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Supply 100% Pure and Organic Pearl Powder with Best Quality
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USD $ 13.0-15.0 / Kilogram 1 Kilogram 10000 Kilogram/Week Baoding Faithful Industry Co., Ltd. Contact Supplier
Kojic acid 501-30-4 /manufacturer/low price/high quality/in stock
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USD $ 10.0-11.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Manufacturer supply skin whitening 99%+ Kojic acid ; Kojic acid dipalmitate powder in stock
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99% Kojic Acid Whitening cream Raw material Kojic Acid powder for soap whitening
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USD $ 14.0-21.0 / Kilogram 1 Kilogram 55 Metric Ton/Month Xi'an Quanao Biotech Co., Ltd. Contact Supplier
Kojic acid
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USD $ 1.0-1.0 / Kilogram 1 Kilogram 6000 Metric Ton/Month Wuxi TAA Chemical Industry Co.,LTD. Contact Supplier
Kojic acid
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Kojic acid manufacturer supplier high quality
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Skin Whitening Kojic Acid Powder
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USD $ 25.0-25.0 / Kilogram 1 Kilogram 10 Metric Ton/Month Shaanxi Greenyo Biotech Co., Ltd. Contact Supplier
Kojic acid for Skin Whitening
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USD $ 15.0-20.0 / Kilogram 1 Kilogram 10 Metric Ton/Day DB BIOTECH CO., LTD Contact Supplier
2-HYDROXYMETHYL-5-HYDROXY-4-PYRONE
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USD $ 44.7-44.7 / Kilogram 1 Kilogram 10 Metric Ton/Month Wuhan ZeShanCheng Biomedical Technology Co., Ltd. Contact Supplier

501-30-4 Usage

Microbial fermentation of kojic acid

Microbial fermentation of kojic acid refers to the process and technology of mass production of kojic acid by microbial fermentation method. Kojic acid is an acidic metabolites produced by Aspergillus oryzae and other microorganisms, soluble in water, ethanol or acetate. Most microorganisms can produce kojic acid for fungi, such as Aspergillus niger (Aspergillus oryzae), A.flavo-oryzae (Beige), Aspergillus flavus, Aspergillus candidus (A.flavus) (A.candidus) (A. clavatus), Aspergillus clavatus, huge Aspergillus (A.giganteus), Aspergillus fumigatus (A.fumigatus), a.tamarii (A.tamarii), Aspergillus WENTII (A.wentii) and a.glaucus (A.glaucus). Some bacteria such as rose Gluconobacter (Gluconobacter roseus), waxy Gluconobacter (G.cerinus) and Pseudomonas aeruginosa (Pseudomonas spp) can also use sugar to produce kojic acid. The basic fermentation process: Sweet potato powder by α-amylase hydrolysis→sterilizing→in the fermentation tank cooling→inoculation of Aspergillus oryzae seed from seed tank)→32 ℃and aerobic fermentation (about 5 days)→fermentation liquid filtration→ kojic acid zinc salt→decompression concentrating→crystallizing→acidification→kojic acid. kojic acid is used for manufacturing of food and daily necessities increase flavor enhancer maltol and ethyl maltol raw materials, but also the production of insecticide, fungicide and a film of dust removal agent of raw materials, and if some aliphatic carboxylic acid occurred acylation, kojic acid ester is obtained, it is raw material for manufacture of whitening cosmetics.
Reference: Zhou Deqing, Xu Shiju. Dictionary of microbiology. Tianjin: Tianjin science and Technology Press.2005.

Chemical Properties

tan powder

Uses

A naturally occurring chelation agent.

