CAS 75927-49-0 2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HCID 5233012)

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Basic information

CAS: 75927-49-0
Standard SMILES: C=CB1OC(C)(C)C(C)(C)O1
InChIKey: DPGSPRJLAZGUBQ-UHFFFAOYSA-N
Molecular formula: C8H15BO2
Average molar mass: 154.02 g/mol
Monoisotopic mass: 154.11651012

Names & identifiers

Preferred name: 2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
IUPAC: 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
English name: Pinacol vinylboronate
Molecular formula: C8H15BO2
Molecular weight: 154.01

Names & synonyms

75927-49-02-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneDTXSID60997301RefChem:471366DTXCID801424306629-384-3Vinylboronic acid pinacol ester4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolaneMFCD001924922-VINYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolanevinylboronic acid pinacolester

Show more names

Picol vinylboroteboronic acid pinacoLAKOS BRN-0470inacol vinylboronatePINACOL VINYLBORONATEVINYLBORONIC ACID PINACOL ESTE

2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolane;Vinylboronic acid pinacol ester1,3,2-Dioxaborolane, 2-ethenyl-4,4,5,5-tetramethyl-vinyl boronic acid pinacol esterPinacolvinylboronate2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolane; 2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4,4,5,5-Tetramethyl-2-(2-vinyl)-1,3,2-dioxaborolane; 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane;Vinylboronic acid pinacol cyclic esterPinacol vinylboronate, stabilized with 0.1% BHTSCHEMBL13544

Database identifiers

Properties

Computed structural properties

Topological polar surface area: 18.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 11
Formal charge: 0
Complexity: 159

Physicochemical properties

Boiling point: 52 · 52-54°C 24mm
Density: 0.908 g/mL · 0.908 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.4300(lit.)
Flash point: 94 °F · 94 °F
storage temp.: -20 °C · -20°C
solubility: Chloroform (Sparingly), Methanol (Slightly)
form: Powder or Low Melting Solid
color: White to yellow
Sensitive: Air Sensitive
Stability: Light Sensitive, Volatile
InChI: InChI=1S/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3
InChIKey: DPGSPRJLAZGUBQ-UHFFFAOYSA-N
SMILES: O1C(C)(C)C(C)(C)OB1C=C
CAS DataBase Reference: 75927 · 75927-49-0(CAS DataBase Reference)
UNSPSC Code: 12352103 · 12352103
NACRES: 22 · NA.22

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (97.8%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesFlam. Liq. 3 (97.8%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: No
ridadr: UN 3272 3/PG 3
hs_code: 29319090
risk_code: 10-43
Signal word: Warning
Symbol(GHS): GHS02,GHS07,GHS09
hazard_code: Xi
safety_code: 16-36/37
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: III
Hazard statements: H226-H317-H411
Limited Quantities: 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Aquatic Chronic 2Flam. Liq. 3Skin Sens. 1

Chemistry & industry

Applications · 2 items

Usessuzuki reaction

UsesReagent used forSuzuki-Miyaura coupling reactionsMizoroki-Heck reactions (cascade reaction)Intramolecular Nozaki-Hiyama-Kishi reactionsStereoselective Cu-catalyzed γ-selective and stereospecific couplingControl of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenesRegio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactionsAsymmetric Birch reductive alkylationReagent used in Preparation of Molecular tubes for lipid sensingEnzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)