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Benzenepropanamide, N-2-propenyl-, also known as allylbenzenepropanamide, is an organic compound with the chemical formula C12H15NO. It is a derivative of benzenepropanamide, where a propenyl (allyl) group replaces the hydrogen atom on the nitrogen atom. Benzenepropanamide, N-2-propenyl- is characterized by its aromatic benzene ring and an amide functional group, which is connected to a propenyl side chain. It is used in various chemical and pharmaceutical applications, such as the synthesis of drugs and other organic compounds. Due to its unique structure, it exhibits specific chemical properties and reactivity, making it an important intermediate in the synthesis of various molecules.

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  • 133055-17-1 Structure
  • Basic information

    1. Product Name: Benzenepropanamide, N-2-propenyl-
    2. Synonyms: N-allyl-3-phenylpropanamide;
    3. CAS NO:133055-17-1
    4. Molecular Formula: C12H15NO
    5. Molecular Weight: 189.257
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 133055-17-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: Benzenepropanamide, N-2-propenyl-(CAS DataBase Reference)
    10. NIST Chemistry Reference: Benzenepropanamide, N-2-propenyl-(133055-17-1)
    11. EPA Substance Registry System: Benzenepropanamide, N-2-propenyl-(133055-17-1)
  • 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: 133055-17-1(Hazardous Substances Data)

133055-17-1 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 133055-17-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,3,0,5 and 5 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 133055-17:
(8*1)+(7*3)+(6*3)+(5*0)+(4*5)+(3*5)+(2*1)+(1*7)=91
91 % 10 = 1
So 133055-17-1 is a valid CAS Registry Number.

133055-17-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(prop-2-enyl)-3-phenylpropanamide

1.2 Other means of identification

Product number -
Other names N-allyl-3-phenylpropanamide

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:133055-17-1 SDS

133055-17-1Relevant articles and documents

Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids

Choudhary, Shivani,Hamann, Henry J.,Ramachandran, P. Veeraraghavan

supporting information, (2020/11/13)

Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.

A Hydroperoxide-Mediated Decarboxylation of α-Ketoacids Enables the Chemoselective Acylation of Amines

Nanjo, Takeshi,Kato, Natsuki,Zhang, Xuan,Takemoto, Yoshiji

supporting information, p. 15504 - 15507 (2019/11/14)

Strategies for the formation of amide bonds, that is, one of the most basic and important transformations in organic synthesis, have so far focused predominantly on dehydration reactions. Herein, we report and demonstrate the practical utility of a novel decarboxylative amidation of α-ketoacids by using inexpensive tert-butyl hydroperoxide (TBHP), which is characterized by high yields, a broad substrate scope, mild reaction conditions, and a unique chemoselectivity. These features enable the synthesis of peptides from amino acid derived α-ketoacids under preservation of the stereochemical information.

Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides

Guissart, Céline,Barros, Andre,Rosa Barata, Luis,Evano, Gwilherm

supporting information, p. 5098 - 5102 (2018/09/13)

An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.

Nickel/Photoredox-Catalyzed Amidation via Alkylsilicates and Isocyanates

Zheng, Shuai,Primer, David N.,Molander, Gary A.

, p. 7957 - 7961 (2017/11/10)

A nickel/photoredox, dual-catalyzed amidation reaction between alkylsilicate reagents and alkyl/aryl isocyanates is reported. In contrast to the previously reported reductive coupling process, this protocol is characterized by mild reaction conditions and the absence of a stoichiometric reductant. A mechanistic hypothesis involving a nickel-isocyanate adduct is proposed based on literature precedent and further validation by experimental results.

Pd(II)-Catalyzed, Picolinamide-Assisted, Z-Selective γ-Arylation of Allylamines to Construct Z-Cinnamylamines

Parella, Ramarao,Babu, Srinivasarao Arulananda

, p. 6550 - 6567 (2017/07/15)

Investigations of Pd(II)-catalyzed, picolinamide-assisted, γ-C(sp2)-H activation and Z-selective arylation of allylamines are reported. The reactions of N-allylpicolinamides with various aryl iodides in the presence of the catalyst Pd(OAc)2 and additive AgOAc have led to the selective γ-arylation of allylamines to construct various cinnamylamines with moderate to good yields and good to high E/Z ratios. To obtain good E/Z ratios, the Pd(II)-catalyzed arylation reaction of N-allylpicolinamides was probed using different additives, directing groups, and reaction conditions. The Pd(II)-catalyzed arylation of an allylamine containing both γ-C(sp2)-H and γ-C(sp3)-H bonds afforded moderate yields of the γ-C(sp2)-H and γ-C(sp3)-H bisarylated cinnamylamines. Although Heck-type γ-arylations of allylamines have generally afforded the E-cinnamylamines, the bidentate directing group picolinamide-directed arylations of allylamines were found to be Z-selective. A plausible mechanism was proposed for the observed regioselectivity and Z-selective arylation of N-allylpicolinamides. Additionally, the Pd(II)-catalyzed arylation of an N-allyl-5-methylisoxazole-3-carboxamide afforded the E-cinnamylamines plausibly via a ligand-free Heck-type reaction mechanism.

