1-Methylpyrazole-4-boronic acid pinacol ester supplier

Name
1-Methyl-4-pyrazole boronic acid pinacol ester
EINECS 616-293-9
CAS No. 761446-44-0
Article Data22
CAS DataBase
Density 1.05 g/cm³
Solubility Slightly soluble in water.
Melting Point 59-64 °C(lit.)
Formula C₁₀H₁₇BN₂O₂
Boiling Point 308.3 °C at 760 mmHg
Molecular Weight 208.068
Flash Point 140.3 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-37/39
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn, F, Xi
Synonyms 1H-Pyrazole,1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;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;
PSA 36.28000
LogP 0.71930

Synthetic route

: 269410-08-4
pyrazole-4-boronic acid pinacol ester

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 4h;	93%
With sodium hydride In tetrahydrofuran at 20℃;	90%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 3h;	72%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 60℃; for 8h; Inert atmosphere;	63%

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 847818-55-7
(1-methyl-1H-pyrazol-4-yl)boronic acid

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

Conditions

Conditions	Yield
With 4 A molecular sieve In tetrahydrofuran at 20℃; for 2h;	80%
With alkaline lipase In tetrahydrofuran; ethanol at -15 - -10℃; for 12h; Concentration; Reagent/catalyst; Molecular sieve; Large scale; Enzymatic reaction;	92.5 kg

: 930-36-9
1-methyl-1H-pyrazole

: 76-09-5
2,3-dimethyl-2,3-butane diol

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

Conditions

Conditions	Yield
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium Stage #2: With Trimethyl borate In tetrahydrofuran at -90℃; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran	80%

: 15803-02-8
4-bromo-1-methyl-1H-pyrazole

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 5h; Inert atmosphere;	27.1%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; Suzuki-Miyaura Coupling;

: 269410-08-4
pyrazole-4-boronic acid pinacol ester

: 74-83-9
methyl bromide

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

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile Inert atmosphere;

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 22038-72-8, 26981-93-1, 51943-20-5
methyldiazene

: C19H43BN2O4

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

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux;

...Expand

: 35852-81-4
4-chloro-1-methyl-1H-pyrazole

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); XPhos In ethanol at 20℃; for 2h;

: 39806-90-1
4-iodo-1-methyl-1H-pyrazole

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Conditions

Conditions	Yield
Stage #1: 4-iodo-1-methyl-1H-pyrazole With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; for 1.5h;	1 g

: 930-36-9
1-methyl-1H-pyrazole

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A: 847818-74-0
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

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

Conditions

Conditions	Yield
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In hexane at 20℃; Glovebox; Inert atmosphere; Stage #2: With 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; Glovebox; Inert atmosphere; Stage #3: 1-methyl-1H-pyrazole In hexane at 20℃; for 5h; Reagent/catalyst; Solvent; Glovebox; Inert atmosphere; Overall yield = 67 percent; regioselective reaction;

Yield

Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In hexane at 20℃; Glovebox; Inert atmosphere;
Stage #2: With 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; Glovebox; Inert atmosphere;
Stage #3: 1-methyl-1H-pyrazole In hexane at 20℃; for 5h; Reagent/catalyst; Solvent; Glovebox; Inert atmosphere; Overall yield = 67 percent; regioselective reaction;

...Expand

: 269410-08-4
pyrazole-4-boronic acid pinacol ester

methyl halide: methyl halide

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

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile

: 15803-02-8
4-bromo-1-methyl-1H-pyrazole

: 76-09-5
2,3-dimethyl-2,3-butane diol

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

Conditions

Conditions	Yield
Stage #1: 4-bromo-1-methyl-1H-pyrazole With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -75 - -65℃; Inert atmosphere; Large scale; Stage #2: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran; hexane; toluene at -75 - 20℃; Large scale;

: 3-bromo-5-trifluoromethylbenzoic acid methyl ester

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

: 1237536-10-5
methyl 3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)benzoate

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃;	100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 3h; Suzuki Coupling;	100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 3h;	100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 3h;	100%

: 1160756-09-1
7-chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4, 3-b ]indole-4-carboxamide

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

: 1160756-20-6
1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-7-(1-methyl-1H-pyrazol-4-yl)-5H-pyrido[4,3-b]indole-4-carboxamide

Conditions

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	100%

: 1430728-70-3
N-(3-(5-bromo-1H-benzo[d]imidazol-1-yl)-5-(1-(phenylsulfonyl)-1H-indol-3-yl)phenyl)acetamide

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

: 1430728-71-4
N-(3-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-5-(1-(phenylsulfonyl)-1H-indol-3-yl)phenyl)acetamide

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; Inert atmosphere;	100%

: 1403396-16-6
3-[1-(4-bromo-2-fluorophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

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

: 1403396-88-2
8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 120℃; for 1h; Microwave irradiation;	100%

: 1403396-34-8
3-[1-(4-bromo-3-fluorophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

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

: 1403396-91-7
8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[3-fluoro-4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 120℃; for 1h; Microwave irradiation;	100%

