piperidine-1-carbaldehyde

• ChemBase ID: 3735
• Molecular Formular: C6H11NO
• Molecular Mass: 113.15764
• Monoisotopic Mass: 113.08406398
• SMILES: O=CN1CCCCC1
• Canonical SMILES: O=CN1CCCCC1
• InChI: InChI=1S/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2
• InChIKey: FEWLNYSYJNLUOO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: piperidine-1-carbaldehyde
• IUPAC Systematic name: Piperidine-1-carbaldehyde
• IUPAC Traditional name: N-formylpiperidine
• Synonyms: N-Carbaldehyde piperidine; NFP; Piperidine-1-carboxaldehyde; 1-Formylpiperidine; 1-Piperidinecarbaldehyde; N-Formylpiperidine; 1-Formylpiperidine; 1-Formylpiperidine; Piperidine-1-carbaldehyde; 哌啶-1-甲醛; 1-甲酰哌啶; N-甲酸基哌啶

Database IDs

• CAS Number: 2591-86-8
• EC Number: 219-986-0
• MDL Number: MFCD00006483
• Beilstein Number: 107697
• PubChem SID: 46508673; 24894793; 160967173
• PubChem CID: 17429
• Chemspider ID: 16486
• DrugBank ID: DB04113
• MeSH Name: N-Formylpiperidine
• Wikipedia Title: N-Formylpiperidine

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.21873112
• LogD (pH = 7.4): 0.21873122
• Log P: 0.21873122
• Molar Refractivity: 31.9108 cm^3
• Polarizability: 12.265093 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.21
• LOG S: 0.4
• Solubility (Water): 2.82e+02 g/l

PROPERTIES

Physical Property

• Melting Point: -31°C; -31°C
• Boiling Point: 221-223°C; 222 °C(lit.); 222°C; 222°C
• Flash Point: 102 °C; 102°C(215°F); 215.6 °F; 91°C
• Density: 1.019; 1.019 g cm^-3; 1.019 g/mL at 25 °C(lit.)
• Refractive Index: 1.484; 1.4840; n20/D 1.484(lit.); n20/D 1.485
• Vapor Pressure: 0.01 kPa; 0.1 mmHg ( 25 °C)

Safety Information

• Storage Warning: Harmful/Irritant/Store under Argon; IRRITANT
• RTECS: TN0380000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 21/22-36/37/38; R21/22, R36/37/38
• Safety Statements: 26-36/37; S26, S36/37
• TSCA Listed: false; 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: H301-H311-H315-H319-H335-H227; H302-H311-H315-H319-H335
• GHS Precautionary statements: P210-P301+P310-P305+P351+P338-P361-P405-P501A; P261-P280-P305 + P351 + P338-P312
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3

Product Information

• Purity: ≥99.0% (GC); 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C6H11NO

DETAILS

DrugBank - DB04113

Drug information: experimental

Sigma Aldrich - F17407

Packaging
100, 500 g in glass bottle
Application
Reactant for:
• Direct amidation of azoles with formamides via metal-free C-H activation in the presence of tert-butyl perbenzoate1
• Vilsmeier-type reactions of pyrazoles with amides in the presence of phosphorous oxychloride2
• CO-free aminocarbonylation of N-substituted formamides with aryl iodides/bromides catalyzed by palladium acetate and Xantphos for synthesis of arylamides3
• Synthesis of alternating copolymers for organic photovoltaic applications4
• One-pot double functionalization of π-deficient heterocyclic lithium reagents5
• Synthesis of thermally stable piezofluorochromic aggregation-induced emission compounds6

Sigma Aldrich - 47725

Other Notes
Used in formyl transfer to Grignard reagents7
Application
Reactant for:
• Direct amidation of azoles with formamides via metal-free C-H activation in the presence of tert-butyl perbenzoate1
• Vilsmeier-type reactions of pyrazoles with amides in the presence of phosphorous oxychloride2
• CO-free aminocarbonylation of N-substituted formamides with aryl iodides/bromides catalyzed by palladium acetate and Xantphos for synthesis of arylamides3
• Synthesis of alternating copolymers for organic photovoltaic applications4
• One-pot double functionalization of π-deficient heterocyclic lithium reagents5
• Synthesis of thermally stable piezofluorochromic aggregation-induced emission compounds6

REFERENCES

• Reaction with Grignard or alkyllithium reagents gives aldehydes in high yield: Angew. Chem. Int. Ed., 20, 878 (1981); Org. Synth. Coll., 7, 451 (1990).