Skip to Content
MilliporeSigma
All Photos(1)

Documents

561673

Sigma-Aldrich

1-Naphthylmagnesium bromide solution

0.25 M slurry in THF

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service