4-Chloropyridine-3-boronic acid pinacol ester

Base Information

• Chemical Name: 4-Chloropyridine-3-boronic acid pinacol ester
• CAS No.: 452972-15-5
• Molecular Formula: C11H15BClNO2
• Molecular Weight: 239.51
• Hs Code.: 2933399090
• European Community (EC) Number: 670-325-6
• DSSTox Substance ID: DTXSID00476867
• Wikidata: Q72458435
• Mol file: 452972-15-5.mol

Synonyms:452972-15-5;4-Chloropyridine-3-boronic acid pinacol ester;4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;4-Chloropyridine-3-boronic acid, pinacol ester;MFCD06798247;4-Chloropyridin-3-ylboronic acid, pinacol ester;4-chloro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;4-Chloropyridine-3-boronicAcidPinacolEster;Pyridine, 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;SCHEMBL166233;(4-CHLOROPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;DTXSID00476867;KTLJNRVZMVZXMR-UHFFFAOYSA-N;AKOS015949908;AB29854;GS-6280;SY023186;AM20051194;CS-0054405;FT-0678866;A25344;A25354;EN300-191084;J-515192;Z3234953204;4-CHLOROPYRIDIN-3-YLBORONIC ACID, PINACOL ESTER 98;4-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxa borolan-2-yl)-pyridine;4-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine

Chemical Property of 4-Chloropyridine-3-boronic acid pinacol ester

Chemical Property:

• Appearance/Colour: cream powder
• Vapor Pressure: 0.000402mmHg at 25°C
• Melting Point: 110 °C
• Refractive Index: 1.505
• Boiling Point: 326.774 °C at 760 mmHg
• PKA: 3.19±0.10(Predicted)
• Flash Point: 151.428 °C
• PSA: 31.35000
• Density: 1.145 cm³
• LogP: 2.03420
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.0884366
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

98% ^*data from raw suppliers

4-Chloropyridine-3-boronic acid, pinacol ester 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CN=C2)Cl
• Uses: 4-Chloropyridine-3-boronic acid pinacol ester, HCl

Technology Process of 4-Chloropyridine-3-boronic acid pinacol ester

There total 4 articles about 4-Chloropyridine-3-boronic acid pinacol ester 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: 41.0%

4-Chloropyridine (626-61-9) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 4-chloro-3-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (452972-15-5)

Guidance literature:

4-Chloropyridine; With lithium diisopropyl amide; In diethyl ether; at -60 ℃; for 0.75h;

With Triisopropyl borate; In diethyl ether; at -60 - 20 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In diethyl ether; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00283-1

Reference yield: 20.0%

3-bromo-4-chloropyridine (36953-42-1) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 4-chloro-3-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (452972-15-5)

Guidance literature:

3-bromo-4-chloropyridine; With n-butyllithium; In diethyl ether; at -78 ℃; for 1h;

With Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In diethyl ether; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00283-1

Reference yield:

2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (557087-01-1) + 4-chlorpyridine hydrochloride (7379-35-3) → 4-chloro-3-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (452972-15-5)

Guidance literature:

2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4-chlorpyridine hydrochloride; With n-butyllithium; diisopropylamine; In diethyl ether; at 0 ℃; for 0.5h; Inert atmosphere;

With lithium diisopropyl amide; In diethyl ether; at 20 ℃; for 2h; Inert atmosphere;

upstream raw materials:

4-Chloropyridine

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

3-bromo-4-chloropyridine

2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

5-[4-(4-chloropyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester

Refernces

• 1、 Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valerie,Bovy, Philippe R.,Rault, Sylvain. "Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters". . p. 3323 - 3328. Retrieved 2007/10/03.