: 1403396-89-3
(8R)-3-[1-(4-bromo-2-fluorophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

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

: 1403396-90-6
(8R)-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water Reflux;	100%

: 1403396-04-2
(8R)-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-[1-(4-chlorophenyl)cyclopropyl]-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

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

: 1403396-43-9
(8R)-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-{1-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

Conditions

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane; water at 140℃; for 2h; Microwave irradiation;	100%

: 1029720-67-9
5-bromo-3-chloroisoquinoline

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

: 1578245-81-4
3-chloro-5-(1-methyl-1H-pyrazol-4-yl)isoquinoline

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 105℃; for 1.5h; Suzuki Coupling; Microwave irradiation;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 110℃; for 2h; Microwave irradiation;

: 1578245-95-0
8-chloro-2-(methylsulfanyl)pyrido[3,4-d]pyrimidine

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

: 1578245-98-3
8-(1-methyl-1H-pyrazol-4-yl)-2-(methylthio)pyrido[3,4-d]pyrimidine

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran; water at 65℃; for 18h;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran at 65℃; for 18h; Suzuki Coupling;	100%

: 3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine

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

: 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 24h; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 24h; Suzuki Coupling; Inert atmosphere;

: tert-butyl (R)-3-(7-bromo-2,2-dioxido-1,4-dihydro-3H-benzo[c][1,2,6]thiadiazin-3-yl)pyrrolidine-1-carboxylate

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

: tert-butyl (R)-3-(7-(1-methyl-1H-pyrazol-4-yl)-2,2-dioxido-1,4-dihydro-3H-benzo[c][1,2,6]thiadiazin-3-yl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 90℃; for 1h; Sealed tube;	100%

: ethyl 9'-(1-(tertbutoxycarbonyl)-1H-pyrazol-4-yl)-10'-methoxy-2'-oxo-2',7'-dihydrospiro[cyclobutane-1,6'pyrido[2,1-a]isoquinoline]-3'-carboxylate

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

: ethyl 10'-methoxy-9'-(1-methyl-1H-pyrazol-4-yl)-2'-oxo-2',7'-dihydrospiro[cyclobutane-1,6'-pyrido[2,1-a]isoquinoline]-3'-carboxylate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane; water at 100℃; Inert atmosphere;	100%

: (S)-4-(4-(5-(1-amino-1-(4-fluorophenyl)ethyl)pyrimidin-2-yl)piperazin-1-yl)-6-bromopyrrolo[1,2-b]pyridazine-3-carbonitrile

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

: (S)-4-(4-(5-(1-amino-1-(4-fluorophenyl)ethyl)pyrimidin-2-yl)piperazin-1-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carbonitrile

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	100%

: 19718-49-1
4-amino-3-iodobenzoic acid methyl ester

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

: methyl 4-amino-3-(1-methyl-1H-pyrazol-4-yl)benzoate

Conditions

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In 1,4-dioxane; water at 90℃; for 8h; Inert atmosphere;	100%

: 2-amino-6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile

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

: 2-amino-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;	100%

: 22282-99-1
4-bromo-2-methylpyridine

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

: 2-methyl-4-(1-methyl-1H-pyrazol-4-yl)pyridine

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 85℃; for 12h; Suzuki Coupling; Inert atmosphere;	100%

: 875-51-4
4-Bromo-2-nitroaniline

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

: 959909-79-6
4-(1-methyl-1H-pyrazol-4-yl)-2-nitroaniline

Conditions

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In ISOPROPYLAMIDE; water at 80℃; for 1h; Suzuki Coupling;	99%
With sodium carbonate In N,N-dimethyl acetamide; water at 80℃; for 1h; Inert atmosphere;	99%
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl acetamide; water at 80℃; for 1h; Suzuki Coupling;	99%

: 117718-92-0
8-amino-3-bromoimidazo<1,2-a>pyrazine

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

: C10H10N6

Conditions

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 80℃; for 16h;	99%
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 80℃; for 16h;	99%

: 1200130-75-1
9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b:4',3'-d]pyrrole-6-carbonitrile

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

: 1200130-78-4
9-benzenesulfonyl-5-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b:4',3'-d]pyrrole-6-carbonitrile

Conditions

Conditions	Yield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; acetonitrile at 140℃; for 0.5h; Microwave irradiation;	99%

: 1346245-14-4
C25H34ClN3O3Si

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

: 1346245-11-1
C29H39N5O3Si

Conditions

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In 1,4-dioxane; water at 80℃; Inert atmosphere;	99%

: 6-bromo-2-(trimethylsilyl)furo[3,2-b]pyridine

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

: C14H17N3OSi

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,2-dimethoxyethane; water for 1.16667h; Inert atmosphere; Reflux;	99%

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

: 78242-20-3
1-methyl-1H-pyrazol-4-ol

Conditions

Conditions	Yield
With water; dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 20℃; for 3h;	99%
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere;	98%
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 5℃; for 0.883333h;	38.2%

