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  2. 91-64-5
Coumarin | 91-64-5

Product name:Coumarin

CAS No:91-64-5
MF:C9H6O2
MW:146.14274263382
MDL:MFCD00006850
CID:34614
PubChem ID:323
Introduction

coumarin(2H-Chromen-2-one),Aka1,2-Benzopyranone,Secondary metabolites widely distributed in the plant kingdom,Often close to studentsCinnamic acid\Flavonoids\LignansIsogenesis,Widely distributed in higher plants,Especially Umbelliferae\Rutaceae\Compositae\Leguminosae\Orchidaceae\Solanaceae\Daphneideraceae\Among the metabolites of plants and microorganisms such as Saxifragaceae and Melilotus.Coumarin under UV light\Visible light and when encountering concentrated sulfuric acid,Can produce blue fluorescence;It can regulate plant growth\Antibacterial and antiviral\Anticoagulant \smooth muscle relaxation \Various biological activities such as UV absorption and radiation resistance.So far, many coumarins have been isolated from citrus plants in Rutaceae.

Names and Identifiers
  • 2H-Chromen-2-one
  • TIMTEC-BB SBB000094
  • O-HYDROXYCINNAMIC ACID LACTONE
  • TONKA BEAN CAMPHOR
  • 5,6-BENZO-2-PYRONE
  • AKOS 212-75
  • 2H-1-BENZOPYRAN-2-ONE
  • 2H-1-BENZOPYAN-2-ONE
  • 1,2-BENZOPYRONE
  • Coumarin
  • COUMARIN(P) PrintBack
  • COUMARIN, INDICATOR
  • chromen-2-one
  • cis-o-CouMarinic acid lactone
  • COUMARINE
  • CouMarinic anhydride
  • CUMARIN
  • Kumarin
  • Rattex
  • Benzo-alpha-pyrone
  • o-Hydroxycinnamic lactone
  • 2-Oxo-1,2-benzopyran
  • Coumarinic lactone
  • Benzo-a-pyrone
  • Kumarin [Czech]
  • 2H-1-Benzopyran, 2-oxo-
  • 5,6-Benzo-alpha-pyrone
  • 2H-Benzo[b]pyran-2-one
  • 2H-Benzo(b)pyran-2-one
  • 1-Benzopyran-2-one
  • Caswell No. 259C
  • o-Coumaric acid
  • Coumarin (8CI)
  • 1,2-Benzopyrone
  • 2-Chromenone
  • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactone
  • 2H-Benzopyran-2-one
  • 5,6-Benzo-2-pyrone
  • Benzo-α-pyrone
  • cis-o-Coumarinic acid lactone
  • Coumarinic anhydride
  • Lympedim
  • NSC 8774
  • o-Hydroxycinnamic acid lactone
  • Rhodiascent Extra Pure
  • Tonka Bean Camphor
  • Cumarin
  • 2H-1-Benzopyran-2-one
  • Tonka bean camphor
  • MLS000028741
  • MLS001148422
  • ConMedNP.1796
  • 2H-benzo[b]pyran-2-one
  • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, d-lactone
  • o-hydroxycinnamic acid delta-lactone
  • MLSMR
  • Coumarine
  • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone
  • MLS002454395
  • SMR000059040
  • MDL:MFCD00006850
  • InChIKey:ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
  • Inchi:1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
  • SMILES:O=C1C=CC2C(=CC=CC=2)O1
  • BRN:383644
Chemical and Physical Properties

Computed Properties

  • Exact Mass: 146.14g/mol
  • Surface Charge: 0
  • XLogP3: 1.4
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Rotatable Bond Count: 0
  • Monoisotopic Mass: 146.036779g/mol
  • Monoisotopic Mass: 146.036779g/mol
  • Topological Polar Surface Area: 26.3Ų
  • Heavy Atom Count: 11
  • Complexity: 196
  • Isotope Atom Count: 0
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Covalently-Bonded Unit Count: 1
  • Tautomer Count: nothing
  • Topological Polar Surface Area: 26.3
  • Surface Charge: 0

