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561673

Sigma-Aldrich

1-Naphthylmagnesium bromide solution

0.25 M slurry in THF

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About This Item

Empirical Formula (Hill Notation):
C10H7BrMg
CAS Number:
703-55-9
Molecular Weight:
231.37
MDL number:
MFCD00015768
UNSPSC Code:
12352103
PubChem Substance ID:
24879961
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

Quality Level

100

concentration

0.25 M slurry in THF

bp

65 °C

density

0.908 g/mL at 25 °C

SMILES string

Br[Mg]c1cccc2ccccc12

InChI

1S/C10H7.BrH.Mg/c1-2-6-10-8-4-3-7-9(10)5-1;;/h1-7H;1H;/q;;+1/p-1

InChI key

PZIIGUMPOSVMSD-UHFFFAOYSA-M

Application

1-Naphthylmagnesium bromide can be used:
  • To prepare unsymmetrical chiral diene ligands, which are applicable in asymmetric transformation reactions.
  • As a starting material in the synthesis of methyl (2Z,4E)-2-methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate, a naphthylnitrobutadiene based anti-proliferative compound.

Legal Information

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

Signal Word

Danger

Hazard Statements

H225,H302,H314,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN7339
SHBM4685
SHBM0937
SHBL6284
SHBK2907

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Design, synthesis, and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: Toward a structure-activity correlation
Petrillo G, et al.
Bioorganic & Medicinal Chemistry, 16(1), 240-247 (2008)
Stefan Abele et al.
The Journal of organic chemistry, 77(10), 4765-4773 (2012-05-04)
An operationally simple and scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene (bod*) ligands relying on an organocatalytic one-pot Michael addition-aldol reaction with cheap 2-cyclohexenone and phenylacetaldehyde is presented. The crystalline bicyclic product 4a (6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one) is transformed into phenylbicyclo[2.2.2]oct-5-en-2-one 2, a versatile

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