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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

functional group

allyl

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

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

419591-VAR:
419591-BULK:
419591-100ML:4548173287515
419591-800ML:4548173287522

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN6815
SHBN0959
SHBL3404
SHBK5503
SHBG5800V

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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]
Tetrahedron Asymmetry, 17, 2465-2465 (2006)
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.
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

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