4-Bromopyrazole supplier | CasNO.2075-45-8

Name
4-Bromopyrazole
EINECS
CAS No. 2075-45-8
Article Data35
CAS DataBase
Density 1.905 g/cm³
Solubility Slightly soluble in water.
Melting Point 93-96 °C(lit.)
Formula C₃H₃BrN₂
Boiling Point 254.999 °C at 760 mmHg
Molecular Weight 146.974
Flash Point 108.038 °C
Transport Information
Appearance White to cream crystalline powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Pyrazole,4-bromo- (6CI,7CI,8CI);4-Bromo-1H-pyrazole;NSC 522023;
PSA 28.68000
LogP 1.17220

Synthetic route

: 288-13-1
NH-pyrazole

: 2075-45-8
4-bromo-1H-pyrazole

Conditions

Conditions	Yield
With bromine In dichloromethane at 0℃;	100%
With N-Bromosuccinimide In water at 20 - 25℃;	100%
With N-Bromosuccinimide In water at 20℃;	100%

: 3112-31-0
3,5-pyrazoledicarboxylic acid

: 2075-45-8
4-bromo-1H-pyrazole

Conditions

Conditions	Yield
With bromine

: potassium 4-bromopyrazolate

: 50901-46-7
Methyl 4-pyridazinyl ketone

A: 2075-45-8
4-bromo-1H-pyrazole

B: C6H5N2O(1-)*K(1+)

Conditions

Conditions	Yield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;

...Expand

: 13745-17-0
4-bromo-1H-pyrazole-3-carboxylic acid

: 2075-45-8
4-bromo-1H-pyrazole

: C10H5BrF2N2O

: 2075-45-8
4-bromo-1H-pyrazole

Conditions

Conditions	Yield
With phosphate buffer at 25℃; Kinetics;

: C11H9BrN2O

: 2075-45-8
4-bromo-1H-pyrazole

Conditions

Conditions	Yield
With phosphate buffer at 25℃; Kinetics;

: C11H9BrN2O

: 2075-45-8
4-bromo-1H-pyrazole

Conditions

Conditions	Yield
With phosphate buffer at 25℃; Kinetics;

: C10H4BrClF2N2O

: 2075-45-8
4-bromo-1H-pyrazole

Conditions

Conditions	Yield
With phosphate buffer at 25℃; Kinetics;

: (4-bromo-1H-pyrazol-1-yl)(p-tolyl)methanone

: 2075-45-8
4-bromo-1H-pyrazole

Conditions

Conditions	Yield
With phosphate buffer at 25℃; Kinetics;

: (S)-flurbiprofenyl 4-bromopyrazolide

A: 2075-45-8
4-bromo-1H-pyrazole

B: 5104-49-4, 51543-38-5, 51543-39-6, 51543-40-9
(S)-(+)-flurbiprofen

Conditions

Conditions	Yield
With water; sodium hydroxide at 4℃; for 24h;

: 288-13-1
NH-pyrazole

: 600-00-0
ethyl 2-bromoisobutyrate

A: 2075-45-8
4-bromo-1H-pyrazole

B: 1040377-17-0
ethyl 2-(4-bromo-1H-pyrazol-1-yl)-2-methylpropanoate

C: ethyl 3-(4-bromo-1H-pyrazol-1-yl)-2-methylpropanoate

Conditions

Conditions	Yield
Stage #1: NH-pyrazole; ethyl 2-bromoisobutyrate With sodium t-butanolate In N,N-dimethyl-formamide Stage #2: With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

...Expand

: 2075-45-8
4-bromo-1H-pyrazole

: 109-92-2
ethyl vinyl ether

: 1024120-52-2
4-bromo-1-(1-ethoxyethyl)-1H-pyrazole

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane at 20℃; for 3h;	100%
With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 3h;	89%
With hydrogenchloride In 1,4-dioxane	89%

: 2075-45-8
4-bromo-1H-pyrazole

: 2-chloro-N-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide

: 2-(4-bromo-1H-pyrazol-1-yl)-N-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃;	100%
With potassium carbonate In acetonitrile at 100℃;

