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497746

Sigma-Aldrich

Butylzinc bromide solution

0.5 M in THF

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About This Item

Linear Formula:
CH3(CH2)3ZnBr
CAS Number:
92273-73-9
Molecular Weight:
202.41
MDL number:
MFCD00671997
UNSPSC Code:
12352103
PubChem Substance ID:
24873140
NACRES:
NA.22

concentration

0.5 M in THF

density

0.958 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CCCC[Zn]Br

InChI

1S/C4H9.BrH.Zn/c1-3-4-2;;/h1,3-4H2,2H3;1H;/q;;+1/p-1

InChI key

HMBGXQKLGHIDMN-UHFFFAOYSA-M

Application

Butylzinc bromide is an organozinc compound, which can be used as a reagent:
  • In palladium-catalyzed Negishi cross-coupling reaction to construct carbon-carbon bond by reacting with organic halides or triflates.
  • To prepare n-butylanisole by treating with 4-bromoanisole in the presence of a tetraphosphine ligand and a palladium catalyst.

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Signal Word

Danger

Hazard Statements

H225,H302,H319,H335,H351

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of all-cis-3-(2-diphenylphosphinoethyl)-1, 2, 4-tris (diphenylphosphinomethyl) cyclopentane (Ditricyp) from dicyclopentadiene
Kondolff I, et al.
Tetrahedron, 63(38), 9514-9521 (2007)
Room-temperature Negishi cross-coupling of unactivated alkyl bromides with alkyl organozinc reagents utilizing a Pd/N-heterocyclic carbene catalyst
Hadei N, et al.
The Journal of Organic Chemistry, 70(21), 8503-8507 (2005)

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