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2-Propen-1-ol, 3-(2-nitrophenyl)-, also known as 3-(2-nitrophenyl)allyl alcohol or cinnamyl alcohol with a nitro group, is an organic compound characterized by the presence of an allyl alcohol moiety and a nitrophenyl group. This molecule has a molecular formula of C9H9NO3 and a molecular weight of 181.17 g/mol. It is a yellowish liquid with a distinct aromatic odor. The compound is derived from the reaction of cinnamyl alcohol with nitrobenzene, where the nitro group is introduced to the phenyl ring. It is used in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals due to its unique reactivity and functional group presence. The compound is sensitive to light and heat, and it is typically stored in a cool, dark place to maintain its stability.

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  • 1504-65-0 Structure
  • Basic information

    1. Product Name: 2-Propen-1-ol, 3-(2-nitrophenyl)-
    2. Synonyms:
    3. CAS NO:1504-65-0
    4. Molecular Formula: C9H9NO3
    5. Molecular Weight: 179.175
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1504-65-0.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: 2-Propen-1-ol, 3-(2-nitrophenyl)-(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2-Propen-1-ol, 3-(2-nitrophenyl)-(1504-65-0)
    11. EPA Substance Registry System: 2-Propen-1-ol, 3-(2-nitrophenyl)-(1504-65-0)
  • 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: 1504-65-0(Hazardous Substances Data)

1504-65-0 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 1504-65-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,0 and 4 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1504-65:
(6*1)+(5*5)+(4*0)+(3*4)+(2*6)+(1*5)=60
60 % 10 = 0
So 1504-65-0 is a valid CAS Registry Number.

1504-65-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-3-(2-nitrophenyl) prop-2-en-1-ol

1.2 Other means of identification

Product number -
Other names 2-nitrocinnamyl alcohol

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:1504-65-0 SDS

1504-65-0Relevant articles and documents

A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles

Carlson, Angela S.,Liu, En-Chih,Topczewski, Joseph J.

, p. 6044 - 6059 (2020)

Developing reactions to generate complex and modular building blocks in a concise and direct fashion remains a contemporary synthetic challenge. This work describes a stereoselective cascade reaction between allylic azides and acrylates that directly generates tetrahydro-pyrrolo-pyrazole ring systems. These products contain up to four contiguous stereocenters, two of which may be tetrasubstituted carbon atoms attached to a nitrogen atom. Over 30 examples are provided with an average isolated yield of 71% (ranging from 40% to 94%). The reaction was easily scaled to use more than one gram of starting material, and the products can be readily diversified.

Hf-MOF catalyzed Meerwein?Ponndorf?Verley (MPV) reduction reaction: Insight into reaction mechanism

Lin, Yamei,Bu, Qingxia,Xu, Jiaxian,Liu, Xiao,Zhang, Xueping,Lu, Guo-Ping,Zhou, Baojing

, (2021/01/25)

Hf-MOF-808 exhibits excellent activity and specific selectivity on the hydrogenation of carbonyl compounds via a hydrogen transfer strategy. Its superior activity than other Hf-MOFs is attributed to its poor crystallinity, defects and large specific surface area, thereby containing more Lewis acid-base sites which promote this reaction. Density functional theory (DFT) computations are performed to explore the catalytic mechanism. The results indicate that alcohol and ketone fill the defects of Hf-MOF to form a six-membered ring transition state (TS) complex, in which Hf as the center of Lewis stearic acid coordinates with the oxygen of the substrate molecule, thus effectively promoting hydrogen transfer process. Other reactive groups, such as –NO2, C = C, -CN, of inadequate hardness or large steric hindrance are difficult to coordinate with Hf, thus weakening their catalytic effect, which explains the specific selectivity Hf-MOF-808 for reducing the carbonyl group.

Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates

Ahmed Fouad, Manar,Ferretti, Francesco,Formenti, Dario,Milani, Fabio,Ragaini, Fabio

supporting information, p. 4876 - 4894 (2021/09/20)

Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.

