161395-96-6

Basic information

• Product Name: E-2-(1-PENTENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• Synonyms: trans-1-Penten-1-ylboronic acid pinacol ester 97%;4,4,5,5-tetramethyl-2-[(E)-pent-1-enyl]-1,3,2-dioxaborolane;(E)-3-hydroxy-2,3-dimethylbutan-2-yl hydrogen pent-1-en-1-ylboronate;E-2-(1-PENTENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;1-PENTENYL-1-BORONIC ACID, PINACOL ESTER;TRANS-1-PENTENYL-1-BORONIC ACID PINACOL ESTER;TRANS-1-PENTENYLBORONIC ACID PINACOL ESTER;TRANS-4,4,5,5-TETRAMETHYL-2-PENT-1-ENYL-1,3,2-DIOXABOROLANE
• CAS NO: 161395-96-6
• Molecular Formula: C11H21BO2
• Molecular Weight: 196.09
• Mol File: 161395-96-6.mol

Chemical Properties

• Boiling Point: 110-111 °C28 mm Hg
• Flash Point: 181 °F
• Appearance: /
• Density: 0.884 g/mL at 25 °C
• Vapor Pressure: 0.442mmHg at 25°C
• Refractive Index: n20/D 1.441
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: E-2-(1-PENTENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(CAS DataBase Reference)
• NIST Chemistry Reference: E-2-(1-PENTENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(161395-96-6)
• EPA Substance Registry System: E-2-(1-PENTENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(161395-96-6)

Safety Data

• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 161395-96-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
E-2-(1-PENTENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is used as a reagent for the BACE-1 inhibitory activity of acyl guanidines. BACE-1 (Beta-secretase 1) is an enzyme that plays a crucial role in the production of amyloid-beta peptides, which are associated with Alzheimer's disease. By inhibiting BACE-1, E-2-(1-PENTENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE can potentially contribute to the development of therapeutic agents for the treatment of Alzheimer's disease.

InChI:InChI=1/C11H21BO2/c1-6-7-8-9-12-13-10(2,3)11(4,5)14-12/h8-9H,6-7H2,1-5H3/b9-8+

Upstream product

• 627-19-0 1-Pentyne 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 109-67-1 1-penten 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 104376-24-1 (E)-1-pentenylboronic acid 

Downstream Products

• 1448718-39-5 C₁₂H₁₅NO₃ 
• 1233667-32-7 C₁₃H₁₈O₂ 
• 1448718-40-8 C₁₃H₁₈O 
• 1448718-41-9 C₁₃H₁₈O 
• 1448718-44-2 C₁₄H₂₀O 
• 1448718-45-3 (1S,2R)-1-cyclohexyl-2-ethylbut-3-en-1-ol 
• 67562-21-4 4,4,5,5-tetramethyl-2-pentyl-1,3,2-dioxaborolane 
• 1425822-02-1 (S,E)-2-amino-N-(4-amino-2-bromo-5-(pent-1-enyl)benzyl)-N-(3-methylbutyl)-4-methylpentanamide 

Relevant articles and documents

Paternò-Büchi reaction versus hydrogen abstraction in the photochemical reactivity of alkenyl boronates with benzophenone

The photochemical reaction between some alkenyl boronates and benzophenone is described. While a pinacol alkenyl boronate derivative gave the corresponding oxetane, the MIDA esters gave a tertiary alcohol derived from allylic hydrogen abstraction by triplet benzophenone and coupling of the radicals thus obtained. A theoretical work at DFT level of theory performed on a MIDA ester explained this behaviour showing that the formation of the tertiary alcohol is the most probable reaction. Furthermore, the theoretical calculations showed that the Paternò-Büchi reaction occurs giving the C,C biradical intermediate and this result is not in agreement with the previous described hypothesis where electron poor alkenes gave mainly the C,O biradical intermediate.

