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117722

Sigma-Aldrich

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:
2094-72-6
Molecular Weight:
198.69
Beilstein:
389960
EC Number:
218-252-7
MDL number:
MFCD00074724
UNSPSC Code:
12352100
PubChem Substance ID:
24847343
NACRES:
NA.22

Quality Level

200

Assay

95%

form

solid

bp

135-136 °C/10 mmHg (lit.)

mp

49-51 °C (lit.)

functional group

acyl chloride

SMILES string

ClC(=O)C12C[C@H]3C[C@H](C[C@H](C3)C1)C2

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-

InChI key

MIBQYWIOHFTKHD-KJZNFTALSA-N

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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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC7100
BCCC6498
BCCC6499
BCCC4876
BCBP3427V

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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)
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
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
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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