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117722

Sigma-Aldrich

1-Adamantanecarbonyl chloride

95%

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Synonym(s):
1-Adamantanecarboxylic acid chloride, 1-Chlorocarbonyladamantane
Empirical Formula (Hill Notation):
C11H15ClO
CAS Number:
Molecular Weight:
198.69
Beilstein:
389960
EC Number:
MDL number:
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

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1 of 4

This Item
320129114189119946
Acetyl chloride reagent grade, 98%

Sigma-Aldrich

320129

Acetyl chloride

Acetyl chloride reagent grade, 98%

Sigma-Aldrich

114189

Acetyl chloride

form

solid

form

liquid

form

liquid

form

-

bp

135-136 °C/10 mmHg (lit.)

bp

52 °C (lit.)

bp

52 °C (lit.)

bp

82 °C/20 mmHg (lit.)

mp

49-51 °C (lit.)

mp

−112 °C (lit.)

mp

−112 °C (lit.)

mp

10-12 °C (lit.)

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

-

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

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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Sigma-Aldrich

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Sigma-Aldrich

100277

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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

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