Welcome to LookChem.com Sign In|Join Free

CAS

  • or
Allyl Benzoate is an organic compound with the chemical formula C10H10O2. It is a colorless liquid with a pleasant, fruity odor and is soluble in organic solvents. It is synthesized by the esterification of allyl alcohol with benzoic acid. Allyl Benzoate is known for its reactivity and is used as a versatile reactant in various chemical reactions.

583-04-0 Suppliers

Post Buying Request

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier
  • 583-04-0 Structure
  • Basic information

    1. Product Name: ALLYL BENZOATE
    2. Synonyms: Allylbenzoate,97%;prop-2-enyl benzoate;BENZOIC ACID ALLYL ESTER;ALLYL BENZOATE;2-Propenyl benzoate;benzoicacid,2-propenylester
    3. CAS NO:583-04-0
    4. Molecular Formula: C10H10O2
    5. Molecular Weight: 162.19
    6. EINECS: 209-494-4
    7. Product Categories: monomer
    8. Mol File: 583-04-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 83-84°C 5mm
    3. Flash Point: 98.4°C
    4. Appearance: /
    5. Density: 1.05
    6. Vapor Pressure: 0.0335mmHg at 25°C
    7. Refractive Index: 1.5160-1.5190
    8. Storage Temp.: N/A
    9. Solubility: soluble in Methanol
    10. CAS DataBase Reference: ALLYL BENZOATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: ALLYL BENZOATE(583-04-0)
    12. EPA Substance Registry System: ALLYL BENZOATE(583-04-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 583-04-0(Hazardous Substances Data)

583-04-0 Usage

Uses

Used in Pharmaceutical Industry:
Allyl Benzoate is used as a reactant in the preparation of stable potassium alkyltrifluoroborates. These potassium alkyltrifluoroborates are used in Suzuki-Miyaura cross-coupling reactions with aryltriflates and arylhalides, which are important reactions in the synthesis of pharmaceutical compounds.
Used in Chemical Industry:
Allyl Benzoate is used as a reactant in the synthesis of various organic compounds, including polymers, fragrances, and flavorings. Its reactivity makes it a valuable building block in the chemical industry.
Used in Research:
Allyl Benzoate is used as a reactant in various research applications, including the study of cross-coupling reactions and the development of new synthetic methods. Its versatility and reactivity make it an important compound for researchers in the field of organic chemistry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 2166, 1992 DOI: 10.1021/jo00033a048Tetrahedron Letters, 29, p. 4513, 1988 DOI: 10.1016/S0040-4039(00)80534-1Synthetic Communications, 5, p. 213, 1975 DOI: 10.1080/00397917508064112

Check Digit Verification of cas no

The CAS Registry Mumber 583-04-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 3 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 583-04:
(5*5)+(4*8)+(3*3)+(2*0)+(1*4)=70
70 % 10 = 0
So 583-04-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O2/c1-2-8-12-10(11)9-6-4-3-5-7-9/h2-7H,1,8H2

583-04-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Allyl Benzoate

1.2 Other means of identification

Product number -
Other names prop-2-enyl benzoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:583-04-0 SDS

583-04-0Relevant articles and documents

Electrochemical esterification via oxidative coupling of aldehydes and alcohols

Smeyne, Dylan,Verboom, Katherine,Bryan, Maria,LoBue, James,Shaikh, Abid

supporting information, (2021/03/26)

An electrolytic method for the direct oxidative coupling of aldehydes with alcohols to produce esters is described. Our method involves anodic oxidation in presence of TBAF as supporting electrolyte in an undivided electrochemical cell equipped with graphite electrodes. This method successfully couples a wide range of alcohols to benzaldehydes with yields ranging from 70 to 90%. The protocol is easy to perform at a constant voltage conditions and offers a sustainable alternative over conventional methods.

Micellar Catalysis for Sustainable Hydroformylation

Calamante, Massimo,Dei, Filippo,Maramai, Samuele,Migliorini, Francesca,Petricci, Elena

, p. 2794 - 2806 (2021/05/03)

It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini's salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.

