5-Norbornene-2-carboxaldehyde

Base Information

• Chemical Name: 5-Norbornene-2-carboxaldehyde
• CAS No.: 5453-80-5
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.167
• Hs Code.: 29122990
• European Community (EC) Number: 226-698-9
• NSC Number: 18897
• DSSTox Substance ID: DTXSID20884162
• Nikkaji Number: J218F
• ChEMBL ID: CHEMBL4549018
• Mol file: 5453-80-5.mol

Synonyms:5-Norbornene-2-carboxaldehyde;5453-80-5;Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde;Bicyclo[2.2.1]hept-5-ene-2-carbaldehyde;2-Formyl-5-norbornene;5-Formylbicyclohept-2-ene;5-Norbornane-2-carboxaldehyde;EINECS 226-698-9;NSC 18897;AI3-10023;Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde;Bicyclo(2.2.1)hept-5-ene-2-carbaldehyde;bicyclo[2.2.1]hept-2-ene-5-carbaldehyde;NSC18897;5-norbornene-2-al;2-Formylnorborna-5-ene;5-norbornene-2-aldehyde;5-Formylbicyclo-2-heptene;5-Norbornene-2-carbaldehyde;norborn-5-en-2-carbaldehyde;2-norbornene-5-carboxaldehyde;SCHEMBL419841;CHEMBL4549018;DTXSID20884162;STR03238;NSC-18897;AKOS000120342;AKOS016842488;AC-4855;Bicyclo[2.2.1]hept-5-en-2-aldehyde;bicyclo-[2,2,1]-hept-5-en-2-aldehyde;Bicyclo[2.2.1]-5-hepten-2-yl-methanal;FT-0600269;N0504;EN300-20204;A830231;J-802154;F2191-0147;Z104477258

Chemical Property of 5-Norbornene-2-carboxaldehyde

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.819mmHg at 25°C
• Refractive Index: n20/D 1.490(lit.)
• Boiling Point: 182.2 °C at 760 mmHg
• Flash Point: 58 °C
• PSA: 17.07000
• Density: 1.162 g/cm³
• LogP: 1.39750
• Storage Temp.: Flammables area
• Water Solubility.: insoluble
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 122.073164938
• Heavy Atom Count: 9
• Complexity: 160

Purity/Quality:

99% Min. ^*data from raw suppliers

5-Norbornene-2-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 23-37/39-26-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC(C1C=C2)C=O
• Uses: 5-Norbornene-2-carboxaldehyde was used in transition metal-catalyzed synthesis of norbornene-derived homopolymers having pendent t-Boc-protected quinizarin moieties for patterned fluorescence images. It acts as Diels-Alder adduct of acrolein and cyclopentadiene. It can be used as protected form of acrolein, from which the double bond may be liberated by cycloreversion, e.g. in a useful synthesis of 2-vinylimidazole. 5-Norbornene-2-carboxaldehyde was used in transition metal-catalyzed synthesis of norbornene-derived homopolymers having pendent t-Boc-protected quinizarin moieties for patterned fluorescence images.

Technology Process of 5-Norbornene-2-carboxaldehyde

There total 31 articles about 5-Norbornene-2-carboxaldehyde 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: 98.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + acrolein (107-02-8,25068-14-8) → 5-Norbornene-2-carboxaldehyde (5453-80-5,19926-90-0)

Guidance literature:

With benzoic acid N'-isopropylhydrazide hydrochloride; In methanol; water; at 20 ℃; for 48h;

DOI:10.1039/b212239a

Reference yield: 92.0%

bicyclo<2.2.1>hept-5-ene-2-carboxaldehyde oxime (90086-80-9,96193-38-3,96193-44-1) → 5-Norbornene-2-carboxaldehyde (5453-80-5,19926-90-0)

Guidance literature:

With cethyltrimethylammonium permanganate; In dichloromethane; at 25 ℃; for 0.25h;

DOI:10.1021/jo00365a042

Reference yield: 91.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + acrolein (107-02-8,25068-14-8) → 5-Norbornene-2-carboxaldehyde (5453-80-5,19926-90-0) + (2R)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (72203-35-1) + (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (58001-94-8)

Guidance literature:

With [Ru(η5-C5H5)((S,S)-BIPHOP-F)(acetone)][SbF6]; lithium diisopropyl amide; In dichloromethane; at -20 ℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique;

DOI:10.1002/hlca.201600139

upstream raw materials:

diethyl ether

cyclopenta-1,3-diene

acrolein

carbon monoxide

Downstream raw materials:

1-norborn-5-en-2-yl-pentane-1,4-dione

<2,5-Methylen-1,2,5,6-tetrahydro-benzaldehyd>-p-amino-benzoylhydrazon

(2,5-Methylen-1,2,5,6-tetrahydro-benzaldehyd)-phenylacetylhydrazon

5-hydroxymethyl-2-norbornene

Refernces

• 1、 He, Xinxin,Wang, Xinyan,Tse, Ying-Lung Steve,Ke, Zhihai,Yeung, Ying-Yeung. "Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis". . p. 12632 - 12642. Retrieved 2021/10/21.
• 2、 Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.,Malkov, Andrei V.. "Oxidative Dehomologation of Aldehydes with Oxygen as a Terminal Oxidant". . p. 6760 - 6762. Retrieved 2017/12/26.