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18280

Sigma-Aldrich

3-Bromopyridine

purum, ≥97.0% (GC)

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About This Item

Empirical Formula (Hill Notation):
C5H4BrN
CAS Number:
626-55-1
Molecular Weight:
158.00
Beilstein:
105880
EC Number:
210-952-0
MDL number:
MFCD00006373
UNSPSC Code:
12352100
PubChem Substance ID:
24851015

grade

purum

Assay

≥97.0% (GC)

refractive index

n20/D 1.571 (lit.)
n20/D 1.571

bp

173 °C (lit.)

density

1.64 g/mL at 25 °C (lit.)

SMILES string

Brc1cccnc1

InChI

1S/C5H4BrN/c6-5-2-1-3-7-4-5/h1-4H

InChI key

NYPYPOZNGOXYSU-UHFFFAOYSA-N

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Application

3-Bromopyridine was used in the synthesis of cis-1-methyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,2-f]pyrindine (a nicotine analog). It was also used in the preparation of 3-pyridylboronic acid.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302,H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

125.6 °F - closed cup

Flash Point(C)

52 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Wenjie Li et al.
The Journal of organic chemistry, 67(15), 5394-5397 (2002-07-20)
3-Pyridylboronic acid was prepared in high yield and bulk quantity from 3-bromopyridine via a protocol of lithium-halogen exchange and "in situ quench". This technique was further studied and evaluated on other aryl halides in the preparation of arylboronic acids.
Hongbin Zhai et al.
Organic letters, 4(25), 4385-4386 (2002-12-06)
[reaction: see text] The title compound, 2, has been synthesized in 45% overall yield in six steps from 3-bromopyridine. The hexahydropyrrolo[3,2-f]pyrindine skeleton was constructed from key intermediate 5, via intramolecular azomethine ylide-alkene [3 + 2] cycloaddition. The present work constitutes

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