24464-63-9

Basic information

• Product Name: N-DECYLBORONIC ACID
• Synonyms: 1-Decylboronic acid, 98%;Decylboronic acid;1-Decaneboronicacid (6CI);RARECHEM AH PB 0104;N-DECYLBORONIC ACID;Decylboronic acid, 98.8%
• CAS NO: 24464-63-9
• Molecular Formula: C₁₀H₂₃BO₂
• Molecular Weight: 186.1
• Mol File: 24464-63-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 76-78°C
• Boiling Point: 297.1 °C at 760 mmHg
• Flash Point: 133.5 °C
• Appearance: /
• Density: 0.883 g/cm³
• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.434
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 10.35±0.43(Predicted)
• Sensitive: Air Sensitive
• BRN: 1743934
• CAS DataBase Reference: N-DECYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-DECYLBORONIC ACID(24464-63-9)
• EPA Substance Registry System: N-DECYLBORONIC ACID(24464-63-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 24464-63-9(Hazardous Substances Data)

Usage

Uses

suzuki reaction

InChI:InChI=1/C10H23BO2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h12-13H,2-10H2,1H3

Upstream product

• 1188-96-1 tridecylborane 
• 688-74-4 boric acid tributyl ester 
• 22086-40-4 (n-decyl)dibromoborane 
• 872-05-9 1-Decene 
• 63076-46-0 2-decyl-[1,3,2]dithiaborolane 
• 22092-92-8 diisopropopylaminoborane 
• 7732-18-5 water 
• 17049-50-2 n-decyl magnesium bromide 
• 14044-65-6 borane-THF 
• 55671-55-1 dibromoborane dimethylsulfide 

Downstream Products

• 1609638-14-3 4'-decyl-2'-hydroxyacetophenone 
• 112-30-1 1-Decanol 
• 2244-07-7 undecanenitrile 

Relevant articles and documents

Migratory aptitudes of simple alkyl groups in the anionotropic rearrangement of quaternary chloromethyl borate species: A combined experimental and theoretical investigation

A combined experimental and theoretical investigation at the DFT and MP2 levels on the boronto-carbon 1,2-shift in "ate species", coming from the quaternization of boranes (A) and boronate (B), is reported. To discuss the different migratory aptitudes of various alkyl groups, we have examined the migration of primary (R = Me, Et), secondary (R = i-Pr), and tertiary (R = t-Bu) alkyl groups. The effect of the counterion Li+ and of the solvent (polarized continuous model (PCM) method) has been considered. The following results are relevant: (a) in all cases, the reaction proceeds via a concerted-type mechanism which explains the retention of configuration at the migrating group and the inversion at the migration terminus experimentally observed. (b) The trend of the migration barriers along the direction primary → secondary → tertiary alkyl group observed in "ate" species A is reversed in boronate species B, in agreement with the experimental evidences. (c) A simple theoretical model is proposed where the barrier trend is the result of a delicate interplay between two opposite factors: (1) a "steric effect", which favors the most sterically demanding migrating groups, and (2) a "charge effect" associated with the partial carbanionic nature of the migrating carbon atom and which favors the less substituted migrating carbons.

Deboronative cyanation of potassium alkyltrifluoroborates: Via photoredox catalysis

A photoredox catalytic method was developed for the direct cyanation of alkyltrifluoroborates. This reaction provides a new and useful transformation of the easily available alkyltrifluoroborates. The photocatalytic reaction can tolerate a variety of functional groups with mild reaction conditions. Mechanistic investigations are consistent with the present reaction following a radical pathway.

Reaction of grignard reagents with diisopropylaminoborane. Synthesis of alkyl, aryl, heteroaryl and allyl boronic acids from organo(diisopropyl)- aminoborane by a simple hydrolysis

Diisopropylaminoborane (BH2-N(iPr)2) is prepared by reacting lithium diisopropylaminoborohydride (iPr-LAB) with trimethylsilyl chloride (TMSCl). Aliphatic, aromatic, and heteroaromatic (diisopropylamino) boranes are readily synthesiz