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1158984-92-9

2-Thiopheneboronic acid MIDA ester, also known as 2-Thiopheneboronic acid MIDA boronate, is a chemical compound derived from thiophene and MIDA (N-Methyliminodiacetic acid). It is a stable boronic acid surrogate that is used in various chemical reactions, particularly in the field of organic synthesis. The compound is characterized by its ability to participate in slow-release cross-coupling reactions, making it a valuable asset in the synthesis of complex organic molecules.

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  • 1158984-92-9 Structure

  • Basic information

    1. Product Name: 2-Thiopheneboronic acid MIDA ester
    2. Synonyms: 2-Thiopheneboronic acid MIDA ester;4-Methyl-2,6-dioxo-8-(thiophen-2-yl)hexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide;2-Thiopheneboronic acid MIDA este
    3. CAS NO:1158984-92-9
    4. Molecular Formula: C9H10BNO4S
    5. Molecular Weight: 239.056
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1158984-92-9.mol

  • Chemical Properties

    1. Melting Point: 189-194°C
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
    8. Solubility: N/A
    9. CAS DataBase Reference: 2-Thiopheneboronic acid MIDA ester(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2-Thiopheneboronic acid MIDA ester(1158984-92-9)
    11. EPA Substance Registry System: 2-Thiopheneboronic acid MIDA ester(1158984-92-9)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 1
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1158984-92-9(Hazardous Substances Data)

1158984-92-9 Usage

Uses

Used in Organic Synthesis:
2-Thiopheneboronic acid MIDA ester is used as a reactant for slow-release cross-coupling reactions. It serves as a stable boronic acid surrogate for classically challenging cross-couplings, allowing for the formation of new carbon-carbon bonds in a controlled manner. This property makes it a valuable tool in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Suzuki Cross-Coupling with MIDA Boronates:
In the field of organic chemistry, 2-Thiopheneboronic acid MIDA ester is used as a reactant in Suzuki Cross-Coupling reactions involving MIDA boronates. This application takes advantage of the compound's stability and reactivity, enabling the formation of carbon-carbon bonds between aryl and vinyl halides or triflates and arylboronic acids. The use of 2-Thiopheneboronic acid MIDA ester in these reactions can lead to improved yields and selectivity, making it an attractive option for chemists working with challenging substrates.

Check Digit Verification of cas no

The CAS Registry Mumber 1158984-92-9 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,1,5,8,9,8 and 4 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1158984-92:
(9*1)+(8*1)+(7*5)+(6*8)+(5*9)+(4*8)+(3*4)+(2*9)+(1*2)=209
209 % 10 = 9
So 1158984-92-9 is a valid CAS Registry Number.

1158984-92-9 Well-known Company Product Price

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  • Aldrich

  • (708828)  2-ThiopheneboronicacidMIDAester  

  • 1158984-92-9

  • 708828-1G

  • 322.92CNY

  • Detail

  • Aldrich

  • (708828)  2-ThiopheneboronicacidMIDAester  

  • 1158984-92-9

  • 708828-5G

  • 1,366.56CNY

  • Detail

1158984-92-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name [2,2'-(Methylimino-κN)diacetato-κO(2-)](2-thienyl)boro

1.2 Other means of identification

Product number -
Other names 2-thiophene-amidoxime

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1158984-92-9 SDS

1158984-92-9Relevant articles and documents

Site-differentiated polyboron arenes prepared by direct C=H borylation and their highly selective Suzuki-Miyaura cross-coupling reactions

Xu, Liang,Ding, Siyi,Li, Pengfei

supporting information, p. 1822 - 1826 (2014/03/21)

Di- and polyboron (hetero)arenes, site-differentiated with MIDA boronyl (MIDA=N-methyliminodiacetic acid) and pinacolato boronyl (Bpin), were prepared by an iridium-catalyzed direct C=H borylation of readily available (hetero)aryl MIDA boronates. The exce

PROCESS FOR THE BORYLATION OF ARENES AND HETEROARYLS

-

Page/Page column 75, (2012/03/26)

This invention relates to a novel process for the borylation of arenes and heteroaryls. The present invention also provides novel borenium cations, which act as electrophiles for electrophilic substitution on the arene or heteroaryl ring, as well as to methodology for the preparation of these cations.

SLOW RELEASE OF ORGANOBORONIC ACIDS IN CROSS-COUPLING REACTIONS

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Page/Page column 35, (2010/04/27)

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1-B-T; where R1 represents an organic group, T represents a conformationalIy rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a pal ladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

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