4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane

• ChemBase ID: 63858
• Molecular Formular: C9H17BO2
• Molecular Mass: 168.04108
• Monoisotopic Mass: 168.13216018
• SMILES: B1(OC(C(O1)(C)C)(C)C)CC=C
• Canonical SMILES: C=CCB1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3
• InChIKey: YMHIEPNFCBNQQU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane
• IUPAC Traditional name: 4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane
• Synonyms: Allylboronic acid, pinacol cyclic ester; 2-(Prop-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Allylboronic acid, pinacol ester; 4,4,5,5-tetramethyl-2-(2-propen-1-yl)-1,3,2-dioxaborolane; 4,4,5,5-tetramethyl-2-(2-propenyl)-1,3,2-dioxaborolane; Allyl pinacol boronate; Pinacolyl 2-propenylboronate; 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Pinacol allylboronate; Allylboronic acid pinacol ester; ALLYLBORONIC ACID PINACOL ESTER; 2-烯丙基-4,4,5,5-四甲基-1,3,2-二氧环戊硼烷; 丙烯基硼酸频哪醇酯; 烯丙基硼酸频哪醇酯; 丙烯基硼酸邻二叔醇酯

Database IDs

• CAS Number: 72824-04-5
• MDL Number: MFCD00013347
• Beilstein Number: 4244068
• PubChem SID: 24859457; 162029597
• PubChem CID: 2763171

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.8201
• LogD (pH = 7.4): 2.8201
• Log P: 2.8201
• Molar Refractivity: 45.2642 cm^3
• Polarizability: 19.709911 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 50-53 °C/5 mmHg(lit.); 50-53°C/5mm; 50-53°C/5mm
• Flash Point: 114.8 °F; 46 °C; 46°C; 60°C(140°F)
• Density: 0.890; 0.896; 0.896 g/mL at 25 °C(lit.)
• Refractive Index: 1.4270; n20/D 1.4268(lit.)

Safety Information

• Storage Warning: Flammable/Irritant/Moisture Sensitive/Store under Argon; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993; UN3272
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38
• Safety Statements: 26-36
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226; H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 97%; 98%; 98+%
• Linear Formula: ((CH3)4C2O2)BCH2CH=CH2

DETAILS

Sigma Aldrich - 324647

Packaging
1, 10 g in glass bottle
Application
Reagent used for
• Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis1
• Intermolecular radical additions2
• Allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids3
• Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes4
• Nucleic acid-templated energy transfer leading to a photorelease reaction5
• Stereoselective indium-catalyzed Hosomi-Sakurai reactions6 Reagent used in Preparation of
• Cyclic sulfone hydroxyethylamines as BACE1 inhibitors for reduction of Amyloid β-Peptides7
• Transmetalation of carbene Ru iodide with Ag carboxylates to give C-H-activated Ru carbene complexes as catalysts for Z-selective olefin metathesis8

REFERENCES

• Reacts with carboxylic acids, in the presence of tri-n-butyltin hydride, to give homoallylic alcohols in good yield: Synthesis, 1573 (2001):
  
• Homoallylic alcohols can also be formed by allylboration of aldehydes; the reaction has been found to be accelerated by Lewis acids, e.g. AlCl₃ or Sc(OTf)₃: J. Am. Chem. Soc., 124, 12414 (2002).