: 2075-45-8
4-bromo-1H-pyrazole

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

: 133560-58-4
4-bromo-1-<2-(trimethylsilyl)ethoxy>methyl-1H-pyrazole

Conditions

Conditions	Yield
Stage #1: 4-bromo-1H-pyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h;	99%
Stage #1: 4-bromo-1H-pyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃; for 16h;	99%
Stage #1: 4-bromo-1H-pyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.583333h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h;	91%

: 2075-45-8
4-bromo-1H-pyrazole

: 75-22-9
trimethylamine-borane

: 16998-93-9
{1-(4-bromo)pyrazolyl}borane

Conditions

Conditions	Yield
	99%
	99%

: 2075-45-8
4-bromo-1H-pyrazole

: 2373-51-5
chloro-methylsulfanyl-methane

: 4-bromo-1-[(methylsulphanyl)methyl]-1H-pyrazole

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃; for 16h;	99%
Stage #1: 4-bromo-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: chloro-methylsulfanyl-methane In N,N-dimethyl-formamide at 20℃;

: 2075-45-8
4-bromo-1H-pyrazole

: pentadeca-7,8-diene

: (S,E)-4-bromo-1-(pentadec-8-en-7-yl)-1H-pyrazole

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); (R)-segphos In toluene at 80℃; for 16h; Schlenk technique; Inert atmosphere; enantioselective reaction;	99%

: 2075-45-8
4-bromo-1H-pyrazole

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

: 4,5,8-tris(4-bromo-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%

: 2075-45-8
4-bromo-1H-pyrazole

: 76-83-5
trityl chloride

: 95162-14-4
4-bromo-1-trityl-1H-pyrazole

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	98.2%
With pyridine; dmap In dichloromethane at 20℃; for 16h;	96%
With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;	89%

: 2075-45-8
4-bromo-1H-pyrazole

: 98-59-9
p-toluenesulfonyl chloride

: 116228-41-2
4-bromo-1H-pyrazol-1-yl(4-methylphenyl)sulfone

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃; for 24h;	98%
With sodium hydroxide In dichloromethane at 0 - 20℃;	98%
With triethylamine In dichloromethane at 20℃; for 3h;	73%
In pyridine for 2h; Heating;	70%
Stage #1: 4-bromo-1H-pyrazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 12h;	63%

: 2075-45-8
4-bromo-1H-pyrazole

: 141699-58-3
3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester

: 877399-34-3
tert-butyl 3-(4-bromo-1H-pyrazol-1-yl)azetidine-1-carboxylate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 110℃; for 0.5h; Microwave irradiation;	98%
With sodium hydride In N,N-dimethyl-formamide at 110℃; for 0.5h; Microwave irradiation;	98%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 110℃; for 0.5h; Inert atmosphere; Microwave irradiation;	98%

: 2075-45-8
4-bromo-1H-pyrazole

: 1129-28-8
3-methoxycarbonylbenzyl bromide

: 1005628-24-9
3-(4-bromo-pyrazol-1-ylmethyl)-benzoic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate In ISOPROPYLAMIDE at 60℃;	98%
Stage #1: 4-bromo-1H-pyrazole With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.7h; Stage #2: 3-methoxycarbonylbenzyl bromide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;	79%

: 2075-45-8
4-bromo-1H-pyrazole

: 98-16-8
3-trifluoromethylaniline

: 1537903-13-1
N-(3-trifluoromethylphenyl)-1H-pyrazol-4-amine

Conditions

Conditions	Yield
With t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; lithium hexamethyldisilazane In tetrahydrofuran at 50℃; for 6h; Inert atmosphere; Sealed tube;	98%

: 2075-45-8
4-bromo-1H-pyrazole

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

: 1150271-23-0
4-bromopyrazole-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In acetonitrile at 20℃; for 2h;	98%
With triethylamine In dichloromethane at 20℃;	93%
In tetrahydrofuran at 30 - 45℃; Large scale;	92%

