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2744-08-3

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2744-08-3 Usage

Uses

(4aR,8aR)-Decahydroisoquinoline is a synthetic building block predominately used in the synthesis of natural products.

Purification Methods

The free base is treated with saturated aqueous picric acid, allowed to stand for 12hours, filtered, washed with MeOH to remove the more soluble trans isomer and recrystallised from MeOH to give pure cis-picrate m 149-150o. The picrate (~5g) is shaken with 5M aqueous NaOH (50mL) and Et2O (150mL) while H2O is added to the aqueous phase to dissolve insoluble Na picrate. The Et2O extract is dried over solid NaOH and then shaken with Al2O3 (Merck for chromatography) until the yellow color of traces of picric acid disappears (this color cannot be removed by repeated shaking with 5-10 M aqueous NaOH). The extract is concentrated to 50mL and dry HCl is bubbled through until separation of the white crystals of the cis-HCl is complete. These are washed with Et2O, dried at 100o and recrystallised from EtOH/EtOAc to yield pure cis-hydrochloride m 182-183o (dried in a vacuum desiccator over KOH) with IR (KBr) 2920, 2820, 1582, 1470, 1445, 1410, 1395, max 1313, 1135, 1080, 990, 870 cm-1 . The pure free base is prepared by dissolving the hydrochloride in 10M aqueous NaOH, extracted with Et2O, dried over solid KOH, filtered and distilled in a vacuum. It has IR (film) max 2920, 2820, 2720, 2560, 1584, 1470, 1445, 1415, 1395, 1315, 1300, 1135, 1080, 1020, 990, 873 cm-1 . The 1HNMR in CDCl3 is characteristically different from that of the trans-isomer. [Armarego J Chem Soc (C) 377 1967, Gray & Heitmeier J Am Chem Soc 80 6274 1958, Witkop J Am Chem Soc 70 2617 1948, Skita Chem Ber 57 1982 1924, Helfer Helv Chim Acta 6 7991923, Beilstein 20 II 73, 20 III/IV 2026.]

Check Digit Verification of cas no

The CAS Registry Mumber 2744-08-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,4 and 4 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2744-08:
(6*2)+(5*7)+(4*4)+(3*4)+(2*0)+(1*8)=83
83 % 10 = 3
So 2744-08-3 is a valid CAS Registry Number.

2744-08-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name cis-Decahydroisoquinoline

1.2 Other means of identification

Product number -
Other names decahydrosoquinoline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2744-08-3 SDS

2744-08-3Relevant articles and documents

-

Gray,Heitmeier

, p. 6274 (1958)

-

-

Witkop

, p. 2617 (1948)

-

Catalyst component, catalyst for olefin polymerization, and process for producing olefin polymer using catalyst

-

, (2012/08/29)

A polymer having high catalyst activity, excellent hydrogen response, high stereoregularity and high yield can be obtained by polymerizing olefins in the presence of a catalyst for olefin polymerization comprising (A) a solid catalyst component containing magnesium, titanium, a halogen, and an electron donor compound, (B) an organoaluminum compound shown by the formula R6pAlQ3-p(R1R2N)m, and (C) an aminosilane compound shown by the formula (R3HN)nR4pSi(OR5)q.

Mechanism of Isomerization of 1,2,3,4-Tetrahydroisoquinoline to 5,6,7,8-Tetrahydroisoquinoline over Raney Nickel

Okazaki, Hiroshi,Onishi, Kiyotaka,Ikefuji, Yoshio,Tamura, Ryuji

, p. 1321 - 1327 (2007/10/02)

The isomerization of 1,2,3,4-tetrahydroisoquinoline to 5,6,7,8-tetrahydroisoquinoline proceeded over Raney nickel at ca. 200 deg C under hydrogen and nitrogen pressure in a closed reactor.Based on kinetic analyses and quantum chemical calculations we propose that the isomerization proceeds through a series of consecutive steps where dehydrogenation and hydrogenation take place in an alternate manner.The isomerization is initiated by dehydrogenation at the C-1 and N positions of 1,2,3,4-tetrahydroisoquinoline to form 3,4-dihydroisoquinoline which, in turn, is rehydrogenated into 3,4,6,7-tetrahydroisoquinoline and 3,4,5,6,7,8-hexahydroisoquinoline.The hexahydroisoquinoline is finally dehydrogenated into the isomerized product.No extra hydrogen appears to be required for the isomerization.Under a nitrogen stream in an open reactor, the selective formation of isoquinoline occurred.

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