2856-63-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorobenzyl cyanide is used as a key intermediate in the synthesis of clopidogrel, a potent platelet aggregation inhibitor. It plays a crucial role in the development of this medication, which is widely prescribed for the prevention of blood clots and the treatment of conditions such as atherosclerosis, recent heart attack, and stroke.
Additionally, due to its unique chemical structure, 2-Chlorobenzyl cyanide can be further utilized in the synthesis of other pharmaceutical compounds, contributing to the development of new drugs and therapies in the healthcare sector.
Used in Agrochemical Industry:
2-Chlorobenzyl cyanide also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various pesticides and insecticides. Its chemical properties make it a valuable component in the development of these products, which are essential for protecting crops and ensuring food security.

InChI:InChI=1/C8H6ClN/c9-8-4-2-1-3-7(8)5-6-10/h1-4H,5H2

Upstream product

• 143-33-9 sodium cyanide 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 151-50-8 potassium cyanide 
• 694-80-4 2-bromo-1-chlorobenzene 
• 17729-59-8 tri-n-butyl(cyanomethyl)stannane 
• 1058649-16-3 2-chloro-1-[(ethoxymethoxy)methyl]benzene 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 1058649-12-9 2-chloro-1-(methoxymethoxy)methyl benzene 
• 773837-37-9 sodium cyanide 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 28321-11-1 1-chloro-2-(2,2-difluorovinyl)benzene 
• 13078-80-3 2-(2-chlorophenyl)ethanamine 
• 7282-58-8 3-(2-chloro-phenyl)-2-thioxo-propionic acid 
• 139109-52-7 3-(2-chloro-phenyl)-2-hydroxyimino-propionic acid 

Downstream Products

• 123517-65-7 (2-chloro-phenyl)-[2]pyridyl-acetonitrile 
• 69849-08-7 2-(2-chlorophenyl)-2-methylpropanenitrile 
• 79101-70-5 1-chloro-2-(nitromethyl)benzene 
• 40061-54-9 2-chlorophenylacetic acid ethyl ester 
• 2444-36-2 2'-chloro-benzeneacetic acid 
• 10268-06-1 2-(2-chlorophenyl)acetamide 
• 673476-96-5 (2-chloro-phenyl)-thioacetic acid amide 
• 21742-26-7 (2-chloro-phenyl)-hydroxyimino-acetonitrile 
• 56239-12-4 5-(2-chloro-phenyl)-pyrimidin-4-ylamine 
• 77186-48-2 2-(2-chloro-phenyl)-acetoacetonitrile 
• 113133-93-0 1,1,1-trichloro-2,2-bis-[2-(2-chloro-phenyl)-acetylamino]-ethane 
• 73775-50-5 2-(4-chloro-phenyl)-4-dimethylamino-butyronitrile 
• 14208-28-7 4-(2-chloro-phenyl)-isothiazolidine-3,5-dithione 
• 68429-15-2 2-(2-Chloro-phenyl)-5-methyl-cyclohexane-1,3-dione 

Relevant academic research and scientific papers

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Concentrated Aqueous Sodium Tosylate as Green Medium for Alkene Oxidation and Nucleophilic Substitution Reactions

A hydrotropic solution of highly concentrated sodium tosylate (NaOTs) can be used as a recyclable medium for the environmentally benign oxidation of conjugated alkenes with H2O2. Both uncatalyzed and metal-catalyzed reactions provided the corresponding oxidation products in higher yields than in pure water or many common organic solvents.

Ionic liquid-induced conversion of methoxymethyl-protected alcohols into nitriles and iodides using [Hmim][NO3]

This Letter reports a one-pot efficient conversion of methoxymethyl-ethers into their corresponding nitriles and iodides using the ionic liquid, 1-methyl-3H-imidazolium nitrate ([Hmim][NO3]) under microwave irradiation. A variety of products were prepared in high yields using this method.

Oxidant-free conversion of primary amines to nitriles

An amide-derived NNN-Ru(II) hydride complex catalyzes oxidant-free, acceptorless, and chemoselective dehydrogenation of primary and secondary amines to the corresponding nitriles and imines with liberation of dihydrogen. The catalyst system tolerates oxidizable functionality and is selective for the dehydrogenation of primary amines (-CH2NH2) in the presence of amines without α-CH hydrogens.

