4-Bromo-3-methylpyrazole supplier

Name
4-Bromo-3-methylpyrazole
EINECS 237-456-7
CAS No. 13808-64-5
Article Data4
CAS DataBase
Density 1.723 g/cm³
Solubility
Melting Point 77-79 °C
Formula C₄H₅BrN₂
Boiling Point 259.9 °C at 760 mmHg
Molecular Weight 161.001
Flash Point 111 °C
Transport Information
Appearance off-white powder
Safety 37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Pyrazole,4-bromo-3-methyl- (8CI);4-Bromo-3-methyl-1H-pyrazole;NSC 50563;
PSA 28.68000
LogP 1.48060

Synthetic route

: 130874-31-6
4-bromo-3-methyl-1-phenylsulphonylpyrazole

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
With potassium hydroxide In methanol for 1h; Heating;	83%
With potassium hydroxide In methanol for 1h; Heating; other 4-bromo-1-phenylsulphonylpyrazoles;	83%

: 1453-58-3
3-Methylpyrazole

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
Stage #1: 3-Methylpyrazole With N-Bromosuccinimide In N,N-dimethyl-formamide at 60℃; Continuous flow reactor; Stage #2: With water; acetic acid In N,N-dimethyl-formamide	49%

3(resp. 5)-methyl-pyrazole: 3(resp. 5)-methyl-pyrazole

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
With water; bromine

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 24424-99-5
di-tert-butyl dicarbonate

: 1021919-24-3
tert-butyl 4-bromo-3-methyl-1H-pyrazole-1-carboxylate

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃;	100%
With sodium carbonate In dichloromethane; water for 2.5h;
With sodium carbonate In dichloromethane at 20℃; for 16h;
With dmap; triethylamine In acetonitrile at 20℃;	0.32 g

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 4,5,8-tris(4-bromo-3-methyl-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 45℃; for 10h; Inert atmosphere; Electrochemical reaction; Green chemistry; diastereoselective reaction;	99%

: 21205-91-4
9-borabicyclo[3.3.1]nonane dimer

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: potassium hydride

: potassium[bis(3-Me-4-Br-pyrazolyl)borate(C8H14)]

Conditions

Conditions	Yield
In toluene for 3h; Inert atmosphere; Schlenk technique; Reflux;	96%

...Expand

: 134419-59-3
4-oxanyl methanesulfonate

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 4-bromo-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 10h;	88%

: 13154-24-0
triisopropylsilyl chloride

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 4-bromo-3-methyl-1-(triisopropylsilyl)-1H-pyrazole

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 72h; Reflux;	86.1%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 124-38-9
carbon dioxide

: 74-88-4
methyl iodide

: 1207853-38-0
methyl 4-bromo-3-methyl-1H-pyrazole-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 4-bromo-3-methyl-1H-pyrazole; carbon dioxide With cesium hydroxide; (hydroxido){N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene}copper(I) In tetrahydrofuran at 40℃; under 1125.11 Torr; for 0.204167h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran Inert atmosphere; regioselective reaction;	85%

...Expand

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 98-80-6
phenylboronic acid

: 13788-84-6
3-Methyl-4-phenyl-1H-pyrazole

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; catacxium A In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;	84%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 108-67-8
1,3,5-trimethyl-benzene

: 4-bromo-1-mesityl-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
With C24H42N3(1+)*ClO4(1-); lithium perchlorate; acetic acid In acetonitrile at 20℃; for 72h; Electrochemical reaction; Sealed tube; Irradiation;	83%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 98-09-9
benzenesulfonyl chloride

: 130874-31-6
4-bromo-3-methyl-1-phenylsulphonylpyrazole

Conditions

Conditions	Yield
With pyridine for 2h; Heating;	82%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 98-80-6
phenylboronic acid

