645-59-0 Usage
Chemical Properties
clear colorless to light yellow liquid
Uses
Different sources of media describe the Uses of 645-59-0 differently. You can refer to the following data:
1. A glucosinolate enzymic hydrolosis product with potential antibacterial activities against plant pathogenic bacteria
2. 3-Phenylpropionitrile was used to study the free enzyme activity of nitrilase AtNIT1.
Definition
ChEBI: A nitrile that is propionitrile in which one of the methyl hydrogens has been replaced by a phenyl group.
Preparation
To a stirred solution of 3-phenylpropanamide (50 mg, 0.34 mmol) in acetonitrile (0.8 mL) at room temperature were successively added formic acid (0.2 mL) and paraformaldehyde (50 mg, 1.67 mmol). The reaction mixture was then refluxed for 12 h, and the solution obtained was cooled to room temperature. Work-up A: The crude mixture was concentrated under reduced pressure, and the residue was subjected to flash chromatography on silica gel (230–240 mesh) eluting with hexane/ethyl acetate (7:3) to yield 3-phenylpropanonitrile (37 mg, 85%). Work-up B: The reaction mixture was diluted with ethyl acetate (10 mL) and washed successively with saturated sodium hydrogen carbonate solution (5 mL) and water (5 mL). The combined aqueous layers were extracted with ethyl acetate (2 × 10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude 3-phenylpropanonitrile was purified as described above (Work-up A).
Synthesis Reference(s)
Journal of the American Chemical Society, 98, p. 4685, 1976 DOI: 10.1021/ja00431a078Chemical and Pharmaceutical Bulletin, 10, p. 427, 1962 DOI: 10.1248/cpb.10.427
General Description
The effect of 3-Phenylpropionitrile on the growth and survival of woodlouse Porcellio scaber has been studied.
Check Digit Verification of cas no
The CAS Registry Mumber 645-59-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 645-59:
(5*6)+(4*4)+(3*5)+(2*5)+(1*9)=80
80 % 10 = 0
So 645-59-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H9N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7H2
645-59-0Relevant articles and documents
A Study of the Sodium Borohydride Reduction of α,β-Acetylenic vs α,β-Olefinic Nitriles
Kulp, Stuart S.,Szarko, Richard
, p. 5573 - 5574 (1988)
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Enantioselective hydrogenation of diaryl-substituted α,β-unsaturated nitriles
Wabnitz, Tobias C.,Rizzo, Simona,G?tte, Carsten,Buschauer, Armin,Benincori, Tiziana,Reiser, Oliver
, p. 3733 - 3736 (2006)
α,β-Unsaturated nitriles can be hydrogenated with enantioselectivities up to 88% ee using chiral ruthenium-diphenylphosphino bisaryl and bisheteroaryl complexes such as ruthenium(II)-BINAP and ruthenium(II)-BINP. Mechanistic investigations indicate that conversion is accelerated by electron-rich ligands and that an additional coordinative group needs be present in order to promote conversion. The chiral products are useful building blocks for the synthesis of histamine H2 agonists of the arpromidine type.
Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones
Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki
supporting information, p. 3799 - 3802 (2022/04/07)
The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.
A Titanium-Catalyzed Reductive α-Desulfonylation
Kern, Christoph,Selau, Jan,Streuff, Jan
supporting information, p. 6178 - 6182 (2021/03/16)
A titanium(III)-catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α-sulfonyl nitriles, circumventing traditional base-mediated α-alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α-desulfonylation of ketones. In addition, a one-pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst-dependent mechanism involving a homolytic C?S cleavage.
