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

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

1-Methyl-4-pyrazole boronic acid pinacol ester Basic information 1-Methyl-4-pyrazole boronic acid pinacol ester Chemical Properties Safety Information 1-Methyl-4-pyrazole boronic acid pinacol ester Usage And Synthesis 1-Methyl-4-pyrazole boronic acid pinacol ester Preparation Products And Raw...

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Product Details:

1-Methyl-4-pyrazole boronic acid pinacol ester Basic information

Product Name:

1-Methyl-4-pyrazole    boronic acid pinacol ester

Synonyms:

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-;1-METHYL-    4-PYRAZOLEBORONIC ACID PINACOL ESTER;1-METHYL-4-(4,4,5,5-TERAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-;1-Methyl-4-pyrazoleboronic    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-trimethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole;1-Methyl-1H-pyrazole-4-boronic acid pinacol;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole1-Methylpyrazole-4-boronic    acid pinacol ester

CAS:

761446-44-0

MF:

C10H17BN2O2

MW:

208.07

EINECS:

1312995-182-4

Product Categories:

Organoborons;Pyrazole;Boronic acid;Heterocyclic Building Blocks;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronate Esters;Organometallic Reagents

Mol File:

761446-44-0.mol

image001.gif


1-Methyl-4-pyrazole boronic acid pinacol ester Chemical Properties

Appearance:

white to light yellow crystal    powder

Density:

1.05 g/cm3

Melting   Point:

59-64ºC

Boiling   Point:

308.3ºC at 760 mmHg

Flash    Point:

140.3ºC

Refractive   Index:

1.505

Storage   Condition:

Refrigerator (+4ºC)

form 

Crystals

color 

Off-white to yellow

Water Solubility 

Slightly soluble in water.

InChIKey

UCNGGGYMLHAMJG-UHFFFAOYSA-N

CAS DataBase Reference

761446-44-0(CAS    DataBase Reference)


Safety Information

Hazard Codes 

Xn,F,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant/Flammable

HazardClass 

IRRITANT

Hs code

2933199090


1-Methyl-4-pyrazole boronic acid pinacol ester Usage And Synthesis

Chemical Properties

White to light yellow crystal    powde

Uses

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

Uses

suzuki reaction

Intermediate as

910462-43-0 4SC-202, 943540-75-8    JNJ-38877605, 917879-39-1 MK-2461,1001917-37-8 MK8033

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Synthesis route

image011_副本.jpg

Reference:

PROGENICS PHARMACEUTICALS, INC. Patent:    WO2009/155527 A2, 2009 ; Location in patent: Page/Page column 137-138 ; WO    2009/155527 A2
Journal of Medicinal Chemistry, , vol. 52, # 24 p.    7934 - 7937

image013_副本.jpg

Reference:

Stewart, Gavin W.; Brands, Karel M. J.; Brewer, Sarah E.; Cowden, Cameron J.; Davies, Antony J.; Edwards, John S.; Gibson, Andrew W.; Hamilton, Simon E.; Katz, Jason D.; Keen, Stephen P.; Mullens, Peter R.; Scott, Jeremy P.; Wallace, Debra J.; Wise, Christopher S. Organic Process Research and Development, 2010 , vol. 14, # 4 p. 849 - 858

image015_副本.jpg

Reference:

Ivachtchenko, Alexandre V.; Kravchenko,    Dmitry V.; Zheludeva, Valentina I.; Pershin, Dmitry G. Journal of Heterocyclic   Chemistry, 2004 , vol. 41, # 6 p. 931 - 939


1-Methyl-4-pyrazole boronic acid pinacol ester Preparation Products And Raw materials

Raw materials

Tetrahydrofuran-->Potassium    hydroxide -->n-Butyllithium-->Iodomethane-->Trimethyl    borate-->Methyl    bromide -->Pinacol-->MOLECULAR    SIEVE-->4-Bromopyrazole


Upstream information

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole; 4-Chlorotoluene; 5-Bromo-2-naphthoic acid; bromomethane; 2-(6-bromo-2,3-dihydro-1,4-benzoxazin-4-yl)-6,6-dimethyl-5,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one; chlorobenzene; 1-Methyl-1H-pyrazole-4-boronic acid; 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole; N-methylpyrazole; iodomethane;


Downtream information

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole; 1-methyl-4-phenylpyrazole; 1-methyl-4-(4-methylphenyl)pyrazole; 6,6-dimethyl-2-[6-(1-methylpyrazol-4-yl)-2,3-dihydro-1,4-benzoxazin-4-yl]-5,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one; 1-[2-(1-methylpyrazol-4-yl)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]-N-(pyridin-2-ylmethyl)methanesulfonamide; 5-(1-methylpyrazol-4-yl)naphthalene-2-carboxylic acid


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