[ CAS No. 14400-67-0 ] {[proInfo.proName]}

Name: 14400-67-0|2,5-Dimethylfuran-3(2H)-one|98%
Brand: Ambeed
SKU: A633485
Price: 7.0 USD
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Quality Control of [ 14400-67-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 14400-67-0 ]

SDS Specification

Alternatived Products of [ 14400-67-0 ]

Product Details of [ 14400-67-0 ]

CAS No. :	14400-67-0	MDL No. :	MFCD00052571
Formula :	C₆H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ASOSVCXGWPDUGN-UHFFFAOYSA-N
M.W :	112.13	Pubchem ID :	85730
Synonyms :		Chemical Name :	2,5-Dimethylfuran-3(2H)-one

Calculated chemistry of [ 14400-67-0 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	29.65
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.77
Log Po/w (XLOGP3) :	0.83
Log Po/w (WLOGP) :	0.88
Log Po/w (MLOGP) :	-0.04
Log Po/w (SILICOS-IT) :	1.28
Consensus Log Po/w :	0.94

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.06
Solubility :	9.81 mg/ml ; 0.0875 mol/l
Class :	Very soluble
Log S (Ali) :	-0.96
Solubility :	12.2 mg/ml ; 0.108 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.85
Solubility :	15.7 mg/ml ; 0.14 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.14

Safety of [ 14400-67-0 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P240-P241+P242+P243-P280-P303+P361+P353-P370+P378-P403+P235-P501	UN#:	1993
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 14400-67-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 14400-67-0 ]

[ 14400-67-0 ] Synthesis Path-Downstream 1~88

1
[ 14400-67-0 ]
[ 76778-00-2 ]
[ 76777-77-0 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 1501 - 1513

2
[ 14400-67-0 ]
[ 7766-48-5 ]
[ 76777-76-9 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 1501 - 1513

3
[ 14400-67-0 ]
[ 64677-33-4 ]
[ 119582-52-4 ]

Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1831 - 1840

4
[ 14400-67-0 ]
[ 119-66-4 ]
[ 67916-05-6 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1985,p. 204 - 205

5
[ 14400-67-0 ]
1,4-benzenebisdiazonium tetrafluoroborate [ No CAS ]
p-phenylenebis(2-azo-2,5-dimethyl-3-furanone) [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1980,vol. 110,p. 419 - 422

6
[ 14400-67-0 ]
1,4-benzenebisdiazonium tetrafluoroborate [ No CAS ]
[ 52204-40-7 ]

Reference： [1]Gazzetta Chimica Italiana,1980,vol. 110,p. 419 - 422

8
[ 14400-67-0 ]
1,3-benzenebisdiazonium hydrogensulfate [ No CAS ]
[ 52204-42-9 ]

Reference： [1]Gazzetta Chimica Italiana,1980,vol. 110,p. 419 - 422

9
[ 14400-67-0 ]
1,3-benzenebisdiazonium hydrogensulfate [ No CAS ]
[ 77086-12-5 ]

Reference： [1]Gazzetta Chimica Italiana,1980,vol. 110,p. 419 - 422

10
[ 14400-67-0 ]
[ 71502-43-7 ]
[ 95104-46-4 ]

Reference： [1]Synthesis,1984,p. 868 - 870
[2]Synthesis,1984,p. 868 - 870

11
[ 14400-67-0 ]
[ 83326-43-6 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 2895 - 2898

12
[ 57556-12-4 ]
[ 14400-67-0 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 505 - 506

13
[ 17492-61-4 ]
[ 14400-67-0 ]
[ 61892-85-1 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1982,vol. 36,p. 1 - 14

14
[ 61892-85-1 ]
[ 14400-67-0 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1982,vol. 36,p. 1 - 14

15
[ 15441-67-5 ]
[ 124-38-9 ]
[ 14400-67-0 ]
[ 4436-75-3 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 3063 - 3068

16
[ 15441-67-5 ]
[ 14400-67-0 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 505 - 506
[2]Tetrahedron Letters,1986,vol. 27,p. 505 - 506

