Cas no 957061-12-0 (3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester)

3-Methoxycarbonyl-5-nitrophenylboronic acid pinacol ester is a boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions due to its stability and reactivity. The pinacol ester group enhances shelf life and handling by protecting the boronic acid moiety from protodeboronation. The nitro and methoxycarbonyl substituents provide versatility for further functionalization, making it valuable in pharmaceutical and materials science research. Its crystalline solid form ensures consistent purity and ease of quantification. This compound is particularly useful in synthesizing complex aromatic systems, where controlled coupling under mild conditions is required. Its stability under air and moisture simplifies storage and experimental workflows.
3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester structure
957061-12-0 structure
Product Name:3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester
CAS No:957061-12-0
MF:C14H18BNO6
MW:307.106824398041
MDL:MFCD09258774
CID:839783
PubChem ID:44119765
Update Time:2025-10-28

3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester Chemical and Physical Properties

Names and Identifiers

    • 3-METHOXYCARBONYL-5-NITROPHENYLBORONIC ACID, PINACOL ESTER
    • Methyl 3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • B-4149
    • OR8574
    • Methyl 3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (ACI)
    • 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester
    • SCHEMBL310549
    • CS-0175568
    • D97426
    • EN300-1706260
    • 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester
    • METHYL3-NITRO-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE
    • methyl 3-nitro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • MFCD09258774
    • BS-23123
    • 3-Methoxycarbonyl-5-nitrophenylboronic acid pinacol ester
    • 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-benzoic acid methyl ester
    • 3-Methoxycarbonyl-5-nitrophenylboronic acid,pinacol ester
    • A1-00804
    • 957061-12-0
    • AKOS022177651
    • 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzoic acid methyl ester
    • 3-(Methoxycarbonyl)-5-nitrobenzeneboronic acid, pinacol ester
    • DB-112665
    • DTXSID00657396
    • KSHZAKDFKZEZJQ-UHFFFAOYSA-N
    • 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester
    • MDL: MFCD09258774
    • Inchi: 1S/C14H18BNO6/c1-13(2)14(3,4)22-15(21-13)10-6-9(12(17)20-5)7-11(8-10)16(18)19/h6-8H,1-5H3
    • InChI Key: KSHZAKDFKZEZJQ-UHFFFAOYSA-N
    • SMILES: N(=O)(C1C=C(C=C(B2OC(C)(C(O2)(C)C)C)C=1)C(OC)=O)=O

Computed Properties

  • Exact Mass: 307.12300
  • Monoisotopic Mass: 307.1227175g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 3
  • Complexity: 445
  • 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: 90.6?2

Experimental Properties

  • PSA: 90.58000
  • LogP: 2.20380

3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester 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%

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3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester Production Method

Additional information on 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester

Comprehensive Guide to 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester (CAS No. 957061-12-0)

3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester (CAS No. 957061-12-0) is a highly versatile boronic acid derivative widely used in organic synthesis, pharmaceutical research, and material science. This compound belongs to the class of arylboronic esters, which are pivotal intermediates in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic chemistry. Its unique structure, featuring a methoxycarbonyl and a nitro group, makes it a valuable building block for designing complex molecules.

The pinacol ester moiety in 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester enhances its stability, making it easier to handle and store compared to its free boronic acid counterpart. This property is particularly beneficial in industrial applications where long-term storage is required. Researchers and chemists frequently search for "boronic ester stability" and "Suzuki coupling reagents," highlighting the relevance of this compound in contemporary chemical research.

One of the most searched topics in synthetic chemistry is "how to improve yield in Suzuki reactions." The use of 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester can address this concern due to its high reactivity and selectivity. The nitro group in the compound can also serve as a directing group in further functionalization reactions, a feature that is often explored in "directed C-H activation" studies.

In pharmaceutical research, 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester is employed in the synthesis of bioactive molecules and drug candidates. The "methoxycarbonyl group" is a common pharmacophore found in many FDA-approved drugs, making this compound a valuable intermediate in medicinal chemistry. Recent trends show increasing interest in "boron-based drugs" and "boronic acids in drug discovery," further underscoring its importance.

From an industrial perspective, the demand for high-purity boronic esters like 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester is on the rise. Manufacturers and suppliers often look for "reliable boronic ester suppliers" and "CAS 957061-12-0 price" to source this compound for large-scale applications. Its role in the production of advanced materials, such as OLEDs and liquid crystals, is another area of growing interest.

Environmental and safety considerations are also critical when working with 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester. While it is not classified as a hazardous material, proper handling and storage are essential to maintain its integrity. Searches related to "safe handling of boronic esters" and "storage conditions for CAS 957061-12-0" are common among laboratory professionals.

In summary, 3-Methoxycarbonyl-5-nitrophenylboronic acid, pinacol ester (CAS No. 957061-12-0) is a multifaceted compound with significant applications in synthetic chemistry, pharmaceuticals, and materials science. Its stability, reactivity, and versatility make it a sought-after reagent in both academic and industrial settings. As research into boron chemistry continues to expand, the relevance of this compound is expected to grow even further.

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