1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Base Information

• Chemical Name: 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• CAS No.: 761446-44-0
• Molecular Formula: C10H17BN2O2
• Molecular Weight: 208.068
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID40378816
• Nikkaji Number: J2.139.002J
• Wikidata: Q72496282
• Mol file: 761446-44-0.mol

Synonyms:761446-44-0;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Methylpyrazole-4-boronic acid pinacol ester;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole;1-methyl-1h-pyrazole-4-boronic acid pinacol ester;MFCD03789259;C10H17BN2O2;1-methylpyrazole-4-boronic acid, pinacol ester;1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-methyl-pyrazole-4-boronic acid pinacol ester;1H-PYRAZOLE, 1-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;1-Methy-4-(4,4,5,5,-tertamethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-methyl pyrazole-4-boronic acid pinacol ester;1-Methyl-4-pyrazole boronic acid pinacol ester;1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1h-pyrazole;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)-1H-pyrazole;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-METHYLPYRAZOLE;1-Methylpyrazole-4-boronicacidpinacol ester;N-Methylpyrazole-4-boronic acid pinacol ester;SCHEMBL119232;DTXSID40378816;BCP26644;CS-M3409;RB2052;STK695158;AKOS005259008;AS-2991;BCP9000053;PB23372;NCGC00334729-01;AC-25837;BP-21255;SY003667;1-methylpyrazol-4-boronic acid pinacol ester;A9655;AM20100745;FT-0649385;M2339;1-Methyl-4-pyrazoleboronic acid pinacol ester;EN300-101866;n-methyl pyrazole-4-boronic acid pinacol ester;AB01326663-02;1-methyl-4-1h-pyrazoleboronic acid pinacol ester;1-Methylpyrazole-4-boronic acid pinacol ester, 95%;Q-103249;1-methyl--1H-pyrazole-4- boronic acid pinacol ester;F0001-2484;Z1336745109;(1-METHYL-1H-PYRAZOL-4-YL)BORONIC ACID PINACOL ESTER;1-METHYL-1H-PYRAZOLE- 4-BORONIC ACID, PINACOL ESTER;1-Methyl-4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-pyrazole;1-methyl-4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole;1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1h -pyrazole;1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazol;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyrazole;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1 H-pyrazole;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h pyrazole;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-pyrazole;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazole;2-(1-Methyl-4-pyrazolyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(1-METHYLPYRAZOL-4-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-methyl-pyrazole;methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Methyl-4-(4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolan-2-yl)-1H-pyrazole;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Methylpyrazole-4-boronic Acid Pinacol Ester

Chemical Property of 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 59-64 °C(lit.)
• Refractive Index: 1.505
• Boiling Point: 308.3 °C at 760 mmHg
• PKA: 2.09±0.10(Predicted)
• Flash Point: 140.3 °C
• PSA: 36.28000
• Density: 1.05 g/cm³
• LogP: 0.71930
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Chloroform (slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 208.1383080
• Heavy Atom Count: 15
• Complexity: 242

Purity/Quality:

98%, ^*data from raw suppliers

1-Methylpyrazole-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, F, Xi
• Hazard Codes: Xn,F,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(N=C2)C
• Uses: 1-Methyl-4-pyrazole boronic acid pinacol ester is a reagent used for:Suzuki-Miyaura cross-coupling reactions1,2,3? ;Transesterification reactions4Reagent used for preparation of? ;Aminothiazoles as γ-secretase modulators5? ;Amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy6? ;Pyridine derivatives as TGF-β1 and activin A signalling inhibitors7? ;MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer8. suzuki reaction It is a reagent used for Suzuki-Miyaura cross-coupling reactions, transesterification reactions. It is involved in several reactions as a reagent for the preparation of aminothiazoles as γ-secretase modulators,amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy, pyridine derivatives as TGF-β1 and active A signaling inhibitors and MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer.

Technology Process of 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

There total 14 articles about 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 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: 93.0%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + methyl iodide (74-88-4) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

Reference yield: 92.0%

→ 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Guidance literature:

With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct; XPhos; In ethanol; at 20 ℃; for 1h;

Reference yield: 80.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (1-methyl-1H-pyrazol-4-yl)boronic acid (847818-55-7) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Guidance literature:

With 4 A molecular sieve; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/jhet.5570410612

upstream raw materials:

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

(1-methyl-1H-pyrazol-4-yl)boronic acid

pyrazole-4-boronic acid pinacol ester

methyl iodide

Downstream raw materials:

3-(1-methyl-1H-pyrazol-4-yl)-cyclohex-2-enone

[(R)-1-({5-Fluoro-2-[2-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-4-ylamino}-methyl)-propyl]-carbamic acid tert-butyl ester

methyl 2-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenyl)acetate

tert-butyl 3-(2-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoate

Refernces

• 1、 -. "AMINOPYRAZINE COMPOUNDS AS HPK1 INHIBITOR AND THE USE THEREOF". Page/Page column 94. . Retrieved 2021/02/26.
• 2、 -. "Method for preparing aryl boronate at room temperature". Paragraph 0020-0022; 0049-0051; 0081-0083. . Retrieved 2019/05/11.