17
[ 14400-67-0 ]
[ 108-45-2 ]
[ 52204-42-9 ]

Reference： [1]Gazzetta Chimica Italiana,1980,vol. 110,p. 419 - 422

18
[ 431-03-8 ]
[ 14400-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium chloride; In water;	EXAMPLE 1 49 g of diacetyl (50 cc) were dissolved in 250 cc of H2 O in a 600 cc beaker. 9.8 g of KOH, dissolved in 175 cc of H2 O, were dripped into the diacetyl solution, kept under stirring and maintained at a temperature between 2° and 5°C. At the end of the dripping and after stopping the cooling, the solution was neutralized with H2 SO4 at 50 percent. To the solution (442 cc) there were admixed 4 cc of concentrated HCl (density 1.18) and the solution was then heated under slow stirring for 6 hours at 95°C. At the end of this operation, the pH of the solution was brought to 5 - 6 with 30 percent NaOH, saturated with NaCl (140 g), and extracted 5 times with ether. The etheric solution was thereupon dried on Na2 SO4. By distillation of the ether, 34.6 g of residue were obtained which, by distillation under vacuum (at 69° - 70°C/12 mm Hg), yielded 19.47 g of 2,5-dimethyl-3-(2H)-furanone.

Reference： [1]Journal of the Chemical Society. Chemical communications,1985,p. 204 - 205
[2]Patent: US3980675,1976,A

19
[ 14400-67-0 ]
[ 106-50-3 ]
[ 52204-40-7 ]

Reference： [1]Gazzetta Chimica Italiana,1980,vol. 110,p. 419 - 422

20
[ 14400-67-0 ]
[ 513-31-5 ]
[ 161551-18-4 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

21
[ 14400-67-0 ]
[ 74-88-4 ]
[ 1559-45-1 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 1501 - 1513

24
[ 14400-67-0 ]
[ 65495-78-5 ]
(E)-4-(2,5-Dimethyl-3-oxo-2,3-dihydro-furan-2-yl)-but-2-enoic acid methyl ester [ No CAS ]
(1S,2R)-2-((S)-2,5-Dimethyl-3-oxo-2,3-dihydro-furan-2-yl)-cyclopropanecarboxylic acid methyl ester [ No CAS ]
(1R,2S)-2-((S)-2,5-Dimethyl-3-oxo-2,3-dihydro-furan-2-yl)-cyclopropanecarboxylic acid methyl ester [ No CAS ]

Reference： [1]Synlett,1999,p. 1391 - 1394

25
[ 14400-67-0 ]
[ 1117-71-1 ]
(1S,2R)-2-((S)-2,5-Dimethyl-3-oxo-2,3-dihydro-furan-2-yl)-cyclopropanecarboxylic acid methyl ester [ No CAS ]
(1R,2S)-2-((S)-2,5-Dimethyl-3-oxo-2,3-dihydro-furan-2-yl)-cyclopropanecarboxylic acid methyl ester [ No CAS ]
(1R,2R,3R,4R)-3-Bromomethyl-1,4-dimethyl-5-oxo-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Synlett,1999,p. 1391 - 1394
[2]Synlett,1999,p. 1391 - 1394

26
[ 14400-67-0 ]
[ 65495-78-5 ]
(1S,2R)-2-((S)-2,5-Dimethyl-3-oxo-2,3-dihydro-furan-2-yl)-cyclopropanecarboxylic acid methyl ester [ No CAS ]
(1R,2S)-2-((S)-2,5-Dimethyl-3-oxo-2,3-dihydro-furan-2-yl)-cyclopropanecarboxylic acid methyl ester [ No CAS ]
(1R,2R,3R,4R)-3-Iodomethyl-1,4-dimethyl-5-oxo-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Synlett,1999,p. 1391 - 1394

27
[ 71502-43-7 ]
[ 14400-67-0 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 5215 - 5223

28
[ 14400-67-0 ]
[ 3587-60-8 ]
[ 805232-85-3 ]

