3-BUTENYLMAGNESIUM BROMIDE

Base Information

• Chemical Name: 3-BUTENYLMAGNESIUM BROMIDE
• CAS No.: 7103-09-5
• Molecular Formula: C4H7 Br Mg
• Molecular Weight: 159.309
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID70392606
• Mol file: 7103-09-5.mol

Synonyms:Magnesium,bromo-3-butenyl- (7CI,8CI,9CI); 1-Butene, magnesium complex;1-(Bromomagnesium)-3-butene; 1-Buten-4-ylmagnesium bromide;3-Buten-1-ylmagnesium bromide; 3-Butenylmagnesium bromide

Chemical Property of 3-BUTENYLMAGNESIUM BROMIDE

Chemical Property:

• Boiling Point: 65 °C
• Flash Point: -30 ºC
• PSA: 0.00000
• Density: 0.937
• LogP: 2.37570
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 157.95815
• Heavy Atom Count: 6
• Complexity: 14

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Butenylmagnesium bromide solution 0.5 M in THF ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,C,Xn
• Statements: 11-14/15-19-34-40-36/37/38
• Safety Statements: 16-26-36/37/39-45-43-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [CH2-]CC=C.[Mg+2].[Br-]
• Uses: Used in a key diastereoselective step in the synthesis of (–)-muricatacin from L-tartaric acid.

Technology Process of 3-BUTENYLMAGNESIUM BROMIDE

There total 5 articles about 3-BUTENYLMAGNESIUM BROMIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

1-bromo-4-butene (5162-44-7) → 4-but-1-enylmagnesium bromide (7103-09-5)

Guidance literature:

With iodine; magnesium; In tetrahydrofuran; at 70 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201605362

Reference yield:

1-bromo-4-butene (5162-44-7) + magnesium (7439-95-4) → 4-but-1-enylmagnesium bromide (7103-09-5)

Guidance literature:

With iodine; In tetrahydrofuran; for 0.5h; Heating / reflux;

Reference yield:

1-bromo-4-butene (5162-44-7) → 4-but-1-enylmagnesium bromide (7103-09-5)

Guidance literature:

With iodine; In diethyl ether; 1.) reflux, 2.) room temp., 30 min;

DOI:10.1021/jo00175a008

upstream raw materials:

1-bromo-4-butene

ethylmagnesium bromide

magnesium

Downstream raw materials:

(E)-hepta-6,3-dien-2-one

But-3-enyltriphenylsilan

((3S,4R)-3-But-3-enyl-3,4-dimethyl-cyclohex-1-enyloxy)-trimethyl-silane

2-methyl-1-hexene

Refernces

• 1、 Sandmeier, Tobias,Carreira, Erick M.. "Enantioselective Synthesis of Cyclic Nitrones by Chemoselective Intramolecular Allylic Alkylation of Oximes". supporting information. p. 9913 - 9918. Retrieved 2021/03/29.
• 2、 Usami, Kaoru,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika. "Visible-Light-Mediated Iminyl Radical Generation from Benzyl Oxime Ether: Synthesis of Pyrroline via Hydroimination Cyclization". supporting information. p. 5714 - 5717. Retrieved 2018/09/21.