117722
1-Adamantanecarbonyl chloride
95%
Synonym(s):
1-Adamantanecarboxylic acid chloride, 1-Chlorocarbonyladamantane
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About This Item
Empirical Formula (Hill Notation):
C11H15ClO
CAS Number:
Molecular Weight:
198.69
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
218-252-7
Beilstein/REAXYS Number:
389960
MDL number:
Assay:
95%
Form:
solid
InChI key
MIBQYWIOHFTKHD-KJZNFTALSA-N
InChI
1S/C11H15ClO/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2/t7-,8+,9-,11-
SMILES string
ClC(=O)C12C[C@H]3C[C@H](C[C@H](C3)C1)C2
assay
95%
form
solid
bp
135-136 °C/10 mmHg (lit.)
Quality Level
functional group
acyl chloride
Related Categories
General description
1-Adamantanecarbonyl chloride on reaction with triethylammonium isopropylphosphite forms mixed anhydride, an efficient capping reagent for the hydrogen-phosphonate DNA synthesis. It is a good substrate for Friedel–Crafts acylation of anisole in the presence of indium metal.
Application
1-Adamantanecarbonyl chloride was used in the preparation of efficient amine-modified oligodeoxynucleotides for fabrication of DNA microarrays.
signalword
Danger
hcodes
Hazard Classifications
Skin Corr. 1B
supp_hazards
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Highly selective catalytic Friedel-Crafts acylation and sulfonylation of activated aromatic compounds using indium metal.
Jang DO, et al.
Tetrahedron Letters, 47(34), 6063-6066 (2006)
Anna K Blakney et al.
Biomacromolecules, 21(6), 2482-2492 (2020-04-07)
Messenger RNA (mRNA) is a promising platform for both vaccines and therapeutics, and self-amplifying RNA (saRNA) is particularly advantageous, as it enables higher protein expression and dose minimization. Here, we present a delivery platform for targeted delivery of saRNA using
Nagendra Kumar Kamisetty et al.
Analytical and bioanalytical chemistry, 387(6), 2027-2035 (2007-01-24)
Amine-modified oligodeoxynucleotides (AMO) are commonly used probe oligodeoxynucleotides for DNA microarray preparation. Two methods are currently used for AMO preparation--use of amine phosphoramidites protected by acid-labile monomethoxytrityl (MMT) groups or alkali-labile trifluoroacetyl (TFA) groups. Because conventional AMO preparation procedures have
Novel activating and capping reagents for improved hydrogen-phosphonate DNA synthesis.
Andrus A, et al.
Tetrahedron Letters, 29(8), 861-864 (1988)
Evgenii S Mozhaitsev et al.
Anti-cancer agents in medicinal chemistry, 19(4), 463-472 (2018-12-14)
The DNA repair enzyme tyrosyl-DNA-phosphodiesterase 1 (TDP1) is a current inhibition target to improve the efficacy of cancer chemotherapy. Previous studies showed that compounds combining adamantane and monoterpenoid fragments are active against TDP1 enzyme. This investigation is focused on the
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