Reference： [1]Synlett,2004,p. 2081 - 2086

29
[ 14400-67-0 ]
[ 76513-69-4 ]
2,5-dimethyl-2-(2-trimethylsilanyl-ethoxymethyl)-furan-3-one [ No CAS ]

Reference： [1]Synlett,2004,p. 2081 - 2086

30
[ 14400-67-0 ]
[ 88023-78-3 ]
[ 805232-86-4 ]

Reference： [1]Synlett,2004,p. 2081 - 2086

31
[ 14400-69-2 ]
[ 14400-67-0 ]

Reference： [1]Synlett,2004,p. 2081 - 2086

32
[ 14400-67-0 ]
[ 610-81-1 ]
2,5-dimethyl-2-(4-hydroxy-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2859 - 2866

33
[ 14400-67-0 ]
[ 364-78-3 ]
2,5-dimethyl-2-(4-fluoro-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2859 - 2866

34
[ 14400-67-0 ]
[ 1635-61-6 ]
2,5-dimethyl-2-(5-chloro-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2859 - 2866

35
[ 14400-67-0 ]
[ 578-46-1 ]
2,5-dimethyl-2-(5-methyl-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2859 - 2866

36
[ 14400-67-0 ]
[ 88-74-4 ]
2,5-dimethyl-2-(2-nitrophenylazo)-3-oxo-2,3-dihydrofuran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2859 - 2866

37
[ 14400-67-0 ]
[ 89-63-4 ]
2,5-dimethyl-2-(4-chloro-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2859 - 2866

38
[ 14400-67-0 ]
[ 89-62-3 ]
2,5-dimethyl-2-(4-methyl-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2859 - 2866

39
[ 14400-67-0 ]
[ 96-96-8 ]
2,5-dimethyl-2-(4-methoxy-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2859 - 2866

40
[ 14400-67-0 ]
[ 693-25-4 ]
2,5-dimethyl-3-pentylfuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 1 m: Synthesis of 2,5-dimethyl-3-pentylfuran; 449 mg of <strong>[14400-67-0]2,5-dimethyl-3(2H)-furanone</strong> are placed in 3 ml of diethyl ether and 2.5 ml of pentyl magnesium bromide solution (2 M in diethyl ether, 5 mmol) are added at 0°C. The mixture is refluxed for 2 h, dilute sulfuric acid is added and the organic phase is separated off. The aqueous phase is extracted twice with diethyl ether, the combined organic phases are dried over sodium sulfate and the solvent is distilled off under vacuum. The crude product is purified by chromatography on silica gel (pentane/diethyl ether).MS (El): 109 (100), 1 10 (51 ), 43 (48), 166 (8), 95 (22), 123 (21 ), 167 (4), 108 (4), 11 1 (4), 41 (3).1H-NMR (CDCI3, 400 MHz): 0.88 (t, 3 H, J = 7.0 Hz), 1.30 (m, 2 H), 1.30 (m, 2 H), 1.47 (m, 2 H), 2.15 (s, 3 H), 2.21 (s, 3 H), 2.24 (t, 2 H, J = 7.2 Hz), 5.75 (s, 1 H). 13C-NMR (CDCI3, 90 MHz): 1 1.3 (CH3), 13.4 (CH3), 14.0 (CH3), 22.5 (CH2), 24.8 (CH2), 30.1 (CH2), 31.5 (CH2), 107.4 (CH), 119.8 (C), 145.0 (C), 148.9 (C).

