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224421

Sigma-Aldrich

sec-Butylmagnesium chloride solution

2.0 M in diethyl ether

Synonym(s):

2-Butylmagnesium chloride, Chloro(1-methylpropyl)magnesium, sec-Butylchloromagnesium

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About This Item

Linear Formula:
CH3CH2CH(CH3)MgCl
CAS Number:
Molecular Weight:
116.87
Beilstein:
3600265
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

reaction suitability

reaction type: Grignard Reaction

concentration

2.0 M in diethyl ether

density

0.828 g/mL at 25 °C

SMILES string

CCC(C)[Mg]Cl

InChI

1S/C4H9.ClH.Mg/c1-3-4-2;;/h3H,4H2,1-2H3;1H;/q;;+1/p-1

InChI key

MJHZUYZQMNONPK-UHFFFAOYSA-M

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Application

sec-Butylmagnesium chloride solution is a Grignard reagent, it can be used in:
  • Metal catalyzed cross-coupling reactions with non-activated aryl chlorides.
  • The synthesis of various alkoxytrichlorosilanes by reacting with tetrachlorosilane and alcohols.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Central nervous system

Supplementary Hazards

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 1

Flash Point(F)

-40.0 °F - closed cup

Flash Point(C)

-40 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Versatile method for introduction of bulky substituents to alkoxychlorosilanes
Masaoka S, et al.
Journal of Organometallic Chemistry, 691(1-2), 182-192 (2006)
An unprecedented iron-catalyzed cross-coupling of primary and secondary alkyl Grignard reagents with non-activated aryl chlorides
Perry MC, et al.
Tetrahedron Letters, 53(33), 4436-4439 (2012)
35 years of palladium-catalyzed cross-coupling with Grignard reagents: how far have we come?
Knappke CEI and von Wangelin AJ
Chemical Society Reviews, 40(10), 4948-4962 (2011)
Jee Myung Yang et al.
BMC ophthalmology, 17(1), 101-101 (2017-06-28)
Physical cooling of the eye surface relieves ocular discomfort, but translating this event to drug treatment of dry eye discomfort not been studied. Here, we synthesized a water-soluble TRPM8 receptor agonist called cryosim-3 (C3, 1-diisopropylphosphorylnonane) which selectively activates TRPM8 (linked

Articles

Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

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