Organic acids

Kojic acid is composed of glucose by Aspergillus Candida in 30~32 ℃ under aerobic fermentation, having the antibacterial effect of organic acid, molecular structure is for substituted gamma pyrone, in naturally occurring γ-pyranone compounds, well-known compounds are only kojic acid and maltol. In 1907, Saito is by Aspergillus isolated kojic acid crystals. In 1912, it was named by Yabuta and in 1924 to determine the structure of kojic acid. In 1953, Arnstela (surface fermentation) and in1971 Kitada Makio (submerged fermentation) using isotope tracing technique converted that kojic acid is glucose without carbon frame fracture direct oxidation and dehydration to form.
Kojic acid is present in the song, it is what people eat, safe use. In recent years, application of a large number of patent documentation report kojic acid was used in cosmetics. Tyrosinase is a key enzyme in melanin formation. Kojic acid can combine with tyrosinase copper chelate and make the loss of activity, which is the whitening effect.Clinical application and experimental results show that kojic acid can generate strong inhibitory effect on human skin melanin, safe and non-toxic, will not be caused sequelae of leukoplakia. Better combination of kojic acid and other agents (such as superoxide dismutase (SOD), placenta extract, amino acids, sunscreen agents and various kinds of plant extracts, etc.). Kojic acid is mainly used for skin whitening products, anti-aging products, sunscreen products, whitening facial cleanser and cosmetics.
Kojic acid has certain antibacterial activity. Gram negative bacteria of kojic acid sodium of sensitive degree is greater than gram positive bacteria, while most other contrary in the antimicrobial substances. Inhibitory effect of kojic acid is far below other antibacterial substances and its antibacterial activity is bacteriostatic rather than sterilization. Kojic acid on yeast, virus and phage is invalid.
The above information is edited by the chemicalbook Han Ya.

Physicochemical properties

Kojic acid crystal is prism shape, acicular, colorless. Kojic acid is soluble in water, alcohol, acetone, slightly soluble in ether, ethyl acetate, chloroform and pyridine, insoluble in most other solvent. Crystallization can be in acetone, ethyl acetate solvent , also be in the 150 to 200℃ by vacuum sublimation. The melting point of the reported in the literature is 151 to 154 ℃. 5,7-diethyl kojic acid and its derivatives respectively at 315 nm and 255nm have specific absorption peaks.
Kojic acid is unstable to light and heat, the concentration 0.5% solution of kojic acid at different pH at a temperature of 100℃ treatment for 3h or sun light shined for 5h. The results at pH 5~7 solution become yellow to tan, but did not change much at pH4.
Effect of kojic acid and ferric chloride is special red, this method can be used for kojic acid quantitative. Kojic acid can be reduced fee Lin reagent and ammoniacal silver nitrate and its molecular structure near the carbonyl has a hydroxyl group, and a variety of metal to form a salt and other hydroxyl can generate ether and ester derivatives.
kojic acid

The safety of kojic acid

Japanese scholars in traditional fermented products of kojic acid to illustrate the kojic acid as the safety of food additives, which can be not limited to add.
Because kojic acid has certain antibacterial and antioxidation, in Japan kojic acid has been widely used in food processing of color protection and transportation of fruits and vegetables, fresh aquatic products, medical anti-inflammatory agent and so on. The Japanese government early in April 1988 approved in cosmetics to add kojic acid as a sunscreen, Xiaoban, white beautiful new pharmaceuticals.
China's Ministry of health approved the first Nanjing Shi Shan Tou pharmaceutical factory production of 142-kojic acid cream cosmetics for special purposes in 1991. In August of 1992, Shanghai Normal University Science and Technology Development Co., Ltd. production of kojic acid as additive in cosmetics by the Shanghai chemical toxicity assessment.
Reference: Wang Boyan, Jin Qirong. Production and application of fermentation acid. Beijing: Chinese Light Industry Press.2007.

Application prospect

Kojic acid which is in food, cosmetics, medicine and other aspects for the efficient application, determines its considerable economic value and great potential for development. For industrialized production of kojic acid, Japan has occupied a leading position, but with the development of society, the progress of science and technology, all the countries in the world in terms of kojic acid production have been corresponding development. These provide a broad space for the development of domestic kojic acid industry .
In short, kojic acid faces new opportunities and challenges as a new food additives in 21st century . Kojic acid is as a new type of preservative and will play an important role in food, cosmetic and pharmaceutical industry .

