3-Cyano-7-hydroxycoumarin

Base Information

• Chemical Name: 3-Cyano-7-hydroxycoumarin
• CAS No.: 19088-73-4
• Molecular Formula: C10H5NO3
• Molecular Weight: 187.155
• Hs Code.: 2932209090
• European Community (EC) Number: 633-779-6
• DSSTox Substance ID: DTXSID20172596
• Nikkaji Number: J736.549G
• Wikidata: Q27454050
• Metabolomics Workbench ID: 74183
• ChEMBL ID: CHEMBL150302
• Mol file: 19088-73-4.mol

Synonyms:3-CHDC;3-cyano-7-hydroxycoumarin

Chemical Property of 3-Cyano-7-hydroxycoumarin

Chemical Property:

• Vapor Pressure: 3.13E-08mmHg at 25°C
• Melting Point: ≥250 °C(lit.)
• Refractive Index: 1.667
• Boiling Point: 436.574 °C at 760 mmHg
• PKA: 7.03 ± 0.20, most acidic, temperature: 25 °C
• Flash Point: 217.832 °C
• PSA: 74.23000
• Density: 1.507 g/cm³
• LogP: 1.37028
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMF: soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 187.026943022
• Heavy Atom Count: 14
• Complexity: 339

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Cyanoumbelliferone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)OC(=O)C(=C2)C#N
• Uses: 3-Cyano-7-hydroxycoumarin has been the most widely used fluorophores for preparing fluorogenic substrates.As a blue-fluorescent probe used as a reference standard. Blue-Fluorescent probe used as a reference standard 3-Cyanoumbelliferone is a calibration standard.

Technology Process of 3-Cyano-7-hydroxycoumarin

There total 8 articles about 3-Cyano-7-hydroxycoumarin 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: 92.0%

7-hydroxy-2-imino-2H-chromene-3-carbonitrile (330996-72-0) → 3-cyano-7-hydroxycoumarin (19088-73-4)

Guidance literature:

Acidic conditions;

DOI:10.1002/jhet.265

Reference yield: 88.0%

ethyl 2-cyanoacetate (105-56-6) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 3-cyano-7-hydroxycoumarin (19088-73-4)

Guidance literature:

With barium(II) hydroxide; In ethanol; water; for 1h; Sonication; Green chemistry;

DOI:10.1134/S1070428021090189

Reference yield: 87.0%

malononitrile (109-77-3) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 3-cyano-7-hydroxycoumarin (19088-73-4)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 4h;

DOI:10.1016/j.dyepig.2021.109447

upstream raw materials:

ethyl 2-cyanoacetate

2,4-Dihydroxybenzaldehyde

malononitrile

7-hydroxy-2-imino-2H-chromene-3-carbonitrile

Downstream raw materials:

3-(benzothiazol-2-yl)coumarin

7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid

Refernces

• 1、 Qiao, Haixia,Meng, Yali,Zhang, Yanxia,Sun, Jiaxing,Wang, Tao,Zhang, Xiaojie,Wang, Feifan,Kang, Yan-Fei. "A simple coumarin-based fluorescent probe for specific detection of cysteine over homocysteine and glutathione". . p. 1461 - 1466. Retrieved 2018.
• 2、 Takenaka,Nakai,Kusabayashi. "NEW LIQUID CRYSTALLINE MATERIAL EXHIBITING A REENTRANT NEMATIC PHASE.". . p. 299 - 305. Retrieved 1983.
• 3、 Nakai,Takenaka,Kusabayashi. "THERMAL AND DIELECTRIC PROPERTIES OF LIQUID CRYSTALS WITH A COUMARIN SKELETON.". . p. 3571 - 3577. Retrieved 1983.
• 4、 Traylor, Matthew J.,Chai, Jack,Clark, Douglas S.. "Simultaneous measurement of CYP1A2 activity, regioselectivity, and coupling: Implications for environmental sensitivity of enzyme-substrate binding". . p. 186 - 193. Retrieved 2011.
• 5、 Dong, Amelia Nathania,Ahemad, Nafees,Pan, Yan,Palanisamy, Uma Devi,Yiap, Beow Chin,Ong, Chin Eng. "Functional and structural characterisation of common cytochrome P450 2D6 allelic variants—roles of Pro34 and Thr107 in catalysis and inhibition". . p. 1015 - 1029. Retrieved 2019.
• 6、 Wei, Lai,Hou, Tao,Li, Jiaqi,Zhang, Xiuli,Zhou, Han,Wang, Zhenyu,Cheng, Junxiang,Xiang, Kaijing,Wang, Jixia,Zhao, Yaopeng,Liang, Xinmiao. "Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle". supporting information. p. 2634 - 2647. Retrieved 2021/04/02.