307531-75-5

Basic information

• Product Name: 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE
• Synonyms: 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE;(E)-1-PENTENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER;(E)-1-Pentene-1,2-diboronicacid;1-cis-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)pentene;Bis(pinacolcyclicester);1-cis-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxoboralan-2-yl)pentene;2,2μ-[(1Z)-1-Propyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane], 1-[cis-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)] pentene;2,2'-[(1Z)-1-Propyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolanel
• CAS NO: 307531-75-5
• Molecular Formula: C17H32B2O4
• Molecular Weight: 322.06
• EINECS: -0
• Mol File: 307531-75-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 301-303
• Boiling Point: 301-303 °C(lit.)
• Flash Point: 169 °F
• Appearance: /
• Density: 0.954 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.455(lit.)
• CAS DataBase Reference: 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE(307531-75-5)
• EPA Substance Registry System: 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE(307531-75-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 307531-75-5(Hazardous Substances Data)

Usage

Description

1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE, also known as (E)-1-Pentene-1,2-diboronic acid bis(pinacol) ester, is an alkenyl boronate ester characterized by its unique chemical structure and stability. It is known for its air and chromatography stability, making it a valuable compound in the field of organic chemistry.

Uses

1. Used in Organic Synthesis:
1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE is used as a reactant in the stereoselective synthesis of γ-boryl substituted homoallylic alcohols. This is achieved by reacting with aromatic aldehydes via a Ru-catalyzed double bond transposition reaction, which is crucial for the development of complex organic molecules with specific stereochemistry.
2. Used in Suzuki-Miyaura Cross-Coupling Reaction:
In the field of organic chemistry, 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE serves as a valuable component in the Suzuki-Miyaura cross-coupling reaction. This reaction is a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of biologically active compounds and pharmaceuticals.
3. Used in the Pharmaceutical Industry:
1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it an attractive candidate for the development of new drugs with potential therapeutic applications.
4. Used in the Chemical Industry:
In the chemical industry, 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE is utilized as a building block for the synthesis of various specialty chemicals, including advanced materials and fine chemicals with specific properties and applications.

Upstream product

• 627-19-0 1-Pentyne 
• 73183-34-3 bis(pinacol)diborane 

Relevant articles and documents

Synthesis of γ-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition

The stereoselective synthesis of anti isomers of γ-boryl-substituted homoallylic alcohols is disclosed. (E)-1,2-Di(boryl)alk-1-enes undergo Ru-catalyzed double-bond transposition with control of the geometry. The in situ generated (E)-1,2-di(boryl)alk-2-enes add to aldehydes in a stereospecific manner. The alkenylboron group within the product is amenable to a variety of synthetic derivatizations.