One-Pot Amide Bond Formation from Aldehydes and Amines via a Photoorganocatalytic Activation of Aldehydes

Papadopoulos, Giorgos N.,Kokotos, Christoforos G.

, p. 7023 - 7028 (2016/08/30)

A mild, one-pot, and environmentally friendly synthesis of amides from aldehydes and amines is described. Initially, a photoorganocatalytic reaction of aldehydes with di-isopropyl azodicarboxylate leads to an intermediate carbonyl imide, which can react with a variety of amines to afford the desired amides. The initial visible light-mediated activation of a variety of monosubstituted or disubstituted aldehydes is usually fast, occurring in a few hours. Following the photocatalytic reaction, addition of the primary amine at room temperature or the secondary amine at elevated temperatures leads to the corresponding amide from moderate to excellent yields without epimerization. This methodology was applied in the synthesis of Moclobemide, a drug against depression and social anxiety.

TEMPO-Catalyzed Oxidative Amidation of Alcohols via Hexafluoroisopropyl Esters

Vatèle, Jean-Michel

, p. 2280 - 2284 (2015/09/28)

Stepwise oxidative amidation of alcohols using trichloroisocyanuric acid, a catalytic amount of TEMPO in combination with pyridine and hexafluoroisopropyl (HFIP) alcohol followed by amines is described. This procedure used HFIP esters as activating esters which were found to be very efficient acylating agents for amide bond formation. This process is compatible with a number of functional groups and acid-sensitive protecting groups.

Direct amidation from alcohols and amines through a tandem oxidation process catalyzed by heterogeneous-polymer-incarcerated gold nanoparticles under aerobic conditions

Soule, Jean-Francois,Miyamura, Hiroyuki,Kobayashi, Shu

supporting information, p. 2614 - 2626 (2013/11/19)

We describe herein a highly elegant and suitable synthesis of amide products from alcohols and amines through a tandem oxidation process that uses molecular oxygen as a terminal oxidant. Carbon-black-stabilized polymer-incarcerated gold (PICB-Au) or gold/cobalt (PICB-Au/Co) nanoparticles were employed as an efficient heterogeneous catalyst depending on alcohol reactivity and generated only water as the major co-product of the reaction. A wide scope of substrate applicability was shown with 42 examples. The catalysts could be recovered and reused without loss of activity by using a simple operation. Gold standard: A highly efficient green method for amide synthesis from alcohols and amines catalyzed by gold nanoparticles stabilized by styrene-based copolymers has been developed (see scheme). Two catalysts have been used with high selectivity depending on the combination of substrates. These Au nanoparticle catalysts can be recovered and reused several times by simple operations. Copyright

Semisynthetic cyclopamine analogues as potent and orally bioavailable hedgehog pathway antagonists

Tremblay, Martin R.,Nevalainen, Marta,Nair, Somarajan J.,Porter, James R.,Castro, Alfredo C.,Behnke, Mark L.,Yu, Lin-Chen,Hagel, Margit,White, Kerry,Faia, Kerrie,Grenier, Louis,Campbell, Matthew J.,Cushing, Jill,Woodward, Caroline N.,Hoyt, Jennifer,Foley, Michael A.,Read, Margaret A.,Sydor, Jens R.,Tong, Jeffrey K.,Palombella, Vito J.,McGovern, Karen,Adams, Julian

supporting information; experimental part, p. 6646 - 6649 (2009/11/30)

Herein is reported the synthesis of a novel class of hedgehog antagonists derived from cyclopamine. The acid sensitive D-ring of cyclopamine was homologated utilizing a sequence of chemoselective cyclopropanation and stereoselective acid-catalyzed rearran

CYCLOPAMINE ANALOGUES AND METHODS OF USE THEREOF

-

Page/Page column 61-62, (2010/10/20)

The present invention provides compositions and methods for modulating smoothened-dependent pathway activation. The present invention provides analogs of cyclopamine that can be used to counteract the phenotypic effects of unwanted activation of a hedgeho

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