: 50877-45-7
4-bromo-3-methyl-1-phenyl-1H-pyrazole

Conditions

Conditions	Yield
With pyridine; oxygen; copper diacetate In dichloromethane at 20℃; for 24h;	82%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 13360-57-1
dimethylamino sulfonyl chloride

: 882689-55-6
4-bromo-3-methyl-pyrazole-1-sulphonic acid dimethylamide

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 6h;	81%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 6h;	81%
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: dimethylamino sulfonyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	54%
Stage #1: 4-bromo-3-methyl-1H-pyrazole With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: dimethylamino sulfonyl chloride In tetrahydrofuran
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h; Stage #2: dimethylamino sulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 3.25h;

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 100-39-0
benzyl bromide

: 1-benzyl-4-bromo-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	80%
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 15℃; for 1h;	60%
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 15℃; for 1h;	60%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 150-76-5
4-methoxy-phenol

: 2-(4-bromo-3-methyl-1H-pyrazol-1-yl)-4-methoxyphenol

Conditions

Conditions	Yield
With dipotassium peroxodisulfate In acetonitrile at 80℃; for 5h; Inert atmosphere; Schlenk technique;	76%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 1357927-37-7
[Ru(2,2′-bipyridine-6,6′-dicarboxylate)((CH3)2SO)2]

: [Ru(2,2′-bipyridine-6,6′-dicarboxylate)(DMSO)(4-bromo-3-methyl-pyrazole)2]

Conditions

Conditions	Yield
In methanol for 0.333333h; Reflux; Inert atmosphere;	75%

: 78385-26-9
3-bromomethyl-3-methyloxetane

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 4-bromo-3-methyl-1-((3-methyloxetan-3-yl)methyl)-1H-pyrazole

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 1.5h; Microwave irradiation;	74.9%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 76-83-5
trityl chloride

: 474706-49-5
4-bromo-3-methyl-1-trityl-1H-pyrazole

Conditions

Conditions	Yield
With triethylamine In chloroform at 20℃; Inert atmosphere;	73%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 2-(4-bromo-3-methyl-1H-pyrazol-1-yl)-4-methoxyphenol

: 2,6-bis(4-bromo-3-methyl-1H-pyrazol-1-yl)-4-methoxyphenol

Conditions

Conditions	Yield
With dipotassium peroxodisulfate In acetonitrile at 80℃; for 5h; Inert atmosphere; Schlenk technique;	72%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 6226-25-1
2,2,2-trifluoroethyl trifluoromethanesulphonate

: 4-bromo-3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 0.5h; Microwave irradiation;	68.4%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 105-36-2
ethyl bromoacetate

: ethyl 2-(4-bromo-3-methyl-1H-pyrazol-1-yl)acetate

Conditions

Conditions	Yield
With sodium hydride; potassium iodide In N,N-dimethyl-formamide; mineral oil at 80℃; for 12h;	68%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 1357927-37-7
[Ru(2,2′-bipyridine-6,6′-dicarboxylate)((CH3)2SO)2]

: [Ru(2,2′-bipyridine-6,6′-dicarboxylate)(4-bromo-3-methyl-pyrazole)3]

Conditions

Conditions	Yield
In methanol for 6h; Reflux; Inert atmosphere;	68%

: 6479-18-1
1-methyl-2(1H)-quinoxalinone

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 3-(4-bromo-3-methyl-1H-pyrazol-1-yl)-1-methylquinoxalin-2(1H)-one

Conditions

Conditions	Yield
With air In acetonitrile at 20℃; for 20h; Irradiation;	60%

: 75-30-9
2-iodo-propane

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 1215295-87-6
4-bromo-1-isopropyl-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 90℃; for 12h;	56%
With caesium carbonate In acetonitrile at 90℃; for 12h;	56%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 141699-59-4
1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate

A: 1076223-99-8
tert-butyl 4-(4-bromo-5-methyl-1H-pyrazol-1-yl)piperidine-1-carboxylate