Food additives

Kojic acid may be developed as a new food additive. As a food preservative sorbic acid is more than the performance of the ideal.
Kojic acid can be used for fresh vegetables, fruits, fresh seafood, such as the cut apple, bananas, potatoes, mushrooms in 0.1% kojic acid solution leaching for 1 hour, can effectively prevent browning. Crab meat and shrimp and other seafood with 0.25%~0.6% kojic acid and 0.1% sodium sulfite solution respectively spray or infiltration method to treat Lentinus edodes, perishable vegetables such as spinach, results at room temperature for 1 day the alteration of mushroom and spinach 4 days later still keeps fresh, rarely atrophy. The dip of cut rose, rose, and so in 0.1% kojic acid solution at room temperature can be fresh for 8 days long. Kojic acid as an antioxidant can prevent oil deterioration and prevent the browning of dough. Combining with Ascorbic acid effect is better.
Kojic acid can replace part of sodium nitrite in color hair color, and can inhibit the conversion of nitrite to carcinogenic nitrosamines.
Studies suggest that the preservation mechanism of kojic acid inhibition of polyphenol oxidase in plants and animal carapace (i.e. tyrosinase).
As mentioned above, kojic acid of antibacterial, antisepsis, fresh-keeping, color protection hair color, antioxidant effect in a body is a potential and the superior performance of food additives.

Extraction and purification of kojic acid

Kojic acid with divalent metal ions can form insoluble metal chelates, and this property can be utilized in the extraction. Secondly, kojic acid is soluble in water but little solubility, temperature on the solubility of great influence, is conducive to the concentration cooling crystallization.
Kojic acid can be as iron reagent. Even with the use of fermented in stainless steel tanks, the fermentation broth was also red brown, this nature influences to extraction and refining process.
Kojic acid was extracted from the fermentation broth by the copper salt precipitation, ethyl acetate extraction, ether by continuous extraction, concentration and crystallization or freezing crystallization. In 20th century 70s, the Beijing daily chemical factory used zinc salt method.

Uses

hydroxystearate nonionic solubilizer

Purification Methods

Crystallise the acid from MeOH (charcoal) by adding Et2O. It sublimes at 150-200o/0.1torr. [Beilstein 18 II 57, 18 III/IV 1145, 18/2 V 516.]

Pest control and crop yield

Kojic acid and divalent heavy metal complexes is better in the control effect of several kinds of plant fungi disease than Bordeaux mixture (a kind of insecticidal and fungicidal agent). The kojic acid complex is easy to prepare, spraying on the leaf adhesion is tightly without damage to the plants. These metals group in a non from form and kojic acid links, so toxic to humans is very low, safer than Bordeaux.
Kojic acid or nicotinic insecticides activator, when dealing with wild melon silk moth (Diaphania hyalinata L.) and (Prodenia eridania cram.), with 5% nicotine sulfate pyrophyllite powder or 5% nicotine bentonite spraying agent adding 5% kojic acid and its toxicity were increased by 35% and 50%, separately.
Kojic acid can also be used alone as a pesticide. Its mechanism is: in the coexistence and insect individual, impact on pest reproduction, disturb the hormone system, then the full eradication of the pest. Unlike conventional insecticides, not only to kill all the pests and the people, are harmless to humans and animals, and does not pollute the environment.
Nickell and Gordon, 1963) has recommended a kojic acid as plant growth stimulant. From recent years patent, kojic acid as the crop yield, increasing agent is a promising. The method is to use kojic acid or its salt spray crop leaves or invasive roots, seeds, promoting crop root, stem and leaf growth and Promoting Blossom and bear fruit, improving the yield and quality. For example: 0.01~1000mg/L kojic acid solution spraying sweet potato seedlings after planting and harvest of sweet potato starch content increased by 10%~20%, the total yield increased by 20%~30%; from flowering to harvest, in foliar spraying concentration is 100mg/L of kojic acid solution of 8 times, tomato maturity, the sugar, the individual weight were significantly increased.
China is the largest producer of hybrid rice, the hybrid rice seeds need to use "920". Considering the kojic acid production, cost advantages, it might make a difference on rice, corn, wheat, and so on of main grain crops production.

