Benzyl 4-oxopiperidine-1-carboxylate

HCID 643496

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Basic information

CAS: 19099-93-5
Standard SMILES: O=C1CCN(C(=O)OCc2ccccc2)CC1
InChIKey: VZOVOHRDLOYBJX-UHFFFAOYSA-N
Molecular formula: C13H15NO3
Average molar mass: 233.26 g/mol
Monoisotopic mass: 233.10519334

Names & identifiers

Preferred name: Benzyl 4-oxopiperidine-1-carboxylate
IUPAC: benzyl 4-oxopiperidine-1-carboxylate
English name: 1-Cbz-4-Piperidone
Molecular formula: C13H15NO3
Molecular weight: 233.26

Names & synonyms

benzyl 4-oxopiperidine-1-carboxylateBenzyl 4-oxo-1-piperidinecarboxylateRefChem:566693606-227-719099-93-51-Cbz-4-PiperidoneN-Benzyloxycarbonyl-4-piperidone1-Cbz-piperidin-4-onen-(benzyloxycarbonyl)-4-piperidone1-(Benzyloxycarbonyl)-4-piperidinoneMFCD00673144N-CBZ-4-piperidone

Show more names

1-CBZ-4-piperidinoneCbz-4-piperidone1-N-CBZ-4-PIPERIDONE1-CARBOBENZOXY-4-PIPERIDONEN-Cbz-piperidone

1-Z-4-Piperidone1-piperidinecarboxylic acid, 4-oxo-, phenylmethyl ester4-Oxo-1-piperidinecarboxylic Acid Benzyl EsterPIPERIDIN-4-ONE, N-CBZ PROTECTEDphenylmethyl 4-oxopiperidinecarboxylateN-Cbz-4-piperidinone1-BENZYLOXYCARBONYL-4-PIPERIDONEN-Cbz-piperid-4-one

Database identifiers

CAS: 19099-93-5
PubChem CID: 643496
DTXSID: DTXSID50349198
EC Number: 606-227-7
Nikkaji: J305.987A

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 46.6 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 17
Formal charge: 0
Complexity: 274

Experimental & physicochemical properties

DrugsDEA NFLIS-Drug Category -> New Drug

Physicochemical properties

Melting point: 38 · 38-41°C
Boiling point: 114 · 114-140 °C/0.25 mmHg (lit.)
Density: 1.172 g/mL · 1.172 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.542(lit.)
Flash point: 110 °C · >110 °C
storage temp.: 2 · Sealed in dry,2-8°C
solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
form: Solid or Lliquid
pka: -1.63 · -1.63±0.20(Predicted)
Specific Gravity: 1.185 · 1.185
color: White to pale yellow
BRN: 1533716 · 1533716
InChI: InChI=1S/C13H15NO3/c15-12-6-8-14(9-7-12)13(16)17-10-11-4-2-1-3-5-11/h1-5H,6-10H2
InChIKey: VZOVOHRDLOYBJX-UHFFFAOYSA-N
SMILES: N1(C(OCC2=CC=CC=C2)=O)CCC(=O)CC1
CAS DataBase Reference: 19099 · 19099-93-5(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H412
Precautionary statements: 264 · P264-P270-P273-P301+P312-P501
PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 23 · 23-24/25-36-26-37/39
WGK Germany: 3 · 3
HS Code: 29333990 · 29333990
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (81.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (81.2%)

Safety data

PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk: 3
hs_code: 29333990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 23-24/25-36-26-37/39
Storage Class: 10 - Combustible liquids
Hazard statements: H302-H412
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 3
Precautionary statements: P264-P270-P273-P301+P312-P501

Chemistry & industry

Applications

UsesProtected piperidinone that can undergo interesting synthetic transformations including the Knoevenagel reaction,1 hetero-Diels-Alder reactions,2 and reactions to form N-(4-piperidinyl)oxindoles.3

General Description1-Cbz-4-Piperidone is the starting material in biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol condensation reactions.