Reference： [1]Patent: WO2007/131834,2007,A1 .Location in patent: Page/Page column 66

41
[ 14400-67-0 ]
[ 623-43-8 ]
C₁₁H₁₆O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 6299 - 6302

42
[ 14400-67-0 ]
[ 14400-69-2 ]

Reference： [1]Synlett,2004,p. 2081 - 2086

43
[ 14400-67-0 ]
(2S,5R)-2-Benzyloxymethyl-2,5-dimethyl-dihydro-furan-3-one [ No CAS ]

Reference： [1]Synlett,2004,p. 2081 - 2086

44
[ 14400-67-0 ]
(2S,5S)-2-Benzyloxymethyl-2,5-dimethyl-dihydro-furan-3-one [ No CAS ]

Reference： [1]Synlett,2004,p. 2081 - 2086

45
[ 14400-67-0 ]
2-benzyloxymethyl-2-methyl-5-(3-buten-1-yl)-3(2H)-furanone [ No CAS ]

Reference： [1]Synlett,2004,p. 2081 - 2086

46
[ 14400-67-0 ]
5-ethyl-2-(4-methoxy-benzyloxymethyl)-2-methyl-furan-3-one [ No CAS ]

Reference： [1]Synlett,2004,p. 2081 - 2086

47
[ 14400-67-0 ]
[ 805232-77-3 ]

Reference： [1]Synlett,2004,p. 2081 - 2086

48
[ 14400-67-0 ]
2-benzyloxymethyl-2-methyl-5-[1-(2-propen-1-yl)-3-buten-1-yl]-3(2H)-furanone [ No CAS ]

Reference： [1]Synlett,2004,p. 2081 - 2086

49
[ 14400-67-0 ]
[ 805232-79-5 ]

Reference： [1]Synlett,2004,p. 2081 - 2086

50
[ 14400-67-0 ]
[ 805232-80-8 ]

Reference： [1]Synlett,2004,p. 2081 - 2086

51
[ 14400-67-0 ]
5-hexyl-2-(4-methoxy-benzyloxymethyl)-2-methyl-furan-3-one [ No CAS ]

Reference： [1]Synlett,2004,p. 2081 - 2086

52
[ 55086-61-8 ]
[ 14400-67-0 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 5215 - 5223

53
[ 14400-67-0 ]
(1R,2S)-2-((S)-2,5-Dimethyl-3-oxo-2,3-dihydro-furan-2-yl)-cyclopropanecarboxylic acid methyl ester [ No CAS ]

Reference： [1]Synlett,1999,p. 1391 - 1394

54
[ 14400-67-0 ]
8-Methyl-6-methylene-11-oxa-bicyclo[6.2.1]undec-1⁽¹⁰⁾-en-4-yn-9-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

55
[ 14400-67-0 ]
(Z)-(6S,8S)-6-Hydroxy-8-methyl-11-oxa-bicyclo[6.2.1]undeca-1⁽¹⁰⁾,4-dien-9-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

56
[ 14400-67-0 ]
[ 161551-16-2 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

57
[ 14400-67-0 ]
[ 161551-19-5 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

58
[ 14400-67-0 ]
[ 161551-26-4 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

59
[ 14400-67-0 ]
[ 161551-20-8 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

60
[ 14400-67-0 ]
2-[2-Hydroxy-5-(tetrahydro-pyran-2-yloxy)-pent-3-ynyl]-2,5-dimethyl-furan-3-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

61
[ 14400-67-0 ]
2-[2-Hydroxy-2-hydroxymethyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-ynyl]-2,5-dimethyl-furan-3-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

62
[ 14400-67-0 ]
(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-11-oxa-bicyclo[6.2.1]undeca-1⁽¹⁰⁾,4-dien-9-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

63
[ 14400-67-0 ]
2-[(Z)-5-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-pent-3-enyl]-2,5-dimethyl-furan-3-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

64
[ 14400-67-0 ]
2-[(Z)-2-(tert-Butyl-diphenyl-silanyloxy)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl]-2,5-dimethyl-furan-3-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

65
[ 14400-67-0 ]
2-[2-(tert-Butyl-diphenyl-silanyloxy)-5-(tetrahydro-pyran-2-yloxy)-pent-3-ynyl]-2,5-dimethyl-furan-3-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 6795 - 6798

66
[ 17492-61-4 ]
[ 14400-67-0 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1982,vol. 36,p. 1 - 14

67
[ 14400-67-0 ]
[ 76777-81-6 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 1501 - 1513

68
[ 14400-67-0 ]
[ 76777-88-3 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 1501 - 1513

