572179
cis-1-Propen-1-ylboronic acid
≥95.0%
Synonym(s):
cis-Propenylboronic acid
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About This Item
Linear Formula:
H3CCH=CHB(OH)2
CAS Number:
Molecular Weight:
85.90
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
InChI
1S/C3H7BO2/c1-2-3-4(5)6/h2-3,5-6H,1H3/b3-2-
SMILES string
C\C=C/B(O)O
InChI key
CBMCZKMIOZYAHS-IHWYPQMZSA-N
assay
≥95.0%
composition
trans isomer, ≤10%
mp
65-70 °C (lit.)
storage temp.
−20°C
Application
cis-1-Propen-1-ylboronic acid can be used:
- As an intermediate in the preparation of furan-2-yl analog of salvinorin A, a psychoactive natural product.
- To synthesize antibacterial polyoxygenated dibenzofuran derivatives from phloroglucinol.
- As a substrate in the palladium-catalyzed cis-vinyl arenes synthesis by reacting with various aryl chlorides.
Other Notes
Contains varying amounts of anhydride
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
219.2 °F - closed cup
flash_point_c
104.00 °C - closed cup
ppe
Eyeshields, Gloves
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Palladium-catalyzed cross-coupling of aryl chlorides with alkenylboronic acids with low E/Z isomerization
Thimmaiah M, et al.
Tetrahedron Letters, 49(39), 5605-5607 (2008)
Synthesis and antibacterial activity of new symmetric polyoxygenated dibenzofurans
Oramas-Royo S, et al.
European Journal of Medicinal Chemistry, 141(9), 178-187 (2017)
Kimberly M Lovell et al.
Bioorganic & medicinal chemistry, 20(9), 3100-3110 (2012-04-03)
Modification of the furan ring of salvinorin A (1), the main active component of Salvia divinorum, has resulted in novel neoclerodane diterpenes with opioid receptor affinity and activity. Conversion of the furan ring to an aldehyde at the C-12 position
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