1,2,3,4-TETRAHYDROISOQUINOLINE
Synthesis Description Reference- Product Name
- 1,2,3,4-TETRAHYDROISOQUINOLINE
- CAS No.
- 91-21-4
- Chemical Name
- 1,2,3,4-TETRAHYDROISOQUINOLINE
- Synonyms
- Tetrahydroisoquinoline;AKOS BB-9293;LABOTEST-BB LTBB000776;1,2,3,4-TetrahydroisoquinoL;3,4-Dihydro-1H-isoquinoline.;1,2,3,4-TETRAHYDROISOQUINOLINE;1,2,3,4-Tetrahydroisochinoline;1,2,3,4-tetrahydro-isoquinolin;1,2,3,4-Tetrahydro-2-isoquinoline;Isoquinoline, 1,2,3,4-tetrahydro-
- CBNumber
- CB5126507
- Molecular Formula
- C9H11N
- Formula Weight
- 133.19
- MOL File
- 91-21-4.mol
1,2,3,4-TETRAHYDROISOQUINOLINE Property
- Melting point:
- −30 °C(lit.)
- Boiling point:
- 232-233 °C(lit.)
- Density
- 1.064 g/mL at 25 °C(lit.)
- vapor pressure
- 3.33-97.9Pa at 20-58.5℃
- refractive index
- n20/D 1.568(lit.)
- Flash point:
- 210 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 20g/l
- form
- Liquid
- pka
- 9.66±0.20(Predicted)
- color
- Clear yellow to brown
- Water Solubility
- Soluble in water at 20°C 20g/L.
- BRN
- 116156
- InChIKey
- UWYZHKAOTLEWKK-UHFFFAOYSA-N
- CAS DataBase Reference
- 91-21-4(CAS DataBase Reference)
- EPA Substance Registry System
- Isoquinoline, 1,2,3,4-tetrahydro- (91-21-4)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H301Toxic if swalloed
H310Fatal in contact with skin
H314Causes severe skin burns and eye damage
H332Harmful if inhaled
H371May cause damage to organs
H412Harmful to aquatic life with long lasting effects
- Precautionary statements
-
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P273Avoid release to the environment.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- T13005
- Product name
- 1,2,3,4-Tetrahydroisoquinoline
- Purity
- 95%
- Packaging
- 25g
- Price
- $49.8
- Updated
- 2024/03/01
- Product number
- T13005
- Product name
- 1,2,3,4-Tetrahydroisoquinoline
- Purity
- 95%
- Packaging
- 100g
- Price
- $98.9
- Updated
- 2024/03/01
- Product number
- T1676
- Product name
- 1,2,3,4-Tetrahydroisoquinoline
- Purity
- >95.0%(GC)
- Packaging
- 25g
- Price
- $48
- Updated
- 2024/03/01
- Product number
- T1676
- Product name
- 1,2,3,4-Tetrahydroisoquinoline
- Purity
- >95.0%(GC)
- Packaging
- 100g
- Price
- $119
- Updated
- 2024/03/01
- Product number
- L08143
- Product name
- 1,2,3,4-Tetrahydroisoquinoline, 97%
- Packaging
- 25g
- Price
- $48.4
- Updated
- 2024/03/01
1,2,3,4-TETRAHYDROISOQUINOLINE Chemical Properties,Usage,Production
Synthesis
To a solution of the isoquinolinone (1.156 g, 9.90 mmol) and tert-butyl alcohol
(0.88 mL, 11.9 mmol) in THF (30 mL) at −78 °C was added liquid ammonia (about
280 mL). Lithium was added in small pieces until the blue coloration persisted, after
which the solution was stirred at −78 °C for 30 min. The blue coloration was dissipated
with piperlyne, 4-methoxybenzyl chloride (4.83 g, 31.00 mmol) in THF (5 mL)
was introduced by syringe, and the mixture was stirred for an additional 150 min at
−78 °C. Solid ammonium chloride was added and then the ammonia was allowed to
evaporate. The pale yellow residue was partitioned between CH2Cl2 (30 mL) and
water (40 mL). The layers were separated, and the aqueous layer was extracted
with CH2Cl2 (2 × 30 mL). The combined organic layers were washed with 10%
sodium thiosulfate solution (20 mL), dried over magnesium sulfate, and concentrated.
Flash chromatography (EtOAc:hexane, 2:1) on silica gave 2.21 g (75%) of the
tetrahydroisoquinolinone.
Reference: Schultz, A. G.; Guzi, T. J.; Larsson, E.; Rahm, R.; Thakker, K.
Bidlack, J. M. J. Org. Chem. 1998, 63, 7795–7804.
Description
1, 2, 3, 4-TETRAHYDROISOQUINOLINE belongs to tetrahydroisoquinoline compound, which is encountered in a number of drugs, tubocurarine, one of the quaternary ammonium muscle relaxants1-3. It is used as a reagent in the preparation of4-(1, 2, 4-oxadiazol-5-yl) piperidine-1-carboxamides as antiproliferative tubulin inhibitors1. It can be used for the synthesis of 1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid (Tic), which has strong applications in peptides and peptidomimetics design and discovery2. 1, 2, 3, 4-tetrahydroisoquinoline has been made into some derivatives with potential for prevention of parkinsonism4, cancer treatment5 and acting as Anticonvulsant Agents6.
Reference
- https://www.alfa.com/en/catalog/L08143/
- https://www.ncbi.nlm.nih.gov/pubmed/21235510
- https://en.wikipedia.org/wiki/Tetrahydroisoquinoline
- Okuda, K, Y. Kotake, and S. Ohta. "Parkinsonism-preventing activity of 1-methyl-1, 2, 3, 4-tetrahydroisoquinoline derivatives in C57BL mouse in vivo. Biological & Pharmaceutical Bulletin 29.7(2006):1401-1403.
- Luca, Laura De, et al. "3D Pharmacophore Models for 1, 2, 3, 4‐Tetrahydroisoquinoline Derivatives Acting as Anticonvulsant Agents." Archiv Der Pharmazie 339.7(2006):388-400.
- Hatano, H, et al. "Tumor-specific cytotoxic activity of 1, 2, 3, 4-tetrahydroisoquinoline derivatives against human oral squamous cell carcinoma cell lines."Anticancer Research 29.8(2009):3079-3086.
Chemical Properties
clear yellow to brown liquid
Uses
1,2,3,4-Tetrahydroisoquinoline is used as a reagent in the preparation of 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides as antiproliferative tubulin inhibitors.
Definition
ChEBI: 1,2,3,4-tetrahydroisoquinoline is a member of isoquinolines.
Synthesis Reference(s)
The Journal of Organic Chemistry, 40, p. 1191, 1975 DOI: 10.1021/jo00897a001
Tetrahedron Letters, 26, p. 4633, 1985 DOI: 10.1016/S0040-4039(00)98771-9
1,2,3,4-TETRAHYDROISOQUINOLINE Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 1,2,3,4-TETRAHYDROISOQUINOLINE manufacturers
- Product
- 1,2,3,4-tetrahydro-isoquinoline 91-21-4
- Price
- US $0.01-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 50 tons
- Release date
- 2020-04-28
- Product
- 1,2,3,4-TETRAHYDROISOQUINOLINE 91-21-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-10-17
- Product
- 1,2,3,4-TETRAHYDROISOQUINOLINE 91-21-4
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 Tons
- Release date
- 2021-10-13