7-Hydroxyisoquinoline

Base Information

• Chemical Name: 7-Hydroxyisoquinoline
• CAS No.: 7651-83-4
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 2933499090
• European Community (EC) Number: 676-883-7
• DSSTox Substance ID: DTXSID90901678
• Nikkaji Number: J1.094.755C
• Wikidata: Q106902827
• Mol file: 7651-83-4.mol

Synonyms:7-Hydroxyisoquinoline;isoquinolin-7-ol;7651-83-4;7-Isoquinolinol;14476-74-5;MFCD00456131;Isoquinolin-7-Ol, 7-Hydroxy-2-Azanaphthalene;7(1H)-Isoquinolinone;NoName_814;7-Isoquinolinol, AldrichCPR;SCHEMBL276615;DTXSID90901678;AKOS001061431;AC-9567;CS-W011000;MB01177;PS-4726;RTE2_000003;SY020018;A9697;AM20061496;FT-0621436;FT-0685558;EN300-05942;J-519272;W-205613;Z56928661

Chemical Property of 7-Hydroxyisoquinoline

Chemical Property:

• Appearance/Colour: yellow solid
• Melting Point: 226-228 °C
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 332.1 °C at 760 mmHg
• PKA: 5.68(at 20℃)
• Flash Point: 154.6 °C
• PSA: 33.12000
• Density: 1.26 g/cm³
• LogP: 1.94040
• Storage Temp.: Keep Cold
• Solubility.: Soluble in methanol and concentrated sulfuric acid.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 145.052763847
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

Isoquinolin-7-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC2=C1C=CN=C2)O
• Uses: 7-Hydroxyisoquinoline is used to study its photophysial behavior in polymer matrices such as polymethyl methacrylate, cellulose acetate, polyvinyl alcohol and sulfonated tetrafluoroethylene based fluoropolymer- copolymer. It also used to prepare quinine. Further, it is used as the material for all optical switching due to its excited state proton transfer (ESPT) effect.

Technology Process of 7-Hydroxyisoquinoline

There total 13 articles about 7-Hydroxyisoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

3-Benzyloxybenzaldehyde (1700-37-4) + 2,2-dimethoxyethylamine (22483-09-6) → isoquinolin-7-ol (7651-83-4)

Guidance literature:

3-Benzyloxybenzaldehyde; 2,2-dimethoxyethylamine; In toluene; Heating;

With trifluoroacetic anhydride; In toluene; at 5 ℃;

With boron trifluoride diethyl etherate; In toluene; at 20 ℃; for 120h;

DOI:10.1039/b417026a

Reference yield: 64.0%

7-methoxyisoquinoline (39989-39-4) → isoquinolin-7-ol (7651-83-4)

Guidance literature:

With hydrogen bromide; Heating;

DOI:10.1016/j.bmcl.2005.10.102

Reference yield:

sulfuric acid (7664-93-9) + (3-hydroxy-benzylidenamino)-acetaldehyde diethylacetal (143247-61-4) → isoquinolin-7-ol (7651-83-4) + 5-hydroxyisoquinoline (2439-04-5)

Guidance literature:

Bei 2-taegigem Behandeln;

DOI:10.1021/ja01221a051

upstream raw materials:

sulfuric acid

(3-hydroxy-benzylidenamino)-acetaldehyde diethylacetal

3-Benzyloxybenzaldehyde

2,2-dimethoxyethylamine

Downstream raw materials:

7-hydroxy-1,2,3,4-tetrahydroisoquinoline

7-aminoisoquinoline

[1-benzyl-2-(isoquinolin-7-yloxy)-ethyl]-carbamic acid tert-butyl ester

[2-(isoquinolin-7-yloxy)-1-phenyl-ethyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Patel, Dinesh G.,Benedict, Jason B.,Kopelman, Roni A.,Frank, Natia L.. "Photochromism of a spirooxazine in the single crystalline phase". . p. 2208 - 2210. Retrieved 2005.
• 2、 Xingjun, Jiang,Jianbo, He,Hongli, Chen,Weiqing, Yang,Yuanyuan, Zhang,Menglin, Ma. "Copper-catalyzed hydrolysis of bromoisoquinolines: Preparation of hydroxyisoquinolines". . p. 65 - 70. Retrieved 2019/01/16.
• 3、 Deprele, Sylvine,Kashemirov, Boris A.,Hogan, James M.,Ebetino, Frank H.,Barnett, Bobby L.,Evdokimov, Artem,McKenna, Charles E.. "Farnesyl pyrophosphate synthase enantiospecificity with a chiral risedronate analog, [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid) (NE-10501): Synthetic, structural, and modeling studies". . p. 2878 - 2882. Retrieved 2008/12/23.