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  • 23350-58-5 Structure
  • Basic information

    1. Product Name: CROTONAMIDE
    2. Synonyms: CROTONAMIDE;TRANS-2-BUTENAMIDE;2-Butenamide;Aids018362;Aids-018362;But-2-enamide
    3. CAS NO:23350-58-5
    4. Molecular Formula: C4H7NO
    5. Molecular Weight: 85.1
    6. EINECS: N/A
    7. Product Categories: Miscellaneous Reagents
    8. Mol File: 23350-58-5.mol
  • Chemical Properties

    1. Melting Point: 158°C
    2. Boiling Point: 218.7°Cat760mmHg
    3. Flash Point: 86°C
    4. Appearance: /
    5. Density: 0.956g/cm3
    6. Vapor Pressure: 0.124mmHg at 25°C
    7. Refractive Index: 1.456
    8. Storage Temp.: Amber Vial, Refrigerator
    9. Solubility: Methanol (Sparingly)
    10. PKA: 15.78±0.50(Predicted)
    11. Water Solubility: very faint turbidity
    12. Stability: Light Sensitive
    13. CAS DataBase Reference: CROTONAMIDE(CAS DataBase Reference)
    14. NIST Chemistry Reference: CROTONAMIDE(23350-58-5)
    15. EPA Substance Registry System: CROTONAMIDE(23350-58-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39
    4. WGK Germany:
    5. RTECS: GQ0700000
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 23350-58-5(Hazardous Substances Data)

23350-58-5 Usage

Chemical Properties

White Powder

Check Digit Verification of cas no

The CAS Registry Mumber 23350-58-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,3,5 and 0 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 23350-58:
(7*2)+(6*3)+(5*3)+(4*5)+(3*0)+(2*5)+(1*8)=85
85 % 10 = 5
So 23350-58-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H7NO/c1-2-3-4(5)6/h2-3H,1H3,(H2,5,6)/b3-2+

23350-58-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name CROTONAMIDE

1.2 Other means of identification

Product number -
Other names Crotonsaeureamid

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:23350-58-5 SDS

23350-58-5Relevant articles and documents

Total Synthesis of Strychnine

Lee, Geun Seok,Namkoong, Gil,Park, Jisook,Chen, David Y.-K.

, p. 16189 - 16193 (2017)

The total synthesis of the flagship Strychnos indole alkaloid, strychnine, has been accomplished. The developed synthetic sequence features a novel vinylogous 1,4-addition, a challenging iodinium salt mediated silyl enol ether arylation, a palladium-catalyzed Heck reaction, and a streamlined late-stage conversion to strychnine. Furthermore, an application of asymmetric counterion-directed catalysis (ACDC) in the context of target-oriented organic synthesis has been rendered access to an optically active material. The synthetic sequence described herein represents the most concise entry to optically active strychnine to date.

Convenient synthesis of various substituted homotaurines from alk-2-enamides

Nai, Youfeng,Xu, Jiaxi

, p. 1355 - 1365 (2013/08/23)

Various substituted homotaurines (=3-aminopropane-1-sulfonic acids) 6 were readily synthesized in satisfactory to good yields via the Michael addition of thioacetic acid to alk-2-enamides 3 (→4), followed by LiAlH4 reduction (→5) and performic acid oxidation (Scheme 1). The configuration of 'anti'-disubstituted homotaurine 'anti'-6h was deduced from the 3-(acetylthio)alkanamide (=S-(3-amino-1,2-dimethyl-3-oxopropyl) ethanethioate)'anti'-4h formed in the Michael addition, which was identified via the Karplus equation analysis, and confirmed by X-ray diffraction analysis. The current route is an efficient method to synthesize diverse substituted homotaurines, including 1-, 2-, and N-monosubstituted, as well as 1,2-, 1,N-, 2,N-, and N,N-disubstituted homotaurines (Table). Copyright

I2-TEMPO as an efficient oxidizing agent for the one-pot conversion of alcohol to amide using FeCl3 as the catalyst

Das, Rima,Chakraborty, Debashis

experimental part, p. 48 - 53 (2012/08/28)

A high yield one-pot method for the synthesis of amides from alcohols is described. The aldehyde was generated in situ using iodine-TEMPO as oxidizing agent followed by intermediate oxime formation through reaction with NH 2OH?HCl and finally rearrangement of oxime catalyzed by FeCl3.

