[ CAS No. 40834-42-2 ]

Name: 5-Hydroxy-4-methylfuran-2(5H)-one
Brand: Ambeed
SKU: A185843
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Quality Control of [ 40834-42-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 40834-42-2 ]

SDS

Alternatived Products of [ 40834-42-2 ]

Product Details of [ 40834-42-2 ]

CAS No. :	40834-42-2	MDL No. :	MFCD07782086
Formula :	C₅H₆O₃	Boiling Point :	328.1°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	114.10	Pubchem ID :	115301
Synonyms :

Computed Properties of [ 40834-42-2 ]

TPSA :Topological Polar Surface Area	46.5	H-Bond Acceptor Count :	3
XLogP3 :	-0.4	H-Bond Donor Count :	1
SP3 :	0.40	Rotatable Bond Count :	0

Safety of [ 40834-42-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 40834-42-2 ]

Upstream synthesis route of [ 40834-42-2 ]
Downstream synthetic route of [ 40834-42-2 ]

[ 40834-42-2 ] Synthesis Path-Upstream 1~10

1
[ 616-02-4 ]
[ 931-23-7 ]
[ 40834-42-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -30 - -15℃; for 3.00 h; Inert atmosphere	A solution of 5.34 g LiAlH(t-BuO)3 (21.00 mmol) in 40 cm3 anhydrous THF was added dropwise over a 30-min period to a solution of 1.68 g citraconic anhydride (6, 15.00 mmol) in 50 cm3 anhydrous THF under a nitrogen atmosphere at - 30 C. The temperature was maintained at - 15 C for 3 h and then the reaction mixture was warmed to ambient temperature. The reaction was quenched with 50 cm3 1 M HCl, the solution was saturated with NaCl, the crude product was extracted with EtOAc (3 9 50 cm3), and the combined organic fraction was dried over MgSO4. The solvent was removed in vacuo. Purification by column chromatography (SiO2, 20percent AcOEt in petroleum ether) afforded 7a (1.023 g,60percent) and 7b (116 mg, 7percent) as yellow oils. TLC: Rf = 0.16 (for 7a), 0.15 (for 7b) (20percent AcOEt in petroleum ether). 7a: 1H NMR (400 MHz, acetone-d6): d = 6.67 (bs, 1H),6.02 (bs, 1H), 5.87 (p, J = 1.5 Hz, 1H), 2.08 (d,J = 1.5 Hz, 3H) ppm; 13C NMR (100 MHz, acetone-d6):d = 171.30 ([C\), 166.65 ([C\), 118.68 (CH), 100.25(CH), 13.15 (CH3) ppm; MS (EI): m/z (percent) = 114.0 ([M?],2), 113.0 (7), 86.0 (61), 85.0 (13), 69.0 (100), 68.0 (82),41.1 (50), 40.1 (65), 39.1 (93).

Reference： [1] Monatshefte fur Chemie, 2018, vol. 149, # 8, p. 1475 - 1480

2
[ 123-38-6 ]
[ 298-12-4 ]
[ 40834-42-2 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 7, p. 627 - 640
[2] Patent: WO2012/7814, 2012, A2. Location in patent: Page/Page column 21-22

3
[ 4744-08-5 ]
[ 10024-89-2 ]
[ 6000-59-5 ]
[ 40834-42-2 ]

Reference： [1] Patent: US5464865, 1995, A

4
[ 123-38-6 ]
[ 563-96-2 ]
[ 40834-42-2 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4889 - 4894

5
[ 83803-81-0 ]
[ 40834-42-2 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 9, p. 1365 - 1370

6
[ 203131-19-5 ]
[ 40834-42-2 ]

Reference： [1] Synlett, 1998, # 1, p. 31 - 32

7
[ 616-02-4 ]
[ 40834-42-2 ]
[ 6124-79-4 ]
[ 22122-36-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 1734 - 1743

8
[ 78920-07-7 ]
[ 40834-42-2 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4889 - 4894

9
[ 78920-13-5 ]
[ 40834-42-2 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4889 - 4894

10
[ 26315-61-7 ]
[ 51043-49-3 ]
[ 40834-42-2 ]
[ 109745-72-4 ]

Reference： [1] Journal of Organic Chemistry, 1987, vol. 52, # 21, p. 4788 - 4790
[2] Journal of Organic Chemistry, 1987, vol. 52, # 21, p. 4788 - 4790

[ 40834-42-2 ] Synthesis Path-Downstream 1~10

1
[ 40834-42-2 ]
[ 54168-84-2 ]

Reference： [1]Journal of the Chemical Society C: Organic,1968,p. 1984 - 1997

2
[ 40834-42-2 ]
[ 56013-01-5 ]
[ 14398-44-8 ]

Reference： [1]Canadian Journal of Chemistry,1975,vol. 53,p. 1943 - 1948

3
[ 40834-42-2 ]
[ 57380-65-1 ]
[ 41438-10-2 ]

Reference： [1]Canadian Journal of Chemistry,1975,vol. 53,p. 1943 - 1948

4
[ 40834-42-2 ]
[ 1067-74-9 ]
[ 3555-79-1 ]

