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Merck
CN

46465

Sigma-Aldrich

1-Adamantyl fluoroformate

technical, ≥90% (T)

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About This Item

Empirical Formula (Hill Notation):
C11H15FO2
CAS Number:
62087-82-5
Molecular Weight:
198.23
Beilstein:
3590131
EC Number:
263-400-6
MDL number:
MFCD00074772
UNSPSC Code:
12352101
PubChem Substance ID:
329757195

Key Documents

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grade

technical

Assay

≥90% (T)

mp

30-32 °C (lit.)
30-32 °C

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

FC(=O)OC12C[C@H]3C[C@H](C[C@H](C3)C1)C2

InChI

1S/C11H15FO2/c12-10(13)14-11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2/t7-,8+,9-,11-

InChI key

PNLZKVOKOVFGMZ-KJZNFTALSA-N

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Other Notes

Reagent suited for the protection of imidazole function of histidine; Used for the protection of ω-amino groups of Lys and Orn; e.g. in fragment condensations; γ,ω-bis-protection of arginine

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

190.4 °F - closed cup

Flash Point(C)

88 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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R. Presentini et al.
International Journal of Peptide and Protein Research, 27, 123-123 (1986)
I.J. Galpin et al.
Tetrahedron, 35, 2771-2771 (1979)
L Moroder et al.
Hoppe-Seyler's Zeitschrift fur physiologische Chemie, 357(11), 1647-1650 (1976-11-01)
1-Adamantyl fluoroformate was prepared from 1-adamantol and fluorophosgene. The cristalline and stable fluoroformate was allowed to react with amino acids to give the corresponding 1-adamantyloxycarbonyl derivatives in consistently high yields. Additonally this new reagent proved to be ideally reactive for
G.W. Kenner et al.
Tetrahedron, 35, 2767-2767 (1979)

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