Basic information
- CAS
269410-08-4- Standard SMILES
CC1(C)OB(c2cn[nH]c2)OC1(C)C- InChIKey
TVOJIBGZFYMWDT-UHFFFAOYSA-N- Molecular formula
- C9H15BN2O2
- Average molar mass
- 194.04 g/mol
- Monoisotopic mass
- 194.12265812
Names & identifiers
- Preferred name
- 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
- IUPAC
- 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
- English name
- 4-Pyrazoleboronic acid pinacol ester
- Molecular formula
- C9H15BN2O2
- Molecular weight
- 194.04
Names & synonyms
269410-08-44-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleDTXSID40378836RefChem:287754DTXCID40329863629-131-7Pyrazole-4-boronic acid pinacol ester4-Pyrazoleboronic acid pinacol ester1h-pyrazole-4-boronic acid pinacol ester4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleMFCD034530631h-pyrazole-4-boronic acid, pinacol ester
Show more names
4-Pyrazoleboronic acid pinaol esterBaricitinib-005Triazolam Impurity 6eboronic acid pinacoLCrizotinib Intermediates 4Pinacol Pyrazol-4-ylboronate
pyrazole-4-boronic acid, pinacol ester4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane1H-Pyrazole, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Baricitinib Impurity 32SCHEMBL98961(1H-PYRAZOL-4-YL)BORONIC ACID PINACOL ESTER4U3BSC724T
Database identifiers
Properties
Computed structural properties
- Topological polar surface area
- 47.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 217
Physicochemical properties
- Melting point
- 142 · 142-146 °C (lit.)
- Boiling point
- 335.4 · 335.4±15.0 °C(Predicted)
- Density
- 1.09 · 1.09±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO, Ethyl Acetate, Methanol
- pka
- 13.36 · 13.36±0.50(Predicted)
- form
- Powder
- color
- Off-white to tan
- Water Solubility
- insoluble
- InChI
- InChI=1S/C9H15BN2O2/c1-8(2)9(3,4)14-10(13-8)7-5-11-12-6-7/h5-6H,1-4H3,(H,11,12)
- InChIKey
- TVOJIBGZFYMWDT-UHFFFAOYSA-N
- SMILES
- N1C=C(B2OC(C)(C)C(C)(C)O2)C=N1
- CAS DataBase Reference
- 269410 · 269410-08-4(CAS DataBase Reference)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (98.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 53 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (98.1%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- No
- hs_code
- 29331990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,F
- hazard_note
- Irritant/Flammable
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
Uses4-Pyrazoleboronic Acid Pinacol Ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.
Uses1H-Pyrazole-4-boronic acid pinacol ester is a useful reagent for Suzuki-Miyaura cross-couplings as well as Ruthenium-catalyzed asymmetric hydrogenation. It is also used as reagent for preparing VEGF, Aurora, RHO (ROCK), Janus Kinase 2, c-MET, ALK, S-nitrsoflutathione reductase, CDC7, Acetyl-CoA carboxylase inhibitors as well as other biologically active compounds.
UsesReagent used forSuzuki-Miyaura cross-couplings Ruthenium-catalyzed asymmetric hydrogenation Reagent used in preparation of inhibitors of many highly significant therapeutic enzymes and kinases containing the privileged scaffold pyrazole, includingVEGF AuroraRho (ROCK)Janus Kinase 2 (JAK) c-MET ALK S-nitrosoglutathione reductase CDC7 Acetyl-CoA carboxylase Prosurvival Bcl-2 protein Viral RNA-Dependent RNA polymerase Long Chain Fatty Acid Elongase 6PI3 AKT Chk1 Protein Kinase B
Upstream & downstream products
Upstream raw materials
Related reactions
797 records
Compound notes
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