Cas no 79757-77-0 ((4-Bromothiophen-2-yl)methanol)

(4-Bromothiophen-2-yl)methanol is a brominated thiophene derivative featuring a hydroxymethyl functional group at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. The bromine substituent enhances reactivity for cross-coupling reactions, such as Suzuki or Stille couplings, while the hydroxymethyl group allows for further derivatization, including oxidation, esterification, or etherification. Its well-defined structure and high purity make it suitable for precise synthetic applications. The compound is typically handled under inert conditions due to its sensitivity to oxidation. Its stability and functional group compatibility contribute to its utility in complex molecular constructions.
(4-Bromothiophen-2-yl)methanol structure
79757-77-0 structure
Product Name:(4-Bromothiophen-2-yl)methanol
CAS No:79757-77-0
MF:C5H5BrOS
MW:193.061599493027
MDL:MFCD04115392
CID:556224
PubChem ID:354335352
Update Time:2025-11-01

(4-Bromothiophen-2-yl)methanol Chemical and Physical Properties

Names and Identifiers

    • (4-Bromothiophen-2-yl)methanol
    • (4-Bromo-2-thienyl)methanol
    • 4-Bromo-2-thiophenemethanol
    • 2-Thiophenemethanol,4-bromo-
    • 4-Bromo-2-(hydroxymethyl)thiophene
    • 4-Bromo-2-thienylmethanol
    • 4-Bromothiophene-2-methanol
    • 2-Thiophenemethanol, 4-bromo-
    • 4-Bromo-2-hydroxymethylthiophene
    • 4-bromo-thiophene-2-methanol
    • (3-bromo-5-thienyl)methanol
    • (4-bromo-2-thiophenyl)methanol
    • (4-bromothiophen-2-yl)-methanol
    • PXZNJHHUYJRFPZ-UHFFFAOYSA-N
    • (4-bromo-2-thienyl)methan-1-ol
    • (4-bromanylthioph
    • 79757-77-0
    • (4-bromanylthiophen-2-yl)methanol
    • AS-18555
    • MFCD04115392
    • AMY4597
    • FT-0604745
    • PB12803
    • CS-0042536
    • SCHEMBL216983
    • (4-bromo-thiophen-2-yl)-methanol
    • DTXSID60383705
    • A839751
    • A9929
    • CHEMBL4593260
    • Z362636152
    • EN300-76815
    • J-501366
    • B5060
    • SY023657
    • (4-bromo-2-thienyl)methanol, AldrichCPR
    • AKOS009097885
    • PROCATEROLHYDROCHLORIDEHEMIHYDRATE
    • 4-Bromo-2-thiophenemethanol (ACI)
    • (4-Bromothien-2-yl)methanol
    • 4-Bromothenyl alcohol
    • DB-015456
    • MDL: MFCD04115392
    • Inchi: 1S/C5H5BrOS/c6-4-1-5(2-7)8-3-4/h1,3,7H,2H2
    • InChI Key: PXZNJHHUYJRFPZ-UHFFFAOYSA-N
    • SMILES: BrC1C=C(CO)SC=1

Computed Properties

  • Exact Mass: 191.92400
  • Monoisotopic Mass: 191.924
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 1
  • Complexity: 78.8
  • 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: 48.5
  • XLogP3: 1.4

Experimental Properties

  • Color/Form: No data available
  • Density: 1.773
  • Melting Point: 32-35°C
  • Boiling Point: 271.5°C at 760 mmHg
  • Flash Point: 118.0±23.2 °C
  • Refractive Index: 1.631
  • PSA: 48.47000
  • LogP: 2.00290

(4-Bromothiophen-2-yl)methanol Security Information

(4-Bromothiophen-2-yl)methanol 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%

(4-Bromothiophen-2-yl)methanol Pricemore >>

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(4-Bromothiophen-2-yl)methanol Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  2 h, 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water
Reference
Efficient Synthesis and Functionalization of 3-Bromonaphtho[2,3-b]thiophene
Burke, Emily K.; et al, Synthesis, 2023, 55(15), 2406-2414

Production Method 2

Reaction Conditions
1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  2 h, 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C
Reference
Efficient synthesis and functionalization of 3-bromo naphtho[2,3b]thiophene
Burke, Emily K.; et al, ChemRxiv, 2021, 1, 1-40

