Bis(pinacolato)diborane

HCID 2733548CAS 73183-34-3
Substructure searchFind similar structures

Basic information

Standard SMILES
CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C
InChIKey
IPWKHHSGDUIRAH-UHFFFAOYSA-N
Molecular formula
C12H24B2O4
Average molar mass
253.9 g/mol
Monoisotopic mass
254.18607005

Overview

Bis(pinacolato)diboron is a 1,3,2-dioxaborolane that is 4,4,5,5-tetramethyl-1,3,2-dioxaborolane in which the boron hydrogen at position 2 is replaced by a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group. It is a reagent used in organic synthesis to synthesise pinacol boronic esters. It has a role as an EC 3.4.24.24 (gelatinase A) inhibitor.

Names & identifiers

Preferred name
Bis(pinacolato)diborane
IUPAC
4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane
English name
Bis(pinacolato)diboron
Molecular formula
C12H24B2O4
Molecular weight
253.94

Names & synonyms

Bis(pinacolato)diboron73183-34-3bis(pinacolato)diboraneDipinacoldiboronPinacol diboraneB2Pin2Diboron pinacol ester4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolaneMiyaura's reagent2,2'-Bi-1,3,2-dioxaborolane, 4,4,4',4',5,5,5',5'-octamethyl-I906W26P4UCHEBI:183312
Show more names
BPINPin2B2(BPin)2B2Pin4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolaneBis(pinacolate)diboron
DTXSID30369935RefChem:569258B(P)DBDTXCID40320971615-925-04,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane)4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolaneMFCD00799570

Database identifiers

CAS
73183-34-3
PubChem CID
2733548
DTXSID
DTXSID30369935
ChEBI
CHEBI:183312
UNII
I906W26P4U
EC Number
615-925-0
Nikkaji
J698.829F

Properties

Computed structural properties

Topological polar surface area
36.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
18

Experimental & physicochemical properties

Chemical ClassesMetals -> Metalloid Compounds (Boron)
Physical DescriptionColorless solid; [Merck Index]

Physicochemical properties

Melting point
137 · 137-140 °C(lit.)
Boiling point
222.6 · 222.6±7.0 °C(Predicted)
Density
0.98 · 0.98
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Powder or Platelets

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 67.3% (107 of 159) of all reports.

Danger

H302 (14.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 159 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 20-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10449
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (14.5%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
No
hs_code
29349990
risk_code
36/37/38-20/21/22
Signal word
Warning

Chemistry & industry

Uses & manufacturing

UsesUsed as a boron source in organic syntheses; [Merck Index]
Applications · 5 items

UsesIt is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis. Unlike some other diboron compounds, B2pin2 is not moisture-sensitive and can be handled in air.

UsesAs a boron source in Pt-mediated diborations, coupling reactions; in Rh-or Ir-mediated borylations of alkanes and arenes, and in carbenoid chemistry.

Usessuzuki reaction

UsesBis(pinacolato)diboron is used as a condensation agent in the preparation poly(arylene)s. Bis(pinacolato)diboron is an organoboranate with potential use as matrix metallo-proteinase (MMP-2) inhibitor.

General DescriptionBis(pinacolato)diboron or (B2pin2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.

Preparation methods · 1 item

PreparationBis(pinacolato)diboron may be prepared by reacting tetrakis(dimethylamino)diboron with pinacol in acidic conditions. The B-B bond length is 1.711(6) Å. The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkanes and alkenes. Using various organorhodium or organoiridium catalysts, it can also be installed onto saturated hydrocarbons: CH3(CH2)6CH3 + [pinB]2 → pinBH + CH3(CH2)7Bpin These reactions proceed via boryl complexes.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Additional notes · 2 items

DefinitionBis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH3)4C2O2B]2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B2pin2.

DefinitionChEBI: Bis(pinacolato)diboron is a 1,3,2-dioxaborolane that is 4,4,5,5-tetramethyl-1,3,2-dioxaborolane in which the boron hydrogen at position 2 is replaced by a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group. It is a reagent used in organic synthesis to synthesise pinacol boronic esters. It has a role as an EC 3.4.24.24 (gelatinase A) inhibitor.

Related reactions

2,619 records
New reaction record

Linked notes

Loading…