91419-52-2

Basic information

• Product Name: 1-Boc-4-cyanopiperidine
• Synonyms: 1-Piperidinecarboxylic acid, 4-cyano-, 1,1-dimethylethyl ester;Boc-4-cyanopiperidine;1-BOC-PIPERIDINE-4-CARBONITRILE;N-Boc-piperidine-4-carbonitrile;N-boc-4-cyanopiperidie;1-N-Boc-4-cyano-piperidine ,98%;1-Boc-4-cyanopiperid;N-tert-Butoxycarbonyl-4-cyanopiperidine
• CAS NO: 91419-52-2
• Molecular Formula: C₁₁H₁₈N₂O₂
• Molecular Weight: 210.27
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Heterocycles;pharmacetical;Pyrans, Piperidines &Piperazines;Piperidine;Piperazine;Aromatics;Pyrans, Piperidines & Piperazines;Heterocyclic Building Blocks
• Mol File: 91419-52-2.mol
• Article Data: 48

Chemical Properties

• Melting Point: 60-62°C
• Boiling Point: 325.3 °C at 760 mmHg
• Flash Point: 150.5 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.07 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• PKA: -3.08±0.40(Predicted)
• CAS DataBase Reference: 1-Boc-4-cyanopiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-4-cyanopiperidine(91419-52-2)
• EPA Substance Registry System: 1-Boc-4-cyanopiperidine(91419-52-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20/21/22-50-36-22
• Safety Statements: 36-36/37/39-61-26
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 91419-52-2(Hazardous Substances Data)

Usage

Description

1-Boc-4-cyanopiperidine is a chemical compound that features a piperidine ring with a cyano group at the 4-position and a tert-butoxycarbonyl (Boc) protecting group at the 1-position. This structure makes it a versatile intermediate in organic synthesis and a valuable building block for the development of various pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
1-Boc-4-cyanopiperidine is used as a reactant for the synthesis of Aminomethylated fluoropiperidines, which are important for the development of protein kinase B inhibitors. These inhibitors play a crucial role in regulating cellular processes and have potential applications in the treatment of various diseases, including diabetes and cancer.
1-Boc-4-cyanopiperidine is also used as a reactant for the synthesis of GlyT1 inhibitors. GlyT1 inhibitors are compounds that block the reuptake of glycine in the brain, which can be beneficial in the treatment of neurological disorders such as schizophrenia and depression.
Additionally, 1-Boc-4-cyanopiperidine is used as a reactant for the synthesis of piperidinecarboxylic acids via nitrilase-catalyzed enantioselective synthesis. These enantioselective methods allow for the production of chiral compounds with high purity, which is essential for the development of effective and safe pharmaceuticals.
Used in Agrochemical Industry:
1-Boc-4-cyanopiperidine is used as a reactant for the replacement in CB2 receptor inhibitors. CB2 receptor inhibitors have potential applications in the development of agrochemicals, as they can modulate the endocannabinoid system in plants, leading to improved growth, stress resistance, and crop yield.
1-Boc-4-cyanopiperidine is also used as a reactant in double addition reactions of methyllithium and n-butyllithium to unsaturated nitriles. These reactions are important in the synthesis of complex organic molecules, which can be used in the development of new agrochemicals and other industrial applications.

InChI:InChI=1/C11H18N2O2/c1-11(2,3)15-10(14)13-6-4-9(8-12)5-7-13/h9H,4-7H2,1-3H3

Upstream product

• 4395-98-6 4-cyanopiperidine 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 91419-48-6 4-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 39546-32-2 4-carboxamidopiperidine 
• 124-63-0 methanesulfonyl chloride 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 141699-59-4 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate 
• 137076-22-3 tert butyl 4-formylpiperidine-1-carboxylate 
• 190446-85-6 tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate 
• 124443-68-1 1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 

Downstream Products

• 91419-58-8 tert-butyl 4-(1H-tetrazol-5-yl)piperidine-1-carboxylate 
• 206989-61-9 4-acetyl-1-(t-butoxycarbonyl)piperidine 
• 4395-98-6 4-cyanopiperidine 
• 269741-29-9 4-(3-fluorobenzoyl)piperidine-1-carboxylic acid tert-butyl ester 
• 912768-78-6 tert-butyl 4-(4-methylbenzoyl)piperidine-1-carboxylate 
• 919284-64-3 tert-butyl 4-[(benzyloxy)methyl]-4-cyanopiperidine-1-carboxylate 
• 280110-63-6 (Z)-tert-butyl 4-(N’-hydroxycarbamimidoyl)piperidine-1-carboxylate 
• 530116-33-7 tert-butyl 4-(1-amino-1-methylethyl)piperidine-1-carboxylate 
• 940868-23-5 tert-butyl 4-(4-{[(4-fluorobenzyl)amino]carbonyl}-5,6-dihydroxypyrimidin-2-yl)piperidine-1-carboxylate 
• 919284-65-4 4-benzyloxymethyl-piperidine-4-carbonitrile 
• 919284-66-5 4-benzyloxymethyl-1-(propane-1-sulfonyl)-piperidine-4-carbonitrile 
• 919284-67-6 C-[4-benzyloxymethyl-1-(propane-1-sulfonyl)-piperidin-4-yl]-methylamine 
• 919284-89-2 1-[4-benzyloxymethyl-1-(propane-1-sulfonyl)-piperidin-4-yl]-ethylamine 
• 919284-91-6 2,4-dichloro-N-{1-[4-hydroxymethyl-1-(propane-1-sulfonyl)-piperidin-4-yl]-ethyl}-benzamide 

Relevant articles and documents

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2

Cyanation of unactivated primary and secondary alkyl mesylates with Zn(CN)2 catalyzed by nickel has been developed. The reaction provides an efficient route for the synthesis of alkyl nitriles with wide substrate scope, good functional group tolerance, and compatibility with heterocyclic compounds. Mechanistic studies indicate that alkyl iodide generated in situ serves as the reactive intermediate and the gradual release of alkyl iodide is crucial for the success of the reaction.

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.