Experimental Properties

  • Odor: Pleasant, fragrant odor resembling that of vanilla beans.
  • Stability Shelf Life: Converted to a dimer on long exposure to light.
  • Decomposition: When heated to decomposition it emits acrid smoke and fumes.
  • Taste: Bitter undertone; nut-like flavor on dilution
  • LogP: 1.79300
  • PSA: 30.21000
  • Merck: 2562
  • Refractive Index: 1.5100 (estimate)
  • Water Partition Coefficient: 1.7 g/L (20 ºC)
  • FEMA: 2744
  • Color/Form: 2000 μg/mL in methanol
  • Solubility: 不溶于冷水,易溶于热水、醇、乙醚、氯仿和****溶液。
  • Sensitiveness: Sensitive to humidity
  • λmax: 275nm
  • PH: Non' uorescence (9.5) to light green ' uorescence (10.5)
  • Odor: Pleasant, fragrant odor resembling that of vanilla beans.
Security Information
  • Symbol: GHS06
  • RTECS:GN4200000
  • WGK Germany:1
  • Safety Term:6.1
  • Safety Instruction:S36-S36/37-S26
  • Packing Group:III
  • Risk Phrases:R20/21/22; R36/37/38; R40
  • Tanda barang berbahaya: Xn Xn
  • Hazardous Material transportation number:UN 2811 6.1/PG 3
  • Hazard Statement:H301
  • Warning Statement:P301+P310
  • Prompt:dangerous
  • Storage Condition:Powder -20°C 3 years   4°C 2 years In solvent -80°C 6 months   -20°C 1 month
  • PackingGroup:III
  • Hazard Category Code:22
  • Signal Word:Danger
  • TSCA:Yes
  • Toxicity:LD50 orally in rats, guinea pigs: 680, 202 mg/kg (Jenner)
  • HazardClass:6.1
Customs Data
  • Customs Data:

    China Customs Code:

    2932201000

    Overview:

    HS:2932201000 coumarin\Methyl coumarin and ethyl coumarin VAT:17.0% Tax refund rate:13.0% Regulatory conditions:nothing Minimum tariff:6.5% general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    HS:2932201000 2h-chromen-2-one VAT:17.0% Tax rebate rate:13.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Synthetic Circuit

Synthetic Circuit 1

Reaction Conditions
1.1 Catalysts: Potassium hydroxide ,  Bismuth silver carbonate oxide (Bi0.88Ag0.17(CO3)O2) Solvents: Dimethylformamide ;  24 h, 110 °C
Reference
Exploiting a silver-bismuth hybrid material as heterogeneous noble metal catalyst for decarboxylations and decarboxylative deuterations of carboxylic acids under batch and continuous flow conditions
Meszaros, Rebeka; et al, Green Chemistry, 2021, 23(13), 4685-4696

Synthetic Circuit 2

Reaction Conditions
1.1 Solvents: Pyridine ;  5 h, heated
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, 0 °C
Reference
Some unusual reactions of Meldrum's acid. Synthesis of cinnamic acids, coumarins and 2-benzyl-1-indanone
Mahulikar, P. P.; et al, Journal of Chemical Research, 2006, (1), 12-14

Synthetic Circuit 3

Reaction Conditions
1.1 Reagents: 1,3-Dibromo-5,5-dimethylhydantoin ,  Water ,  Pyridine, hydrofluoride (1:9) Solvents: Dichloromethane
Reference
Fluorination studies using difluoroiodotoluene
Greaney, Michael Francis, 1999, , ,

Synthetic Circuit 4

Reaction Conditions
1.1 Reagents: 1,1′-Carbonyldiimidazole ,  Water Solvents: Anisole ;  5 min, rt
1.2 Catalysts: Dabco ;  48 h, rt
Reference
A water-promoted catalytic hydrodecarboxylation of conjugated carboxylic acids under open air conditions at room temperature
Wang, Zhan-Yong; et al, Green Chemistry, 2023, 25(8), 3040-3045

Synthetic Circuit 5

Reaction Conditions
1.1 Solvents: Acetonitrile ;  27 h, rt
Reference
Combinatorial discovery of two-photon photoremovable protecting groups
Pirrung, Michael C.; et al, Proceedings of the National Academy of Sciences of the United States of America, 2003, 100(22), 12548-12553

Synthetic Circuit 6

Reaction Conditions
1.1 Reagents: Cuprous chloride Solvents: Acetonitrile
1.2 Reagents: Sodium hydroxide Solvents: Water
Reference
Thiocarbonyl to carbonyl group transformation using cuprous chloride and sodium hydroxide
Narasimhamurthy, N.; et al, Tetrahedron Letters, 1986, 27(33), 3911-12

Synthetic Circuit 7

Reaction Conditions
1.1 Catalysts: Di-μ-chlorotetrakis(2-phenylpyridine)diiridium Solvents: Acetonitrile ;  36 h, rt
Reference
Synthesis of (Z)-Cinnamate Derivatives via Visible-Light-Driven E-to-Z Isomerization
Shu, Penghua; et al, SynOpen, 2019, 3(4), 103-107

Synthetic Circuit 8

Reaction Conditions
1.1 Reagents: Benzoyl peroxide ,  N-Bromosuccinimide Solvents: Carbon tetrachloride ;  2 h, reflux; reflux → 0 °C
1.2 Reagents: Sodium carbonate Solvents: Water ;  0 °C
Reference
Aromatization of Stobbe reaction products
Jabbar, Saba; et al, Asian Journal of Chemistry, 2002, 14(3-4), 1799-1800