Reference： [1]Journal of the Chemical Society C: Organic,1968,p. 1984 - 1997

5
[ 40834-42-2 ]
BF₄OEt₃ [ No CAS ]
[ 62054-50-6 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 209 - 212

8
[ 55809-36-4 ]
[ 40834-42-2 ]
5-(5-tert-butyl-1,2-isoxazol-3-yl)amino-4-methyl-2,5-dihydrofuran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In toluene; for 8h;Reflux;	5-Hydroxy-4-methyl-2,5-dihydrofuran-2-one (1000 mg, 8.76 mmol, 1.0 equiv) and 3-amino-5-tert-butyl-1,2-isoxazole (1351 mg, 9.64 mmol, 1.1 equiv) were dissolved in abs. toluene (20 ml) and stirred under reflux conditions for 8 h. After cooling to room temperature, the reaction mixture was filtered off with suction and, after thorough drying, 5-(5-tert-butyl-1,2-isoxazol-3-yl)amino-4-methyl-2,5-dihydrofuran-2-one was isolated without any further purification in the form of a colorless solid (1470 mg, 71% of theory).). 1H-NMR (400 MHz, CDCl3 delta, ppm) 6.12 (m, 1H), 5.96 (d, 1H), 5.65 (s, 1H), 4.95 (br. d, 1H), 2.14 (s, 3H), 1.31 (s, 9H). 5-(5-tert-Butyl-1,2-isoxazol-3-yl)amino-4-methyl-2,5-dihydrofuran-2-one (150 mg, 0.64 mmol, 1.0 equiv) was dissolved in diethyl carbonate (1.54 ml, 20 equiv) and stirred at a temperature of 120 C. for 8 h. After cooling to room temperature, the reaction mixture was filtered off with suction, and final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethoxycarbonyloxy-4-methyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (63 mg, 32% of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 6.95 (s, 1H), 6.68 (s, 1H), 6.02 (m, 1H), 4.37-4.32 (m, 2H), 2.12 (s, 3H), 1.39 (t, 3H), 1.34 (s, 9H).

Reference： [1]Patent: US2020/79765,2020,A1.Location in patent: Paragraph 0200-0201

9
[ 40834-42-2 ]
[ 1095823-39-4 ]
5-(5-chloro-4-trifluoromethylpyridin-2-yl)amino-4-methyl-2,5-dihydrofuran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In toluene; for 16h;Reflux;	5-Hydroxy-4-methyl-2,5-dihydrofuran-2-one (300 mg, 2.63 mmol, 1.0 equiv) and 2-amino-5-chloro-4-trifluoromethylpyridine (568 mg, 2.89 mmol, 1.1 equiv) were dissolved in abs. toluene (12 ml) and stirred under reflux conditions for 16 h. After cooling to room temperature, the reaction mixture was filtered off with suction and, after thorough drying, 5-(5-chloro-4-trifluoromethylpyridin-2-yl)amino-4-methyl-2,5-dihydrofuran-2-one was isolated without any further purification in the form of a colorless solid (530 mg, 68% of theory).). 1H-NMR (400 MHz, d6-DMSO delta, ppm) 8.43 (s, 1H), 8.36 (d, 1H), 7.06 (s, 1H), 6.78 (d, 1H), 6.15 (m, 1H), 2.07 (s, 3H). 5-(5-Chloro-4-trifluoromethylpyridin-2-yl)amino-4-methyl-2,5-dihydrofuran-2-one (250 mg, 0.85 mmol, 1.0 equiv) was dissolved in propionic anhydride (2.22 g, 20 equiv) and stirred at a temperature of 155 C. for 4 h. After cooling to room temperature, the reaction mixture was filtered off with suction, and final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethylcarbonyloxy-4-methyl-1-(5-chloro-4-trifluoromethylpyridin-2-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (35 mg, 12% of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.67 (s, 1H), 8.39 (s, 1H), 7.42 (s, 1H), 6.02 (m, 1H), 2.39-2.32 (m, 2H), 2.08 (s, 3H), 1.17 (t, 3H).

Reference： [1]Patent: US2020/79765,2020,A1.Location in patent: Paragraph 0198-0199

10
[ 108-05-4 ]
[ 40834-42-2 ]
[ 180063-09-6 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 1215 - 1222

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[ 40834-42-2 ]

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
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H370	Causes damage to organs
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H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 40834-42-2 ]

Quality Control of [ 40834-42-2 ]

Related Doc. of [ 40834-42-2 ]

Product Details of [ 40834-42-2 ]

Computed Properties of [ 40834-42-2 ]

Safety of [ 40834-42-2 ]

Application In Synthesis of [ 40834-42-2 ]

[ 40834-42-2 ] Synthesis Path-Upstream 1~10

[ 40834-42-2 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 40834-42-2 ]

Alcohols

Esters

Related Parent Nucleus of [ 40834-42-2 ]

Furans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 40834-42-2 ]

Related Parent Nucleus of
[ 40834-42-2 ]