2-bromopyridine

• ChemBase ID: 69500
• Molecular Formular: C5H4BrN
• Molecular Mass: 157.99596
• Monoisotopic Mass: 156.95271113
• SMILES: c1(ccccn1)Br
• Canonical SMILES: Brc1ccccn1
• InChI: InChI=1S/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H
• InChIKey: IMRWILPUOVGIMU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromopyridine
• IUPAC Traditional name: 2-bromopyridine
• Synonyms: 2-Bromopyridine; 2-Bromopyridine; 2-溴吡啶

Database IDs

• CAS Number: 109-04-6
• EC Number: 203-641-6
• MDL Number: MFCD00006219
• Beilstein Number: 105789
• PubChem SID: 24892038; 162035226
• PubChem CID: 7973

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7298084
• LogD (pH = 7.4): 1.7298476
• Log P: 1.729848
• Molar Refractivity: 32.3661 cm^3
• Polarizability: 12.334084 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 192-194 °C(lit.); 192-194°C; 192-194°C
• Flash Point: 194 °F; 54°C; 90 °C; 97°C(207°F)
• Density: 1.625; 1.657; 1.657 g/mL at 25 °C(lit.)
• Refractive Index: 1.572; 1.5720; n20/D 1.57; n20/D 1.572(lit.)

Safety Information

• Storage Warning: IRRITANT; Toxic/Light Sensitive/Store under Argon
• RTECS: US3850000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2929; UN2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 24/25-36/37/38; R:22
• Safety Statements: 16-36/37-45; 26-36/37-45; S:36/37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H310-H315-H319-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P302 + P350-P305 + P351 + P338-P310; P280H-P305+P351+P338-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2929 6.1/PG 2

Product Information

• Purity: ≥98.0% (GC); 95+%; 97%; 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C5H4BrN

DETAILS

MP Biomedicals - 05214729

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B80100

Packaging
25, 100, 500 g in glass bottle

REFERENCES

• Reaction with n-BuLi gives 2-lithio-pyridine. Subsequent reaction at low temperatures with PCl₃ gives, as the major product, 2,2'-bipyridine, along with a low yield of the expected tris(2-pyridyl)phosphine. POCl₃ or SOCl₂ also promote the symmetrical coupling reaction: Heteroatom. Chem., 5, 409 (1994). In contrast, reaction with LDA in THF at -78^o results in lithiation at the 3-position, giving access to 3-substituted 2-bromopyridines: Synthesis, 235, 237 (1982). See also: Org. Lett., 3, 835 (2001).
• Bromopyridines can be converted to the Grignards by Mg exchange with i-PrMgCl: Tetrahdron Lett., 40, 4339 (1999).