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2158-14-7 molecular structure
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4-acetamidobenzene-1-sulfonyl azide

ChemBase ID: 145939
Molecular Formular: C8H8N4O3S
Molecular Mass: 240.23912
Monoisotopic Mass: 240.03171114
SMILES and InChIs

SMILES:
CC(=O)Nc1ccc(cc1)S(=O)(=O)N=[N+]=[N-]
Canonical SMILES:
CC(=O)Nc1ccc(cc1)S(=O)(=O)N=[N+]=[N-]
InChI:
InChI=1S/C8H8N4O3S/c1-6(13)10-7-2-4-8(5-3-7)16(14,15)12-11-9/h2-5H,1H3,(H,10,13)
InChIKey:
NTMHWRHEGDRTPD-UHFFFAOYSA-N

Cite this record

CBID:145939 http://www.chembase.cn/molecule-145939.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-acetamidobenzene-1-sulfonyl azide
IUPAC Traditional name
4-acetamidobenzenesulfonyl azide
Synonyms
p-ABSA
4-Acetamidobenzenesulfonyl azide
对乙酰氨基苯磺酰叠氮
4-乙酰氨基苯磺酰叠氮
4-乙酰胺基 苯磺酰基叠氮
CAS Number
2158-14-7
MDL Number
MFCD00029626
Beilstein Number
2219568
PubChem SID
24865269
162240139
PubChem CID
5129185

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5129185 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.31138  H Acceptors
H Donor LogD (pH = 5.5) 0.3478259 
LogD (pH = 7.4) 0.3478254  Log P 0.46187156 
Molar Refractivity 57.636 cm3 Polarizability 21.74883 Å3
Polar Surface Area 92.67 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
104-111 °C expand Show data source
107-111 °C(lit.) expand Show data source
107-111°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
26-37 expand Show data source
26-37/39 expand Show data source
TSCA Listed
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
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95.0% (HPLC) expand Show data source
97% expand Show data source
Grade
purum expand Show data source
Linear Formula
CH3CONHC6H4SO2N3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 404764 external link
Packaging
5, 25 g in glass bottle
Application
Hydroazidation Catalyst for Facile Preparation of OrganoazidesDiazo transfer agent.1,2,3
Reagent for synthesis of: Monosaccharide-derived alcohols Non-peptidic NK3 receptor antagonistsReagent for: A late-stage intermolecular C-H olefination Intramolecular isomuenchnone cycloaddition approach to antitumor agents Rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates Suzuki-Miyaura cross coupling reaction
Sigma Aldrich - 00245 external link
Other Notes
Diazo-transfer reagent: synthesis of α-diazo esters7,8
Application
Reagent for synthesis of: Monosaccharide-derived alcohols1 Non-peptidic NK3 receptor antagonists2Reagent for: A late-stage intermolecular C-H olefination3 Intramolecular isomuenchnone cycloaddition approach to antitumor agents4 Rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates5 Suzuki-Miyaura cross coupling reaction6

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Diazo transfer agent. Recommended as a safer alternative to tosyl azide for diazo transfer reactions, in the presence of a base, e.g. Et3N or DBU, with active methylene compounds. A further advantage of the reagent is that the by-product sulfonamide is removable by trituration with water: Synth. Commun., 17, 1709 (1987). For illustrative examples, with subsequent cyclization using Rhodium(II) acetate, L15152, as a route to highly substituted furans, see: Tetrahedron, 44, 3343 (1988); Org. Synth. Coll., 9, 422 (1998):
  • • For a further example, see: Org. Synth. Coll., 9, 155 (1998).
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PATENTS

PATENTS

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INTERNET

INTERNET

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