ChemicalBook > CAS DataBase List > N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE

N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE

Product Name
N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE
CAS No.
66207-23-6
Chemical Name
N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE
Synonyms
benzyl 3,6-dihydropyridine-1(2H)-carboxylate;Benzyl 5,6-dihydropyridine-1(2H);1-Cbz-1,2,3,6-tetrahydropyridine;N-CBZ-1,2,5,6-TETRAHYDROPYRIDINE;N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE;benzyl 3,6-dihydro-2H-pyridine-1-carboxylate;benzyl 5,6-dihydropyridine-1(2H)-carboxylate;1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine;benzyl 1,2,3,6-tetrahydropyridine-1-carboxylate;Phenylmethyl 3,6-dihydro-1(2H)-pyridinecarboxylate
CBNumber
CB5432211
Molecular Formula
C13H15NO2
Formula Weight
217.26
MOL File
66207-23-6.mol
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N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE Property

Boiling point:
334.6±41.0 °C(Predicted)
Density 
1.148±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
pka
-1.46±0.20(Predicted)
Appearance
Colorless to light yellow Liquid
InChI
InChI=1S/C13H15NO2/c15-13(14-9-5-2-6-10-14)16-11-12-7-3-1-4-8-12/h1-5,7-8H,6,9-11H2
InChIKey
YWKYQRWNOXUYJK-UHFFFAOYSA-N
SMILES
C1N(C(OCC2=CC=CC=C2)=O)CC=CC1
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Safety

HS Code 
2933399990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H311Toxic in contact with skin

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC
Product number
D446760
Product name
3,6-Dihydro-1(2H)-pyridinecarboxylicAcidPhenylmethylEster
Packaging
50g
Price
$825
Updated
2021/12/16
SynQuest Laboratories
Product number
4H56-1-8N
Product name
Benzyl 5,6-dihydropyridine-1(2H)-carboxylate
Purity
95%
Packaging
1g
Price
$150
Updated
2021/12/16
SynQuest Laboratories
Product number
4H56-1-8N
Product name
Benzyl 5,6-dihydropyridine-1(2H)-carboxylate
Purity
95%
Packaging
250mg
Price
$50
Updated
2021/12/16
ChemScene
Product number
CS-W022589
Product name
Benzyl5,6-dihydropyridine-1(2H)-carboxylate
Purity
98.45%
Packaging
5g
Price
$76
Updated
2021/12/16
ChemScene
Product number
CS-W022589
Product name
Benzyl5,6-dihydropyridine-1(2H)-carboxylate
Purity
98.45%
Packaging
10g
Price
$133
Updated
2021/12/16
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N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE Chemical Properties,Usage,Production

Uses

3,6-Dihydro-1(2H)-pyridinecarboxylic Acid Phenylmethyl Ester is used in the synthesis of potent antibacterials targeting type IIA topoisomerases. Also used in the synthesis of inhibitors of papain-like cathespin proteases.

Synthesis

694-05-3

501-53-1

66207-23-6

General procedure: A mixed solution of 1,2,5,6-tetrahydropyridine (36.1 g, 1 eq.), sodium carbonate (1.5 eq.) and water (45 eq.) was cooled in an ice water bath. Benzyl chloroformate (1.1 eq.) was slowly added dropwise over a period of 1 h. The reaction was kept at 5 °C for 2 h. The reaction was then slowly warmed to room temperature and continued for 16 h. The reaction was completed with the addition of saturated table water. After completion of the reaction, the reaction mixture was diluted with saturated saline and the product was extracted with ethyl acetate (EtOAc). The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give an oily crude product. The crude product was purified by fast column chromatography (elution gradient: 10% ethyl acetate/hexane to 100% ethyl acetate) to afford the target compound benzyl 5,6-dihydropyridine-1(2H)-carboxylate (36.2, 99% yield) as a colorless oil.EIMS (m/z): calculated value of C13H15NO2 (M++1) 218.26, measured value 218.10 EIMS (m/z).

References

[1] Tetrahedron Letters, 2002, vol. 43, # 23, p. 4289 - 4293
[2] Journal of Organic Chemistry, 1991, vol. 56, # 9, p. 3133 - 3137
[3] Patent: WO2011/29046, 2011, A1. Location in patent: Page/Page column 193
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1254 - 1259
[5] Tetrahedron, 2006, vol. 62, # 14, p. 3284 - 3291

N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE Suppliers

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66207-23-6, N-CBZ-1,2,3,6-TETRAHYDROPYRIDINERelated Search:

Benzoyl peroxide

  • N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE
  • N-CBZ-1,2,5,6-TETRAHYDROPYRIDINE
  • benzyl 5,6-dihydropyridine-1(2H)-carboxylate
  • 1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine
  • benzyl 1,2,3,6-tetrahydropyridine-1-carboxylate
  • benzyl 3,6-dihydro-2H-pyridine-1-carboxylate
  • 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-, phenylmethyl ester
  • benzyl 3,6-dihydropyridine-1(2H)-carboxylate
  • Benzyl 5,6-dihydropyridine-1(2H)
  • benzyl 3,6-dihydropyridine-1(2H)-carboxylate66207-23-6
  • 1-Cbz-1,2,3,6-tetrahydropyridine
  • 3,6-Dihydro-1(2H)-pyridinecarboxylic Acid Phenylmethyl Ester
  • 4-Isoxazolecarboxylicacid,5-hydroxy-5-methyl-,ethylester
  • Phenylmethyl 3,6-dihydro-1(2H)-pyridinecarboxylate
  • 66207-23-6
  • Heterocycle-Pyridine series