3,5-dibromopyridine

• ChemBase ID: 13729
• Molecular Formular: C5H3Br2N
• Molecular Mass: 236.89202
• Monoisotopic Mass: 234.8632231
• SMILES: c1(cncc(c1)Br)Br
• Canonical SMILES: Brc1cncc(c1)Br
• InChI: InChI=1S/C5H3Br2N/c6-4-1-5(7)3-8-2-4/h1-3H
• InChIKey: SOSPMXMEOFGPIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-dibromopyridine
• IUPAC Traditional name: 3,5-dibromopyridine
• Synonyms: 3,5-Dibromo-pyridine; NSC 6209; 3,5-Dibromopyridine; 3,5-Dibromopyridine; 3,5-二溴吡啶

Database IDs

• CAS Number: 625-92-3
• EC Number: 210-916-4
• MDL Number: MFCD00014634
• Beilstein Number: 108477
• PubChem SID: 24847407; 24861148; 160977036
• PubChem CID: 69369

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.2930095
• LogD (pH = 7.4): 2.2930777
• Log P: 2.2930787
• Molar Refractivity: 39.1467 cm^3
• Polarizability: 15.432079 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light-Yellow Solid
• Melting Point: 110 - 115°C; 110-113°C; 110-115 °C; 110-115 °C(lit.); 110-115°C; 111-112°C
• Hydrophobicity(logP): 2.484

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38; 36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H311-H332-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P361-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (GC); 95%; 98%; 98+%; 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C5H3Br2N

DETAILS

Sigma Aldrich - 120162

Packaging
10 g in glass bottle

REFERENCES

• With n-BuLi at -30 ^o, selective metallation occurs by exchange with one Br atom: J. Org. Chem., 16,1485 (1951). In contrast, using LDA in THF at -100 ^o, lithiation can be accomplished at the 4-position. Subsequent reaction with an electrophile can be followed by lithiation with n-BuLi to give 3-bromo-4,5-disubstituted pyridines: Tetrahedron Lett ., 37, 2565 (1996):