2,7-Bis(bromomethyl)naphthalene

Base Information

• Chemical Name: 2,7-Bis(bromomethyl)naphthalene
• CAS No.: 38309-89-6
• Molecular Formula: C12H10Br2
• Molecular Weight: 314.019
• Hs Code.: 2903999090
• European Community (EC) Number: 625-096-7
• DSSTox Substance ID: DTXSID10452319
• Nikkaji Number: J812.001C
• Wikidata: Q72444442
• Mol file: 38309-89-6.mol

Synonyms:2,7-Bis(bromomethyl)naphthalene;38309-89-6;2,7-Bis(brommethyl)naphthalen;SCHEMBL2888187;DTXSID10452319;2,7-Bis(bromomethyl)naphthalene, >=97.0% (HPLC)

Chemical Property of 2,7-Bis(bromomethyl)naphthalene

Chemical Property:

• Vapor Pressure: 7.95E-06mmHg at 25°C
• Melting Point: 146-150 °C
• Refractive Index: 1.685
• Boiling Point: 386.3 °C at 760 mmHg
• Flash Point: 219.2 °C
• PSA: 0.00000
• Density: 1.72 g/cm³
• LogP: 4.62960
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 313.91288
• Heavy Atom Count: 14
• Complexity: 163

Purity/Quality:

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

2,7-Bis(bromomethyl)naphthalene ≥97.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC2=C1C=CC(=C2)CBr)CBr
• Uses: Precursor for catalyst O,O′-Diallyl-N,N′-(2,7-naphthalindiyldimethyl)-bis-(hydrocinchonidinium) dibromide.

Technology Process of 2,7-Bis(bromomethyl)naphthalene

There total 4 articles about 2,7-Bis(bromomethyl)naphthalene 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: 98.0%

2,7-dimethylnaphthalene (582-16-1) → 2,7-bis(bromomethyl)naphthalene (38309-89-6)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80 ℃; for 9h;

DOI:10.1021/ja042848j

Reference yield:

2,7-Dihydroxynaphthalene (582-17-2) → 2,7-bis(bromomethyl)naphthalene (38309-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 1,4-dioxane / 4.33 h / 0 - 22 °C / Inert atmosphere

2: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / diethyl ether; tetrahydrofuran / 0 - 40 °C / Inert atmosphere

3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 80 °C / Inert atmosphere

With pyridine; N-Bromosuccinimide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; diethyl ether; 2: |Kumada Cross-Coupling;

DOI:10.1002/chem.201703024

Reference yield:

methanesulfonic acid 1,1,1-trifluoro-1,1'-(2,7-naphthalenedidyl) ester (151391-00-3) → 2,7-bis(bromomethyl)naphthalene (38309-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / diethyl ether; tetrahydrofuran / 0 - 40 °C / Inert atmosphere

2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 80 °C / Inert atmosphere

With N-Bromosuccinimide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; tetrachloromethane; diethyl ether; 1: |Kumada Cross-Coupling;

DOI:10.1002/chem.201703024

upstream raw materials:

2,7-dimethylnaphthalene

2,7-Dihydroxynaphthalene

methanesulfonic acid 1,1,1-trifluoro-1,1'-(2,7-naphthalenedidyl) ester

Downstream raw materials:

1,4-di-(2,7)naphtha-cyclohexane

1,2-bis-(7-methyl-[2]naphthyl)-ethane

(2,7-naphthylenedimethylene)bis[triphenylphosphonium bromide]

2,7-Bis-(m-methylstyryl)-naphthalin

Refernces

• 1、 Borkent,J.H.,Laarhoven,W.H.. "-". . p. 2565 - 2567. Retrieved 1978.
• 2、 Sakyiamah, Maxwell M.,Kobayakawa, Takuya,Fujino, Masayuki,Konno, Makoto,Narumi, Tetsuo,Tanaka, Tomohiro,Nomura, Wataru,Yamamoto, Naoki,Murakami, Tsutomu,Tamamura, Hirokazu. "Design, synthesis and biological evaluation of low molecular weight CXCR4 ligands". supporting information. p. 1130 - 1138. Retrieved 2019/02/16.
• 3、 Schaack, Cédric,Sidler, Eric,Trapp, Nils,Diederich, Fran?ois. "Helical Threads: Enantiomerically Pure Carbo[6]Helicene Oligomers". supporting information. p. 14153 - 14157. Retrieved 2017/10/17.