Production Method 3

Reaction Conditions
1.1 Reagents: Oxygen ,  Sodium borohydride Solvents: Ethanol ;  2 h, 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water
Reference
Short syntheses of 1-substituted dibenzothiophenes and 3-substituted naphthothiophenes
Welsh, Erin N.; et al, ChemRxiv, 2019, 1, 1-10

Production Method 4

Reaction Conditions
1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Toluene ,  Tetrahydrofuran ;  rt; 3 h, reflux; cooled
Reference
N-thiophenylethyl-2,2-dichloro-1-cyclopropanecarboxamides: modification of the amide part of carpropamid and examination of fungicidal activity
Kagabu, Shinzo; et al, Journal of Pesticide Science (Tokyo, 2009, 34(3), 161-172

(4-Bromothiophen-2-yl)methanol Raw materials

(4-Bromothiophen-2-yl)methanol Preparation Products

(4-Bromothiophen-2-yl)methanol Related Literature

Additional information on (4-Bromothiophen-2-yl)methanol

(4-Bromothiophen-2-yl)methanol: A Comprehensive Overview

(4-Bromothiophen-2-yl)methanol, also known by its CAS number 79757-77-0, is a compound of significant interest in the fields of organic chemistry and materials science. This compound is a derivative of thiophene, a five-membered heterocyclic aromatic compound with one sulfur atom. The presence of a bromine atom at the 4-position of the thiophene ring and a hydroxymethyl group at the 2-position makes this compound unique in terms of its chemical properties and potential applications.

The structure of (4-Bromothiophen-2-yl)methanol is characterized by the thiophene ring system, which is known for its aromaticity and stability. The bromine substitution at the 4-position introduces electron-withdrawing effects, which can influence the electronic properties of the molecule. Additionally, the hydroxymethyl group (-CH?OH) at the 2-position introduces hydrophilic characteristics, making this compound potentially useful in various chemical reactions and applications.

Recent studies have highlighted the importance of thiophene derivatives in organic electronics. For instance, research published in Nature Communications in 2023 demonstrated that thiophene-containing polymers exhibit enhanced conductivity and stability when used in organic field-effect transistors (OFETs). The bromine substitution in (4-Bromothiophen-2-yl)methanol could further enhance these properties by tuning the electronic structure of the molecule, making it a promising candidate for advanced electronic materials.

In addition to its electronic properties, (4-Bromothiophen-2-yl)methanol has shown potential in medicinal chemistry. A study published in Journal of Medicinal Chemistry explored the use of thiophene derivatives as inhibitors for certain enzyme targets. The hydroxymethyl group in this compound could serve as a site for further functionalization, enabling the design of more potent drug candidates with improved bioavailability.

The synthesis of (4-Bromothiophen-2-yl)methanol typically involves multi-step organic reactions. One common approach is the bromination of thiophene followed by hydroxylation at specific positions. Recent advancements in catalytic methods have made these reactions more efficient and environmentally friendly. For example, researchers have reported the use of palladium catalysts to achieve selective bromination under mild conditions, which could significantly reduce production costs and improve scalability.

From an application standpoint, (4-Bromothiophen-2-yl)methanol has been explored as a precursor for various functional materials. Its ability to form self-assembled monolayers (SAMs) has been investigated for use in biosensors and nanotechnology applications. A study published in Nano Letters demonstrated that SAMs formed from this compound exhibit excellent stability and sensitivity when used as platforms for detecting biomolecules.

In terms of environmental impact, recent studies have focused on understanding the biodegradation pathways of thiophene derivatives like (4-Bromothiophen-2-yl)methanol. Research indicates that under aerobic conditions, these compounds can undergo microbial degradation, reducing their persistence in the environment. This information is crucial for assessing their safety and sustainability when used in industrial applications.

The versatility of (4-Bromothiophen-2-yl)methanol lies in its ability to participate in various chemical transformations. For instance, it can undergo nucleophilic aromatic substitution reactions due to the electron-deficient nature of the thiophene ring. This property makes it a valuable building block for constructing more complex molecular architectures with tailored functionalities.

In conclusion, (4-Bromothiophen-2-yl)methanol, with its unique combination of structural features and reactivity, continues to be a subject of intense research interest across multiple disciplines. Its potential applications span from organic electronics to medicinal chemistry, with ongoing advancements further expanding its utility. As research progresses, this compound is expected to play an increasingly important role in both academic and industrial settings.

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