69
[ 14400-67-0 ]
2-(2-butynyl)-2-methyl-5-<1-(phenylseleno)ethyl>-3(2H)-furanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 1501 - 1513

70
[ 3031-66-1 ]
[ 14400-67-0 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 505 - 506
[2]Tetrahedron Letters,1986,vol. 27,p. 505 - 506

71
[ 105653-96-1 ]
[ 14400-67-0 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 505 - 506

72
[ 14400-67-0 ]
[ 3658-77-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; potassium hydrogencarbonate; In methanol; water; ethyl acetate;	EXAMPLE 1 378 g of 2,5-dimethyl-2H-furan-3-one are added to a solution of 304 g of potassium bicarbonate in 420 ml of methanol and 420 ml of water, and 372 ml of 30percent (w/w) hydrogen peroxide are then added over 1 hour, under stirring, the temperature being kept between 30° and 40° C. After stirring for 2 hours at about 20° C., the starting material and the desired product are extracted from the reaction medium in 500 ml of ethyl acetate using a liquid-liquid extraction apparatus. The solvent is removed under vacuum to give 160 g of a brownish oil, which is distilled under reduced pressure. The fraction distilling at about 100° C. under 250 Pa is isolated and crystallized from twice its weight of ethyl acetate or isopropyl ether. This gives 25 g of 2,5-dimethyl-4-hydroxy-2H-furan-3-one. 40 g of starting material are recovered from the fraction distilling below 100° C. and may be recycled.

Reference： [1]Patent: US5171867,1992,A

73
[ 14400-67-0 ]
TBSOTf [ No CAS ]
[ 406224-39-3 ]

Yield	Reaction Conditions	Operation in experiment
3.6 g (89%)	With triethanolamine; In dichloromethane;	A. 3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2,5-dimethylfuran (222A) 2,5-Dimethyl-3(3H)-furanone (2.00 g, 17.8 mmol) was dissolved in methylene chloride (180 mL). TEA (7.43 mL, 53.5 mmol) was added followed by TBSOTf (4.92 mL, 21.4 mmol) at 25° C. After 1 h, the reaction was concentrated in vacuo and the resulting slurry was run through a silica gel column conditioned with 3percent TEA in hexanes. The product was eluted with 3percent TEA/hexanes to give 3.6 g (89percent) of compound 222A as an orange oil which was used directly in subsequent reactions.

Reference： [1]Patent: US2004/77605,2004,A1

74
[ 14400-67-0 ]
[ 92287-46-2 ]
[ 1192511-89-9 ]

Yield	Reaction Conditions	Operation in experiment
80%		2,5-dimethyl-2-(7-methoxynaphthalen-2-yldiazenyl)furan-3(2H)-one To a suspension of 2-amino-7-methoxynaphthalene (5 g, 28,8 mmol) in H2O (72 ml), HCl conc. (14,5 ml) was added, it was then cooled down in an ice bath, and a solution of NaNO2 (2,14 g, 31,1 nnmol) in H2O (18 ml) was added dropwise maintaining the mixture at stirring at 0C during 30 minutes. The previous solution was diluted with water (140 ml), <strong>[14400-67-0]2,5-dimethyl-2,3-dihydrofuran-3-one</strong> (3,63 g, 31,4 mmol) was added and was left at stirring during 2 hrs at room temperature. It was then extracted with ethylic ether several times and the collection of organic phases was washed with water until a neutral pH was achieved, and it was dried over sodium sulfate. 6,8 g (80 percent) of 2,5-dimethyl-2-(7-methoxynaphthalen-2-yldiazenyl)furan-3-one were obtained in the form of a reddish coloured oil. 1H-NMR (300 MHz, DMSO-d6) delta ppm: 8,35 (d, J=1,9Hz, 1H), 7.9 (dd, J=3,1Hz, J'= 9,0Hz, 2H), 7,6 (d, J=2,6Hz, 1H), 7,5 (dd, J=2,0Hz, J'=8,8Hz, 1H), 7,25 (dd, J=2,6Hz, J'=8,9Hz, 1H), 5,75 (s, 1H), 3,9 (s, 3H), 2,45 (s, 3H), 1,65 (s, 3H).

