Synthesis Description Reference
ChemicalBook > CAS DataBase List > 1,2,3,4-TETRAHYDROISOQUINOLINE

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
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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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
NX4900000
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29334900
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T13005
Product name
1,2,3,4-Tetrahydroisoquinoline
Purity
95%
Packaging
25g
Price
$49.8
Updated
2024/03/01
Sigma-Aldrich
Product number
T13005
Product name
1,2,3,4-Tetrahydroisoquinoline
Purity
95%
Packaging
100g
Price
$98.9
Updated
2024/03/01
TCI Chemical
Product number
T1676
Product name
1,2,3,4-Tetrahydroisoquinoline
Purity
>95.0%(GC)
Packaging
25g
Price
$48
Updated
2024/03/01
TCI Chemical
Product number
T1676
Product name
1,2,3,4-Tetrahydroisoquinoline
Purity
>95.0%(GC)
Packaging
100g
Price
$119
Updated
2024/03/01
Alfa Aesar
Product number
L08143
Product name
1,2,3,4-Tetrahydroisoquinoline, 97%
Packaging
25g
Price
$48.4
Updated
2024/03/01
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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

  1. https://www.alfa.com/en/catalog/L08143/
  2. https://www.ncbi.nlm.nih.gov/pubmed/21235510
  3. https://en.wikipedia.org/wiki/Tetrahydroisoquinoline
  4. 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.
  5. 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.
  6. 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

2-PhenylethylaMine Ethanol Ethyl formate Sodium sulfate Trifluoroacetic acid Paraformaldehyde Chloroform Diethyl ether Sodium bicarbonate Acetic acid Methanol Sodium hydroxide

Preparation Products

6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
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View Lastest Price from 1,2,3,4-TETRAHYDROISOQUINOLINE manufacturers

Henan Aochuang Chemical Co.,Ltd.
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
Hebei Zhanyao Biotechnology Co. Ltd
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
Zhuozhou Wenxi import and Export Co., Ltd
Product
1,2,3,4-Tetrahydroisoquinoline 91-21-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27

91-21-4, 1,2,3,4-TETRAHYDROISOQUINOLINERelated Search:

THIAZOLIDINE Tetrahydrothiophen-3-one DL-LAUDANOSINE 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride DL-LAUDANOSOLINE HYDROBROMIDE TRIHYDRATE (+/-)-TETRAHYDROPAPAVEROLINE HYDROBROMIDE (+)-Bicuculline 1,2,3,4-TETRAHYDROISOQUINOLINE 1,2,3,4-L-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID 1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 1,2,3,4-D-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID (S)-N-tert-Butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide BOC-TIC-OH 3-CARBOXY-1,2,3,4-TETRAHYDROISOQUINOLINE 3-CARBOXY-1,2,3,4-TETRAHYDROISOQUINOLINE (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline Drotaverin hydrochloride

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