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Sigma-Aldrich

Benzylmagnesium chloride solution

2.0 M in THF

Synonym(s):

(Phenylmethyl)magnesium chloride, Benzylchloromagnesium, Chloro(phenylmethyl)magnesium

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About This Item

Linear Formula:
C6H5CH2MgCl
CAS Number:
6921-34-2
Molecular Weight:
150.89
Beilstein:
878506
MDL number:
MFCD00000469
UNSPSC Code:
12352103
PubChem Substance ID:
24853532
NACRES:
NA.22
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Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

2.0 M in THF

density

1.031 g/mL at 25 °C

functional group

phenyl

SMILES string

Cl[Mg]Cc1ccccc1

InChI

1S/C7H7.ClH.Mg/c1-7-5-3-2-4-6-7;;/h2-6H,1H2;1H;/q;;+1/p-1

InChI key

NRAFPLGJPPJUNB-UHFFFAOYSA-M

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General description

Benzylmagnesium chloride is an organometallic compound that acts as a Lewis acid and a strong base.[1]

Application

Benzylmagnesium chloride (Grignard reagent) can be used as an alkylating reagent:
  • For alkylating quinolyl-functionalized Cp−chromium(III) complexes which are used as precursors for the preparation of active olefin polymerization catalysts.[2]
  • In the synthesis of 2,3-disubstituted benzopyran-4-ones[3], 6-chloro-8-methylpurine derivative[4], and phenylalanine derivatives.[5]

Signal Word

Danger

Hazard Statements

H225,H314,H335,H336,H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000187002
0000187002
0000192392
SHBN7508
SHBN4363

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A novel synthesis of 2, 3-disubstituted benzopyran-4-ones and application to the solid phase
Harikrishnan LS and Showalter HD H
Tetrahedron, 56(4), 515-519 (2000)
A facile three-step synthesis of 1, 2-amino alcohols using the Ellman homochiral tert-butylsulfinamide
Barrow JC, et al.
Tetrahedron Letters, 42(11), 2051-2054 (2001)
Dichotomy in regioselective cross-coupling reactions of 6, 8-dichloropurines with phenylboronic acid and methylmagnesium chloride: synthesis of 6, 8-disubstituted purines
Hocek M, et al.
Synthesis, 2004(06), 889-894 (2004)
Benzylmagnesium Chloride
Herman G
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Quinolyl-functionalised Cp-chromium polymerisation catalysts: synthesis and crystal structures of alkylation products
Enders M, et al.
Journal of Organometallic Chemistry, 687(1), 125-130 (2003)
View All Related Papers

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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