TRANS-5-NORBORNENE-2,3-DICARBONYL CHLORIDE

Base Information

• Chemical Name: TRANS-5-NORBORNENE-2,3-DICARBONYL CHLORIDE
• CAS No.: 4582-21-2
• Molecular Formula: C9H8 Cl2 O2
• Molecular Weight: 219.067
• Hs Code.: 2917209090
• European Community (EC) Number: 224-967-5
• NSC Number: 512760,103156
• DSSTox Substance ID: DTXSID80963447
• Nikkaji Number: J1.386.786K
• Mol file: 4582-21-2.mol

Synonyms:5-Norbornene-2,3-dicarbonylchloride, trans- (8CI); Bicyclo[2.2.1]hept-5-ene-2,3-dicarbonyl dichloride,(2-endo,3-exo)-; NSC 103156;endo,exo-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyclic acid dichloride;endo,exo-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic dichloride;trans-3,6-Endomethylene-1,2,3,6-tetrahydrophthaloyl chloride; trans-5-Norbornene-2,3-dicarbonylchloride

Chemical Property of TRANS-5-NORBORNENE-2,3-DICARBONYL CHLORIDE

Chemical Property:

• Vapor Pressure: 0.032mmHg at 25°C
• Refractive Index: n20/D 1.517(lit.)
• Boiling Point: 243.3°Cat760mmHg
• Flash Point: 133.5°C
• PSA: 34.14000
• Density: 1.453g/cm³
• LogP: 1.95550
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 217.9901349
• Heavy Atom Count: 13
• Complexity: 270

Purity/Quality:

98%min ^*data from raw suppliers

trans-3,6-Endomethylene-1,2,3,6-tetrahydrophthaloyl chloride 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 23-26-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C=CC1C(C2C(=O)Cl)C(=O)Cl

Technology Process of TRANS-5-NORBORNENE-2,3-DICARBONYL CHLORIDE

There total 5 articles about TRANS-5-NORBORNENE-2,3-DICARBONYL CHLORIDE 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: 100.0%

fumaryl dichloride (627-63-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → endo,exo-bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid dichloride (4582-21-2)

Guidance literature:

In toluene; Heating;

DOI:10.1016/S0960-894X(98)00143-7

Reference yield: 98.0%

norbornene-5,6-dicarboxylic acid (1200-88-0) → endo,exo-bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid dichloride (4582-21-2)

Guidance literature:

With oxalyl dichloride; In N,N-dimethyl-formamide; benzene; for 4h; Reflux;

DOI:10.24820/ark.5550190.p010.654

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → endo,exo-bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid dichloride (4582-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetone; H₂O / 50 °C

2: oxalyl chloride; DMF

With oxalyl dichloride; N,N-dimethyl-formamide; In water; acetone;

DOI:10.1021/ol0352759

upstream raw materials:

fumaryl dichloride

cyclopenta-1,3-diene

norbornene-5,6-dicarboxylic acid

Downstream raw materials:

(+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol

1,4-Endomethylen-cyclohex-5-en-trans-2,3-dicarbonsaeurediamid

dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Acetic acid (1S,2R,3R,4R)-3-acetoxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

Refernces

• 1、 ?apan, Irfan,Servi, Süleyman. "Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons". . p. 131 - 142. Retrieved 2018/10/26.
• 2、 Moore, Joel D.,Byrne, Robert J.,Vedantham, Punitha,Flynn, Daniel L.,Hanson, Paul R.. "High-Load, ROMP-Generated Oligomeric Bis-acid Chlorides: Design of Soluble and Insoluble Nucleophile Scavengers". . p. 4241 - 4244. Retrieved 2007/10/03.