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301981

Sigma-Aldrich

5,6,7,8-Tetrahydroisoquinoline

95%

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About This Item

Empirical Formula (Hill Notation):
C9H11N
CAS Number:
36556-06-6
Molecular Weight:
133.19
EC Number:
253-098-4
MDL number:
MFCD00012168
UNSPSC Code:
12352100
PubChem Substance ID:
24858223
NACRES:
NA.22

assay

95%

form

liquid

refractive index

n20/D 1.545 (lit.)

bp

106-108 °C/13 mmHg (lit.)

density

1.03 g/mL at 25 °C (lit.)

SMILES string

C1CCc2cnccc2C1

InChI

1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h5-7H,1-4H2

InChI key

HTMGQIXFZMZZKD-UHFFFAOYSA-N

Related Categories

General description

Reduction of 5,6,7,8-tetrahydroisoquinoline with sodium in ethanol gives trans-decahydroquinolines. 5,6,7,8-Tetrahydroisoquinoline is also referred as Bz-tetrahydroisoquinoline.

Application

5,6,7,8-Tetrahydroisoquinoline was used in total synthesis of (±)-desoxycodeine-D. It was also used in the synthesis of 7,8-dihydroisoquinolin-5(6H)-one.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

212.0 °F - closed cup

flash_point_c

100 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reduction of 5, 6, 7, 8-tetrahydroquinolines and 2, 3, 4, 5, 6, 7, 8, 10-octahydroquinolines to trans-decahydroquinolines.
Vierhapper FW and Eliel EL.
The Journal of Organic Chemistry, 40(19), 2734-2742 (1975)
A Convenient Synthesis 7, 8-Dihydroisoquinolin-5 (6H)-One.
Lardenois P, et al.
Synthetic Communications, 26(12), 2305-2308 (1996)
Total synthesis of (?)-desoxycodeine-d: a novel route to the morphine skeleton.
Liou J-P and Cheng C-Y.
Tetrahedron Letters, 41(6), 915-918 (2000)
Preparation of cis-and trans-Decahydroisoquinolines and of Bz-Tetrahydroisoquinoline.
Witkop B.
Journal of the American Chemical Society, 70(8), 2617-2619 (1948)

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