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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:
15366-08-2
Molecular Weight:
116.87
Beilstein:
3600265
MDL number:
MFCD00000467
UNSPSC Code:
12352103
PubChem Substance ID:
24853437
NACRES:
NA.22

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

H225,H260,H302,H314,H336

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

EUH019

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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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)
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)
Versatile method for introduction of bulky substituents to alkoxychlorosilanes
Masaoka S, et al.
Journal of Organometallic Chemistry, 691(1-2), 182-192 (2006)
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

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

Selective Metalation and Additions

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

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