Cas no 850568-72-8 (Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)

Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is a boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions. Its stable dioxaborolane structure enhances shelf life and handling, while the tert-butyl ester group offers improved solubility and reactivity. This compound is valuable in pharmaceutical and materials science research for constructing complex aromatic frameworks.
Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate structure
850568-72-8 structure
Product Name:Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
CAS No:850568-72-8
MF:C17H25BO4
MW:304.189005613327
MDL:MFCD03453055
CID:719830
PubChem ID:354333902
Update Time:2025-06-17

Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical and Physical Properties

Names and Identifiers

    • tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • 4-(tert-Butoxycarbonyl)benzeneboronic acid pinacol ester
    • 4-(tert-Butoxycarbonyl)phenylboronic acid pinacol ester
    • Benzoic acid,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester
    • NULL
    • BM559
    • OR4118
    • 4-Boc-phenylboronic Acid Pinacol Ester
    • 2-(4-tert-Butoxycarbonylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic Acid tert-Butyl Ester
    • 4-(TERT-BUTOXYCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER
    • 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl ester
    • 4-(tert-Butoxycarbonyl)phenylboronic acid, pinacol ester, AldrichCPR
    • GNXLDEFJAZGNCJ-UH
    • 1,1-Dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (ACI)
    • 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid tert-butyl ester
    • 4-(Boc-)-phenylboronic acid
    • EN300-7372455
    • SY056873
    • AKOS015950765
    • 4-(t-Butoxycarbonyl)phenylboronic acid pinacol ester
    • GNXLDEFJAZGNCJ-UHFFFAOYSA-N
    • 850568-72-8
    • MFCD03453055
    • Z1741981029
    • (4-(TERT-BUTOXYCARBONYL)PHENYL)BORONIC ACID PINACOL ESTER
    • DTXSID20402582
    • SCHEMBL900346
    • 4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-Benzoic Acid 1,1-Dimethylethyl Ester
    • B5132
    • 4-Tert-butoxycarbonylphenylboronic acid pinacol ester
    • BCP11508
    • CS-W012104
    • DS-16076
    • Tert-butyl4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • MDL： MFCD03453055
    • Inchi： 1S/C17H25BO4/c1-15(2,3)20-14(19)12-8-10-13(11-9-12)18-21-16(4,5)17(6,7)22-18/h8-11H,1-7H3
    • InChI Key： GNXLDEFJAZGNCJ-UHFFFAOYSA-N
    • SMILES： O=C(C1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1)OC(C)(C)C

Computed Properties

  • Exact Mass: 304.18500
  • Monoisotopic Mass: 304.185
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 4
  • Complexity: 401
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 44.8

Experimental Properties

  • Color/Form: No data available
  • Density: 1.04
  • Melting Point: 128-132
  • Boiling Point: 389.1℃ at 760 mmHg
  • Flash Point: 189.1±23.2 °C
  • Refractive Index: 1.517
  • PSA: 44.76000
  • LogP: 2.94110

Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Security Information

Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Customs Data

  • HS CODE：2934999090
  • Customs Data：

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Pricemore >>

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Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium acetate Solvents: 1,4-Dioxane ;  5 min, rt
1.2 Reagents: Oxygen Catalysts: (SP-4-1)-[5,10,15,20-Tetrakis(4-methylphenyl)-21H,23H-porphinato(2-)-κN21,κN22,κ… ;  6 h, 110 °C
Reference
Pd(II)-Porphyrin Complexes - the First Use as Safer and Efficient Catalysts for Miyaura Borylation
Rao, Kanusu Umamaheswara; Venkateswarlu, Katta, Synlett, 2018, 29(8), 1055-1060

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  30 min; 18 h, 80 °C
Reference
Ultrahigh Surface Area Zirconium MOFs and Insights into the Applicability of the BET Theory
Wang, Timothy C.; Bury, Wojciech; Gomez-Gualdron, Diego A.; Vermeulen, Nicolaas A.; Mondloch, Joseph E.; et al, Journal of the American Chemical Society, 2015, 137(10), 3585-3591

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  overnight, reflux
Reference
Non-Catalytic Benefits of Ni(II) Binding to an Si(111)-PNP Construct for Photoelectrochemical Hydrogen Evolution Reaction: Metal Ion Induced Flat Band Potential Modulation
Gurrentz, Joseph M. ; Rose, Michael J., Journal of the American Chemical Society, 2020, 142(12), 5657-5667

Production Method 4

Reaction Conditions
1.1 Reagents: sec-Butyllithium Solvents: Tetrahydrofuran ,  Hexane ,  Cyclohexane ;  0.055 s, -28 °C
1.2 Solvents: Tetrahydrofuran ;  2.2 s, -28 °C
1.3 Reagents: Hydrochloric acid Solvents: Water
Reference
Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki-Miyaura coupling without intentionally added base
Nagaki, Aiichiro; Moriwaki, Yuya; Yoshida, Jun-ichi, Chemical Communications (Cambridge, 2012, 48(91), 11211-11213

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium methoxide Solvents: 1,2-Dimethoxyethane ;  10 min, 30 °C
1.2 30 °C; 1 h, 30 °C
Reference
Anomalous Reactivity of Silylborane: Transition-Metal-Free Boryl Substitution of Aryl, Alkenyl, and Alkyl Halides with Silylborane/Alkoxy Base Systems
Yamamoto, Eiji; Izumi, Kiyotaka; Horita, Yuko; Ito, Hajime, Journal of the American Chemical Society, 2012, 134(49), 19997-20000

