Description

1-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS No. 1151802-22-0) is a high-purity boronic ester derivative with the molecular formula C₁₂H₁₉BN₂O₂. This compound features a cyclopropyl-substituted pyrazole core coupled with a pinacol boronate ester group, making it a versatile intermediate in Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. Its stable dioxaborolane moiety ensures excellent handling and storage properties under inert conditions. Ideal for pharmaceutical research, agrochemical development, and materials science, this reagent is supplied as a crystalline solid with ≥95% purity (HPLC). Suitable for use in organic synthesis, medicinal chemistry, and as a building block for advanced boron-containing compounds.

Properties

• CAS Number: 1151802-22-0
• Complexity: 302
• IUPAC Name: 1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole
• InChI: InChI=1S/C12H19BN2O2/c1-11(2)12(3,4)17-13(16-11)9-7-14-15(8-9)10-5-6-10/h7-8,10H,5-6H2,1-4H3
• InChI Key: NLWYVKHISUTBMY-UHFFFAOYSA-N
• Exact Mass: 234.1539580
• Molecular Formula: C12H19BN2O2
• Molecular Weight: 234.10
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(N=C2)C3CC3
• Topological: 36.3
• Monoisotopic Mass: 234.1539580
• Synonyms: 1151802-22-0, 1-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, DTXSID20731526, DTXCID10682270, 810-240-5, 1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole, 1-Cyclopropyl-1H-pyrazole-4-boronic acid pinacol ester, 1-Cyclopropyl-4-(pinacolylboronate)-pyrazole, 1-cyclopropyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, MFCD16659007, 1H-PYRAZOLE, 1-CYCLOPROPYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, NLWYVKHISUTBMY-UHFFFAOYSA-N, 1-Cyclopropylpyrazole-4-boronic Acid Pinacol Ester, 1-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-di…, SCHEMBL1987497, (1-CYCLOPROPYL-1H-PYRAZOL-4-YL)BORONIC ACID PINACOL ESTER, BCP11791, BBL102020, STL555819, AKOS015946259, CS-W000818, GS-5768, SB11811, SY029125, DB-060704, EN300-1671393, 1-(Cyclopropyl)1H-pyrazole-4-boronic acid pinacol ester, Z2044739104, 1- cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 1-cyclopropyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1h-pyrazole, 1-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, AldrichCPR, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-cyclopropyl-1H-pyrazole, 1-Cyclopropyl-4-(4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolan-2-yl)-1H-pyrazole

Application

This compound serves as a key intermediate in the synthesis of bioactive molecules, particularly in medicinal chemistry for the development of kinase inhibitors and other heterocyclic pharmaceuticals. Its boronate ester functionality enables efficient cross-coupling reactions with aryl halides under palladium catalysis. Researchers also utilize it in the preparation of fluorescent probes and boron-based polymers. The cyclopropyl group enhances metabolic stability in drug candidates.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H317 (50%): May cause an allergic skin reaction [Warning Sensitization, Skin]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (50%)
• Skin Irrit. 2 (100%)
• Skin Sens. 1 (50%)
• Eye Irrit. 2A (100%)
• Acute Tox. 4 (50%)
• STOT SE 3 (100%)

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