Reference： [1]Patent: EP2113501,2009,A1 .Location in patent: Page/Page column 21

75
[ 14400-67-0 ]
[ 13101-88-7 ]
[ 1192511-85-5 ]

Yield	Reaction Conditions	Operation in experiment
95%		1.- 2,5-dimethyl-2-(6-methoxynaphthalen-2-yldiazenyl)furan-3(2H)-one To a suspension of 2-amino-6-methoxynaphthalene (2.6 g, 15 mmol) in H2O (40 ml), HCl conc. was added (8 ml), it was cooled in an ice bath and a NaNO2 solution (1.19 g, 17.3 mmol) in H2O (18 ml) was added dropwise shaking the mixture at 0C during 30 minutes. The previous solution was diluted in H2O (80 ml), 2,5-dimethylfuran-2,3-dihydrofuran-3-one (1.94 g, 17.3 mmol) was added and was left shaking during 2 hrs at room temperature resulting in a yellow precipitate. It was filtered, washed with water and dried. It was thereby obtained 2,5-dimethyl-2-(6-methoxynaphthalen-2-yldiazenyl)furan-3-one (4.22 g, 95 percent) in a solid crude form of an ocre-yellow color that was used directly in the following synthesis step. 1H-NMR (300 MHz, CDCl3) delta ppm: 8.35 (s, 1H), 7.85 (d, J=8,8Hz, 1H), 7.75-7.7 (m, 2H), 7.2 (m, 2H), 5.55 (s, 1H), 3.95 (s, 3H), 2.45 (s, 3H), 1.75 (s, 3H).

Reference： [1]Patent: EP2113501,2009,A1 .Location in patent: Page/Page column 19

76
[ 14400-67-0 ]
[ 91-59-8 ]
[ 1192140-19-4 ]

Yield	Reaction Conditions	Operation in experiment
64%		To a suspension of naphthalen-2-amine (2,86 g, 20 mmol) in H2O (12 mL) was added HCl conc. (5 mL) and cooled in an ice bath, and subsequently, a NaNO2 solution (1,48 g, 21,5 nnmol in H2O (8 mL)) was added drop-wise maintaining the stirring mixture at 0C during 20 minutes. The previous solution was diluted in H2O (25 mL) and <strong>[14400-67-0]2,5-dimethylfuran-3(2H)-one</strong> (2.48 g, 22 mmol) was added, and left stirring during 1,5 hours at a room temperature, thereby resulting in a thick oil of orange color. Ethyl ether was added and the organic phase was washed with water, saturated solution of NaHCO3 and water. The organic phase was poured, dried, and eliminated at a reduced pressure thereby obtaining 2,5-dimethyl-2-(naphthalen-2-yldiazenyl)furan-3(2H)-one (4,5 g, 16,9 mmol, 84,5percent) in the form of a thick oil of orange color that solidified on standing and that could be used in the following reaction without purification. In fact, the previously mentioned crude oil was purified, prior to the next synthetic step by chromatography on silica gel using CH2Cl2 as eluant obtaining 2,5-dimethyl-2-(naphthalen-2-yldiazenyl)furan-3(2H)-one (3,4 g, 12,8 mmol, 64,0percent) as an orange solid material. P.f. 76-77C. 1H RMN (300 MHz, CDCl3) delta 1,80 (s, 3H), 2,48 (s, 3H), 5.56 (s, 1H), 7,56 (m, 2H), 7,79-7,89 (m, 3H), 7,98 (m, 1H), 8,42 (s, 1H).