Definition

ChEBI: A pyranone that is 4H-pyran substituted by a hydroxy group at position 5, a hydroxymethyl group at position 2 and an oxo group at position 4. It has been isolated from the fungus Aspergillus oryzae.

Application and use

Used in cosmetics, food additives, pharmaceutical etc,Used for quantitative analysis of ferric iron reagent.
1.kojic acid is widely used in food production. In the pas, because of oxidation resistance, it has been used for kojic acid grease to prevent rancidity. Recent reports, kojic acid has sterilization and insect resistance, as food preservatives, preservatives, color protection agent has obvious effect, can replace chemical preservatives, which is widely used in meat dish processing color, fresh fruits and vegetables, antiseptic raw food, but also can be used as cut flowers preservation and conservation agent to extend shelf life. Kojic acid is added in the food, do not influence the taste, aroma and texture and hinder the conversion of nitrite in paired human carcinogenic nitrosamines, which hinder or inhibition of cured meat products upgrading has a very important significance. Agricultural production, kojic acid can be used as biological pesticide, used as an insecticide, and can be used as bio fertilizer, regardless of the spraying or root application, the yield of grain and vegetables income effect is remarkable.
2. as a food flavoring agent of maltol and ethyl maltol raw materials.
3.kojic acid can be used to produce cephalosporin antibiotic raw materials.
4.In addition that kojic acid is widely used in food processing, but also has good freckle, whitening beauty effect. Kojic acid and its derivatives such as acetate has certain antibacterial and on the skin without a one-time stimulus and cumulative irritation, can be used as a preservative in cosmetics and food. Can strongly absorb ultraviolet light, used lonely or compatibility with all kinds of sunscreen products such as soap and so on. Treatment and prevention and treatment of skin pigmentation such as the formation of chloasma, dosage of 1~2.5% effect is obvious. It helps to keep moisture, reduce skin wrinkles. In activities ,it can be with dandruff remover.
5. It can be used for seasoning and manufacturing raw materials of kojic acid and ethyl maltol leaves skin pigment.

Add whitening whitening cosmetics and kojic acid in food

Kojic acid is a tyrosinase inhibitor, preemptive combined with tyrosinase copper ions, making the copper ions lose effect, can inhibit the synthesis of dopachrome.
Kojic acid can inhibit 5,6-two hydroxy indole (DHI) polymerization, inhibition of DHICA oxidase activity.
Addition of kojic acid in cosmetics can have skin care, moisturizing, whitening, bright, sunscreen, freckle function. Forms have cream, lotion, emulsion, soft membrane powder, clay, powder and so on.
The earliest (1987) domestic developed and obtained the approval of the Ministry of health of the symbol (1991) is Nanjing Shi Shan Tou pharmaceutical factory 142-kojic acid freckle cream, kojic acid content is 1.5%, 2.0% in two sizes. Mainly used for pigmentation, chloasma, pregnancy spots, coffee spot), secondary pigment siderosis and melanosis, on chloasma total efficiency above 85% in the treatment of a variety of colors.
Three Ming Feng reports containing 1% or 2.5% of kojic acid cream is used for chloasma, sunshine and senile spots, inflammation that leads to pigment accumulation and patients with freckles, paint for two months, on 204 cases of statistical results is: effective symptom is alleviated) more than 93 cases (accounted for 45.6%); slightly effective (symptoms relieved slightly) more than 151 cases (74%); kojic acid dosage 1% and 2.5% difference.
Kojic acid, when heated and in the light, is easy to be yellowing, thus affecting the shelf life of kojic acid in cosmetics. Cryopreservation, adding ascorbic acid and hydroxyl methoxy phenyl ketone (2-hydroxy-4-dimethoxy diphenyl ketone) etc. shading agent can enhance its stability.

