153749-89-4

Basic information

• Product Name: N-Boc-2-Cyanopiperidine
• Synonyms: (+/-)-1-N-BOC-2-CYANO-PIPERIDINE;1-N-BOC-2-CYANO-PIPERIDINE;2-CYANO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;TERT-BUTYL2-CYANOPIPERIDINE-1-CARBOXYLATE;1-Piperidinecarboxylic acid, 2-cyano-, 1,1-dimethylethyl ester;1-N-BOC-2-CYANOPIPERDINE;1-BOC-2-CYANOPIPERIDINE 98+%;1-tert-Butoxycarbonyl-2-cyanopiperidine
• CAS NO: 153749-89-4
• Molecular Formula: C₁₁H₁₈N₂O₂
• Molecular Weight: 210.27
• Product Categories: Pyrans, Piperidines &Piperazines;Piperidine;Pyrans, Piperidines & Piperazines
• Mol File: 153749-89-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 62-67℃
• Boiling Point: 325.3 °C at 760 mmHg
• Flash Point: 150.5 °C
• Appearance: White to pale brown/Powder
• Density: 1.07 g/cm³
• Vapor Pressure: 0.000232mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: 2-8°C
• PKA: -4.85±0.40(Predicted)
• CAS DataBase Reference: N-Boc-2-Cyanopiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-2-Cyanopiperidine(153749-89-4)
• EPA Substance Registry System: N-Boc-2-Cyanopiperidine(153749-89-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 37
• RIDADR: UN3439
• WGK Germany: 3
• HazardClass: 6.1
• Hazardous Substances Data: 153749-89-4(Hazardous Substances Data)

Usage

General Description

N-Boc-2-Cyanopiperidine is a chemical compound with the molecular formula C12H20N2O2. It is a derivative of piperidine and contains a N-Boc (tert-butoxycarbonyl) protecting group and a cyano group. N-Boc-2-Cyanopiperidine is used in organic synthesis as a building block for the preparation of various pharmaceuticals and agrochemicals. N-Boc-2-Cyanopiperidine is known to be a versatile intermediate for the synthesis of a variety of biologically active molecules and can be utilized in the development of new drugs and other important chemical products.

InChI:InChI=1/C11H18N2O2/c1-11(2,3)15-10(14)13-7-5-4-6-9(13)8-12/h9H,4-7H2,1-3H3/t9-/m0/s1

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 119910-09-7 N-tert-butoxycarbonyl-2-ethoxypiperidine 
• 42457-10-3 piperidine-2-carbonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 388077-74-5 rac-N-(tert-butoxycarbonyl)piperidine-2-carboxamide 
• 98303-20-9 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 75844-69-8 t-butyl piperidinecarboxylate 
• 110-89-4 piperidine 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 123387-55-3 1-t-butoxycarbonyl-2-tributylstannylpiperidine 
• 4043-87-2 pipecolic Acid 

Downstream Products

• 960294-15-9 tert-butyl 2-(2-chloroethyl)-2-cyanopiperidine-1-carboxylate 
• 661458-47-5 3-(3-piperidin-2-yl-[1,2,4]oxadiazol-5-yl)-benzonitrile 
• 934660-93-2 [14C]-GDC-0973 
• 934665-56-2 tert-butyl (S)-2-{1-[3,4-difluoro-2-(2-fluoro-4-iodophenylamino)benzoyl]-3-hydroxy-3-azetidinyl}perhydropyridine-1-carboxylate 
• 1369665-02-0 (S)-[3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl][3-hydroxy-3-(piperidin-2-yl)azetidin-1-yl]methanone hemifumarate 
• 934662-91-6 cobimetinib 
• 934665-56-2 (R,S) tert-butyl 2-{1-[3,4-difluoro-2-(2-fluoro-4-iodophenylamino)benzoyl]-3-hydroxy-3-azetidinyl}-1-piperidinecarboxylate 
• 934666-39-4 (R,S) tert-butyl 2-(3-hydroxy-3-azetidinyl)-1-piperidinecarboxylate 
• 1510798-88-5 tert-butyl 2-benzyl-2-cyanopiperidine-1-carboxylate 
• 439287-95-3 tert-butyl 2-[(Z)-amino(hydroxyimino)methyl]piperidine-1-carboxylate 
• 439287-95-3 2-(N-hydroxycarbamimidoyl)-piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Enantioselective total syntheses of ropivacaine and its analogues

An alternative asymmetric synthesis of ropivacaine and analogues employing the 'cation pool' strategy and host/guest supramolecular co-catalysis approach is presented. In this study, chiral auxiliaries, several soft nucleophiles as well as one-pot conditions for anodic oxidation, followed by nucleophilic addition, have been applied.

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.

C(sp3)?H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis

Inspired by the reaction mechanism of photo-induced DNA cleavage in nature, a C(sp3)?H cyanation reaction promoted by visible-light photoredox/phosphate hybrid catalysis was developed. Phosphate radicals, generated by one-electron photooxidation of phosphate salt, functioned as a hydrogen-atom-transfer catalyst to produce nucleophilic carbon radicals from C(sp3)?H bonds with a high bond-dissociation energy. The resulting carbon radicals were trapped by a cyano radical source (TsCN) to produce the C?H cyanation products. Due to the high functional-group tolerance and versatility of the cyano group, the reaction will be useful for realizing streamlined building block syntheses and late-stage functionalization of drug-like molecules.