21715-90-2

Basic information

• Product Name: N-Hydroxy-5-norbornene-2,3-dicarboximide
• Synonyms: HONB;LABOTEST-BB LT00112336;N-HYDROXY-5-NORBORNENE-2,3-DICARBOXYLIC ACID IMIDE;N-HYDROXY-5-NORBORNENE-2,3-DICARBOXYLIMIDE;N-HYDROXY-5-NORBORNENE-2,3-DICARBOXIMIDE;N-HYDROXYBICYCLO[2.2.1]HEPT-5-ENE-2,3-DICARBOXYLIC ACID IMIDE;N-HYDROXYBICYCLO[2.2.1]HEPT-5-ENE-2,3-DICARBOXIMIDE;3(2h)-dione,3a,4,7,7a-tetrahydro-2-hydroxy-7-methano-1h-isoindole-1
• CAS NO: 21715-90-2
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17
• EINECS: 244-538-6
• Product Categories: Medical Intermediates;Coupling Reagent;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry
• Mol File: 21715-90-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 165-170 °C(lit.)
• Boiling Point: 311.69°C (rough estimate)
• Flash Point: 164.1 °C
• Appearance: white to off-white crystalline powder
• Density: 1.2822 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Soluble in ethanol
• PKA: 9.00±0.20(Predicted)
• BRN: 13540
• CAS DataBase Reference: N-Hydroxy-5-norbornene-2,3-dicarboximide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Hydroxy-5-norbornene-2,3-dicarboximide(21715-90-2)
• EPA Substance Registry System: N-Hydroxy-5-norbornene-2,3-dicarboximide(21715-90-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 21715-90-2(Hazardous Substances Data)

Usage

Description

N-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.

Chemical Properties

white to off-white crystalline powder

Uses

Different sources of media describe the Uses of 21715-90-2 differently. You can refer to the following data:
1. N-Hydroxy-5-norbornene-2,3-dicarboximide(HONB) is used in solution-phase peptide synthesis. Used in the synthesis of enkephalin analogs.
2. Inhibits racemization in peptide synthesis using DCC as condensing agent.
3. It decreases racemization in peptide synthesis and inhibits formation of N-acylureas.

Purification Methods

Dissolve the imide in CHCl3, filter, evaporate and recrystallise from EtOAc. IR (nujol): max 1695, 1710 and 1770 (C=O), and 3100 (OH) cm-1. The O-acetyl derivative has m 113-114o (from EtOH) with IR bands at max 1730, 1770 and 1815 cm-1 only, and the O-benzoyl derivative has m 143-144o (from propan-2-ol or *C6H6). [Bauer & Miarka J Org Chem 24 1293 1959, Fujino et al. Chem Pharm Bull Jpn 22 1857 1974]. [Beilstein 21/10 V 188.]

InChI:InChI=1/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-/m1/s1

Upstream product

• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 5433-80-7 cis-N-sulphonyloxy-5-norbornene-endo-2,3-dicarboximide 
• 108-91-8 cyclohexylamine 
• 110-91-8 morpholine 
• 123-75-1 pyrrolidine 
• 110-89-4 piperidine 

Downstream Products

• 66449-93-2 Boc-Lys(Z)-ONB 
• 109826-35-9 (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 
• 204187-32-6 (S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 
• 100898-22-4 Phenyl-acetic acid (1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 
• 100898-23-5 2-Chloro-benzoic acid (1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 
• 24147-30-6 N-benzoyloxy-5-norbornene-endo-2,3-dicarboximide 
• 99502-89-3 Chlorameisensaeure-N-hydroxy-norborn-5-en-2,3-dicarboximidester 
• 1154758-31-2 N-(4-nitrobenzyl carbonate)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imide 
• 109210-41-5 Boc-Tyr-Met-Gly-ONB 
• 5433-80-7 cis-N-sulphonyloxy-5-norbornene-endo-2,3-dicarboximide 
• 109336-31-4 2-(3,4-dichloro-benzenesulfonyloxy)-(3ac,7ac)-3a,4,7,7a-tetrahydro-4r,7c-methano-isoindole-1,3-dione 

Relevant articles and documents

Clarification of stereochemistry aspects for N-hydroxy-5-norbornene-2,3-dicarboximide derivatives and elucidation of them by experimental and theoretical investigations, including the synthesis of N, N'-bis-(5-exo-norbornene-2,3-dicarboxyimidyl) carbonate

Ambiguities about the stereochemistry of N-hydroxy- 5-norbornene-2, 3-dicarboximide and N, N'-bis-(5- norbornene-2, 3-dicarboxyimidyl) carbonate and confusing naming of N-hydroxy-5-norbornene-2, 3- dicarboximide and its corresponding anhydride by literature and chemical sellers were addressed. This considered the stereochemistry itself as well as the description thereof. The unclear points could be elucidated by scientific deliberations and by practical and theoretical experiments. N, N'-bis-(5-exonorbornene- 2, 3-dicarboxyimidyl) carbonate was synthesised for the first time and for comparison, the exo and endo isomer of N-hydroxy-5-norbornene-2, 3-dicarboximide and N, N'-bis-(5-endo-norbornene-2, 3-dicarboxy-imidyl) carbonate were manufactured. The molecular structures of N-hydroxy-5-endo-norbornene-2, 3-dicarboximide and N, N'-bis-(5-endo-norbornene-2, 3-dicarboxyimidyl) carbonate have been investigated by X ray crystallography. The stereochemistry assignments of corresponding exo-endo isomers pairs were studied by various NMR experiments and the thermodynamical heat of formation were calculated by theoretical methods. The exo-endo isomers pairs can be differed easily by the chemical shifts of special atoms. For the 13C-NMR experiment is this salient atom the methylene bridge carbon and in the case of 1H-NMR experiment this role fulfilled by the protons which defines the exo-endo isomerism. Using theoretical concepts, we could illustrate that the exo carbonate is thermodynamically more stable than its corresponding endo isomer. For the exo and endo isomers of N-hydroxy-5-norbornene-2, 3-dicarboximide and their corresponding anhydrides, the exo isomers were just slightly favoured. These results underlined the experimental facts that the equilibration of them ends in a rate of nearly fifty-fifty.

Aminolysis of 2,3-[Cyclopenten-3',5'-diyl]-endo-N-(2",4"-dinitrophenoxy)succinimide with Morpholine, Piperidine, Pyrrolidine and Cyclohexylamine in Ethyl Acetate

-

On the knowledge of N-hydroxy-isoindoles. 33. Report on hydroxylamine-derivatives

-