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21715-90-2 molecular structure
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(1R,2S,6R,7S)-4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

ChemBase ID: 151434
Molecular Formular: C9H9NO3
Molecular Mass: 179.17266
Monoisotopic Mass: 179.05824315
SMILES and InChIs

SMILES:
C1[C@@H]2C=C[C@H]1[C@@H]1[C@H]2C(=O)N(C1=O)O
Canonical SMILES:
ON1C(=O)[C@@H]2[C@H](C1=O)[C@H]1C[C@@H]2C=C1
InChI:
InChI=1S/C9H9NO3/c11-8-6-4-1-2-5(3-4)7(6)9(12)10(8)13/h1-2,4-7,13H,3H2/t4-,5+,6-,7+
InChIKey:
ZUSSTQCWRDLYJA-UMRXKNAASA-N

Cite this record

CBID:151434 http://www.chembase.cn/molecule-151434.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2S,6R,7S)-4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
IUPAC Traditional name
(1R,2S,6R,7S)-4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Synonyms
HONB
N-Hydroxybicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imide
N-Hydroxy-5-norbornene-2,3-dicarboxylic acid imide
N-羟基-5-降冰片烯-2,3-二甲酰亚胺
N-羟基-5-降冰片烯-2,3-二甲酰亚胺
CAS Number
21715-90-2
EC Number
244-538-6
MDL Number
MFCD00065691
Beilstein Number
13540
PubChem SID
24853563
162245587
PubChem CID
6541657

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 6541657 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.1724677  H Acceptors
H Donor LogD (pH = 5.5) -0.1905442 
LogD (pH = 7.4) -0.6079052  Log P -0.18144734 
Molar Refractivity 44.4054 cm3 Polarizability 16.86843 Å3
Polar Surface Area 57.61 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
165-170 °C(lit.) expand Show data source
166-169 °C expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
≥96.0% (T) expand Show data source
97% expand Show data source
Grade
purum expand Show data source
Empirical Formula (Hill Notation)
C9H9NO3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 226378 external link
Packaging
50 g in glass bottle
Sigma Aldrich - 56055 external link
Other Notes
Excellent reagent to be used in combination with DCC for peptide synthesis; the reagent decreases racemization, inhibits formation of N-acylureas and affords peptides in high yields1,2; the corresponding chloroformate can be used for the introduction of various amino-protecting groups3

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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