B: 1092500-89-4
tert-butyl 4-(4-bromo-3-methyl-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With sodium hydride In mineral oil at 70℃;	A 27% B 53%
With sodium hydride In N,N-dimethyl acetamide; mineral oil at 70℃;	A 27% B 53%
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate In N,N-dimethyl-formamide at 95℃; for 1h;
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate In N,N-dimethyl-formamide; mineral oil at 90℃; for 4h;

...Expand

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 352-33-0
1-Chloro-4-fluorobenzene

: 4-bromo-1-(4-chlorophenyl)-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 36h; Sealed tube; Inert atmosphere; Irradiation; Electrolysis;	52%

: 41731-23-1
2-bromo-5-methyl-1,3-thiazole

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: C8H8BrN3S

Conditions

Conditions	Yield
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-bromo-5-methyl-1,3-thiazole In N,N-dimethyl-formamide at 20 - 90℃;	50%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 98420-99-6
4-bromo-2-(n-propyl)pyridine

: 4-(4-bromo-3-methyl-1H-pyrazol-1-yl)-2-propylpyridine

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In N,N-dimethyl acetamide at 1140℃; for 6h; Sealed tube;	49%

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 2-[(4-bromo-3-methylpyrazol-1-yl)methoxy]ethyltrimethylsilane

Conditions

Conditions	Yield
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 25℃; for 4h;	44.22%

: 3034-53-5
2-bromo-1,3-thiazole

: 13808-64-5
4-bromo-3-methyl-1H-pyrazole

: C7H6BrN3S

Conditions

Conditions	Yield
Stage #1: 4-bromo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-bromo-1,3-thiazole In N,N-dimethyl-formamide at 20 - 90℃;	42%

4-Bromo-3-methylpyrazole Chemical Properties

The Molecular Structure of 4-Bromo-3-methylpyrazole (CAS NO.13808-64-5):

Empirical Formula: C₄H₅BrN₂
Molecular Weight: 160.9999
IUPAC Name: 4-bromo-5-methyl-1H-pyrazole
Appearance: white to cream-colored powder
Product Categories: Pyrazines;pharmacetical;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrazoles;PyrazolesHeterocyclic Building Blocks
Nominal Mass: 160 Da
Average Mass: 160.9999 Da
Monoisotopic Mass: 159.963603 Da
Index of Refraction: 1.584
Molar Refractivity: 31.29 cm³
Molar Volume: 93.4 cm³
Surface Tension: 50.5 dyne/cm
Density: 1.723 g/cm³
Flash Point: 111 °C
Enthalpy of Vaporization: 47.75 kJ/mol
Boiling Point: 259.9 °C at 760 mmHg
Vapour Pressure: 0.0204 mmHg at 25°C
Melting Point: 76.5 °C
log P (octanol-water): 1.500
Atmospheric OH Rate Constant: 2.79E-11 cm³/molecule-sec at 25°C
InChI
InChI=1/C4H5BrN2/c1-3-4(5)2-6-7-3/h2H,1H3,(H,6,7)
Smiles
c1(c(n[nH]c1)C)Br

4-Bromo-3-methylpyrazole Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 37/39-26
S37/39: Wear suitable gloves and eye/face protection
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

4-Bromo-3-methylpyrazole Specification

4-Bromo-3-methylpyrazole (CAS NO.13808-64-5) is also called as 4-Bromo-3-methyl-1H-pyrazole ; 3-Methyl-4-bromopyrazole ; 4-Bromo-3-methylpyrazole,97% ; 4-Bromo-3-methylpyrazole 97% ; 1H-pyrazole, 4-bromo-3-methyl- ; 3-Methyl-4-bromo-1h-pyrazole .

Product Name

4-Bromo-3-methylpyrazole

Synthetic route

4-Bromo-3-methylpyrazole Chemical Properties

4-Bromo-3-methylpyrazole Safety Profile

4-Bromo-3-methylpyrazole Specification

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