2-(Methoxymethoxy)phenylboronic acid

Base Information

• Chemical Name: 2-(Methoxymethoxy)phenylboronic acid
• CAS No.: 115377-93-0
• Molecular Formula: C8H11BO4
• Molecular Weight: 181.984
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID80447196
• Nikkaji Number: J1.247.559D
• Wikidata: Q72490231
• Mol file: 115377-93-0.mol

Synonyms:2-(METHOXYMETHOXY)PHENYLBORONIC ACID;115377-93-0;[2-(methoxymethoxy)phenyl]boronic Acid;MFCD10566597;(2-(Methoxymethoxy)phenyl)boronic acid;Boronic acid, B-[2-(methoxymethoxy)phenyl]-;SCHEMBL3654163;DTXSID80447196;SPJBOWONADYEPF-UHFFFAOYSA-N;2-(Methoxymethoxy)phenylboronicacid;AKOS006304553;AS-55631;SY104605;CS-0134705;FT-0723772;D71361;B-[2-(METHOXYMETHOXY)PHENYL]BORONIC ACID;A893888

Chemical Property of 2-(Methoxymethoxy)phenylboronic acid

Chemical Property:

• PSA: 58.92000
• Density: 1.19
• LogP: -0.65090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 182.0750390
• Heavy Atom Count: 13
• Complexity: 142

Purity/Quality:

98% ^*data from raw suppliers

2-(Methoxymethoxy)phenylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1OCOC)(O)O

Technology Process of 2-(Methoxymethoxy)phenylboronic acid

There total 7 articles about 2-(Methoxymethoxy)phenylboronic acid 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: 71.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-2-(methoxymethoxy)benzene (68314-54-5) + water (7732-18-5) → ortho-methoxymethyleneoxyphenylboronic acid (115377-93-0)

Guidance literature:

1-bromo-2-(methoxymethoxy)benzene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 2h; Inert atmosphere;

water; With ammonium chloride; In tetrahydrofuran; pentane; Inert atmosphere;

DOI:10.1016/j.bmc.2017.10.030

Reference yield: 45.2%

1-bromo-2-(methoxymethoxy)benzene (68314-54-5) → ortho-methoxymethyleneoxyphenylboronic acid (115377-93-0)

Guidance literature:

1-bromo-2-(methoxymethoxy)benzene; With n-butyllithium; In diethyl ether; at -65 ℃; for 1.16667h; Inert atmosphere;

With triethyl borate; In diethyl ether; at -65 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.molstruc.2008.12.006

Reference yield: 45.2%

triethyl borate (150-46-9) + 1-bromo-2-(methoxymethoxy)benzene (68314-54-5) + sulfuric acid (7664-93-9) → ortho-methoxymethyleneoxyphenylboronic acid (115377-93-0)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; under Ar atm.; Et2O cooled to -65°C; n-BiLi in hexane added slowly to stirred solvent; bromide dropped; mixt. stirred for 1 h at -65°C; (EtO)3B dropped; mixt. stirred for 1 h at -65°C; H2SO4 quickly added; temp. rose until about 20; phases sepd.; aq. phase extd. (Et2O); solvent (about 3/4 vol.) removed (vac.); H2O added; evapd. for 0.5 h; aq. phase removed by decantation; hexane added; slurry kept at 4°C for 11 d; solid filtered off; dissolved (acetone/H2O); standing at room;

DOI:10.1016/j.molstruc.2008.12.006

upstream raw materials:

Trimethyl borate

O-methoxymethylphenol

1-bromo-2-(methoxymethoxy)benzene

triethyl borate

Downstream raw materials:

4-formyl-12-(2-oxymethylenemethoxyphenyl)-[2.2]paracyclophane

2-methoxymethoxyphenylboronic acid MIDA ester

2-hydroxyphenylboronic acid MIDA ester

Refernces

• 1、 Fukuda, Tsutomu,Umeki, Teppei,Tokushima, Keiji,Xiang, Gao,Yoshida, Yuki,Ishibashi, Fumito,Oku, Yusuke,Nishiya, Naoyuki,Uehara, Yoshimasa,Iwao, Masatomo. "Design, synthesis, and evaluation of A-ring-modified lamellarin N analogues as noncovalent inhibitors of the EGFR T790M/L858R mutant". supporting information. p. 6563 - 6580. Retrieved 2017/11/17.
• 2、 Oishi,Yamamoto. "Polymerization of t-butyl vinyl ether mediated by an aluminum Lewis acid-TrF system and its complex structure-tacticity correlation". . p. 1445 - 1454. Retrieved 2007/10/03.