N-Hydroxy-5-norbornene-2,3-dicarboximide

Base Information

• Chemical Name: N-Hydroxy-5-norbornene-2,3-dicarboximide
• CAS No.: 21715-90-2
• Molecular Formula: C9H9NO3
• Molecular Weight: 179.175
• Hs Code.: 29280090
• European Community (EC) Number: 244-538-6
• NSC Number: 100740,12953
• DSSTox Substance ID: DTXSID60885178
• Nikkaji Number: J208.586K
• Mol file: 21715-90-2.mol

Synonyms:N-hydroxy-5-norbornene-2,3-dicarboximide

Chemical Property of N-Hydroxy-5-norbornene-2,3-dicarboximide

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 165-170 °C(lit.)
• Refractive Index: 1.673
• Boiling Point: 347.7 °C at 760 mmHg
• PKA: 9.00±0.20(Predicted)
• Flash Point: 164.1 °C
• PSA: 57.61000
• Density: 1.574 g/cm³
• LogP: 0.12060
• Storage Temp.: Store at RT.
• Solubility.: Soluble in ethanol
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 306

Purity/Quality:

99% ^*data from raw suppliers

N-Hydroxy-5-norbornene-2,3-dicarboximide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C3C2C(=O)N(C3=O)O
• 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.
• Uses: N-Hydroxy-5-norbornene-2,3-dicarboximide(HONB) is used in solution-phase peptide synthesis. Used in the synthesis of enkephalin analogs. Inhibits racemization in peptide synthesis using DCC as condensing agent. It decreases racemization in peptide synthesis and inhibits formation of N-acylureas.

Technology Process of N-Hydroxy-5-norbornene-2,3-dicarboximide

There total 8 articles about N-Hydroxy-5-norbornene-2,3-dicarboximide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide (21715-90-2,397299-61-5)

Guidance literature:

With hydroxylamine hydrochloride; sodium carbonate; In water; at 20 ℃; for 3h;

Reference yield: 9.0%

cis-N-sulphonyloxy-5-norbornene-endo-2,3-dicarboximide (5433-80-7) → endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide (21715-90-2,397299-61-5)

Guidance literature:

cis-N-sulphonyloxy-5-norbornene-endo-2,3-dicarboximide; With aluminium trichloride; In benzene; for 2h; Heating;

With hydrogenchloride; In ethanol;

DOI:10.1080/10426500008046610

Reference yield:

2,3-(cyclopenten-endo-3',5'-diyl)-N-(2,4-dinitrophenoxy)succinimine → 2,4-Dinitrophenol (51-28-5) + endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide (21715-90-2,397299-61-5)

Guidance literature:

With sodium hydroxide; In acetonitrile; at 35 ℃; Rate constant; var. conc. of reagents;

upstream raw materials:

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

piperidine

pyrrolidine

morpholine

Downstream raw materials:

2-(3,4-dichloro-benzenesulfonyloxy)-(3ac,7ac)-3a,4,7,7a-tetrahydro-4r,7c-methano-isoindole-1,3-dione

N-benzoyloxy-5-norbornene-endo-2,3-dicarboximide

cis-N-sulphonyloxy-5-norbornene-endo-2,3-dicarboximide

Boc-Tyr-Met-Gly-ONB

Refernces

• 1、 Abbady,Kandeel,Youssef. "Base catalysed lossen rearrangement of N-sulphonyloxy-2,3-norborn-5-enedicarboximide". . p. 55 - 64. Retrieved 2007/10/03.
• 2、 Bhattacharjee, Gurudas,Singh, Ashok Kumar,Saikia, Ranjumoni,Yadav, Sudha. "Base-catalysed nucleophilic aromatic substitution reaction: Difference in reactivity between endo- and exo-2,3-(cyclopenten-3',5'-diyl)-N-(2",4"-dinitrophenoxy)succinimides with hydroxide ion and piperidine". . p. 1214 - 1217. Retrieved 2007/10/02.