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4-Bromopyrazole

4-Bromopyrazole structure

CAS No:
2075-45-8
Formula:
C3H3BrN2
Chemical Name:
4-Bromopyrazole
Synonyms:
1H-Pyrazole,4-bromo-;Pyrazole,4-bromo-;4-Bromo-1H-pyrazole;4-Bromopyrazole;NSC 522023
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

White to cream crystalline powder

4-Bromopyrazole Basic Attributes

Molecular Weight：

146.97

Exact Mass：

146.97

NSC Number：

522023

DSSTox ID：

DTXSID50174826

HScode：

2933199090

Characteristics

PSA：

28.7

XLogP3：

0.3

Appearance：

White to cream crystalline powder

Density：

1.9±0.1 g/cm3

Melting Point：

94-96 °C

Boiling Point：

255°C at 760 mmHg

Flash Point：

108.0±19.8 °C

Refractive Index：

1.602

Water Solubility：

Slightly soluble in water.

Vapor Pressure：

0.027mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S26-S37/39

RTECS Number：

UQ6200000

Marks：

Xi:Irritant;

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

4-bromopyrazole

4-Bromopyrazole Use and Manufacturing

Methods of Manufacturing

Step 1[00249j To a slurry of 1H-pyrazole (10 g, 147 mmol) in water (150 mL) at room temperature was added NBS (26.1 g, 147 mmol) in one portion. Reaction became milky white and was allowed to stir at room temperature for 24 h. The reaction mixture was extracted with EtOAc (2 x 100 mL). The combined EtOAc extracts were washed with aqueous Na25203 and brine then dried over Na2504, and concentrated under reduced pressure to afford a light tan oil as 21.5 g (100percent) of as a light tan oil that solidified upon standing. HPLC Peak RT = 0.87 mm.step 1To a solution of lH-pyrazole (10 g, 147 mmol)NBS (26.1 g, 147 mmol) was added to the slurry in water (150 mL) at one time (note: exotherm) and the mixture became milky white and stirred overnight at rt. The reaction mixture was then extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with aqueous Na2S2O3 and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide the desired product as 4-bromo-lH-pyrazole (21.5 g, 146 mmol, 100percent yield), which solidifies after standing.A solution of 150 g (2.2 mol) of pyrazole and 703 g (4.4 mol, 2.0 eq.) of bromine in 3 L of water was refluxed for 1 h. General procedure: A round-bottom flask equipped with a magnetic stir bar and a rubber septum was charged with Pr4-Bromopyrazole (21).; Pyrazole (13, 34.0 g, 0.5 mol) and NBS (89.0 g, 0.5 mol, 1.0 equiv) were suspended in water (625 ml). The resulting suspension was stirred over night at room temperature. The reaction mixture was then extracted with EtOAc (2.x.100 mL). The combined EtOAc extracts was washed with aqueous Na4-Bromopyrazole (22) [0163] Pyrazole (19, 34.0 g, 0.5 mol) and NBS (89.0 g, 0.5 mol, 1.0 equiv) were suspended in water (625 ml) at ambient temperature. The resulting suspension was stirred at ambient temperature for overnight. The reaction mixture was then extracted with EtOAc (2×100 mL). The combined EtOAc extracts were washed with aqueous Na4-bromo-l H-pyrazole (A)Bromine (76.4 mL, 1.49 mol) was added dropwise over a period of 2 h to a stirred and cooled (<15 General procedure: 1-benzyl-4-chloro-3, 5-dimethyl-1H-pyrazole. To a 16 mL vial containing 1-benzyl-3, 5-dimethyl-1H-pyrazole (196 mg, 1.05 mmol) and a magnetic stir bar, 0.7 mL of water and 0.3 mL of ethyl acetate was added. Next, NaCl (123 mg, 2 mmol) was added and the vial was placed in a room temperature water bath to control exotherms. Finally, Oxone (322 mg, 0.52 mmol or 1.05 mmol KHSO

Uses

4-Bromopyrazole can be used as starting material employed in a synthesis of 1,4′-bipyrazoles and in suzuki reaction. suzuki reaction As a mono substituted pyrozole, 4-Bromopyrazole can be used as Inhibitor of human liver alcohol dehydrogenase and used in mutagenicity study with the L-arabinose resistance test of Salmonella typhimurium.

Computed Properties

Molecular Weight:146.97
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:145.94796
Monoisotopic Mass:145.94796
Topological Polar Surface Area:28.7
Heavy Atom Count:6
Complexity:48.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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