Bifunctional water activation for catalytic hydration of organonitriles

Daw, Prosenjit,Sinha, Arup,Rahaman, S. M. Wahidur,Dinda, Shrabani,Bera, Jitendra K.

experimental part, p. 3790 - 3797 (2012/06/18)

Treatment of [Rh(COD)(μ-Cl)]2 with excess tBuOK and subsequent addition of 2 equiv of PIN?HBr in THF afforded [Rh(COD)(κC2-PIN)Br] (1) (PIN = 1-isopropyl-3-(5,7-dimethyl-1, 8-naphthyrid-2-yl)imidazol-2-ylidene, COD = 1,5-cyclooctadiene). The X-ray structure of 1 confirms ligand coordination to "Rh(COD)Br" through the carbene carbon featuring an unbound naphthyridine. Compound 1 is shown to be an excellent catalyst for the hydration of a wide variety of organonitriles at ambient temperature, providing the corresponding organoamides. In general, smaller substrates gave higher yields compared with sterically bulky nitriles. A turnover frequency of 20 000 h-1 was achieved for the acrylonitrile. A similar Rh(I) catalyst without the naphthyridine appendage turned out to be inactive. DFT studies are undertaken to gain insight on the hydration mechanism. A 1:1 catalyst-water adduct was identified, which indicates that the naphthyridine group steers the catalytically relevant water molecule to the active metal site via double hydrogen-bonding interactions, providing significant entropic advantage to the hydration process. The calculated transition state (TS) reveals multicomponent cooperativity involving proton movement from the water to the naphthyridine nitrogen and a complementary interaction between the hydroxide and the nitrile carbon. Bifunctional water activation and cooperative proton migration are recognized as the key steps in the catalytic cycle.

FeIII-catalyzed synthesis of primary amides from aldehydes

Gowda, Ravikumar R.,Chakraborty, Debashis

supporting information; experimental part, p. 2226 - 2229 (2011/06/17)

A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl3 in water is described. A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl3 in water is described. Copyright

Efficient nitrile hydration mediated by RuII catalysts in micellar media

Cavarzan, Alessandra,Scarso, Alessandro,Strukul, Giorgio

experimental part, p. 790 - 794 (2010/09/05)

Efficient nitrile hydration to the corresponding amide derivatives is observed in water using poorly soluble [RuCl2(η6- arene)(PR3)] catalysts 1 with the aid of surfactants to ensure substrate and catalyst solubilization, and enabling ligand effect study on catalytic activity. Amide yields of 40 to 95% can be observed with a variety of aromatic and aliphatic nitriles using the optimized catalyst system, [RuCl 2(p-cymene)(PPh2OEt)]/Triton X-114. Catalyst separation and recycling is possible.

Enzymatic nitrile hydrolysis catalyzed by nitrilase ZmNIT2 from maize. An unprecedented β-hydroxy functionality enhanced amide formation

Mukherjee, Chandrani,Zhu, Dunming,Biehl, Edward R.,Parmar, Rajiv R.,Hua, Ling

, p. 6150 - 6154 (2007/10/03)

To explore the synthetic potential of nitrilase ZmNIT2 from maize, the substrate specificity of this nitrilase was studied with a diverse collection of nitriles. The nitrilase ZmNIT2 showed high activity for all the tested nitriles except benzonitrile, producing both acids and amides. For the hydrolysis of aliphatic, aromatic nitriles, phenylacetonitrile derivatives and dinitriles, carboxylic acids were the major products. Unexpectedly, amides were found to be the major products in nitrilase ZmNIT2-catalyzed hydrolysis of β-hydroxy nitriles. The hydrogen bonding between the hydroxyl group and nitrogen in the enzyme-substrate complex intermediates that disfavors the loss of ammonia and formation of acyl-enzyme intermediate, which was further hydrolyzed to acid, was proposed to be responsible for the unprecedented β-hydroxy functionality assisted high yield of amide formation.

Niobium pentachloride promoted conversion of carboxylic acids to carboxamides: Synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures

Nery, Marcelo S.,Ribeiro, Renata P.,Lopes, Claudio C.,Lopes, Rosangela S. C.

, p. 272 - 276 (2007/10/03)

A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.

Synthesis and Reactions of Iodo Lactams

Knapp, Spencer,Levorse, Anthony T.

, p. 4006 - 4014 (2007/10/02)

The synthesis of a series of iodo lactams has been achieved by a new cyclization method that depends on generating N,O-bis(trimethylsilyl)imidate derivatives as intermediates.Treatment of an unsaturated amide with trimethylsilyl triflate in pentane and then iodine in tetrahydrofuran gives the iodo lactam.Some reactions of this new difunctional group with bases, nucleophiles, and Michael acceptors leading to functionalized or elaborated lactams are presented.In general, iodo lactams undergo direct SN2 reactions with reactive (but weakly basic) nucleophiles like azide and triphenylphosphine and elimination or decomposition in the presence of bases or basic nucleophiles.Sodium hydride may be used to generate an N-acylaziridine intermediate, which can be opened with azide to deliver an azido lactam with overall retention of stereochemistry.Silver-assisted solvolysis of iodo lactams gives the hydroxy lactams with retention of configuration, probably also because of participation by the lactam nitrogen.The sodium salt of 5-(iodomethyl)-2-pyrrolidinone (3), generated at -20 deg C, undergoes an annulation reaction with unsaturated esters (but not sulfones), leading to pyrrolizidine derivatives.

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