Uses

Converted to maltol and ethyl maltol, flavor-enhancing additives. Food additive to inhibit tyrosinase.
InChI:InChI=1/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2

501-30-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (K3125)  Kojic acid   501-30-4 K3125-25G 4,058.73CNY Detail
Sigma (K3125)  Kojic acid   501-30-4 K3125-10G 2,035.80CNY Detail
Sigma (K3125)  Kojic acid   501-30-4 K3125-5G 1,129.05CNY Detail
Sigma-Aldrich (95197)  Kojic acid  analytical standard 501-30-4 95197-100MG 615.42CNY Detail
Alfa Aesar (A10760)  Kojic acid, 99%    501-30-4 100g 6385.0CNY Detail
Alfa Aesar (A10760)  Kojic acid, 99%    501-30-4 25g 1990.0CNY Detail
Alfa Aesar (A10760)  Kojic acid, 99%    501-30-4 5g 472.0CNY Detail

501-30-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name kojic acid

1.2 Other means of identification

Product number -
Other names 2-(hydroxymethyl)-5-hydroxy-4H-pyran-4-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:501-30-4 SDS

501-30-4Synthetic route

5-acetoxy-2-acetoxymethyl-4H-pyran-4-one
26209-93-8

5-acetoxy-2-acetoxymethyl-4H-pyran-4-one

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With sodium methylate In methanol for 1h;95%
With methanol; ammonia
chlorokojic acid
7559-81-1

chlorokojic acid

acetone
67-64-1

acetone

A

allomaltol
644-46-2

allomaltol

B

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

C

iodokojic acid
16065-34-2

iodokojic acid

D

iodoacetone
3019-04-3

iodoacetone

Conditions
ConditionsYield
With sodium iodide at 45℃; for 24h; Substitution;A n/a
B n/a
C 78%
D n/a
5-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)-2-(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)-4H-pyran-4-one

5-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)-2-(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)-4H-pyran-4-one

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With silica gel In methanol at 60℃; for 3h; Inert atmosphere;70%
2-keto-D-glucose

2-keto-D-glucose

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
Stage #1: 2-keto-D-glucose With sodium acetate; acetic anhydride In N,N-dimethyl-formamide for 23h;
Stage #2: With sodium methylate In methanol for 1h;
20%
D-xylose
58-86-6

D-xylose

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With Aspergillus oryzae Bei der Vergaerung;
D-sorbitol
50-70-4

D-sorbitol

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
durch Aspergillus oryzae;
D-galactitol
608-66-2

D-galactitol

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
bei der Einw.von Aspergillus oryzae;
L-arabinose
5328-37-0

L-arabinose

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With Aspergillus oryzae Bei der Vergaerung;
glycerol
56-81-5

glycerol

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With aspergillus glaucus Bei der Vergaerung;
bei der Einw.von Aspergillus glaucus;
D-xylose
58-86-6

D-xylose

aspergillus flavus

aspergillus flavus

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

D-glucose
50-99-7

D-glucose

aspergillus flavus

aspergillus flavus

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

D-myo-inositol
87-89-8

D-myo-inositol

aspergillus oryzae

aspergillus oryzae

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

5‑benzyloxy‑4H‑pyran‑4‑one‑2‑ylmethyl adamantan‑1‑ylacetate

5‑benzyloxy‑4H‑pyran‑4‑one‑2‑ylmethyl adamantan‑1‑ylacetate

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen under 258.776 Torr; for 0.166667h;
comenic acid
499-78-5

comenic acid

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: neat (no solvent) / 30 °C / Inert atmosphere; Schlenk technique; Glovebox
2: silica gel / methanol / 3 h / 60 °C / Inert atmosphere
View Scheme
D-Glucose
2280-44-6

D-Glucose

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ammonium hydroxide / 0.75 h / pH 6 / Enzymatic reaction
2.1: sodium acetate; acetic anhydride / N,N-dimethyl-formamide / 23 h
2.2: 1 h
View Scheme
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

