N-Hydroxynorborn-5-en-2,3-dicarboximid

3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione

HCID 89529CAS 21715-90-2

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Grundinformationen

Standard-SMILES: O=C1C2C3C=CC(C3)C2C(=O)N1O
InChIKey: ZUSSTQCWRDLYJA-UHFFFAOYSA-N
Summenformel: C9H9NO3
Durchschnittliche Molmasse: 179,17 g/mol
Monoisotopische Masse: 179,05824315

Überblick

reagent used in peptide synthesis; structure

Namen und Bezeichner

Bevorzugter Name: 3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione
IUPAC: 4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Lokaler Name: N-Hydroxynorborn-5-en-2,3-dicarboximid
Englischer Name: N-Hydroxy-5-norbornene-2,3-dicarboximide
Summenformel: C9H9NO3
Molmasse: 179.17

Namen und Synonyme

21715-90-2N-Hydroxy-5-norbornene-2,3-dicarboximideDTXSID608851784,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy-RefChem:8301273a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneDTXCID401024572244-538-62-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dioneHONB4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione4-Hydroxy-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione

Weitere Namen anzeigen

N-HYDROXY-5-NORBORNENE-2,3-DICARBOXYLIC ACID IMIDEHONB N-HYDROXY-5-NORBORNENE-2.3-DICARBOXYLIMIDEN-HYDROXY-5-NORBORNENE-2,3-DICARBOXYLIMIDEN-HYDROXY-5-NORBORNENE-2,3-DICARBOXIMIDE (HONB)N-Hydroxy-5-norborneLABOTEST-BB LT00112336Endo-N-Hydroxy-5-Norbornene-2,N-Hydroxynorborna-5-ene-2,3-dicarbimide

SCHEMBL6052Oprea1_006565N-Hydroxy-5-norbornene-2.3-dicarboxylic imideNSC12953EINECS 244-538-6MFCD00167583NSC-12953N-Hydroxybicyclo[2.2.1]-5-heptene-2,3-dicarboximide

Datenbank-Bezeichner

CAS: 21715-90-2
PubChem CID: 89529
DTXSID: DTXSID60885178
EC Number: 244-538-6
Nikkaji: J208.586K

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -0,2
Polarare Oberfläche (TPSA): 57,6 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 0
Schwere Atome: 13
Formalladung: 0
Komplexität: 306

Physikochemische Eigenschaften

Schmelzpunkt: 165 · 165-170 °C (lit.)
Siedepunkt: 311.69 °C · 311.69°C (rough estimate)
Dichte: 1.2822 · 1.2822 (rough estimate)
Brechungsindex: 1.56 · 1.5600 (estimate)
storage temp.: 2 · Sealed in dry,2-8°C
Löslichkeit: Soluble in ethanol
pka: 9 · 9.00±0.20(Predicted)
Aggregatzustand: Solid
Farbe: Off-White
BRN: 13540 · 13540
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
InChIKey: ZUSSTQCWRDLYJA-UHFFFAOYSA-N
SMILES: C1(=O)C2C(C3CC2C=C3)C(=O)N1O
CAS Datenbank: 21715 · 21715-90-2(CAS DataBase Reference)
EPA chemische Informationen: 4 · 4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy- (21715-90-2)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 4.2% (2 of 48) of reports.

Warning

H315 (95.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Status: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23986

4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (95.8%)

Sicherheitsdaten

wgk: 3
tsca: TSCA listed
hs_code: 29280090
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Verwendung und Herstellung

General Manufacturing Information4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy-: ACTIVE

Anwendungen · 2 Einträge

BeschreibungN-Hydroxy-5-norbornene-2,3-dicarboximide (NHD) is a compound that has antiviral activity and is used to treat HIV infections. It inhibits the reverse transcriptase enzyme in the virus, which blocks the synthesis of viral DNA. The ferroelectric properties of NHD were first observed by observing changes in its melting point when mixed with water. This property makes it useful for diagnosis purposes. In animal studies, a dose of 5 mg/kg was found to be effective against cancer cells and the drug showed no toxicity in humans at doses up to 500 mg/day. The optimal reaction conditions for NHD are pH 6 and temperature 45 degrees Celsius.

VerwendenN-Hydroxy-5-norbornene-2,3-dicarboximide(HONB) is used in solution-phase peptide synthesis. Used in the synthesis of enkephalin analogs.