694-05-3

Basic information

• Product Name: 1,2,3,6-TETRAHYDROPYRIDINE
• Synonyms: delta3-Piperidine;Pyridine, 1,2,3,6-tetrahydro-;Pyridine, 1,2,5,6-tetrahydro-;1,2,3,6-Tetrahydropyridine 97%;1,2,3,6-Tetrahydropyridine,98%;3,6-Dihydro-2H-pyridine;3-piperideine;1,2,5,6 TETRAHYDROPYRIDINE
• CAS NO: 694-05-3
• Molecular Formula: C₅H₉N
• Molecular Weight: 83.13
• EINECS: 211-766-2
• Product Categories: Pyridines;Heterocyclic Compounds;C5;Heterocyclic Building Blocks
• Mol File: 694-05-3.mol

Chemical Properties

• Melting Point: −48 °C(lit.)
• Boiling Point: 108 °C(lit.)
• Flash Point: 61 °F
• Appearance: White to pale yellow-cream/Powder
• Density: 0.911 g/mL at 25 °C(lit.)
• Vapor Pressure: 23.3mmHg at 25°C
• Refractive Index: n20/D 1.48(lit.)
• PKA: 10.22±0.10(Predicted)
• CAS DataBase Reference: 1,2,3,6-TETRAHYDROPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,6-TETRAHYDROPYRIDINE(694-05-3)
• EPA Substance Registry System: 1,2,3,6-TETRAHYDROPYRIDINE(694-05-3)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39
• RIDADR: UN 2410 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 694-05-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2,3,6-Tetrahydropyridine is used as a synthetic intermediate for the preparation of various pharmaceuticals, agrochemicals, and other organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
1,2,3,6-Tetrahydropyridine is used as a key building block in the development of new drugs and drug candidates. Its ability to form ene-endo-spirocyclic ammonium ylids enables the [2,3]-sigmatropic rearrangement to pyrroloazepinones and oxazepinones, which are important structural motifs in medicinal chemistry.
Used in Agrochemical Industry:
1,2,3,6-Tetrahydropyridine is also utilized in the agrochemical sector for the synthesis of novel pesticides and insecticides. Its unique properties allow for the development of more effective and targeted agrochemicals, contributing to improved crop protection and yield.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

1,2,3,6-TETRAHYDROPYRIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

InChI:InChI=1/C5H9N/c1-2-4-6-5-3-1/h1-2,6H,3-5H2

Upstream product

• 110-86-1 pyridine 
• 85839-08-3 1-cyano-1,2,3,6-tetrahydropyridine 
• 462-08-8 pyridin-3-ylamine 
• 92885-06-8 N-chloro-1,2,5,6-tetrahydropyridine 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 40240-12-8 1-benzyl-1,2,3,6-tetrahydropyridine 
• 52003-32-4 ethyl 1,2,3,6-tetrahydropyridine-1-carboxylate 
• 2876-13-3 N-benzylpyridinium chloride 
• 694-55-3 N-methyl-3,4-didehydropiperidine 
• 2589-31-3 N-benzylpyridinium bromide 
• 100-39-0 benzyl bromide 

Downstream Products

• 106320-87-0 1-(2-chloro-phenoxy)-3-(3,6-dihydro-2H-[1]pyridyl)-propan-2-ol 
• 100718-11-4 (3,6-dihydro-2H-[1]pyridyl)-phenyl-acetic acid methyl ester 
• 101255-85-0 1-[2-(2-o-tolyloxy-ethoxy)-ethyl]-1,2,3,6-tetrahydro-pyridine 
• 18513-75-2 1-(1,2,3,6-tetrahydropyridin-1-yl)ethan-1-one 
• 71785-91-6 (5,6-dihydropyridin-1(2H)-yl)(phenyl)methanone 
• 109816-13-9 (3,6-dihydro-2H-[1]pyridyl)-acetic acid-(2,6-dimethyl-anilide) 
• 101114-58-3 1-(3,6-dihydro-2H-[1]pyridyl)-3-phenoxy-propan-2-ol 
• 97-57-4 1-(3,6-dihydro-2H-[1]pyridyl)-3-o-tolyloxy-propan-2-ol 
• 40240-41-3 1-chlorocarbonyl-3,6-dihydro-1(2H)-pyridine 
• 85908-52-7 phenyl-3 (tetrahydro-1,2,3,6 pyridyl-1)-1 propanethiol-2 
• 139021-47-9 1-(1'-bromoacroyl)-1,2,5,6-tetrahydropyridine 
• 85838-94-4 N-Boc-1,2,3,6-tetrahydropyridine 
• 131269-82-4 2-(1,2,3,6-Tetrahydropyridin-1-yl)-benzonitril 
• 109270-63-5 (5,6-dihydropyridin-1(2H)-yl)(2-iodophenyl)methanone 

Relevant articles and documents

Efficient and chemoselective reduction of pyridines to tetrahydropyridines and piperidines via rhodium-catalyzed transfer hydrogenation

Promoted by iodide anion the rhodium complex dimer, [Cp RhCl 2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6-tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH-Et 3N) mixture at 40 °C, with catalyst loadings as low as 0.005mol% being feasible. Copyright

Synthesis and antibacterial activity of novel fluoroquinolones containing substituted piperidines

The design and synthesis of new fluoroquinolone antibacterial agents having substituted piperidine rings at the C-7 position are described. Most of the new compounds demonstrated high in vitro antibacterial activity. Several of them exhibited significant activities against Gram-positive organisms, which were more potent than those of gemifloxacin, Linezolid, and vancomycin.

Substituted tetrahydropyridine derivatives acting on 5-HT receptors

PCT No. PCT/GB96/02763 Sec. 371 Date Apr. 29, 1998 Sec. 102(e) Date Apr. 29, 1998 PCT Filed Nov. 13, 1996 PCT Pub. No. WO97/18204 PCT Pub. Date May 22, 1997Compounds having formula I, or salts or prodrugs thereof: are selective agonists of the 5-HT1D alpha receptor and are useful in the treatment of migraine and associated conditions.

THE NOVEL REDUCTION OF PYRIDINE DERIVATIVES WITH SAMARIUM DIIODIDE

Pyridine was rapidly reduced into piperidine with samarium diiodide in the presence of water at room temperature in excellent yield.On the similar reactions of pyridine derivatives bearing chloro, amino and cyano functionalities with samarium diiodide-H2O-THF system, these functionalities were partly eliminated with this system to afford pyridine or piperidine.Furthermore, pyridinecarboxamides were reduced with this system to give the corresponding methylpyridines and 2-pyridinecarboxylic acid was reduced to give 2-methylpyridine as the major products.

SYNTHESE D'IMINES CYCLIQUES NON-STABILISEES PAR REACTIONS GAZ-SOLIDE SOUS VIDE ET THERMOLYSE-ECLAIR (1,2).

Unstabilized cyclic imines 1-4 were synthetized in gram-scale by vacuum dehydrochlorination of N-chlorocycloamines.Azirine 5 was prepared by flash vacuum thermolysis of the corresponding vinylazide 19.All the new compounds were characterized at low temperature by 1H, 13C NMR and IR spectroscopy.