Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

117722

Sigma-Aldrich

1-Adamantanecarbonyl chloride

95%

Synonym(s):

1-Adamantanecarboxylic acid chloride, 1-Chlorocarbonyladamantane

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C11H15ClO
CAS Number:
Molecular Weight:
198.69
Beilstein/REAXYS Number:
389960
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

solid

bp

135-136 °C/10 mmHg (lit.)

mp

49-51 °C (lit.)

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

Looking for similar products? Visit Product Comparison Guide

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

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

supp_hazards

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service