[ CAS No. 49619-82-1 ] {[proInfo.proName]}

Name: 49619-82-1|3-Bromo-4H-chromen-4-one|98%
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Quality Control of [ 49619-82-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 49619-82-1 ]

Product Details of [ 49619-82-1 ]

CAS No. :	49619-82-1	MDL No. :	MFCD00017337
Formula :	C₉H₅BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IQIGYNPOESZBDJ-UHFFFAOYSA-N
M.W :	225.04	Pubchem ID :	521256
Synonyms :

Calculated chemistry of [ 49619-82-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.18
TPSA :	30.21 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	2.45
Log Po/w (WLOGP) :	2.56
Log Po/w (MLOGP) :	1.56
Log Po/w (SILICOS-IT) :	3.13
Consensus Log Po/w :	2.36

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.4
Solubility :	0.0905 mg/ml ; 0.000402 mol/l
Class :	Soluble
Log S (Ali) :	-2.73
Solubility :	0.421 mg/ml ; 0.00187 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.47
Solubility :	0.00761 mg/ml ; 0.0000338 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.46

Safety of [ 49619-82-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 49619-82-1 ]

* 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 [ 49619-82-1 ]

[ 49619-82-1 ] Synthesis Path-Downstream 1~88

1
[ 110-89-4 ]
[ 49619-82-1 ]
[ 40302-79-2 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3435 - 3438
[2]Bulletin de la Societe Chimique de France,1958,p. 325,328

2
[ 110-89-4 ]
[ 98592-23-5 ]
[ 60-29-7 ]
[ 49619-82-1 ]

Reference： [1]Bulletin de la Societe Chimique de France,1958,p. 325,328

3
[ 49619-82-1 ]
[ 108-91-8 ]
3-cyclohexylimino-chroman-4-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 3999

4
[ 98592-23-5 ]
[ 49619-82-1 ]

Reference： [1]Bulletin de la Societe Chimique de France,1958,p. 325,328

5
[ 58264-72-5 ]
[ 49619-82-1 ]

Reference： [1]Bulletin de la Societe Chimique de France,1958,p. 325,328
[2]Synthesis,2004,p. 2641 - 2644

6
[ 123-75-1 ]
[ 49619-82-1 ]
[ 33592-93-7 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3435 - 3438

7
[ 288-32-4 ]
[ 49619-82-1 ]
[ 42879-93-6 ]
3-Bromo-2-imidazol-1-yl-chroman-4-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 441 - 443

8
[ 292638-84-7 ]
[ 49619-82-1 ]
[ 115237-37-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2597 - 2604
[2]Australian Journal of Chemistry,2010,vol. 63,p. 1582 - 1593

9
[ 622-42-4 ]
[ 49619-82-1 ]
[ 140473-26-3 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 993 - 996

10
[ 79-24-3 ]
[ 49619-82-1 ]
[ 140473-23-0 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 993 - 996
[2]Tetrahedron Letters,1992,vol. 33,p. 993 - 996

11
[ 49619-82-1 ]
[ 7713-79-3 ]
[ 140483-34-7 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 997 - 1000

12
[ 49619-82-1 ]
[ 1116-98-9 ]
[ 140483-31-4 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 997 - 1000

13
[ 49619-82-1 ]
[ 2483-57-0 ]
[ 140473-25-2 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 993 - 996

14
[ 49619-82-1 ]
[ 69555-14-2 ]
[ 140483-35-8 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 997 - 1000

