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17190-29-3

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17190-29-3 Usage

Description

3-Hydroxy-3-phenylpropionitrile, also known as 3-Phenyl-3-hydroxypropanenitrile (CAS# 17190-29-3), is a β-hydroxynitrile compound that belongs to the class of aryl substituted α-aminophenylacetonitriles. It is synthesized through an asymmetric 1,2-addition reaction by reacting lithioacetonitrile with benzaldehyde. This organic compound is characterized by its unique chemical structure and properties, making it a versatile molecule for various applications in the field of organic synthesis.

Uses

Used in Organic Synthesis:
3-Hydroxy-3-phenylpropionitrile is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block for the development of new molecules with potential applications in pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Hydroxy-3-phenylpropionitrile is used as a starting material for the synthesis of various drug candidates. Its reactivity and structural diversity enable the development of novel therapeutic agents with improved pharmacological properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Flavor and Fragrance Industry:
3-Hydroxy-3-phenylpropionitrile is also used in the flavor and fragrance industry, where it contributes to the characteristic aroma of certain essential oils, such as Orange Oil. Its unique scent profile makes it a valuable component in the creation of various perfumes, colognes, and other fragrance products.
Used in Chemical Research:
In the field of chemical research, 3-Hydroxy-3-phenylpropionitrile serves as a model compound for studying various reaction mechanisms and exploring new synthetic methodologies. Its reactivity and structural features provide valuable insights into the behavior of similar molecules, leading to a better understanding of organic chemistry and the development of innovative synthetic strategies.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 366, 1983 DOI: 10.1021/jo00151a017Synthetic Communications, 24, p. 1433, 1994 DOI: 10.1080/00397919408011747Tetrahedron Letters, 26, p. 155, 1985 DOI: 10.1016/S0040-4039(00)61867-1

Check Digit Verification of cas no

The CAS Registry Mumber 17190-29-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,1,9 and 0 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 17190-29:
(7*1)+(6*7)+(5*1)+(4*9)+(3*0)+(2*2)+(1*9)=103
103 % 10 = 3
So 17190-29-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9,11H,6H2

17190-29-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-hydroxy-3-phenylpropanenitrile

1.2 Other means of identification

Product number -
Other names 3-phenyl-3-hydroxypropanecarbonitrile

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:17190-29-3 SDS

17190-29-3Relevant articles and documents

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.

Cellulosic CuI Nanoparticles as a Heterogeneous, Recyclable Catalyst for the Borylation of α,β-Unsaturated Acceptors in Aqueous Media

Zhou, Lijie,Han, Biao,Zhang, Yaoyao,Li, Bojie,Wang, Liansheng,Wang, Jianying,Wang, Xianbao,Zhu, Lei

, p. 3220 - 3229 (2021/03/06)

Abstract: We have demonstrated that cellulosic CuI nanoparticles could perform as an efficient heterogeneous catalyst for the synthesis of useful organoboron compounds. Desired β-borylation products were all obtained in good to excellent yields under mild

Reaction of electrogenerated cyanomethyl anion with cyclohexylisocyanate: Synthesis of N-(cyclohexylcarbamoyl) acetamide. An unexpected product

Bortolami, Martina,Feroci, Marta,Pandolfi, Fabiana,Petrucci, Rita,Rocco, Daniele,Scarano, Vincenzo,Zollo, Giuseppe

, (2020/10/21)

The contamination with water of the cathodic ACN-Et4NBF4 solution gave us the opportunity to investigate alkyl isocyanate reactivity toward electrogenerated anions. The cathodic reduction of a ACN-Et4NBF4 solution led to the formation of both hydroxide and cyanomethyl anions. The reaction of the catholyte with cyclohexylisocyanate led to the exclusive formation of acetamidated product, with no traces of cyanomethylated one. On the contrary, when reacting with benzaldehyde only the cyanomethylated was isolated. Considering that the acetamidated product of benzaldehyde is reported to be unstable (thus its formation cannot be excluded), various experiments were carried out in order to understand the anomalous reactivity of cyclohexylisocyanate. Moreover, computational analysis allowed to state the higher stability of acetamidated product with respect to the cyanomethylated one. The possibility of a concerted reaction, instead of acetamide anion formation prior to the reaction, is still an open question.

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