Photocatalytic atom transfer radical addition to olefins utilizing novel photocatalysts

Voutyritsa, Errika,Triandafillidi, Ierasia,Tzouras, Nikolaos V.,Nikitas, Nikolaos F.,Pefkianakis, Eleftherios K.,Vougioukalakis, Georgios C.,Kokotos, Christoforos G.

supporting information, (2019/05/24)

Photocatalysis is a rapidly evolving area of research in modern organic synthesis. Among the traditional photocatalysts, metal-complexes based on ruthenium or iridium are the most common. Herein, we present the synthesis of two photoactive, ruthenium-based complexes bearing pyridine-quinoline or terpyridine ligands with extended aromatic conjugation. Our complexes were utilized in the atom transfer radical addition (ATRA) of haloalkanes to olefins, using bromoacetonitrile or bromotrichloromethane as the source of the alkyl group. The tailor-made ruthenium-based catalyst bearing the pyridine-quinoline bidentate ligand proved to be the best-performing photocatalyst, among a range of metal complexes and organocatalysts, efficiently catalyzing both reactions. These photocatalytic atom transfer protocols can be expanded into a broad scope of olefins. In both protocols, the photocatalytic reactions led to products in good to excellent isolated yields.

An Atom-Economic and Stereospecific Access to Trisubstituted Olefins through Enyne Cross Metathesis Followed by 1,4-Hydrogenation

Ratsch, Friederike,Schmalz, Hans-Günther

supporting information, p. 785 - 792 (2018/01/27)

The combination of intermolecular enyne cross metathesis and subsequent 1,4-hydrogenation opens a stereocontrolled and atom-economic access to trisubstituted olefins. By investigating different combinations of functionalized alkyne and alkene substrates, we found that the outcome (yield, E / Z ratio) of the Grubbs II-catalyzed enyne cross-metathesis step depends on the substrate's structure, the amount of the alkene (used in excess), and the (optional) presence of ethylene. In any case, the 1,4-hydrogenation, catalyzed by 1,2-dimethoxybenzene-Cr(CO) 3, proceeds stereospecifically to yield exclusively the E -products from both the E- and Z- 1,3-diene intermediates obtained by metathesis. A rather broad scope and functional group compatibility of the method is demonstrated by means of 15 examples.

The Goldilocks Principle in Phase Labeling. Minimalist and Orthogonal Phase Tagging for Chromatography-Free Mitsunobu Reaction

Szigeti, Mariann,Dobi, Zoltán,Soós, Tibor

, p. 2869 - 2874 (2018/03/09)

An inexpensive and chromatography-free Mitsunobu methodology has been developed using low molecular weight and orthogonally phase-tagged reagents, a tert-butyl-tagged highly apolar phosphine, and a water-soluble DIAD analogue. The byproduct of the Mitsunobu reactions can be removed by sequential liquid-liquid extractions using traditional solvents such as hexanes, MeOH, water, and EtOAc. Owing to the orthogonal phase labeling, the spent reagents can be regenerated. This new variant of the Mitsunobu reaction promises to provide an alternative and complementary solution for the well-known separation problem of the Mitsunobu reaction without having to resort to expensive, large molecular weight reagents and chromatography.

Metal-Free Decarboxylative Trichlorination of Alkynyl Carboxylic Acids: Synthesis of Trichloromethyl Ketones

Jayaraman, Aravindan,Cho, Eunjeong,Irudayanathan, Francis Mariaraj,Kim, Jimin,Lee, Sunwoo

, p. 130 - 141 (2017/12/26)

2,2,2-Trichloroacetophenone derivatives were synthesized via decarboxylative trichlorination from arylpropiolic acids and trichloroisocyanuric acid (TCCA). The reaction was performed in the presence of water at room temperature, and the desired products were obtained in good yields. The reaction showed good functional group tolerance towards halide, cyano, nitro, ketone, ester and aldehyde groups. In addition, the 2,2,2-trichloroacetophenone derivatives were readily transformed into esters, amides, and hydrazides. Based on experiments with H218O (water-18O), we proposed a cationic reaction pathway as the mechanism and suggested two different pathways for producing aryl- and alkyl-substituted propiolic acids. (Figure presented.).