5-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyran-4-one
5443-45-8

5-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.5h;100%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

chlorokojic acid
7559-81-1

chlorokojic acid

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 0.166667h;100%
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane for 3h; Inert atmosphere; chemoselective reaction;100%
With thionyl chloride at 20℃; for 3h;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate
2169-68-8

ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate

ethyl 2-amino-4-(4-chlorophenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate

ethyl 2-amino-4-(4-chlorophenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Heating;99%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

2-amino-4-(phenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

2-amino-4-(phenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Product distribution; Heating; reaction with arylmethylenemalonitrile derivatives;99%
With piperidine In ethanol for 0.166667h; Heating;99%
With β‐cyclodextrin In water at 70℃; for 1h; Reagent/catalyst; Green chemistry;96%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-chlorobenzylidenemalonodinitrile
1867-38-5

4-chlorobenzylidenemalonodinitrile

2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Heating;99%
In water at 100℃; Michael Addition; Microwave irradiation; Sealed tube; Green chemistry;96%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate
2017-87-0

ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate

ethyl 2-amino-6-(hydroxymethyl)-4-(4-methoxyphenyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate

ethyl 2-amino-6-(hydroxymethyl)-4-(4-methoxyphenyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Heating;99%
With piperidine In ethanol for 4h; Cycloaddition; Heating;28%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

benzyl bromide
100-39-0

benzyl bromide

5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one
15771-06-9

5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 80℃;99%
With potassium carbonate In ethanol; water for 2h; Reflux;98%
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h;90%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

vinyl acetate
108-05-4

vinyl acetate

7-O-acetylkojic acid
25552-08-3

7-O-acetylkojic acid

Conditions
ConditionsYield
novozyme 435 In acetonitrile at 50℃; Enzymatic reaction;99%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

6,6',6

6,6',6"-(((nitrilotris(ethane-2,1-diyl))tris(azanediyl))tris(methylene))tris(3-hydroxy-4H-pyran-4-one)

Conditions
ConditionsYield
In ethanol; chloroform at 20℃; for 1h;98.5%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone
118708-61-5

5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Reflux;90%
dichloro(benzene)ruthenium(II) dimer
37366-09-9

dichloro(benzene)ruthenium(II) dimer

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

(η6-C6H6)RuCl(5-hydroxy-2-(hydroxymethyl)-4-pyrone)
1204169-40-3

(η6-C6H6)RuCl(5-hydroxy-2-(hydroxymethyl)-4-pyrone)

Conditions
ConditionsYield
With NaOMe In methanol byproducts: NaCl; kojic acid and NaOMe in dry MeOH stirred for 10 min; Ru complex added, stirred for 5 h; rotary evapd. to dryness; taken in CH2Cl2; soln. filtered, concd. to 3 ml, then Et2O excess added; left for 2 h at room temp.; ppt. collected, washed with Et2O; dried in vac.;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

malononitrile
109-77-3

malononitrile

2-amino-6-(hydroxymethyl)-8-oxo-4-m-tolyl-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
876710-04-2

2-amino-6-(hydroxymethyl)-8-oxo-4-m-tolyl-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene immobilized on silica In neat (no solvent) at 20℃; for 0.05h;98%
In water at 50℃; for 0.0833333h; Sonication;97%
With nanozeolite clinoptilolite In water at 95℃; for 0.333333h; Green chemistry;95%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(4-fluorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
797028-50-3

2-amino-4-(4-fluorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
In water at 50℃; for 0.1h; Sonication;98%
With nanozeolite clinoptilolite In water at 95℃; for 0.25h; Green chemistry;96%
With nano-silica sulfuric acid In water for 0.416667h; Reflux; Green chemistry;95%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

malononitrile
109-77-3

malononitrile

2-amino-4-(pyridine-3-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
625376-09-2

2-amino-4-(pyridine-3-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
In water at 50℃; for 0.0833333h; Sonication;98%
With Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 In ethanol for 0.833333h; Reflux; Green chemistry;85%
furfural
98-01-1

furfural

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

malononitrile
109-77-3

malononitrile

2-amino-4-(furan-2-yl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
873570-71-9