Regio- And diastereoselective Pd-catalyzed aminochlorocyclization of allylic carbamates: scope, derivatization, and mechanism

Ariga, Elaine Miho,Carita Correra, Thiago,Matsushima, Jullyane Emi,McIndoe, J. Scott,Moreira Ribeiro, Francisco Wanderson,Omari, Isaac,Papa Spadafora, Bruna,Rodrigues, Alessandro,Soares, Priscila Machado Arruda,Vinhato, Elisangela,de Oliveira-Silva, Diogo

supporting information, p. 5595 - 5606 (2021/07/02)

The regio- and diastereoselective synthesis of oxazolidinonesviaa Pd-catalyzed vicinal C-N/C-Cl bond-forming reaction from internal alkenes of allylic carbamates is reported. The oxazolidinones are obtained in yields of 44 to 95% with high to excellent diastereoselectivities (from 6?:?1 to >20?:?1 dr) from readily available precursors. This process is scalable, and the products are suitable for the synthesis of useful amino alcohols. A detailed theoretical and experimental mechanistic study was carried out to describe that the reaction proceeds through ananti-aminopalladation of the alkene followed by an oxidative C-Pd(ii) cleavage with retention of the carbon stereochemistry to yield the major diastereomer. The role of Cu(ii) in a C-Cl bond-forming mechanism step has also been proposed.

Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion

Hayashi, Yujiro,Koshino, Seitaro,Kwon, Eunsang,Monde, Kenji,Taniguchi, Tohru

supporting information, p. 15786 - 15794 (2021/10/14)

Enantiodivergent one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source. A domino organocatalyst-mediated enantioselective Michael reaction and aldol condensation provided centrally chiral dihydronaphthalenes with excellent enantioselectivity, from which an enantiodivergent chirality conversion from central-to-axial chirality was achieved. Both enantiomers of biaryls were obtained with excellent enantioselectivity. All transformations can be conducted in a single reaction vessel. A plausible reaction mechanism for the enantiodivergence is proposed.

Microwave-heated γ-Alumina Applied to the Reduction of Aldehydes to Alcohols

Dhokale, Bhausaheb,Susarrey-Arce, Arturo,Pekkari, Anna,Runemark, August,Moth-Poulsen, Kasper,Langhammer, Christoph,H?relind, Hanna,Busch, Michael,Vandichel, Matthias,Sundén, Henrik

, p. 6344 - 6355 (2020/10/28)

The development of cheap and robust heterogeneous catalysts for the Meerwein-Ponndorf-Verley (MPV) reduction is desirable due to the difficulties in product isolation and catalyst recovery associated with the traditional use of homogeneous catalysts for MPV. Herein, we show that microwave heated γ-Al2O3 can be used for the reduction of aldehydes to alcohols. The reaction is efficient and has a broad substrates scope (19 entries). The products can be isolated by simple filtration, and the catalyst can be regenerated. With the use of microwave heating, we can direct the heating to the catalyst rather than to the whole reaction medium. Furthermore, DFT was used to study the reaction mechanism, and we can conclude that a dual-site mechanism is operative where the aldehyde and 2-propoxide are situated on two adjacent Al sites during the reduction. Additionally, volcano plots were used to rationalize the reactivity of Al2O3 in comparison to other metal oxides.

Method for synthesizing unsaturated primary alcohol

-

Paragraph 0044-0048, (2019/08/20)

The invention discloses a method for synthesizing an unsaturated primary alcohol. The method comprises the following steps: adding an unsaturated aldehyde, a transition metal catalyst iridium complexand isopropyl alcohol in a reaction container, heating the reaction mixture in an oil bath, carrying out a reaction for a plurality of hours, then carrying out cooling to room temperature, removing the solvent by rotating evaporation, and then carrying out column separation to obtain the target compound. According to the invention, the unsaturated aldehyde is used as a raw material, isopropyl alcohol is used as a hydrogen source and the solvent, and the unsaturated primary alcohol is generated through hydrogen transfer under participation of the transition metal iridium catalyst. The method has the following remarkable advantages: 1) the reaction temperature is low; 2) cheap, safe and non-toxic isopropanol is used; 3) the catalyst usage amount is low, and reaction atom economy is high; and4) selectivity is good. Therefore, the method meets the requirements of green chemistry and has a wide development prospect.

Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity

Li, Baoli,Ni, Shuaishuai,Mao, Fei,Chen, Feifei,Liu, Yifu,Wei, Hanwen,Chen, Wenhua,Zhu, Jin,Lan, Lefu,Li, Jian

, p. 224 - 250 (2018/02/10)

CrtN has been identified as an attractive and druggable target for treating pigmented Staphylococcus aureus infections. More than 100 new compounds were synthesized, which target the overwhelming the defects of the CrtN inhibitor 1. Analogues 23a and 23b demonstrated a significant activity against pigmented S. aureus Newman and 13 MRSA strains (IC50 = 0.02-10.5 nM), along with lower hERG inhibition (IC50 > 30 μM, ~10-fold decrease in comparison with 1). Furthermore, 23a and 23b were confirmed to reduce the staphylococcal load in the kidney and heart in a mouse model with normal treatment deeper than pretreatment ones, comparable even with vancomycin and linezolid. Remarkably, 23a could strongly block the pigment biosynthesis of these nine multidrug-resistant MRSA strains, including excellent activity against LRSA strains and VISA strains in vivo, and all of which demonstrated that 23a has a huge potential against intractable MRSA, VISA, and LRSA issues as a therapeutic drug.

Novel Staphyloxanthin Inhibitors with Improved Potency against Multidrug Resistant Staphylococcus aureus

Ni, Shuaishuai,Li, Baoli,Chen, Feifei,Wei, Hanwen,Mao, Fei,Liu, Yifu,Xu, Yixiang,Qiu, Xiaoxi,Li, Xiaokang,Liu, Wenwen,Hu, Linghao,Ling, Dazheng,Wang, Manjiong,Zheng, Xinyu,Zhu, Jin,Lan, Lefu,Li, Jian

supporting information, p. 233 - 237 (2018/03/21)

Diapophytoene desaturase (CrtN) is a potential novel target for intervening in the biosynthesis of the virulence factor staphyloxanthin. In this study, 38 1,4-benzodioxan-derived CrtN inhibitors were designed and synthesized to overwhelm the defects of leading compound 4a. Derivative 47 displayed superior pigment inhibitory activity, better hERG inhibitory properties and water solubility, and significantly sensitized MRSA strains to immune clearance in vitro. Notably, 47 displayed excellent efficacy against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate MRSA, VISA), and NRS271 (linezolid-resistant MRSA, LRSA) comparable to that of linezolid and vancomycin in vivo.

Transfer Hydrogenation of Aldehydes and Ketones with Isopropanol under Neutral Conditions Catalyzed by a Metal-Ligand Bifunctional Catalyst [Cp?Ir(2,2′-bpyO)(H2O)]

Wang, Rongzhou,Tang, Yawen,Xu, Meng,Meng, Chong,Li, Feng

, p. 2274 - 2281 (2018/02/23)

A Cp?Ir complex bearing a functional bipyridonate ligand [Cp?Ir(2,2′-bpyO)(H2O)] was found to be a highly efficient and general catalyst for transfer hydrogenation of aldehydes and chemoselective transfer hydrogenation of unsaturated aldehydes with isopropanol under neutral conditions. It was noteworthy that many readily reducible or labile functional groups such as nitro, cyano, ester, and halide did not undergo any change under the reaction conditions. Furthermore, this catalytic system exhibited high activity for transfer hydrogenation of ketones with isopropanol. Notably, this research exhibited new potential of metal-ligand bifunctional catalysts for transfer hydrogenation.

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