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341800

Sigma-Aldrich

1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione

98%

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About This Item

Empirical Formula (Hill Notation):
C11H10O2
CAS Number:
51175-59-8
Molecular Weight:
174.20
MDL number:
MFCD00083094
UNSPSC Code:
12352100
PubChem Substance ID:
24860998
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

mp

77-79 °C (lit.)

SMILES string

O=C1C=CC(=O)[C@H]2[C@@H]3C[C@@H](C=C3)[C@@H]12

InChI

1S/C11H10O2/c12-8-3-4-9(13)11-7-2-1-6(5-7)10(8)11/h1-4,6-7,10-11H,5H2/t6-,7+,10+,11-

InChI key

FQLRTGXTYFCECH-FIPCFZRWSA-N

General description

1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione can be prepared by Diels-Alder reaction of cyclopentadiene and 1,4-benzoquinone.

Application

1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione may be used in the synthesis of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (the ′cage′ compound) via the intramolecular [2+2]-photocycloaddition reaction.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBF1963V
07118LE
15620MR
10713KS
13607DN

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Photochemical synthesis of a ?cage? compound in a microreactor: Rigorous comparison with a batch photoreactor.
Aillet T, et al.
Chemical Engineering and Processing, 64, 38-47 (2013)

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