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359351

Sigma-Aldrich

3-Isochromanone

98%

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About This Item

Empirical Formula (Hill Notation):
C9H8O2
CAS Number:
4385-35-7
Molecular Weight:
148.16
Beilstein:
123692
EC Number:
224-493-9
MDL number:
MFCD00043005
UNSPSC Code:
12352100
PubChem Substance ID:
24862071
NACRES:
NA.22

Assay

98%

mp

80-82 °C (lit.)

functional group

ester

SMILES string

O=C1Cc2ccccc2CO1

InChI

1S/C9H8O2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-4H,5-6H2

InChI key

ILHLUZUMRJQEAH-UHFFFAOYSA-N

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General description

3-Isochromanone has been reported to be isolated from the fungus Nigrospora sp. PSU-F12. An improved Knoevenagel condensation of 3-isochromanone with aromatic aldehydes has been achieved by microwave irradiation on solid supports in the presence of various catalysts. Synthesis of 3-isochromanone via Beayer-Villiger rearrangement has been reported.

Application

3-Isochromanone may be used as starting reagent in the synthesis of of BDPBI (7-bromo-1,4-dihydro-2-phenyl-4,4-bis(4-pyridinylmethyl)2H-isoquinolin-3-one dihydrochloride).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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
MKBB4403
19529KR
11821DU
11325AA
11212BU

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András Vass et al.
Journal of biochemical and biophysical methods, 69(1-2), 179-187 (2006-05-09)
An improved Knoevenagel condensation of 3-isochromanone and aromatic aldehydes can be achieved by microwave irradiation on solid supports in the presence of various catalysts. This synthetic method offers some major advantages, especially the possibility to change the ratio of E/Z
Vatcharin Rukachaisirikul et al.
Archives of pharmacal research, 33(3), 375-380 (2010-04-03)
Nigrosporanenes A (1) and B (2), two new cylohexene derivatives, and tyrosol (3) were isolated from the sea fan-derived fungus Nigrospora sp. PSU-F11, whereas five known compounds: 4-hydroxybenzoic acid (4), aplysiopsene D (5), 3-isochromanone (6), (-)-drimenin (7) and diketopiperazine derivative
3-Isochromanone.
Markgrar JH and Basta SJ.
Synthetic Communications, 2(3), 139-141 (1972)
Chia Hsien Lin et al.
Pharmacology, 67(4), 202-210 (2003-02-22)
The pharmacological effects of BDPBI (7-bromo-1,4-dihydro-2-phenyl-4,4-bis(4-pyridinylmethyl)2H-isoquinolin-3-one dihydrochloride) were tested on isolated endothelium-containing or denuded aorta of the guinea pig. BDPBI with the formula C(27)H(24)BrCl(2)N(3)O was synthesized starting with 3-isochromanone. In the endothelium-containing preparations of the aortic rings, phenylephrine (PHE; 10

Articles

Knoevenagel Condensation Reaction

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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