2-amino-4-(furan-2-yl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
In water at 50℃; for 0.0833333h; Sonication;98%
With nanozeolite clinoptilolite In water at 95℃; for 0.333333h; Green chemistry;97%
With β‐cyclodextrin In water at 70℃; for 1h; Green chemistry;93%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With nanozeolite clinoptilolite In water at 95℃; for 0.3h; Green chemistry;98%
With nano Fe3O4(at) SiO2(at)BenzIm-Fc[Cl]/ZnCl2 In ethanol; water at 20℃; for 0.133333h; Sonication;98%
With sulfonic acid functionalized MCM-41 In water at 90℃; for 0.666667h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Green chemistry;97%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(4-methylphenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile

2-amino-4-(4-methylphenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile

Conditions
ConditionsYield
With nano Fe3O4(at) SiO2(at)BenzIm-Fc[Cl]/ZnCl2 In ethanol; water at 20℃; for 0.133333h; Sonication;98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene immobilized on silica In neat (no solvent) at 20℃; for 0.05h;97%
With ferrocene functionalized ionic liquid supported on silica coated Fe3O4 magnetic nanoparticles In ethanol; water at 25℃; for 0.166667h; Catalytic behavior; Solvent; Sonication;95%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

malononitrile
109-77-3

malononitrile

4-chloro-3-nitro-benzaldehyde
16588-34-4

4-chloro-3-nitro-benzaldehyde

2-amino-4-(4-chloro-3-nitrophenyl)-6-hydroxymethyl-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
1613234-40-4

2-amino-4-(4-chloro-3-nitrophenyl)-6-hydroxymethyl-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With nano-silica sulfuric acid In water for 0.2h; Reflux; Green chemistry;98%
With s-triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles In water at 100℃; for 0.5h; Green chemistry;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(4-cyanophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile
1613234-41-5

2-amino-4-(4-cyanophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile

Conditions
ConditionsYield
With sulfonic acid functionalized MCM-41 In water at 90℃; for 0.583333h; Green chemistry;98%
With nano-silica sulfuric acid In water for 0.25h; Reflux; Green chemistry;94%
With Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 In ethanol for 0.25h; Reflux; Green chemistry;92%
With β‐cyclodextrin In water at 70℃; for 1h; Green chemistry;90%
With lipase from Aspergillus niger In ethanol; water at 20℃; for 3.5h; Enzymatic reaction;90%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

2-((4-fluorophenyl)(hydroxy)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one

2-((4-fluorophenyl)(hydroxy)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; for 24h;98%
With potassium modified alumina catalysts (CAT3) In 1,4-dioxane; water at 20℃; for 24h; Aldol Condensation; Green chemistry;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

1-naphthaldehyde
66-77-3

1-naphthaldehyde

malononitrile
109-77-3

malononitrile

2‑amino‑6‑hydroxymethyl‑4‑(naphthalen‑1‑yl)‑8‑oxo‑4,8‑dihydropyrano[3,2‑b]pyran‑3‑carbonitrile

2‑amino‑6‑hydroxymethyl‑4‑(naphthalen‑1‑yl)‑8‑oxo‑4,8‑dihydropyrano[3,2‑b]pyran‑3‑carbonitrile

Conditions
ConditionsYield
With s-triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles In water at 100℃; for 0.5h; Green chemistry;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

malononitrile
109-77-3

malononitrile

2‑amino‑6‑(hydroxymethyl)‑4‑(4‑nitrophenyl)‑8‑oxo‑4,8‑dihydropyrano[3,2‑b]pyran‑3‑carbonitrile

2‑amino‑6‑(hydroxymethyl)‑4‑(4‑nitrophenyl)‑8‑oxo‑4,8‑dihydropyrano[3,2‑b]pyran‑3‑carbonitrile

