixed organocopper reagents, 2. Selective n-alkyl transfer in tri-n-butylphosphine-catalyzed acylation of n-alkyl phenylzincs; an atom economic synthesis of n-alkyl aryl ketones

Erdik, Ender,Pekel, ?zgen ?mür

, p. 1501 - 1503 (2009)

Tri-n-butylphosphine-catalyzed acylation...

H2-Generation from Alcohols by the MOF-Based Noble Metal-Free Photocatalyst Ni/CdS/TiO2@MIL-101

Tilgner, Dominic,Klarner, Mara,Hammon, Sebastian,Friedrich, Martin,Verch, Andreas,De Jonge, Niels,Kümmel, Stephan,Kempe, Rhett

, p. 842 - 847 (2019)

The synthesis of important classes of ch...

Oxidative rearrangement of internal alkynes to give one-carbon-shorter ketones via manganese porphyrins catalysis

Sheng, Wen-Bing,Jiang, Qing,Luo, Wei-Ping,Guo, Can-Cheng

, p. 5691 - 5693 (2013)

Oxidative rearrangement of internal alky...

Synthesis of Functionalized Ketones from Acid Chlorides and Organolithiums by Extremely Fast Micromixing

Nagaki, Aiichiro,Sasatsuki, Kengo,Ishiuchi, Satoshi,Miuchi, Nobuyuki,Takumi, Masahiro,Yoshida, Jun-ichi

, p. 4946 - 4950 (2019)

Synthesis of ketones containing various ...

Catalytic and chemoselective oxidation of activated alcohols and direct conversion of diols to lactones with in situ-generated bis-IBX catalyst

Seth, Saona,Jhulki, Samik,Moorthy, Jarugu Narasimha

, p. 2445 - 2452 (2013)

The twisted 3,3′-diiodo-2,2′,6,6′-tetram...

Preparation of ketones via the palladium-catalyzed cross-coupling of acid chlorides with trialkylboranes

Kabalka, George W.,Malladi, Rama R.,Tejedor, David,Kelley, Shane

, p. 999 - 1001 (2000)

Trialkylboranes react with acid chloride...

A remarkable effect of ionic liquids in transition-metal-free aerobic oxidation of benzylic alcohols

Oda, Yoshiro,Hirano, Koji,Satoh, Tetsuya,Kuwabata, Susumu,Miura, Masahiro

, p. 5392 - 5394 (2011)

The transition-metal-free aerobic oxidat...

A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids

Haddach, Mustapha,McCarthy, James R.

, p. 3109 - 3112 (1999)

The cross-coupling reaction of acid chlo...

Contra-Thermodynamic Positional Isomerization of Olefins

Zhao, Kuo,Knowles, Robert R.

supporting information, p. 137 - 144 (2022/01/19)

A light-driven method for the contra-the...

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge

supporting information, p. 1372 - 1377 (2022/02/23)

A Rh(I)-catalyzed ketone Suzuki-Miyaura ...

Nickel-Catalyzed Reductive Acylation of Carboxylic Acids with Alkyl Halides and N-Hydroxyphthalimide Esters Enabled by Electrochemical Process

Guo, Lin,Xia, Raymond Yang,Xia, Wujiong,Yang, Chao,Zhang, Haoxiang,Zhou, Xiao

supporting information, (2022/03/31)

A sustainable Ni-catalyzed reductive acy...

Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides

Yang, Jianping,Massaro, Luca,Krajangsri, Suppachai,Singh, Thishana,Su, Hao,Silvi, Emanuele,Ponra, Sudipta,Eriksson, Lars,Ahlquist, M?rten S. G.,Andersson, Pher G.

supporting information, p. 21594 - 21603 (2021/12/27)

We present a highly efficient convergent...

1009-14-9 Process route

benzonitrile
100-47-0

benzonitrile

phenyl butyl ketone
1009-14-9

phenyl butyl ketone

phenyl isopropyl ketone
611-70-1

phenyl isopropyl ketone

Conditions
Conditions Yield
In tetrahydrofuran; at 25 ℃; for 24h;
92 % Spectr.
7 % Spectr.
3-benzoyl-1-phenyl-hexane-1,2-dione

3-benzoyl-1-phenyl-hexane-1,2-dione

water
7732-18-5

water

phenyl butyl ketone
1009-14-9

phenyl butyl ketone

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
Conditions Yield
 
 

1009-14-9 Upstream products

  • 54431-11-7
    54431-11-7

    valerophenone phenylhydrazone

  • 128-09-6
    128-09-6

    N-chloro-succinimide

  • 583-03-9
    583-03-9

    1-Phenyl-1-pentanol

  • 110-59-8
    110-59-8

    pentanonitrile

1009-14-9 Downstream products

  • 101708-94-5
    101708-94-5

    1-phenyl-pentane-1,2-dione-2-oxime

  • 855752-80-6
    855752-80-6

    (+/-)-5-hydroxy-5-phenyl-dodecane

  • 538-68-1
    538-68-1

    pentylbenzene

  • 583-03-9
    583-03-9

    1-Phenyl-1-pentanol

;