3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione (HCID 89529)

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

Database identifiers

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

Properties

Computed structural properties

XLogP: -0.2
Topological polar surface area: 57.6 Å²
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)
UNSPSC Code: 12352300 · 12352300
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29280090 · 29280090
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 2 items

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
Hazard statements: H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Uses & manufacturing

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

Applications · 4 items

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.