: 2075-45-8
4-bromo-1H-pyrazole

: 629-73-2
1-Hexadecene

: (S)-4-bromo-1-(hexadec-1-en-3-yl)-1H-pyrazole

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; JoSPOPhos SL-J688-2; pyridinium p-toluenesulfonate In toluene at 80℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	98%

: 2075-45-8
4-bromo-1H-pyrazole

: 824-94-2
p-methoxybenzyl chloride

: 4-bromo-1-(4-methoxybenzyl)-1H-pyrazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h;	98%

: 2075-45-8
4-bromo-1H-pyrazole

: 766-85-8
3-methoxy-1-iodobenzene

: 4-bromo-1-(3-methoxyphenyl)-1-hydropyrazole

Conditions

Conditions	Yield
With copper(l) iodide; L-valine; potassium carbonate In dimethyl sulfoxide at 100℃; for 48h; Inert atmosphere;	98%
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 110℃; for 48h; Inert atmosphere;	89%
With copper(l) iodide; L-valine; potassium carbonate In dimethylsulfoxide-d6 at 110℃; for 48h;	89%

: 2075-45-8
4-bromo-1H-pyrazole

: pentacosa-12,13-diene

: (S,E)-4-bromo-1-(pentacos-13-en-12-yl)-1H-pyrazole

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); (R)-segphos In toluene at 80℃; for 16h; Schlenk technique; Inert atmosphere; enantioselective reaction;	98%

: 2075-45-8
4-bromo-1H-pyrazole

: copper(II) choride dihydrate

: 1112-67-0
tetrabutyl-ammonium chloride

: [N(n-C4H9)4]2[Cu3(μ3-Cl)2(μ-4-bromopyrazolato)3Cl3]

Conditions

Conditions	Yield
With NaOH In dichloromethane byproducts: NaCl; stirring of equimolar amts. of CuCl2*2H2O, 4-bromopyrazole, NaOH and N(C4H9)4Cl in CH2Cl2 for 12 h at ambient temp.; filtration, treatment with Et2O, filtration, washing with Et2O, recrystn. from CH2Cl2/Et2O; elem. anal.;	97%

...Expand

: 462-08-8
pyridin-3-ylamine

: 2075-45-8
4-bromo-1H-pyrazole

: 1369433-25-9
N-(pyridin-3-yl)-1H-pyrazol-4-amine

Conditions

Conditions	Yield
With t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; lithium hexamethyldisilazane In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Sealed tube;	97%

: 2075-45-8
4-bromo-1H-pyrazole

: 103-63-9
1-phenyl-2-bromoethane

: 4-bromo-1-(2-phenylethyl)pyrazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25 - 90℃; for 14h;	97%
With potassium carbonate In acetonitrile at 90℃; for 12h;	70%

: 2075-45-8
4-bromo-1H-pyrazole

: 104367-27-3
hepta-3,4-diene-1,7-diyldibenzene

: (S,E)-4-bromo-1-(tridec-7-en-6-yl)-1H-pyrazole

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); (R)-segphos In toluene at 80℃; for 16h; Schlenk technique; Inert atmosphere; enantioselective reaction;	97%

: 2075-45-8
4-bromo-1H-pyrazole

: 14686-89-6
(1,2:5,6)-di-O-isopropylidene-D-gulose

: 3-(4-bromo-1H-pyrazol-1-yl)-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-galactofuranose

Conditions

Conditions	Yield
Stage #1: (1,2:5,6)-di-O-isopropylidene-D-gulose With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0 - 10℃; for 1h; Stage #2: 4-bromo-1H-pyrazole With caesium carbonate In N,N-dimethyl-formamide for 18h; Cooling with ice;	97%

: 2075-45-8
4-bromo-1H-pyrazole

: 62-53-3
aniline

: phenyl-(1H-pyrazol-4-yl)-amine

Conditions

Conditions	Yield
With t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; lithium hexamethyldisilazane In tetrahydrofuran at 50℃; for 6h; Inert atmosphere; Sealed tube;	96%
With sodium t-butanolate; tert-butyl XPhos; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 110℃; for 24h;	94%

