2-Chloro-1,3,2-benzodioxaborole

Base Information

• Chemical Name: 2-Chloro-1,3,2-benzodioxaborole
• CAS No.: 55718-76-8
• Molecular Formula: C6H4BClO2
• Molecular Weight: 154.361
• Hs Code.: 2934999090
• European Community (EC) Number: 628-352-6
• DSSTox Substance ID: DTXSID10399755
• Nikkaji Number: J510.753I
• Wikidata: Q82202468
• Mol file: 55718-76-8.mol

Synonyms:55718-76-8;2-Chloro-1,3,2-benzodioxaborole;B-Chlorocatecholborane;2-Chlorobenzo[d][1,3,2]dioxaborole;Beta-chlorocatecholborane;1,3,2-Benzodioxaborole, 2-chloro-;chlorocatecholborane;SCHEMBL28709;B-Chlorocatecholborane, 97%;DTXSID10399755;AZYGEWXDKHFOKB-UHFFFAOYSA-N;2-Chloro-1,3-dioxa-2-boraindan;3,3-DIETHOXY-PROPIONICACID;MFCD00043395;2-chloro-2H-1,3,2-benzodioxaborole;AKOS025213343;AS-55608;C1669;CS-0142780;FT-0691596;D89444;A902520

Chemical Property of 2-Chloro-1,3,2-benzodioxaborole

Chemical Property:

• Vapor Pressure: 0.906mmHg at 25°C
• Melting Point: 56-58 °C(lit.)
• Refractive Index: 1.536
• Boiling Point: 186.554 °C at 760 mmHg
• Flash Point: 66.626 °C
• PSA: 18.46000
• Density: 1.32 g/cm³
• LogP: 1.68150
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 153.9992872
• Heavy Atom Count: 10
• Complexity: 119

Purity/Quality:

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

2-?Chloro-?1,?3,?2-?benzodioxaborole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F
• Hazard Codes: F,C
• Statements: 11-14-34-37
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC2=CC=CC=C2O1)Cl
• Uses: B-Chlorocatecholborane can be used:To prepare 2-arachidonoylglycerol by acetal cleavage of cis-arachidonoylbenzylidene glycerol.To prepare metal boryl complexes (Rh and Ir complexes) through oxidative addition.To remove the trityl group in one of the key steps for the synthesis of (?)-dictyostatin.

Technology Process of 2-Chloro-1,3,2-benzodioxaborole

There total 2 articles about 2-Chloro-1,3,2-benzodioxaborole 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: 70.0%

[OsCl(η6-p-cymene)(1,3-bis(2,6-diisopropylphenyl)imidazolylidene)][trifluoromethanesulfonate] + benzo[1,3,2]dioxaborole (274-07-7) → 2-chloro-1,3,2-benzodioxaborole (55718-76-8) + [OsH2(η6-p-cymene)(1,3-bis(2,6-diisopropylphenyl)imidazolylidene)(catecholborane(-1H))][trifluoromethanesulfonate]

Guidance literature:

In diethyl ether; dichloromethane; at 20 ℃;

DOI:10.1021/om400188z

Reference yield:

(o-C6H4O2)BSH (57100-59-1) → sulfur (10544-50-0) + 2-chloro-1,3,2-benzodioxaborole (55718-76-8) + hydrogen sulfide (7783-06-4)

Guidance literature:

With chlorine;

Reference yield: 100.0%

2-chloro-1,3,2-benzodioxaborole (55718-76-8) + 2-phenylethynylphenol (92151-73-0) → C20H13BO3 (1581275-98-0)

Guidance literature:

In diethyl ether; at -78 - 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.organomet.5b00939

upstream raw materials:

(o-C₆H₄O₂)BSH

benzo[1,3,2]dioxaborole

Downstream raw materials:

catechol butyl borate

2-(benzylthio)benzo[d][1,3,2]dioxaborole

(4-methylphenylthio)catecholborane

2-(phenylethynyl)benzo[d][1,3,2]dioxaborole

Refernces