Conditions
ConditionsYield
With s-triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles In water at 100℃; for 0.333333h; Green chemistry;98%
With sulfonic acid functionalized MCM-41 In water at 90℃; for 0.583333h; Green chemistry;98%
With C5H6NO3S(1+)*F6P(1-) In neat (no solvent) at 90℃; for 0.25h; Reagent/catalyst;92%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

formaldehyd
50-00-0

formaldehyd

1-(4-fluorophenylmethyl)piperazine
70931-28-1

1-(4-fluorophenylmethyl)piperazine

2-((4-(4-fluorobenzyl)piperazin-1-yl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one

2-((4-(4-fluorobenzyl)piperazin-1-yl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
In methanol at 20℃; Mannich Aminomethylation;98%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

2-Amino-6-methylpyridine
1824-81-3

2-Amino-6-methylpyridine

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

C18H17N3O4

C18H17N3O4

Conditions
ConditionsYield
With hyper-cross-linked β-cyclodextrin nanosponge In ethanol for 0.25h; Solvent; Time; Mannich Aminomethylation; Reflux;98%
piperazine
110-85-0

piperazine

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

formaldehyd
50-00-0

formaldehyd

6,6'-(piperazine-1,4-diylbis(methylene))bis(5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one)

6,6'-(piperazine-1,4-diylbis(methylene))bis(5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one)

Conditions
ConditionsYield
Stage #1: piperazine; formaldehyd In ethanol at 20℃; for 0.5h;
Stage #2: 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one In ethanol for 5h;
97%
1) EtOH, H2O, 30 min, 2) EtOH, H2O, room temperature, 1 h; Yield given. Multistep reaction;
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-(trifluoromethylthio)benzaldehyde
4021-50-5

4-(trifluoromethylthio)benzaldehyde

malononitrile
109-77-3

malononitrile

6-amino-7-cyano-2-hydroxymethyl-8-[(4-trifluoromethylthio)phenyl]-4,8-dihydropyrano[3,2-b]pyran-4-one

6-amino-7-cyano-2-hydroxymethyl-8-[(4-trifluoromethylthio)phenyl]-4,8-dihydropyrano[3,2-b]pyran-4-one

Conditions
ConditionsYield
With triethylamine In ethanol for 0.25h; Heating;97%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

propionic acid anhydride
123-62-6

propionic acid anhydride

2-propionyloxymethyl-4H-pyran-4-on-5-yl propionate
1092474-58-2

2-propionyloxymethyl-4H-pyran-4-on-5-yl propionate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;97%
indole
120-72-9

indole

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

benzaldehyde
100-52-7

benzaldehyde

2-((1H-indol-3-yl)(phenyl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one
1261077-99-9

2-((1H-indol-3-yl)(phenyl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
Stage #1: 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one; benzaldehyde With FAU zeolite nanoparticles In neat (no solvent) at 110℃; for 0.166667h; Green chemistry;
Stage #2: indole In neat (no solvent) Temperature; Green chemistry;
97%
With Zn4O(BDC)3 supported on NiFe2O4 nanoparticles In neat (no solvent) at 110℃; for 1h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Concentration;92%
With indium(III) chloride at 120℃; for 1.08333h; neat (no solvent);85%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

malononitrile
109-77-3

malononitrile

2-amino-4-(thiophen-2-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
625376-15-0

2-amino-4-(thiophen-2-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
In water at 50℃; for 0.1h; Sonication;97%
With s-triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles In water at 100℃; for 0.416667h; Green chemistry;95%
With nanozeolite clinoptilolite In water at 95℃; for 0.3h; Green chemistry;92%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

indole-2,3-dione
91-56-5

indole-2,3-dione

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2'-amino-6'-(hydroxymethyl)-2,8'-dioxo-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-3'-carboxylate
884213-99-4

ethyl 2'-amino-6'-(hydroxymethyl)-2,8'-dioxo-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-3'-carboxylate

Conditions
ConditionsYield
With N-doped graphene quantum dots modified with CuO (0D)/ZnO (1D) heterojunction In water for 0.25h;97%
With 1,4-diaza-bicyclo[2.2.2]octane In methanol at 60℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Solvent;94%
With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane for 0.583333h; Reflux;89%

501-30-4Upstream product

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