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262579

Sigma-Aldrich

2-(Bromomethyl)tetrahydro-2H-pyran

98%

Synonym(s):

Tetrahydro-2H-pyran-2-methyl bromide

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About This Item

Empirical Formula (Hill Notation):
C6H11BrO
CAS Number:
34723-82-5
Molecular Weight:
179.05
MDL number:
MFCD00010116
UNSPSC Code:
12352100
PubChem Substance ID:
24855752
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.489 (lit.)

bp

153 °C (lit.)

mp

−59-−58 °C (lit.)

density

1.397 g/mL at 25 °C (lit.)

SMILES string

BrCC1CCCCO1

InChI

1S/C6H11BrO/c7-5-6-3-1-2-4-8-6/h6H,1-5H2

InChI key

MHNWCBOXPOLLIB-UHFFFAOYSA-N

General description

Cross-coupling reaction of 2-(bromomethyl)tetrahydro-2H-pyran with potassium heteroaryltrifluoroborates has been investigated.

Application

2-(Bromomethyl)tetrahydro-2H-pyran has been used in the preparation of tellurated heterocycles, 2-[(2-thienyltelluro)methyl]tetrahydrofuran and [(2-thienyltelluro)methyl]tetrahydro-2H-pyran.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

149.0 °F - closed cup

flash_point_c

65 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Tellurated heterocycles, 2-[(2-thienyltelluro)methyl]tetrahydrofuran and [(2-thienyltelluro)methyl]tetrahydro-2H-pyran: Synthesis and complexation reactions with Pd(II), Pt(II), Hg(II), Ru(II) and Cu(I)
Bali S, et al.
Journal of Organometallic Chemistry, 691(18), 3788-3796 (2006)
Gary A Molander et al.
Organic letters, 12(24), 5783-5785 (2010-11-26)
A method for the cross-coupling of alkyl electrophiles with various potassium aryl- and heteroaryltrifluoroborates has been developed. Nearly stoichiometric amounts of organoboron species could be employed to cross-couple a large variety of challenging heteroaryl nucleophiles. Several functional groups were tolerated

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