Solvent- and metal-free hydroboration of alkynes under microwave irradiation

Boronic esters are versatile building blocks extensively used in organic chemistry and essential to a variety of coupling reactions. In this work, the hydroboration reactions of alkynes were performed without metal catalysts using concomitant microwave ir

Isonicotinate Ester Catalyzed Decarboxylative Borylation of (Hetero)Aryl and Alkenyl Carboxylic Acids through N-Hydroxyphthalimide Esters

Decarboxylative borylation of aryl and alkenyl carboxylic acids with bis(pinacolato)diboron was achieved through N-hydroxyphthalimide esters using tert-butyl isonicotinate as a catalyst under base-free conditions. A variety of aryl carboxylic acids possessing different functional groups and electronic properties can be smoothly converted to aryl boronate esters, including those that are difficult to decarboxylate under transition-metal catalysis, offering a new method enabling use of carboxylic acid as building blocks in organic synthesis. Mechanistic analysis suggests the reaction proceeds through coupling of a transient aryl radical generated by radical decarboxylation with a pyridine-stabilized persistent boryl radical. Activation of redox active esters may proceed via an intramolecular single-electron-transfer (SET) process through a pyridine-diboron-phthalimide adduct and accounts for the base-free reaction conditions.

FRUSTRATED LEWIS PAIRS

Novel compounds containing a Frustrated Lewis Pair are disclosed herein, as well as their use in small molecule activation, in catalysis and/or in the detection of small molecules such as nitrous oxide. The compounds are of formula (I) where Q, W, Y, Z, rings A and B, R1, R2, a and b are as herein defined:

Copper-catalyzed regioselective hydroboration of terminal alkynes in aqueous medium

A mild and environment-friendly copper-catalyzed hydroboration of terminal alkynes in aqueous medium was reported. Regioselectivity control was achieved in the presence of cyclodextrin-bispyridine ligand (CD-1). This protocol was successfully applied to inactivated terminal alkynes. Moreover, the ligand was recovered and reused without any loss of activity over five cycles.

Superparamagnetic copper ferrite nanoparticles catalyzed aerobic, ligand-Free, regioselective hydroboration of alkynes: Influence of synergistic effect

We discovered a general and comprehensive approach for the regioselective hydroboration of terminal and internal alkynes to synthesize vinylboronates using inexpensive and magnetically separable copper ferrite nanoparticles at low catalyst loading using Bis(pinacolato)diboron in the absence of ligand and additives, under mild and greener conditions. A diverse range of functional groups was tolerated in the reaction, including allene and enones, and the corresponding boronates were obtained in high yields under air. Moreover, the assynthesized alkenylboronates were used as precursors to prepare wide variety of vinylorgano chalcogenides regioselectively, in high yields. The present protocol enable the conversion of Csp-H bonds to make Csp2-B bonds via activation of B-B bond, followed by formation of Csp2-Se (Te or S) bonds via activation of Se (Te or S)- Se (Te or S) bonds in a regioselective manner. Deuterium isotope labeling studies showed that the proton source of vinyl boronate stem from the solvent employed.

Regiodivergent Iodocyclizations for the Highly Diastereoselective Synthesis of syn - And anti -Hydroxyl-Isochromanones and -Isobenzofuranones: Concise Synthesis of the Isochromanone Core of the Ajudazols

An efficient synthetic strategy to access hydroxyl-isochromanone and -isobenzofurans from readily available joint alkene precursors by a regiodivergent one-pot iodocyclization-substitution tandem process is reported. The cyclizations proceed with excellen

Rhodium-catalyzed dehydrogenative borylation of aliphatic terminal alkenes with pinacolborane

Aliphatic terminal alkenes react with pinacolborane at ambient temperature to afford dehydrogenative borylation compounds as the major product when iPr-Foxap is used as the ligand with cationic rhodium(I) in the presence of norbornene, which acts as the s

Ligand-free hydroboration of alkynes catalyzed by heterogeneous copper powder with high efficiency

Regioselective hydroboration of terminal and internal alkynes is realized by using 10 mol% copper powder (0.3-1 μm) at room temperature. 24 alkynes were efficiently converted into vinylboronates in up to 96% yield without addition of any ligand or additiv

Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid

We report a highly diastereo- and enantioselective synthesis of anti homoallylic alcohols from terminal alkynes via (E)-1-alkenylboronates based upon two catalytic reactions: a cationic iridium complex-catalyzed olefin transposition of (E)-1-alkenylboronates and a chiral phosphoric acid-catalyzed allylation reaction of aldehydes.