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497894

Sigma-Aldrich

4-Cyanobutylzinc bromide solution

0.5 M in THF

Synonym(s):

Bromo(4-cyanobutyl)zinc

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About This Item

Linear Formula:
NC(CH2)4ZnBr
CAS Number:
226570-68-9
Molecular Weight:
227.42
MDL number:
MFCD01316996
UNSPSC Code:
12352103
PubChem Substance ID:
24873153
NACRES:
NA.22

concentration

0.5 M in THF

density

0.971 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Br[Zn]CCCCC#N

InChI

1S/C5H8N.BrH.Zn/c1-2-3-4-5-6;;/h1-4H2;1H;/q;;+1/p-1

InChI key

HJYQQTDSYHJSLL-UHFFFAOYSA-M

Related Categories

Application

4-Cyanobutylzinc bromide is an organozinc compound, which can be used as a reactant in palladium-catalyzed Negishi cross-coupling reaction to construct carbon-carbon bonds by coupling with organic halides or triflates.
It can also be used as a reactant to prepare:
  • 5-(3-Thienyl)pentanenitrile by reacting with 3-bromothiophene in the presence of a nickel catalyst.
  • α-Cyanobutyl vinylphosphonates by palladium-catalyzed Negishi coupling vinylation reaction with α-(pseudo)halo vinylphosphonates.

Legal Information

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H319,H335,H351

Precautionary Statements

P261 - P281 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-6.2 °F - (THF)

Flash Point(C)

-21.2 °C - (THF)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

497894-50ML:4548173163055
497894-BULK:
497894-VAR:

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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An efficient method for the synthesis of 3-alkylthiophenes bearing functional groups on the side chain: imides and amides
D Jian, et al.
Synthetic Metals, 139(1), 81-88 (2003)
Palladium-catalysed coupling of α-halo vinylphosphonate and α-phosphonovinyl sulfonate with alkylzincs: straightforward and versatile synthesis of ?-alkyl vinylphosphonates
Zhang Li, et al.
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 5(9), 1457-1461 (2018)
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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