Bromozinc(1+);heptanenitrile

Base Information

• Chemical Name: Bromozinc(1+);heptanenitrile
• CAS No.: 312624-28-5
• Molecular Formula: C₇H₁₂BrNZn
• Molecular Weight: 255.473
• DSSTox Substance ID: DTXSID30412511
• Mol file: 312624-28-5.mol

Synonyms:bromozinc(1+);heptanenitrile;312624-28-5;DTXSID30412511;J-018324

Chemical Property of Bromozinc(1+);heptanenitrile

Chemical Property:

• Vapor Pressure: 0.679mmHg at 25°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 23.79000
• Density: g/cm³
• LogP: 3.27118
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 252.94445
• Heavy Atom Count: 10
• Complexity: 79.6

Purity/Quality:

99% ^*data from raw suppliers

6-Cyanohexylzinc bromide solution 0.5M in THF ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xn
• Statements: 19-22-36/38-40-36/37-14-11
• Safety Statements: 16-26-33-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [CH2-]CCCCCC#N.[Zn+]Br
• Uses: 6-Cyanohexylzinc bromide is an organozinc compound, which can be used as a reactant in palladium-catalyzed Negishi cross-coupling reaction to construct carbon-carbon bonds by coupling with organic halides or triflates.It can also be used as a reactant to synthesize: Cyanohexyl substituted aryl derivatives by palladium catalyzed coupling reaction with aryl bromides. Methyl 5-(6-cyanohexyl)-3-methylfuran-2-carboxylate, a key intermediate which is used in the preparation of cyclic furfuryl ether via Wittig rearrangement.

Technology Process of Bromozinc(1+);heptanenitrile

There total 1 articles about Bromozinc(1+);heptanenitrile 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:

7-bromo-heptanonitrile (20965-27-9) + zinc (7440-66-6) → 6-cyanohexylzinc bromide (312624-28-5)

Guidance literature:

With N,N-dimethyl acetamide; for 4h; Milling;

DOI:10.1002/anie.201806480

Reference yield: 82.0%

Ethyl 4-bromobenzoate (5798-75-4) + 6-cyanohexylzinc bromide (312624-28-5) → ethyl 4-(6-cyanohexyl)benzoate

Guidance literature:

With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; tetrabutylammomium bromide; for 4h; Milling;

DOI:10.1002/anie.201806480

Reference yield:

6-cyanohexylzinc bromide (312624-28-5) → heptanenitrile (629-08-3)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; for 0.333333h;

DOI:10.1002/anie.201806480

upstream raw materials:

7-bromo-heptanonitrile

zinc

Downstream raw materials:

heptanenitrile

Refernces

• 1、 Fulton, Tyler J.,Alley, Phebe L.,Rensch, Heather R.,Ackerman, Adriana M.,Berlin, Cameron B.,Krout, Michael R.. "Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N, N-Dimethylacetamide". . p. 14723 - 14732. Retrieved 2018/11/23.