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Safety Information

520322

Sigma-Aldrich

2-Cyanobenzylzinc bromide solution

0.5 M in THF

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About This Item

Linear Formula:
NCC6H4CH2ZnBr
CAS Number:
199465-66-2
Molecular Weight:
261.43
MDL number:
MFCD01311397
UNSPSC Code:
12352103
PubChem Substance ID:
24874105
NACRES:
NA.22

concentration

0.5 M in THF

density

0.993 g/mL at 25 °C

functional group

nitrile

storage temp.

2-8°C

SMILES string

Br[Zn]Cc1ccccc1C#N

InChI

1S/C8H6N.BrH.Zn/c1-7-4-2-3-5-8(7)6-9;;/h2-5H,1H2;1H;/q;;+1/p-1

InChI key

LQRNYQAXNZETFP-UHFFFAOYSA-M

Application

2-Cyanobenzylzinc bromide can be used as a reactant:
  • In the metal-catalyzed Negishi cross-coupling reactions to prepare aryl or heteroaryl derivatives via carbon-carbon bond formation.
  • To synthesize 4-(2-Cyanobenzyl)-3′-(trifluoromethyl)biphenyl by reacting with aryl nonaflate in the presence of Pd(dba)2 as a catalyst.
  • To prepare 2-[(2-cyanophenyl)methyl] benzamide by treating with 2-iodobenzamide using a nickel catalyst.

Legal Information

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

Signal Word

Danger

Hazard Statements

H225,H319,H335,H336,H351

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH014,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

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

520322-VAR:
520322-50ML:4548173165196
520322-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBF7229V
SHBF3097V
17297JJ
06126HH
04004AH

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Improved nickel-catalyzed cross-coupling reaction conditions between ortho-substituted aryl iodides/nonaflates and alkylzinc iodides in solution and in the solid-phase
Jensen AE, et al.
Tetrahedron, 56(25), 4197-4201 (2000)
Visible-Light-Induced Nickel-Catalyzed Negishi Cross-Couplings by Exogenous-Photosensitizer-Free Photocatalysis
Abdiaj I, et al.
Angewandte Chemie (International Edition in English), 57(28), 8473-8477 (2018)
Palladium-catalyzed cross-coupling reactions with aryl nonaflates: a practical alternative to aryl triflates
Rottlander M and Knochel P
The Journal of Organic Chemistry, 63(1), 203-208 (1998)

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