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680249

Sigma-Aldrich

trans-2-Chloromethylvinylboronic acid pinacol ester

97%

Synonym(s):

(E)-2-(3-Chloro-1-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, E-2-Chloromethylvinylboronic acid pinacol ester

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About This Item

Empirical Formula (Hill Notation):
C9H16BClO2
CAS Number:
153724-93-7
Molecular Weight:
202.49
MDL number:
MFCD09260446
UNSPSC Code:
12352103
PubChem Substance ID:
24885550
NACRES:
NA.22

Quality Level

100

Assay

97%

refractive index

n20/D 1.4603

bp

57-62 °C/0.3-0.4 mmHg

density

1.028 g/mL at 25 °C

functional group

chloro

SMILES string

CC1(C)OB(OC1(C)C)\C=C\CCl

InChI

1S/C9H16BClO2/c1-8(2)9(3,4)13-10(12-8)6-5-7-11/h5-6H,7H2,1-4H3/b6-5+

InChI key

HLBDNUSUVDDICF-AATRIKPKSA-N

Related Categories

Application

trans-2-Chloromethylvinylboronic acid pinacol ester is a common reactant of Suzuki coupling reaction. It can be used to prepare:
  • Readout reagent that helps in providing qualitative and quantitative readouts in enzyme biomarker detection assays.
  • Boronated enynes, which on Au(I) catalyzed cycloisomerization yield various dienyl boronates.
  • α-Methyl-substituted boronates for the allylation of ketones to yield homoallylic tertiary alcohols.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP7570
MKCM4549
MKCJ9874
MKCJ0109
MKBX0050V

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Gold-catalyzed cycloisomerization reactions of boronated enynes
Lee JCH and Hall DG
Tetrahedron Letters, 52(2), 321-324 (2011)
Design, synthesis, and characterization of small-molecule reagents that cooperatively provide dual readouts for triaging and, when necessary, quantifying point-of-need enzyme assays
Brooks AD, et al.
The Journal of Organic Chemistry, 80(21), 10437-10445 (2015)
Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates
Fandrick KR, et al.
Organic Letters, 12(17), 3748-3751 (2010)

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