Reference： [1]Patent: EP2112139,2009,A1 .Location in patent: Page/Page column 11

77
[ 14400-67-0 ]
[ 6972-71-0 ]
[ 1443765-09-0 ]

Yield	Reaction Conditions	Operation in experiment
95%		General procedure: To a suspension of 2-Nitroanilines 2a?2g (10mmol) in water (5mL) and hydrochloric acid (37percent, 2.5mL), a solution of sodium nitrite (0.74g, 10.75mmol) in water (4mL) at 0°C was added dropwise. The mixture was stirred for 1h, diluted with water (30mL) and made acid with concentrated hydrochloric acid (2mL). In the case of 2b,f the reactions were carried out at room temperature. To this solution, freshly distilled <strong>[14400-67-0]2,5-dimethyl-3-oxo-2,3-dihydrofuran</strong> [36] (1.24g, 11mmol) was added and the mixture was stirred for 1h at room temperature. The crude residue was collected by filtration. After drying, it was purified by column chromatography using a dichloromethane/ethyl acetate mixture in gradient as eluent and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 345 - 356

78
[ 14400-67-0 ]
[ 6641-64-1 ]
[ 1443765-10-3 ]

Yield	Reaction Conditions	Operation in experiment
78%		General procedure: To a suspension of 2-Nitroanilines 2a?2g (10mmol) in water (5mL) and hydrochloric acid (37percent, 2.5mL), a solution of sodium nitrite (0.74g, 10.75mmol) in water (4mL) at 0°C was added dropwise. The mixture was stirred for 1h, diluted with water (30mL) and made acid with concentrated hydrochloric acid (2mL). In the case of 2b,f the reactions were carried out at room temperature. To this solution, freshly distilled <strong>[14400-67-0]2,5-dimethyl-3-oxo-2,3-dihydrofuran</strong> [36] (1.24g, 11mmol) was added and the mixture was stirred for 1h at room temperature. The crude residue was collected by filtration. After drying, it was purified by column chromatography using a dichloromethane/ethyl acetate mixture in gradient as eluent and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 345 - 356

79
[ 14400-67-0 ]
[ 6393-40-4 ]
[ 1443765-11-4 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: To a suspension of 2-Nitroanilines 2a?2g (10mmol) in water (5mL) and hydrochloric acid (37percent, 2.5mL), a solution of sodium nitrite (0.74g, 10.75mmol) in water (4mL) at 0°C was added dropwise. The mixture was stirred for 1h, diluted with water (30mL) and made acid with concentrated hydrochloric acid (2mL). In the case of 2b,f the reactions were carried out at room temperature. To this solution, freshly distilled <strong>[14400-67-0]2,5-dimethyl-3-oxo-2,3-dihydrofuran</strong> [36] (1.24g, 11mmol) was added and the mixture was stirred for 1h at room temperature. The crude residue was collected by filtration. After drying, it was purified by column chromatography using a dichloromethane/ethyl acetate mixture in gradient as eluent and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 345 - 356

80
[ 14400-67-0 ]
[ 400-98-6 ]
2,5-dimethyl-2-(2-nitrophenylazo-4-trifluoromethyl)-3-oxo-2,3-dihydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		General procedure: To a suspension of 2-Nitroanilines 2a?2g (10mmol) in water (5mL) and hydrochloric acid (37percent, 2.5mL), a solution of sodium nitrite (0.74g, 10.75mmol) in water (4mL) at 0°C was added dropwise. The mixture was stirred for 1h, diluted with water (30mL) and made acid with concentrated hydrochloric acid (2mL). In the case of 2b,f the reactions were carried out at room temperature. To this solution, freshly distilled <strong>[14400-67-0]2,5-dimethyl-3-oxo-2,3-dihydrofuran</strong> [36] (1.24g, 11mmol) was added and the mixture was stirred for 1h at room temperature. The crude residue was collected by filtration. After drying, it was purified by column chromatography using a dichloromethane/ethyl acetate mixture in gradient as eluent and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 345 - 356

