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3-Bromothiophene-5-boronic acid, with the molecular formula C4H3BO2SBr, is a boronic acid derivative featuring a bromine atom attached to a thiophene ring. 3-BROMOTHIOPHENE-5-BORONIC ACID is known for its role in Suzuki-Miyaura cross-coupling reactions, a significant method in organic synthesis, and is recognized for its potential in the creation of pharmaceuticals, agrochemicals, and materials for electronic devices.

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  • 499769-92-5 Structure
  • Basic information

    1. Product Name: 3-BROMOTHIOPHENE-5-BORONIC ACID
    2. Synonyms: 3-BROMOTHIOPHENE-5-BORONIC ACID;4-BROMOTHIOPHENE-2-BORONIC ACID;4-Bromo-2-thienylboronic acid;AKOS BRN-0374;3-BroMo-5-thiopheneboronic acid;(4-BroMothiophen-2-yl)boronic acid
    3. CAS NO:499769-92-5
    4. Molecular Formula: C4H4BBrO2S
    5. Molecular Weight: 206.85
    6. EINECS: N/A
    7. Product Categories: Boronic Acid
    8. Mol File: 499769-92-5.mol
  • Chemical Properties

    1. Melting Point: 126.6℃
    2. Boiling Point: 347.11 °C at 760 mmHg
    3. Flash Point: 163.727 °C
    4. Appearance: /
    5. Density: 1.879 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
    8. Solubility: N/A
    9. CAS DataBase Reference: 3-BROMOTHIOPHENE-5-BORONIC ACID(CAS DataBase Reference)
    10. NIST Chemistry Reference: 3-BROMOTHIOPHENE-5-BORONIC ACID(499769-92-5)
    11. EPA Substance Registry System: 3-BROMOTHIOPHENE-5-BORONIC ACID(499769-92-5)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22
    3. Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 499769-92-5(Hazardous Substances Data)

499769-92-5 Usage

Uses

Used in Organic Synthesis:
3-Bromothiophene-5-boronic acid is used as a key intermediate in organic synthesis for the production of various organic compounds. Its ability to participate in Suzuki-Miyaura cross-coupling reactions makes it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Bromothiophene-5-boronic acid is used as a precursor in the synthesis of pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
3-Bromothiophene-5-boronic acid is utilized as a starting material in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals to improve crop protection and yield.
Used in Material Science for Electronic Devices:
In the field of material science, particularly for electronic devices, 3-Bromothiophene-5-boronic acid is employed in the development of new materials with specific electronic properties, such as semiconductors and conductors, enhancing the performance of electronic components and devices.

Check Digit Verification of cas no

The CAS Registry Mumber 499769-92-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,9,9,7,6 and 9 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 499769-92:
(8*4)+(7*9)+(6*9)+(5*7)+(4*6)+(3*9)+(2*9)+(1*2)=255
255 % 10 = 5
So 499769-92-5 is a valid CAS Registry Number.

499769-92-5Downstream Products

499769-92-5Relevant articles and documents

SREBP INHIBITORS COMPRISING A THIOPHENE CENTRAL RING

-

Paragraph 0353-0354, (2021/08/06)

Provided herein are compounds comprising a three-ring core and pharmaceutically acceptable salts, solvates, tautomers, isotopes, or isomers thereof. Also provided herein are methods of inhibiting a component of the sterol regulatory element binding protein (SREBP) pathway, such as an SREBP or SREBP cleavage activating protein (SCAP), using these compounds, or pharmaceutically acceptable salts, solvates, tautomers, isotopes, or isomers thereof. Further provided are methods of treating a disorder in a subject in need thereof, such as liver disease, non-alcoholic steatohepatitis, insulin resistance, or cancer.

Preparation of brominated 2-alkoxythiophenes via oxidation and etherification of 2-thienyltrifluoroborate salts

Tietz, Jonathan I.,Seed, Alexander J.,Sampson, Paul

supporting information, p. 5058 - 5061 (2013/01/15)

The synthesis of ring brominated long-chain 2-alkoxythiophenes is reported, involving mild (Oxone) oxidation of readily prepared 2-thienyltrifluoroborate salts followed by Mitsunobu etherification. Both procedures are operationally straightforward and use inexpensive reagents. Using this approach, several novel mono- and dibrominated octyloxythiophenes with previously elusive substitution patterns were prepared. One such compound was elaborated to a novel 5-alkoxythieno[3,2-b]thiophene-2-carboxylate ester, marking the first synthetic entry into this family of compounds.

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