Synthesis of Esters by Functionalisation of CO2

-

Paragraph 0135, (2017/09/06)

The invention relates to a method for (I) producing a carboxylic ester of formula (I). Said method comprises the steps of: a) bringing an organosilane/borane of formula Si or B into contact with CO2, in the presence of a catalyst and an electrophilic compound of formula (III), the groups R1, R2, R3, R4, R5, Y, and M′ being as defined in claim 1; and optionally b) recovering the compound of formula (I) produced.

Synthesis and biological evaluation of 2-alkoxycarbonylallyl esters as potential anticancer agents

Ronayne, Conor T.,Solano, Lucas N.,Nelson, Grady L.,Lueth, Erica A.,Hubbard, Skyler L.,Schumacher, Tanner J.,Gardner, Zachary S.,Jonnalagadda, Sravan K.,Gurrapu, Shirisha,Holy, Jon,Mereddy, Venkatram R.

supporting information, p. 776 - 780 (2017/02/18)

The reaction of carboxylic acids with Baylis-Hillman reaction derived α-bromomethyl acrylic esters readily provide 2-(alkoxycarbonyl)allyl esters in good to excellent yields. These functionalized allyl esters have been evaluated for their cell proliferation inhibition properties against breast cancer (MDA-MB-231 and 4T1) and pancreatic cancer (MIAPaCa-2) cell lines to explore their potential as anticancer agents. Several of the synthesized derivatives exhibit good potency against all three cancer cell lines. Our structure activity relationship (SAR) studies on 2-carboxycarbonyl allyl esters indicate that substituted aromatic carboxylic acids provide enhanced activity compared to substituted aliphatic carboxylic acid analogs. Di- and tri-allyl esters derived from di-and tri-carboxylic acids exhibit higher inhibition of cell proliferation than mono esters. Further SAR studies indicate that the double bond in the 2-(alkoxycarbonyl)allyl ester is required for its activity, and there is no increase in activity with increased chain length of the alkoxy group. Two lead candidate compounds have been identified from the cell proliferation inhibition studies and their preliminary mechanism of action as DNA damaging agents has been evaluated using epifluorescence and western blot analysis. One of the lead compounds has been further evaluated for its systemic toxicity in healthy CD-1 mice followed by anticancer efficacy in a triple negative breast cancer MDA-MB-231 xenograft model in NOD-SCID mice. These two in vivo studies indicate that the lead compound is well tolerated in healthy CD-1 mice and exhibits good tumor growth inhibition compared to breast cancer drug doxorubicin.

Environmental Polymer Degradation: Using the Distonic Radical Ion Approach to Study the Gas-Phase Reactions of Model Polyester Radicals

Taggert, Bethany I.,O'Hair, Richard A. J.,Wille, Uta

, p. 5290 - 5300 (2017/07/28)

A novel precursor to the distonic O- and C-centered radical cations Oxo+O? and Oxo+C? was designed and synthesized, which represents model systems for radicals produced during polyester degradation. The precursor is equipped with a nitrate functional group, which serves as a masked site for these alkoxyl and carbon radicals that are unleashed through collision-induced dissociation (CID). Oxo+O? and Oxo+C? feature a cyclic carboxonium ion as permanent charge tag to enable monitoring their ion-molecule reactions on the millisecond to second time scale in the ion trap of the mass spectrometer. The reactions of Oxo+O? and Oxo+C? with cyclohexene, cyclohexadiene, ethyl acetate, 1,1-dimethoxyethane, and 1,2-dimethoxyethane, which exhibit structural features present in both intact and defective polyesters, were explored through product and kinetic studies to identify "hot spots" for radical-induced damage in polyesters. All reactions with Oxo+O? were extremely fast and proceeded predominantly through HAT. Oxo+C? was about two orders of magnitude less reactive and did not noticeably damage aliphatic ester moieties through hydrogen abstraction on the time scale of our experiments. Radical addition to alkene π systems was identified as an important pathway for C-radicals, which needs to be included in polymer degradation mechanisms.

Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols

Chen, Zhengwang,Wen, Yuelu,Fu, Yejuan,Chen, Hai,Ye, Min,Luo, Guotian

supporting information, p. 981 - 985 (2017/05/05)

Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro-ethane solvent with good catalytic activity.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 583-04-0