3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione
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Basic information
- CAS
21715-90-2- Standard SMILES
O=C1C2C3C=CC(C3)C2C(=O)N1O- InChIKey
ZUSSTQCWRDLYJA-UHFFFAOYSA-N- Molecular formula
- C9H9NO3
- Average molar mass
- 179.17 g/mol
- Monoisotopic mass
- 179.05824315
Overview
reagent used in peptide synthesis; structure
Names & identifiers
- Preferred 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
- English name
- N-Hydroxy-5-norbornene-2,3-dicarboximide
- Molecular formula
- C9H9NO3
- Molecular weight
- 179.17
Names & synonyms
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
Show more names
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
Properties
Computed structural propertiesFilling in
- XLogP
- -0.2
- Topological polar surface area
- 57.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 306
Physicochemical properties
- Melting point
- 165 · 165-170 °C (lit.)
- Boiling point
- 311.69 °C · 311.69°C (rough estimate)
- Density
- 1.2822 · 1.2822 (rough estimate)
- refractive index
- 1.56 · 1.5600 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Soluble in ethanol
- pka
- 9 · 9.00±0.20(Predicted)
- form
- Solid
- color
- 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 DataBase Reference
- 21715 · 21715-90-2(CAS DataBase Reference)
- EPA Substance Registry System
- 4 · 4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy- (21715-90-2)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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.
Hazard information
Regulatory Information
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%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29280090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Uses & manufacturing
General Manufacturing Information4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy-: ACTIVE
Applications
DescriptionN-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.
UsesInhibits racemization in peptide synthesis using DCC as condensing agent.
UsesN-Hydroxy-5-norbornene-2,3-dicarboximide(HONB) is used in solution-phase peptide synthesis. Used in the synthesis of enkephalin analogs.
UsesIt decreases racemization in peptide synthesis and inhibits formation of N-acylureas.
Related reactions
64 records
Compound notes
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