2-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 83622-41-7
• Molecular Formula: C7H13BCl2O2
• Molecular Weight: 210.896
• European Community (EC) Number: 870-870-1
• DSSTox Substance ID: DTXSID40453031
• Nikkaji Number: J1.955.239J
• Wikidata: Q82274007
• Mol file: 83622-41-7.mol

Synonyms:83622-41-7;2-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 2-(dichloromethyl)-4,4,5,5-tetramethyl-;SCHEMBL3332568;DTXSID40453031;GQFQFYFLABSDDS-UHFFFAOYSA-N;MFCD27976342;AKOS028108839;AS-55673;Pinacol (dichloromethyl) boronate, >=95%;CS-0061124;D4615;W17646;EN300-6222218;A902221;Z1861999629;2-Dichloromethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Refractive Index: n/D 1.4511
• Boiling Point: 103 °C(Press: 20 Torr)
• PSA: 18.46000
• Density: 1.1423
• LogP: 2.84140
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 210.0385652
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

97% ^*data from raw suppliers

Pinacol (dichloromethyl) boronate ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C(Cl)Cl
• Uses: Pinacol (dichloromethyl) boronate is a general reagent that was employed by Prof. Greg C. Fu and coworkers to achieve the iterative synthesis of asymmetric (secondary) alkyl boronate esters. These can be further derivatized through a growing suite of chemical transformations developed in the last decade (cross coupling, oxidation, amination, halogenation) that proceed with stereochemical fidelity.

Technology Process of 2-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 4 articles about 2-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 89.0%

Trimethyl borate (121-43-7,63156-11-6) + 2,3-dimethylbutane-2,3-diol hexahydrate → pinacol dichloromethylboronic ester (83622-41-7)

Guidance literature:

With n-butyllithium; dichloromethane; In benzene; byproducts: H2O; (Ar); trimethylborate reacted with CH2Cl2 and n-C4H9Li/hexane accordingto Rathke's method, solvent removed (vac.), taken up in C6H6 with pinacol hexahydrate, refluxed for 72 h; cooled to room temp., fractionally distd. (inert gas); elem. anal.;

DOI:10.1016/S0022-328X(00)85850-7

Reference yield: 40.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + Trimethyl borate (121-43-7,63156-11-6) + dichloromethane (75-09-2) → pinacol dichloromethylboronic ester (83622-41-7)

Guidance literature:

dichloromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 1h;

Trimethyl borate; In tetrahydrofuran; hexane; for 0.5h;

2,3-dimethyl-2,3-butane diol; In benzene; for 48h; Inert atmosphere; Reflux;

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + (dichloromethyl)boronic acid (62260-98-4) → pinacol dichloromethylboronic ester (83622-41-7)

Guidance literature:

In benzene; for 48h; Heating;

DOI:10.1021/ja039550y

upstream raw materials:

2,3-dimethyl-2,3-butane diol

(dichloromethyl)boronic acid

Trimethyl borate

dichloromethane

Downstream raw materials:

(E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(Z)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-((1E,3E)-4-(2,4-dimethoxyphenyl)buta-1,3-dienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

C₁₉H₂₉BO₄