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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

680249-1G:
680249-5G:
680249-BULK:
680249-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP7570
MKCM4549
MKCJ9874
MKCJ0109
MKBX0050V

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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)
Gold-catalyzed cycloisomerization reactions of boronated enynes
Lee JCH and Hall DG
Tetrahedron Letters, 52(2), 321-324 (2011)

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