5597-27-3

Basic information

• Product Name: 3-METHYLENE-2-NORBORNANONE
• Synonyms: 3-Methylene-2-norbornanone,97%;3-Methylene-2-norbornanone 97%;2-Norbornanone, 3-methylene-;Bicyclo[2.2.1]heptan-2-one, 3-methylene-;3-METHYLENE-2-NORBORNANONE;3-METHYLENEBICYCLO[2.2.1]HEPTAN-2-ONE;3-methylenenorbornan-2-one;3-Methylene-2-norbornanone,90%
• CAS NO: 5597-27-3
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.16
• EINECS: 227-009-4
• Product Categories: Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 5597-27-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 69-71 °C11 mm Hg(lit.)
• Flash Point: 131 °F
• Appearance: clear brown liquid
• Density: 0.997 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.715mmHg at 25°C
• Refractive Index: n20/D 1.493(lit.)
• CAS DataBase Reference: 3-METHYLENE-2-NORBORNANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLENE-2-NORBORNANONE(5597-27-3)
• EPA Substance Registry System: 3-METHYLENE-2-NORBORNANONE(5597-27-3)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 5597-27-3(Hazardous Substances Data)

Usage

Chemical Properties

clear brown liquid

Uses

3-Methylene-2-norbornanone can be used as a reactant to prepare:3-(2-(4-methoxyphenyl)-2-oxoethyl)bicyclo[2.2.1]heptan-2-one by reacting with 4-anisaldehyde in the presence of tetrabutylammonium decatungstate (TBADT) photocatalyst. 2-Aryl-3-methylene-endo-norbornanols by treating with corresponding aryl lithium reagents.

InChI:InChI=1/C8H10O/c1-5-6-2-3-7(4-6)8(5)9/h6-7H,1-4H2/t6-,7+/m1/s1

Upstream product

• 50-00-0 formaldehyd 
• 497-38-1 2-norbornanone 
• 497-38-1 Norbornan-2-on 
• 74713-07-8 3-(diethylaminomethyl)bicyclo[2.2.1]heptan-2-one 
• 5597-29-5 3-methylenenbicyclo<2.2.1>heptan-endo-2-ol 
• 99173-09-8 (+/-)-3endo-acetoxymethyl-norbornan-2-one 
• 694-92-8 2-methylnorborn-2-ene 
• 497-35-8 2-methylenebicyclo[2.2.1]heptane 

Downstream Products

• 82741-93-3 3-benzylbicyclo<2.2.1>heptan-2-one 
• 89164-93-2 C₁₅H₁₇⁽¹⁺⁾ 
• 89164-90-9 C₁₅H₁₇⁽¹⁺⁾ 
• 89164-91-0 C₁₄H₁₄F⁽¹⁺⁾ 
• 89164-92-1 C₁₄H₁₄Cl⁽¹⁺⁾ 
• 89164-95-4 C₁₄H₁₄F⁽¹⁺⁾ 
• 89164-96-5 C₁₄H₁₄Cl⁽¹⁺⁾ 
• 89164-89-6 C₁₅H₁₇O⁽¹⁺⁾ 
• 89164-98-7 C₁₄H₁₃Cl₂⁽¹⁺⁾ 
• 89164-97-6 C₁₅H₁₄F₃⁽¹⁺⁾ 
• 1069086-86-7 3-{[(4-hydroxyphenyl)sulfanyl]methyl}bicyclo[2.2.1]heptan-2-one 
• 1069086-95-8 3-({[2-(hydroxymethyl)phenyl]sulfanyl}methyl)bicyclo[2.2.1]heptan-2-one 
• 1421789-46-9 4-(3-bromophenyl)-3-azatricyclo[6.2.1.0*2,7*]undeca-2⁽⁷⁾,3,5-triene 
• 1421789-42-5 C₄₁H₄₀N₂OPt 

Relevant articles and documents

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Process for the preparation of bicyclic diketone salts

The present invention relates to a process for the preparation of bicyclic 1,3-diketone salts of formula I wherein R1, R2, R3 and R4 are each independently of the others hydrogen or C1-C4alkyl; A and E are each independently of the other C1-C2alkylene, which may be substituted once or up to four times by a C1-C4alkyl group, and M+ is an alkali metal ion, alkaline earth metal ion or ammonium ion, by oxidation of a compound of formula II to a compound of formula III and subsequent conversion to a compound of formula I either in the presence of a base and a catalytic amount of a cyanide or in the presence of an alkali metal alcoholate or alkaline earth metal alcoholate, and to novel bicyclic enol lactone intermediates of formula III for use in that process.

Radical Reactions of Bicycloheptan-3-spiro-2'-oxiranes

Tributyltin hydride reduction of 2-bromo- and 2-keto-bicycloheptan-3-spiro-2'-oxiranes gives ring opening of the oxirane-ringes via intermediate 3-(spiro-2'-oxiranyl)bicycloheptan-2-yl radicals, whereas reduction of the analogous 2-(thiocarbonyl)imidazolides) unusually yields the 2-methoxy derivatives and does not proceed by the expected normal fragmentation to yield 3-(spiro-2'-oxiranyl)bicycloheptan-2-yl radicals and subsequent ring-opening of the oxirane rings.