20850-49-1

Basic information

• Product Name: 3-Methyl-2-(3,4-dimethoxyphenyl)butyronitrile
• Synonyms: 2-(3,4-Dimethoxyphenyl)-2-isopropylacetonitrile;BENZENEACETONITRILE,3,4-DIMETHOXY-A-(1-METHYLETHYL)-;α-Isopropyl-3,4-dimethoxybenzeneacetonitrile;2-(3,4-DiMethoxy phenyl)-ó-Methylbutyronitrile;2-(3,4-DiMethoxy phenyl)-d-Methylbutyronitrile;2-(3,4-DiMethoxy phenyl)-β-Methylbutyronitrile;Verapamil Impurity K;3-METHYL-2-(3,4-DIMETHOXYPHENYL)BUTYRONITRILE
• CAS NO: 20850-49-1
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.28
• EINECS: 244-082-8
• Product Categories: (intermediate of rerapamil hcl);Aromatics
• Mol File: 20850-49-1.mol
• Article Data: 23

Chemical Properties

• Melting Point: 46-49°C
• Boiling Point: 327.3 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: Pale yellow solid
• Density: 1.023 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3-Methyl-2-(3,4-dimethoxyphenyl)butyronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-(3,4-dimethoxyphenyl)butyronitrile(20850-49-1)
• EPA Substance Registry System: 3-Methyl-2-(3,4-dimethoxyphenyl)butyronitrile(20850-49-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 20850-49-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

(Verapamil EP Impurity K)

InChI:InChI=1/C13H17NO2/c1-9(2)11(8-14)10-5-6-12(15-3)13(7-10)16-4/h5-7,9,11H,1-4H3

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 75-30-9 2-iodo-propane 
• 1195-98-8 2-methyl-2-phenylpropionitrile 
• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 7677-24-9 trimethylsilyl cyanide 
• 67031-41-8 1-(3,4-dimethoxyphenyl)-2-methylpropan-1-ol 
• 102201-29-6 α-isopropyl-veratryl chloride 
• 92040-70-5 dimethoxyphenyl isopropyl acetonitrile 
• 109-70-6 1.3-chlorobromopropane 
• 14046-55-0 isobutyryl-3,4-dimethoxybenzene 
• 105-39-5 chloroacetic acid ethyl ester 
• 110-71-4 1,2-dimethoxyethane 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 75-26-3 isopropyl bromide 

Downstream Products

• 156896-96-7 γ-Cyano-γ-3,4-dimethoxyphenyl-γ-isopropyl-1-buten 
• 27487-83-8 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile 
• 252013-91-5 ethyl 3-cyano-3-(3,4-dimethyloxyphenyl)-2,2,4-trimethylpentanoate 
• 36770-70-4 2-(3,4-dimethoxyphenyl)-5-hydroxy-2-(methylethyl)pentanenitrile 
• 320593-44-0 ethyl 3-cyano-3-isopropyl-3-(3,4-dimethoxyphenyl)propionate 
• 105779-73-5 (2R)-1-(3,4-dimethoxyphenyl)-2-t-butoxycarbonylamino-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane 
• 20850-51-5 α-iso-propyl-3,4-dihydroxyphenylacetonitrile 
• 23313-68-0 verapamil hydrochloride 
• 36622-29-4 (S)-verapamil 
• 156896-96-7 (4S)-(+)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutene 
• 156896-96-7 (4R)-(-)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutene 

Relevant articles and documents

Method for synthesizing α - isopropyl -3 and 4 -methoxyacetonitrile

The invention belongs to the technical field of organic synthesis, and particularly discloses a synthesis method α - isopropyl -3 and 4 -methoxyacetonitrile. To 3, 4 - dimethoxyphenyl acetic acid as a raw material, 2 - (3, 4 - dimethoxyphenyl) acetamide is formed through acylation reaction, and 3, 4 -methoxyphenyl acetonitrile are obtained by dehydration, and α - isopropyl -3 and 4 -methoxyacetonitrile are formed by alkylation reaction. The starting materials are cheap and easily available. The method avoids the use of highly toxic crisis reagents, is mild in reaction conditions, simple in post-treatment, short in synthetic route and high in yield.

A Concise and Modular Three-Step Synthesis of (S)-Verapamil using an Enantioselective Rhodium-Catalyzed Allylic Alkylation Reaction

A concise and modular asymmetric synthesis of the calcium channel blocker (S)-verapamil is described. This approach employs an enantioselective rhodium-catalyzed allylic alkylation reaction between an α-isopropyl-substituted benzylic nitrile and allyl benzoate to construct the challenging acyclic quaternary stereocenter. The terminal olefin then serves as a convenient synthetic handle for a hydroamination to introduce the phenethylamine moiety, furnishing (S)-verapamil in three steps and 55% overall yield, thus providing the most efficient synthesis of this important pharmaceutical reported to date. Furthermore, given the modular nature of the synthesis, it can be readily modified to prepare structurally related bioactive agents.

HIGHLY WATER-SOLUBLE SALTS OF A SHORT ACTING PHENYLALKYLAMINE CALCIUM CHANNEL BLOCKER AND USES THEREOF

The present invention includes surprisingly water-soluble salts of a phenylalkylamine compound that are potent antagonists of L-type calcium channels. Aqueous solutions including salts of the instant invention are formulated for nasal administration and provide a novel therapeutic platform for the treatment of stable angina, migraine, and cardiac arrhythmia, such as paroxysmal supraventricular tachycardia.