7-tert-Butoxybicyclo(2.2.1)hepta-2,5-diene

Base Information

• Chemical Name: 7-tert-Butoxybicyclo(2.2.1)hepta-2,5-diene
• CAS No.: 877-06-5
• Molecular Formula: C11H16O
• Molecular Weight: 164.247
• Hs Code.: 2902190000
• European Community (EC) Number: 212-885-2
• NSC Number: 120548
• DSSTox Substance ID: DTXSID40236563
• Nikkaji Number: J195.167J,J953.389C
• Wikidata: Q83118530
• Mol file: 877-06-5.mol

Synonyms:877-06-5;7-tert-Butoxynorbornadiene;7-tert-Butoxybicyclo(2.2.1)hepta-2,5-diene;7-Norbornadienyl tert-butyl ether;7-tert-Butoxy-2,5-norbornadiene;7-Norbornadienyl t-butyl ether;7-[(2-methylpropan-2-yl)oxy]bicyclo[2.2.1]hepta-2,5-diene;7-tert-butoxybicyclo[2.2.1]hepta-2,5-diene;EINECS 212-885-2;Bicyclo(2.2.1)hepta-2,5-diene, 7-(1,1-dimethylethoxy)-;Bicyclo[2.2.1]hepta-2,5-diene, 7-(1,1-dimethylethoxy)-;7-(tert-butoxy)bicyclo[2.2.1]hepta-2,5-diene;NSC120548;7-t-butoxynorbornadiene;SCHEMBL3954916;7-Norbornadadienyl t-butyl ether;DTXSID40236563;7-tert-Butoxynorborna-2,5-diene;MFCD00082303;NSC 120548;NSC-120548;7-tert-Butoxy-2,5-norbornadiene, 96%;FT-0621482;(1s,4s)-7-tert-butoxybicyclo[2.2.1]hepta-2,5-diene;Bicyclo[2.2.1]hepta-2,5-dien-7-yl tert-butyl ether #;(1alpha,4alpha)-7-tert-Butoxybicyclo[2.2.1]hepta-2,5-diene

Chemical Property of 7-tert-Butoxybicyclo(2.2.1)hepta-2,5-diene

Chemical Property:

• Vapor Pressure: 0.317mmHg at 25°C
• Refractive Index: n20/D 1.469(lit.)
• Boiling Point: 70-72 °C14 mm Hg(lit.)
• Flash Point: 127 °F
• PSA: 9.23000
• Density: 0.936 g/mL at 25 °C(lit.)
• LogP: 2.54210
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 164.120115130
• Heavy Atom Count: 12
• Complexity: 202

Purity/Quality:

98%,99%, ^*data from raw suppliers

7-tert-Butoxy-2,5-norbornadiene 96% ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC1C2C=CC1C=C2

Technology Process of 7-tert-Butoxybicyclo(2.2.1)hepta-2,5-diene

There total 13 articles about 7-tert-Butoxybicyclo(2.2.1)hepta-2,5-diene 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: 81.0%

anti-7-tert-butoxynorbornadien-2-yl triflate + cyclohexylmagnesiumchloride (931-51-1) → anti-7-tert-butoxy-2-cyclohexylnorbornadiene + 7-tert-butoxynorbornadiene (877-06-5)

Guidance literature:

With iron(III) acetylacetonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; at -25 ℃; Inert atmosphere;

DOI:10.1055/s-0028-1083352

Reference yield: 75.0%

anti-7-tert-butoxynorbornadien-2-yl triflate + isopropylmagnesium chloride (1068-55-9) → anti-7-tert-butoxy-2-isopropylnorbornadiene + 7-tert-butoxynorbornadiene (877-06-5)

Guidance literature:

With iron(III) acetylacetonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; at -25 ℃; Inert atmosphere;

DOI:10.1055/s-0028-1083352

Reference yield: 68.0%

anti-7-tert-butoxynorbornadien-2-yl triflate + cyclopentylmagnesium chloride (32916-51-1) → anti-7-tert-butoxy-2-cyclopentylnorbornadiene + 7-tert-butoxynorbornadiene (877-06-5)

Guidance literature:

With iron(III) acetylacetonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; at -25 ℃; Inert atmosphere;

DOI:10.1055/s-0028-1083352

upstream raw materials:

3-t-Butoxyquadricyclane

1-bromo-butane

cycloheptyl bromide

chlorocyclobutane

Downstream raw materials:

7-t-butoxy-4-phenylsulfonyl-4-azatetracyclo<3.3.0.0^2,8.0^3,6>octane

7-t-butoxy-4-(4'-chlorophenylsulfonyl)-4-azatetracyclo<3.3.0.0^2,8.0^3,6>octane

7-(4-methylphenyl)bicyclo<2.2.1>heptadiene

7-(4-fluorophenyl)bicyclo<2.2.1>heptadiene

Refernces

• 1、 Alfano, Angelo J.. "Gas-phase pyrolysis mechanism and kinetics of 3-t-butoxyquadricyclane". . p. 481 - 487. Retrieved 1996.
• 2、 Nagarkar, Amit A.,Yasir, Mohammad,Crochet, Aurelien,Fromm, Katharina M.,Kilbinger, Andreas F. M.. "Tandem Ring-Opening–Ring-Closing Metathesis for Functional Metathesis Catalysts". supporting information. p. 12343 - 12346. Retrieved 2016/10/13.
• 3、 Tsui, Gavin C.,Marquand, Paul Le,Allen, Anna,Tam, William. "Synthesis of anti-2,7-disubstituted norbornadienes". experimental part. p. 609 - 619. Retrieved 2009/07/11.