: 2075-45-8
4-bromo-1H-pyrazole

: 75-03-6
ethyl iodide

: 71229-85-1
1-ethyl-4-bromo-1H-pyrazole

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In water; dimethyl sulfoxide at 20℃;	96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	84%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	84%

: 2075-45-8
4-bromo-1H-pyrazole

: 459-46-1
4-Fluorobenzyl bromide

: 251925-14-1
4-bromo-1-(4-fluorobenzyl)-1H-pyrazole

Conditions

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 12h;	96%
Stage #1: 4-bromo-1H-pyrazole With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.333333h; Stage #2: 4-Fluorobenzyl bromide In DMF (N,N-dimethyl-formamide) at 20℃; for 1h; Stage #3: With water In DMF (N,N-dimethyl-formamide) at 0℃;	86%

: 2075-45-8
4-bromo-1H-pyrazole

: 36865-41-5
3-bromopropanol methyl ether

: 1183903-41-4
4-bromo-1-(3-methoxypropyl)-1H-pyrazole

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃;	96%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;	94%
With caesium carbonate In N,N-dimethyl-formamide at 50℃;

: 2075-45-8
4-bromo-1H-pyrazole

: 1588-44-9
6-phenyl-1-hexene

: (S)-4-bromo-1-(6-phenylhex-1-en-3-yl)-1H-pyrazole

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; JoSPOPhos SL-J688-2; pyridinium p-toluenesulfonate In toluene at 80℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	96%

: 2075-45-8
4-bromo-1H-pyrazole

: 542-69-8
1-iodo-butane

: 957062-61-2
4-bromo-1-butyl-1H-pyrazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 13h;	96%

: 2075-45-8
4-bromo-1H-pyrazole

: 51834-97-0
6-methoxypyridine-3-ol

: 2-(4-bromo-1H-pyrazol-1-yl)-6-methoxypyridin-3-ol

Conditions

Conditions	Yield
With tert-butylammonium hexafluorophosphate(V) In dichloromethane at 23℃; Inert atmosphere; Electrochemical reaction;	96%

4-Bromopyrazole Chemical Properties

IUPAC Name: 4-Bromo-1H-pyrazole
Synonyms of 1H-Pyrazole, 4-bromo- (CAS NO.2075-45-8): 4-Bromopyrazole ; 4-Brompyrazole ; 5-23-04-00172 (Beilstein Handbook Reference) ; BRN 0106510 ; NSC 522023 ; 1H-Pyrazole, 4-bromo- (9CI) ; Pyrazole, 4-bromo-
CAS NO: 2075-45-8
Classification Code: Drug / Therapeutic Agent ; Mutation data
Molecular Formula of 1H-Pyrazole, 4-bromo- (CAS NO.2075-45-8): C₃H₃BrN₂
Molecular Weight: 146.9733
Molecular Structure:

Melting point: 93-96 °C
H bond acceptors: 2
H bond donors: 1
Polar Surface Area: 17.82 Å²
Index of Refraction: 1.601
Molar Refractivity: 26.46 cm³
Molar Volume: 77.1 cm³
Surface Tension: 56.4 dyne/cm
Density of 1H-Pyrazole, 4-bromo- (CAS NO.2075-45-8): 1.904 g/cm³
Flash Point: 108 °C
Enthalpy of Vaporization: 47.26 kJ/mol
Boiling Point: 255 °C at 760 mmHg
Vapour Pressure: 0.0268 mmHg at 25°C

4-Bromopyrazole Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	367mg/kg (367mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 178, Pg. 199, 1971.

4-Bromopyrazole Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: UQ6200000
Hazard Note: Irritant
HazardClass: IRRITANT

Product Name

4-Bromopyrazole

Synthetic route

4-Bromopyrazole Chemical Properties

4-Bromopyrazole Toxicity Data With Reference

4-Bromopyrazole Safety Profile

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