(R)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl

Base Information

• Chemical Name: (R)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl
• CAS No.: 179866-74-1
• Molecular Formula: C₂₄H₂₀Br₂O₄
• Molecular Weight: 532.228
• Hs Code.: 2909309090
• European Community (EC) Number: 633-811-9,634-031-1
• Nikkaji Number: J2.580.979C,J944.856J
• Mol file: 179866-74-1.mol

Synonyms:179866-74-1;211560-97-3;(S)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene;(R)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl;(R)-(+)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl;389867-61-2;(S)-6,6'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl;(R)-(+)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene;6-bromo-1-[6-bromo-2-(methoxymethoxy)naphthalen-1-yl]-2-(methoxymethoxy)naphthalene;6,6'-DIBROMO-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;6,6'-DIBROMO-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHALENE;MFCD03788936;(S)-(-)-6,6'-DIBROMO-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHALENE;(S)-(-)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl;SCHEMBL1305573;UPLLZDVWXACTEG-UHFFFAOYSA-N;AKOS015913110;AKOS016000618;SC11854;BS-52952;CS-0035243;CS-0086007;D4882;D4883;FT-0666482;FT-0703168;PK04_181215;D90346;E72678;J-011474;J-013887;2,2'-Di(methoxymethoxy)-6,6'-dibromo-1,1'-binaphthalene;(aR)-2,2'-Bis(methoxymethoxy)-6,6'-dibromo-1,1'-binaphthalene;(R)-(+)-6,6'-dibromo-2,2'-di(methoxymethyl)oxy-1,1'-binaphthyl;(S)-(-)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene, 97%

Chemical Property of (R)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl

Chemical Property:

• Melting Point: 129-133 °C(lit.)
• Boiling Point: 553.012 °C at 760 mmHg
• Flash Point: 232.823 °C
• PSA: 36.92000
• Density: 1.525 g/cm³
• LogP: 7.15040
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Toluene
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 531.97078
• Heavy Atom Count: 30
• Complexity: 489

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

(R)-6,6''-Dibromo-2,2''-bis(methoxymethoxy)-1,1''-binaphthyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 25-26-36/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCOC1=C(C2=C(C=C1)C=C(C=C2)Br)C3=C(C=CC4=C3C=CC(=C4)Br)OCOC
• Uses: An intermediate in the symmetric synthesis of BINOL-terpyridine ligands, and the starting material for the preparation of a variety of 6,6' and 3,3'-substituted BINOLS. .

Technology Process of (R)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl

There total 5 articles about (R)-6,6'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 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: 90.0%

(S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol (79082-80-7) + chloromethyl methyl ether (107-30-2) → (R)-6,6'-dibromo-2,2'-dimethoxymethoxy-1,1'-binaphthalene (211560-97-3,389867-61-2,179866-74-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(00)01486-6

Reference yield: 86.5%

(S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol (79082-80-7) + methoxymethoxy chloride (150587-19-2) → (R)-6,6'-dibromo-2,2'-dimethoxymethoxy-1,1'-binaphthalene (211560-97-3,389867-61-2,179866-74-1)

Guidance literature:

(S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 1h; Inert atmosphere;

methoxymethoxy chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 4.5h; Inert atmosphere;

DOI:10.1021/ol400790d

Reference yield:

1,1'-bi-2-naphthol (602-09-5) → (R)-6,6'-dibromo-2,2'-dimethoxymethoxy-1,1'-binaphthalene (211560-97-3,389867-61-2,179866-74-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: bromine / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.2: 4.5 h / 0 - 20 °C / Inert atmosphere

With bromine; sodium hydride; In tetrahydrofuran; dichloromethane; mineral oil;

DOI:10.1021/ol400790d

upstream raw materials:

(S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol

chloromethyl methyl ether

β-naphthol

1,1'-bi-2-naphthol

Refernces

• 1、 Hu, Qiao-Sheng,Vitharana, Dilrukshi,Zheng, Xiao-Fan,Wu, Chi,Kwan, Chi Man Simon,Pu, Lin. "Poly(1,1′-bi-2-naphthol)s: Synthesis, characterization, and application in Lewis acid catalysis". . p. 8370 - 8377. Retrieved 1996.
• 2、 Bai, Xiao-Li,Liu, Xu-Dong,Wang, Mang,Kang, Chuan-Qing,Gao, Lian-Xun. "Synthesis of new bis-BINOLs linked by a 2,2e′-bipyridine bridge". . p. 458 - 464. Retrieved 2007/10/03.