Pd-catalyzed cyanation of benzyl chlorides with nontoxic K 4[Fe(CN)6]

Non-toxic K4[Fe(CN)6] was demonstrated to be effective as a green cyanating agent for the cyanation of alkyl halides using PPh3/Pd(OAc)2 as a catalyst system. The presented method allowed a series of benzyl chlorides to be smoothly cyanated in up to 88% yield. In order to avoid or suppress the deactivation of the catalyst, the reaction was required to be performed in a stringent inert ambiance.

Microwave-promoted, one-pot conversion of alkoxymethylated protected alcohols into their corresponding nitriles, bromides, and iodides using [bmim][InCl4] as a green catalyst

The Lewis acid room temperature ionic liquid, [bmim][InCl4], was found to be an efficient and green catalyst for the highly chemoselective and one-pot conversion of MOM- or EOM-ethers into their corresponding nitriles, bromides, and iodides under microwave irradiation. The procedures are simple, rapid, and high yielding. The catalyst exhibited a remarkable reactivity and is reusable.

On rearrangements by cyclialkylations of arylpentanols to 2,3-dihydro-1H-indene derivatives. Part 5. The acid-catalyzed cyclialkylation of 2-(2-chlorophenyl)-2,4-dimethylpentan-3-ol

The mechanism proposed in [1] to explain the surprising result of the cyclialkylation of 4-(2-chlorophenyl)- 2,4-dimethylpentan-2-ol (3, R = Me), which gives not only the 'normal' product, i.e., the 4-chloro-2,3-dihydro-1,1,3,3-tetramethyl- (4), but also the isomer trans-4-chloro-2,3-dihydro-1,1,2,3-tetramethyl-1H-inden (5), could be differentiated in two sections (cf. Scheme 2): the first from 3 to the intermediary ion IIa?IIb, and the second from the latter ions to the final product 5. For the first section, a sufficiently satisfactory explanation has been given in [1]; the second section has received important support from the mechanisms of the cyclialkylation of 2,4-dimethyl-2-phenylpentan-3-ol (6), the precursor of II′a, the ion IIa without the o-Cl substituent (cf. Schemes 2, 3 and 5 and [4]). The present communication gives an explanation of the influence of the o-Cl substituent: a mechanism is proposed for the very complex cyclialkylation of 2-(2-chlorophenyl)-2,4-dimethylpentan-3-ol (11; cf. Scheme 9). Both mechanism may be considered as definitive. It is very surprising that, by the cyclialkylation of the compounds 1, 3, 8, 11, 15, and 17, only compound 1 gives the 'normal' product: the cyclialkylation of all other phenylpentanols follows complex pathways including Et, i-Pr, and Ph migrations, which could not be expected. In addition, it has been established that the transformation of 21 to 22 (cf. Scheme 12) and that of 23 to 24 (cf. Scheme 13) occur through two consecutive 1,2- and not through a single 1,3-hydride migration or through an elimination-addition process (cf. Scheme 13). It can be assumed that the transformation of ion IV (the 2-(2-chlorophenyl)-3,4-dimethylpent-2-ylium ion) to the ion V (the 4-(2-chlorophenyl)-3,4-dimethylpent-2-ylium ion (both shown in Scheme 9 as D-isomers) occurs through the same pathway.

Degradation of 3-aryl-2-hydroxyiminopropionic acids into arylacetonitriles using 1,1'-carbonyldiimidazole or 2,2'-oxalyldi(o-sulfobenzimide)

1,1'-Carbonyldiimidazole (1) is a useful reagent for the preparation of arylacetonitriles (9) from 3-aryl-2-hydroxyiminopropionic acids (8), and 2,2'-oxalyldi (o-sulfobenzimide) (2) can also be used for this purpose under essentially neutral conditions.

Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents

A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: STR1 wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R1 and R2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.

PALLADIUM CATALYZED REACTION OF ARYL BROMIDES WITH CYANOMETHYLTRIBUTYLTIN. AROMATIC CYANOMETHYLATION

Palladium catalyzed reaction of aryl bromides with cyanomethyltributyltin gave arylacetonitriles in moderate yields.Aryl bromides having strong electron-withdrawing groups (such as acyl, cyano, nitro, etc.) cannot be applied to the reaction.