1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol

Basic Information

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CAS Number

5843-65-2

Molecular Formula

C16H17NO3

Molecular Weight

271.32 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Basic Physical Properties

Physical State

Powder

Melting Point

242-244°C

Boiling Point

522.4°Cat760mmHg

Density

1.317

Flash Point

209.6°C

Solubility

,Acetontrile

Refractive Index

1.666

SMILES

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C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O

InChI

InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2

InChIKey

WZRCQWQRFZITDX-UHFFFAOYSA-N

LogP

2.2329

Topological Polar Surface Area

72.72 Å²

Hydrogen Bond Donor/Acceptor

4 / 4

Complexity

317

Safety Information

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Storage Conditions

2-8℃

Synonyms & References

English

(+-)-Norcoclaurine
1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol #
AMY36791
Norcoclaurine
CHEBI:18418
(R)-Higenamine
(+/-)-DEMETHYLCOCLAURINE
XH164059
1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Isoquinolin-6,7-diol, 1,2,3,4-tetrahydro-1-[4-hydroxybenzyl]-
(+-)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol
(RS)-norcoclaurine
UNII-TBV5O16GAP
5843-65-2
AC-26394
6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline
Higenamine
DL-DEMETHYLCOCLAURINE
WZRCQWQRFZITDX-UHFFFAOYSA-N
C06346
Coclaurine, O-demethyl-, (+-)-
DTXSID70973974
Demethyl-Coclaurine
6,7-Dihydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline
s3294
DB12779
FS-8108
1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
6,7-ISOQUINOLINEDIOL, 1,2,3,4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-
TBV5O16GAP
HIGENAMINE [WHO-DD]

MDL Number

MFCD01736979

FAQ

What are the physical and chemical properties of 1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol (CAS: 5843-65-2)?

1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol has a crystalline form and a molecular weight of 252.25 g/mol. It is sparingly soluble in water but more soluble in alcoholic and chlorinated solvents. The compound is relatively stable, with limited reactivity towards common inorganic acids and bases. It does not undergo typical nucleophilic substitution reactions due to the stable aromatic ring structure and the sp3 hybridized nitrogen atom.

How is 1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol (CAS: 5843-65-2) typically synthesized?

1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol is typically synthesized by a multistep process involving the construction of the aromatic core via coupling reactions, followed by ring expansion and hydroxylation. Catalysts such as palladium on carbon and Lewis acids are commonly used, with high yields and good selectivity reported in the literature. The exact conditions can vary depending on the specific starting materials and desired purity of the product.

What industries use 1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol (CAS: 5843-65-2)?

1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol finds applications in the pharmaceutical industry for the development of potential drug candidates, particularly in anti-inflammatory and analgesic therapies. It is also used in the production of electronic materials, where its conductivity properties make it suitable for certain semiconductor applications. Additionally, it may be used in the formulation of certain polymers and as a component in sensors.

What precautions should be taken when handling 1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol (CAS: 5843-65-2)?

When handling 1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol, appropriate personal protective equipment (PPE) should be worn, including gloves, safety goggles, and a lab coat. It should be stored in a well-ventilated area or in a fume hood to prevent inhalation of any vapors. In case of spillage, the area should be ventilated and the spill cleaned up using appropriate absorbent materials. The safety data sheet (SDS) should be consulted for detailed handling procedures and emergency response measures.