: 7745-93-9
2-bromo-4-nitrotoluene

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

: 1-methyl-4-(2-methyl-5-nitrophenyl)-1H-pyrazole

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 90℃; for 10h; Inert atmosphere;	99%

: 1292317-56-6
tert-butyl 4-(4-bromo-2-cyanophenoxy)piperidine-1-carboxylate

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

: C21H26N4O3

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In water; N,N-dimethyl-formamide at 80℃; for 16h; Suzuki Coupling; Inert atmosphere;	99%

: 1123169-45-8
tert-butyl 6-bromo-3,4-dihydroquinoline-1(2H)-carboxylate

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

: tert-butyl 6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl 6-bromo-3,4-dihydroquinoline-1(2H)-carboxylate; 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole With caesium carbonate In 1,4-dioxane; water for 0.333333h; Suzuki Coupling; Inert atmosphere; Stage #2: With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate In 1,4-dioxane; water at 100℃; for 2.16667h; Suzuki Coupling; Inert atmosphere;	99%
With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; caesium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	99%
With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; caesium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	99%

: 6-bromo-4-methoxy-2-methylpyrazolo[1,5-a]pyridine-3-carbonitrile

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

: 4-methoxy-2-methyl-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;	99%

: 188582-62-9
4-bromo-2-fluorobenzyl alcohol

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

: 1418201-67-8
4-(4-hydroxymethyl-3-fluorophenyl)-1-methyl-1H-pyrazole

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h;	98%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In tetrahydrofuran; water at 160℃; for 0.166667h; Sealed tube; Microwave irradiation;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran; water at 160℃; for 0.166667h; Microwave irradiation; Sealed tube;

: 5-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-4-methoxy-2-(methylthio)pyrimidine

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

: 4-methoxy-5-(6-methyl-5-((2-( 1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(methylthio)pyrimidine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 4h; Inert atmosphere;	98%

: 5-bromo-1-methyl-N-[2-(trifluoromethyl)pyridin-4-yl]-1H-indole-3-carboxamide

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

: 1-methyl-5-(1-methyl-1H-pyrazol-4-yl)-N-[2-(trifluoromethyl)pyridin-4-yl]-1H-indole-3-carboxamide

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 1.5h;	98%

: methyl 4-bromo-1-(4-bromo-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylate

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

: methyl 4-bromo-1-(5-(isopropylthio)-4-(1-methyl-1H-pyrazol-4-yl)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylate

Conditions

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In tetrahydrofuran at 90℃; for 16h; Inert atmosphere; Sealed tube;	98%
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In tetrahydrofuran at 20 - 90℃; for 16h; Inert atmosphere; Sealed tube;	94%

1-Methylpyrazole-4-boronic acid pinacol ester Chemical Properties

Molecule structure of 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS NO.761446-44-0):

IUPAC Name: 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole
Molecular Weight: 208.06518 g/mol
Molecular Formula: C₁₀H₁₇BN₂O₂
Density: 1.05 g/cm³
Melting Point: 59-64 °C(lit.)
Boiling Point: 308.3 °C at 760 mmHg
Flash Point: 140.3 °C
Index of Refraction: 1.505
Molar Refractivity: 58.29 cm³
Molar Volume: 196.4 cm³
Surface Tension: 32.1 dyne/cm
Enthalpy of Vaporization: 52.71 kJ/mol
Vapour Pressure: 0.00125 mmHg at 25 °C
Storage Temp.: refrigerator (+4 °C)
H-Bond Acceptor: 3
Rotatable Bond Count: 1
Exact Mass: 208.138308
MonoIsotopic Mass: 208.138308
Topological Polar Surface Area: 36.3
Heavy Atom Count: 15
Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(N=C2)C
InChI: InChI=1S/C10H17BN2O2/c1-9(2)10(3,4)15-11(14-9)8-6-12-13(5)7-8/h6-7H,1-5H3
InChIKey: UCNGGGYMLHAMJG-UHFFFAOYSA-N
Product Categories of 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS NO.761446-44-0): Organoborons;Pyrazole;Boronic acid;Heterocyclic Building Blocks

1-Methylpyrazole-4-boronic acid pinacol ester Safety Profile

Hazard Codes: Harmful Xn, Flammable F, Irritant Xi
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant/Flammable
HazardClass: IRRITANT

1-Methylpyrazole-4-boronic acid pinacol ester Specification

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS NO.761446-44-0) is also named as 1H-pyrazole, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- ; 1-Methyl-1H-pyrazole-4-boronic acid, pinacol ester ; 1-Methyl-4-pyrazoleboronic acid pinacol ester ; 1-Methylpyrazole-4-Boronic Acid Pinacol Ester . 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS NO.761446-44-0) is white to light yellow crystal powder.

Product Name

1-Methyl-4-pyrazole boronic acid pinacol ester

Synthetic route

1-Methylpyrazole-4-boronic acid pinacol ester Chemical Properties

1-Methylpyrazole-4-boronic acid pinacol ester Safety Profile

1-Methylpyrazole-4-boronic acid pinacol ester Specification

Related Products

Hot Products