6-chloropyridine-3-carbonyl chloride

• ChemBase ID: 84520
• Molecular Formular: C6H3Cl2NO
• Molecular Mass: 176.00012
• Monoisotopic Mass: 174.95916908
• SMILES: n1cc(ccc1Cl)C(=O)Cl
• Canonical SMILES: Clc1ccc(cn1)C(=O)Cl
• InChI: InChI=1S/C6H3Cl2NO/c7-5-2-1-4(3-9-5)6(8)10/h1-3H
• InChIKey: FMEBIWNKYZUWFV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloropyridine-3-carbonyl chloride
• IUPAC Traditional name: 6-chloropyridine-3-carbonyl chloride
• Synonyms: 6-Chloropyridine-3-carbonyl chloride; 6-Chloronicotinoyl chloride; 6-Chloronicotinoyl chloride; 6-氯烟酰氯

Database IDs

• CAS Number: 66608-11-5; 58757-38-3
• MDL Number: MFCD00051775
• Beilstein Number: 115927
• PubChem SID: 162071636; 24874669
• PubChem CID: 2782165

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7707074
• LogD (pH = 7.4): 1.7707078
• Log P: 1.7707078
• Molar Refractivity: 40.8819 cm^3
• Polarizability: 15.2336855 Å^3
• Polar Surface Area: 29.96 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 48-51 °C(lit.); 48-52°C; 48-52°C
• Boiling Point: 84-85°C/3mm; 84-85°C/3mm
• Flash Point: 110 °C; 110°C; 230 °F

Safety Information

• Storage Warning: Corrosive/Air Sensitive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C6H3Cl2NO

DETAILS

Sigma Aldrich - 528102

Packaging
25 g in glass bottle

REFERENCES

• Acylation of dimethyl malonate has been carried out using the combination of triethylamine and magnesium chloride (see Diethyl malonate, A15468, and Triethylamine, A12646, for discussion), followed by one-pot hydrolysis-decarboxylation of the acylmalonate derivative in wet DMSO, to give 5-acetyl-2-chloropyridine in good yield: Tetrahedron, 48, 9233 (1992).