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419591

Sigma-Aldrich

3-Butenylmagnesium bromide solution

0.5 M in THF

Synonym(s):

1-(Bromomagnesium)-3-butene, 1-Buten-4-ylmagnesium bromide, Bromo(but-3-enyl)magnesium, Bromo-3-buten-1-ylmagnesium

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About This Item

Linear Formula:
H2C=CHCH2CH2MgBr
CAS Number:
7103-09-5
Molecular Weight:
159.31
MDL number:
MFCD00209554
UNSPSC Code:
12352103
PubChem Substance ID:
24866263
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65 °C

density

0.937 g/mL at 25 °C

SMILES string

Br[Mg]CCC=C

InChI

1S/C4H7.BrH.Mg/c1-3-4-2;;/h3H,1-2,4H2;1H;/q;;+1/p-1

InChI key

SMLLHQBZPPSOSR-UHFFFAOYSA-M

Application

Synthetic building block that can undergo ring-formation reactions facilitated by ruthenium catalysts.
Used in a key diastereoselective step in the synthesis of (–)-muricatacin from L-tartaric acid.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH018,EUH019

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

-22.0 °F - closed cup

Flash Point(C)

-30 °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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Jehrod B Brenneman et al.
Organic letters, 6(8), 1329-1331 (2004-04-09)
A concise synthesis of the potent nAChR agonist (+)-anatoxin-a (1) has been completed in a series of only nine chemical operations and 27% overall yield from commercially available D-methyl pyroglutamate (4). The synthesis features a novel procedure for the diastereoselective
Tetrahedron Asymmetry, 17, 2465-2465 (2006)
Aleksandar Ivkovic et al.
Organic letters, 6(8), 1221-1224 (2004-04-09)
The combination of alkene metathesis and beta-fragmentation offers an efficient entry into (Z)-configured medium-ring cycloalkenes. The versatility of this method is demonstrated by the total synthesis of Periplanone C, a semiochemical of Periplaneta americana. [reaction: see text]
Toshio Honda et al.
Organic letters, 6(1), 87-89 (2004-01-03)
[reaction: see text] A diastereoselective total synthesis of securinine in optically pure form was achieved by employing ring-closing metathesis of the corresponding dienyne compound as a key step.

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