Synthetic Circuit 9

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt → 140 °C
1.2 Catalysts: (SP-4-1)-Dichlorobis[1-(dicyclohexylphosphino-κP)piperidine]palladium Solvents: Tetrahydrofuran ;  24 h, 140 °C; 140 °C → rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  rt
Reference
Mizoroki-Heck Reactions Catalyzed by Dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium: Palladium Nanoparticle Formation Promoted by (Water-Induced) Ligand Degradation
Oberholzer, Miriam; et al, Advanced Synthesis & Catalysis, 2012, 354(4), 627-641

Synthetic Circuit 10

Reaction Conditions
1.1 Solvents: Ethanol ;  rt
Reference
Photoconversion of o-hydroxycinnamates to coumarins and its application to fluorescence imaging
Cho, Sung-Youl; et al, Tetrahedron Letters, 2009, 50(33), 4769-4772

Synthetic Circuit 11

Reaction Conditions
1.1 Solvents: Benzene
Reference
Photocyclization reactions. Part 8. Synthesis of 2-quinolone, quinoline, and coumarin derivatives using trans-cis isomerization by photoreaction
Horaguchi, Takaaki; et al, Journal of Heterocyclic Chemistry, 2002, 39(1), 61-67

Synthetic Circuit 12

Reaction Conditions
1.1 Catalysts: Potassium carbonate ,  Tetrabutylammonium bromide ;  1 h, 135 - 140 °C; 6 h, 135 - 140 °C
1.2 Reagents: Sodium carbonate Solvents: Water ;  pH 8, rt
Reference
Design, synthesis, antifungal activity, and 3D-QSAR of coumarin derivatives
Wei, Yan; et al, Journal of Pesticide Science (Tokyo, 2018, 43(2), 88-95

Synthetic Circuit 13

Reaction Conditions
1.1 Catalysts: Grubbs second generation catalyst Solvents: Dichloromethane ;  24 h, 45 °C
Reference
Aldehyde-Assisted Ruthenium(II)-Catalyzed C-H Oxygenations
Yang, Fanzhi; et al, Angewandte Chemie, 2014, 53(42), 11285-11288

Synthetic Circuit 14

Reaction Conditions
1.1 Catalysts: Grubbs second generation catalyst Solvents: Dichloromethane ;  overnight, rt
Reference
Simple synthesis of versatile coumarin scaffolds
Lay, Luigi, Synthetic Communications, 2006, 36(15), 2203-2209
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sc-205637A-50g 50g ¥263.00 05 Sep. 2023
sc-205637-10g 10g ¥196.00 05 Sep. 2023
sc-205637A-50 g 50g ¥263.00 10 Jul. 2023
sc-205637-10 g 10g ¥196.00 10 Jul. 2023
Brand:lifechemical Supplier:Life Chemicals
No. Purity Stock Specification Price update time operate
F3096-1712-10g 95%+ 10g $84.0/ ¥610.11 06 Sep. 2023
F3096-1712-5g 95%+ 5g $60.0/ ¥435.79 06 Sep. 2023
F3096-1712-2.5g 95%+ 2.5g $40.0/ ¥290.53 06 Sep. 2023
F3096-1712-1g 95%+ 1g $21.0/ ¥152.53 06 Sep. 2023
F3096-1712-0.5g 95%+ 0.5g $19.0/ ¥138.00 06 Sep. 2023
F3096-1712-0.25g 95%+ 0.25g $18.0/ ¥130.74 06 Sep. 2023
Brand:lktlabs Supplier:LKT Labs
No. Purity Stock Specification Price update time operate
C5782-50 g ≥98% In stock 50g $78.80 / ¥572.34 11 Jul. 2023
C5782-10 g ≥98% In stock 10g $47.30 / ¥343.55 11 Jul. 2023
Brand:ambeed Supplier:Ambeed
No. Purity Stock Specification Price update time operate
A633268-1kg 99+% 中国:-/USA:- 1kg $49.0/ ¥355.90 02 Sep. 2023
A633268-500g 99+% 中国:-/USA:- 500g $27.0/ ¥196.11 02 Sep. 2023
A633268-100g 99+% 中国:-/USA:- 100g $12.0/ ¥87.16 02 Sep. 2023
A633268-25g 99+% 中国:-/USA:- 25g $10.0/ ¥72.63 02 Sep. 2023
A633268-10g 99+% 中国:-/USA:- 10g $8.0/ ¥58.11 02 Sep. 2023
A633268-1g 99+% 中国:-/USA:- 1g $6.0/ ¥43.58 02 Sep. 2023
A633268-100mg 99+% 中国:-/USA:- 100mg $5.0/ ¥36.32 02 Sep. 2023
Brand:TCI Supplier:梯希爱(上海)化成工业发展有限公司
No. Purity Stock Specification Price update time operate
C0395-500G >99.0%(GC) 上海:1/天津:1/日本:24 500g ¥535.00 14 Jun. 2023
C0395-25G >99.0%(GC) 上海:3/天津:3/日本:≥40 25g ¥185.00 14 Jun. 2023
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