81
[ 14400-67-0 ]
[ 89-62-3 ]
[ 851517-37-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a suspension of 2-Nitroanilines 2a?2g (10mmol) in water (5mL) and hydrochloric acid (37percent, 2.5mL), a solution of sodium nitrite (0.74g, 10.75mmol) in water (4mL) at 0°C was added dropwise. The mixture was stirred for 1h, diluted with water (30mL) and made acid with concentrated hydrochloric acid (2mL). In the case of 2b,f the reactions were carried out at room temperature. To this solution, freshly distilled <strong>[14400-67-0]2,5-dimethyl-3-oxo-2,3-dihydrofuran</strong> [36] (1.24g, 11mmol) was added and the mixture was stirred for 1h at room temperature. The crude residue was collected by filtration. After drying, it was purified by column chromatography using a dichloromethane/ethyl acetate mixture in gradient as eluent and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 345 - 356

82
[ 14400-67-0 ]
[ 89-63-4 ]
[ 851517-40-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a suspension of 2-Nitroanilines 2a?2g (10mmol) in water (5mL) and hydrochloric acid (37percent, 2.5mL), a solution of sodium nitrite (0.74g, 10.75mmol) in water (4mL) at 0°C was added dropwise. The mixture was stirred for 1h, diluted with water (30mL) and made acid with concentrated hydrochloric acid (2mL). In the case of 2b,f the reactions were carried out at room temperature. To this solution, freshly distilled <strong>[14400-67-0]2,5-dimethyl-3-oxo-2,3-dihydrofuran</strong> [36] (1.24g, 11mmol) was added and the mixture was stirred for 1h at room temperature. The crude residue was collected by filtration. After drying, it was purified by column chromatography using a dichloromethane/ethyl acetate mixture in gradient as eluent and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 345 - 356

83
[ 14400-67-0 ]
[ 1635-61-6 ]
[ 851517-43-6 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a suspension of 2-Nitroanilines 2a?2g (10mmol) in water (5mL) and hydrochloric acid (37percent, 2.5mL), a solution of sodium nitrite (0.74g, 10.75mmol) in water (4mL) at 0°C was added dropwise. The mixture was stirred for 1h, diluted with water (30mL) and made acid with concentrated hydrochloric acid (2mL). In the case of 2b,f the reactions were carried out at room temperature. To this solution, freshly distilled <strong>[14400-67-0]2,5-dimethyl-3-oxo-2,3-dihydrofuran</strong> [36] (1.24g, 11mmol) was added and the mixture was stirred for 1h at room temperature. The crude residue was collected by filtration. After drying, it was purified by column chromatography using a dichloromethane/ethyl acetate mixture in gradient as eluent and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 345 - 356

84
[ 14400-67-0 ]
(+)-tert-butyldimethyl[(1S,2R,5S)-5-methyl-2-[(S)-4-(phenylsulfonyl)-4-[(1R,2R,3R,4S)-1,3,4-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]but-1-en-2-yl]cyclohexyl]oxy}silane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 9223 - 9232

85
[ 14400-67-0 ]
(+)-tert-butyldimethyl[(1S,2R,5S)-5-methyl-2-[(R)-4-(phenylsulfonyl)-4-[(1R,2R,3R,4S)-1,3,4-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]but-1-en-2-yl]cyclohexyl]oxy}silane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 9223 - 9232

86
[ 14400-67-0 ]
(-)-(1S,2R,5S)-5-methyl-2-{4-(phenylsulfonyl)-4-[(1R,2R,3R,4S)-1,3,4-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]but-1-en-2-yl}cyclohexanol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 9223 - 9232

87
[ 14400-67-0 ]
(+)-(1S,2R,5S)-5-methyl-2-{(R)-4-(phenylsulfonyl)-4-[(1R,2R,3R,4S)-1,3,4-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]but-1-en-2-yl}cyclohexanol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 9223 - 9232

88
[ 14400-67-0 ]
(+)-(1S,2R,5S)-5-methyl-2-{4-[(1R,2R,3R,4S)-1,3,4-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]but-1-en-2-yl}cyclohexanol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 9223 - 9232
[2]Journal of Organic Chemistry,2013,vol. 78,p. 9223 - 9232

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Ghs Precautionary Statements

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P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
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P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
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
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
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. 14400-67-0 ] {[proInfo.proName]}

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[ 14400-67-0 ] Synthesis Path-Downstream 1~88

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Ketones

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Furans

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