Production Method 6

Reaction Conditions
1.1 Reagents: Sodium tert-butoxide Solvents: Toluene ,  Tetrahydrofuran ;  6 h, 80 °C
Reference
Chemoselective Coupling of 1,1-Bis[(pinacolato)boryl]alkanes for the Transition-Metal-Free Borylation of Aryl and Vinyl Halides: A Combined Experimental and Theoretical Investigation
Lee, Yeosan; Baek, Seung-yeol; Park, Jinyoung; Kim, Seoung-Tae ; Tussupbayev, Samat ; et al, Journal of the American Chemical Society, 2017, 139(2), 976-984

Production Method 7

Reaction Conditions
1.1 Solvents: Diethyl ether ;  rt; 1.5 h, rt
1.2 Reagents: Water ;  rt
Reference
Effect of the functionalisation route on a Zr-MOF with an Ir-NHC complex for catalysis
Carson, Fabian; Martinez-Castro, Elisa; Marcos, Rocio; Miera, Greco Gonzalez; Jansson, Kjell; et al, Chemical Communications (Cambridge, 2015, 51(54), 10864-10867

Production Method 8

Reaction Conditions
1.1 Reagents: Tosyl chloride Solvents: Pyridine ;  15 h, rt
Reference
Arrangement of proteinogenic α-amino acids on a cyclic peptide comprising alternate biphenyl-cored ζ-amino acids
Tashiro, Shohei; Chiba, Masayuki; Shionoya, Mitsuhiko, Chemistry - An Asian Journal, 2017, 12(10), 1087-1094

Production Method 9

Reaction Conditions
1.1 Solvents: Tetrahydrofuran ;  10 min, -78 °C; -78 °C → rt; 1 h, rt
1.2 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  6 h, reflux
Reference
3D-printed cartridge system for in-flow photo-oxygenation of 7-aminothienopyridinones
Rastelli, Ettore J. ; Yue, Doris; Millard, Caroline; Wipf, Peter, Tetrahedron, 2021, 79,

Production Method 10

Reaction Conditions
1.1 Solvents: Diethyl ether ;  30 min, rt; 2 h, rt
Reference
A Metal-Organic Framework with Covalently Bound Organometallic Complexes
Oisaki, Kounosuke; Li, Qiaowei; Furukawa, Hiroyasu; Czaja, Alexander U.; Yaghi, Omar M., Journal of the American Chemical Society, 2010, 132(27), 9262-9264

Production Method 11

Reaction Conditions
1.1 Reagents: Sodium hydride Catalysts: Cuprous iodide Solvents: Tetrahydrofuran ;  6 - 12 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt
Reference
Formation of Arylboronates by a CuI-Catalyzed Coupling Reaction of Pinacolborane with Aryl Iodides at Room Temperature
Zhu, Wei; Ma, Dawei, Organic Letters, 2006, 8(2), 261-263

Production Method 12

Reaction Conditions
1.1 Reagents: Tripotassium phosphate ,  Methanaminium, N-[(dimethylamino)fluoromethylene]-N-methyl-, hexafluorophosphate… Catalysts: Bis(1,5-cyclooctadiene)nickel ,  Tricyclohexylphosphine Solvents: 1,4-Dioxane ;  24 h, 60 °C
Reference
Ni-Catalyzed Deoxygenative Borylation of Phenols Via O-Phenyl-uronium Activation
Liu, Xiaojie; Xu, Biping; Su, Weiping, ACS Catalysis, 2022, 12(15), 8904-8910

Production Method 13

Reaction Conditions
1.1 Reagents: Potassium methoxide Solvents: 1,2-Dimethoxyethane ;  10 min, 30 °C
1.2 1 h, 30 °C; 30 °C → 0 °C
1.3 Reagents: Tetrabutylammonium fluoride ;  3 h, 0 °C
Reference
Formal Nucleophilic Boryl Substitution of Organic Halides with Silylborane/Alkoxy Base System
Yamamoto, Eiji; Izumi, Kiyotaka; Horita, Yuko; Ukigai, Satoshi; Ito, Hajime, Topics in Catalysis, 2014, 57(10-13), 940-945

Production Method 14

Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  overnight, 100 °C
Reference
A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal-Organic Framework
Johnson, Jacob A.; Petersen, Brenna M.; Kormos, Attila; Echeverria, Elena; Chen, Yu-Sheng; et al, Journal of the American Chemical Society, 2016, 138(32), 10293-10298

Production Method 15

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Catalysts: 1,10-Phenanthroline Solvents: Dimethyl sulfoxide ,  Toluene ;  24 h, 110 °C
1.2 Reagents: Water
Reference
Competing Dehalogenation versus Borylation of Aryl Iodides and Bromides under Transition-Metal-Free Basic Conditions
Niu, Yi-Jie; Sui, Guo-Hui; Zheng, Hong-Xing; Shan, Xiang-Huan; Tie, Lin; et al, Journal of Organic Chemistry, 2019, 84(17), 10805-10813

Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Raw materials

Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Preparation Products

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(CAS:850568-72-8)Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
Order Number:A841134
Stock Status:in Stock
Quantity:100g/500g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 06:52
Price ($):266.0/980.0

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Amadis Chemical Company Limited
(CAS:850568-72-8)Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
A841134
Purity:99%/99%
Quantity:100g/500g
Price ($):266.0/980.0
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