15
[ 49619-82-1 ]
[ 1765-93-1 ]
[ 36136-90-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; benzene; at 80℃; for 16h;Inert atmosphere;	4'-fluoroisoflavone was prepared on large scale according to a procedure from Suzuki and Miyaura (Hoshino et al., 1988; herein incorporated by reference in its entirety). To a flame-dried 500 mL round bottom flask was added <strong>[49619-82-1]3-bromochromone</strong> (50 mmol, 11.25 g), 4-fluorophenylboronic acid (55 mmol, 7.69 g) and NazC03 (100 mmol, 10.6 g). The solids were dissolved in a mixture of benzene (100 mL) and water (50 mL), and the system was purged with N2 for 10-15 minutes. The Pd(PPh3)4 catalyst (2.5 mmol, 2.89 g) was then added, at which time the reaction turned a bright orange. The flask was equipped with a reflux condenser and the reaction was heated to reflux (80 C) overnight. After approximately 16 h, the reaction was cooled to 23C and was diluted with EtOAc (250 mL), then the crude material was passed through a plug of silica with EtOAc as the eluent. The organic material was dried over Na2S04 and concentrated to give a dark brown solid that was adsorbed onto silica gel using DCM. Material purified by flash column chromatography (Si02, 20% EtOAc/hexanes) to afford 4'- fluoroisoflavone (8.14 g, 67% yield) as a yellow-orange solid that showed minor impurities by 1H NMR spectroscopy. Slightly impure material was taken onto the next step of the synthesis without further purification. Product was confirmed by NMR and ultra-performance liquid chromatography/mass spectrometry (UPLCMS).
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; benzene; at 80℃; for 16h;	4'-fluoroisoflavone was prepared on large scale according to a procedure from Suzuki and Miyaura (Hoshino et al, Bull. Chem. Soc. Jpn. 61, 3008-3010 (1988)). To a flame-dried 500 mL round bottom flask was added <strong>[49619-82-1]3-bromochromone</strong> (50 mmol, 11.25 g), 4- fluorophenylboronic acid (55 mmol, 7.69 g) and Na2C03(100 mmol, 10.6 g). The solids were dissolved in a mixture of benzene (100 mL) and water (50 mL), and the system was purged with N2for 10-15 minutes. The Pd(PPh3)4catalyst (2.5 mmol, 2.89 g) was then added, at which time the reaction turned a bright orange. The flask was equipped with a reflux condenser and the reaction was heated to reflux (80 C) overnight. After approximately 16 h, the reaction was cooled to 23 C and was diluted with EtOAc (250 mL), then the crude material was passed through a plug of silica with EtOAc as the eluent. The organic material was dried over Na2S04and concentrated to give a dark brown solid that was adsorbed onto silica gel using DCM. Material purified by flash column chromatography (Si02, 20% EtO Ac/hexanes) to afford 4'-fluoroisoflavone (8.14 g, 67% yield) as a yellow-orange solid that showed minor impurities by 'H NMR spectroscopy. Slightly impure material was taken onto the next step of the synthesis without further purification. NMR (500 MHz, CDCb) d 8.35 (dd, J = 8.0, 1.6 Hz, 1H), 8.05 (s, 1H), 7.73 (ddd, J = 8.7, 7.1, 1.7 Hz, 1H), 7.61 - 7.54 (m, 2H), 7.53 (dd, J= 8.4, 1.1 Hz, 1H), 7.48 (ddd, J = 8.2, 7.0, 1.1 Hz, 1H), 7.17 (ap t , J = 8.7 Hz, 2H);13C NMR (126 MHz, CDCl3): d 176.2, 163.8, 161.8, 156.2, 152.9, 133.8, 130.7, 127.8, 126.4, 125.4, 124.5, 118.1, 115.5; UPLCMS: Mass calculated for C15H9F02, [M+H]+, 241. Found 241.

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010
[2]Patent: WO2016/73897,2016,A1 .Location in patent: Page/Page column 41
[3]Nature Communications,2018,vol. 9
[4]Patent: WO2019/157150,2019,A1 .Location in patent: Page/Page column 53; 54; 55

16
[ 49619-82-1 ]
[ 16419-60-6 ]
3-(o-tolyl)-4H-chromen-4-one [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010
[2]Tetrahedron,2006,vol. 62,p. 3395 - 3401
[3]Chemical Communications,2015,vol. 51,p. 925 - 928

17
[ 49619-82-1 ]
[ 5720-05-8 ]
[ 58113-12-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010

18
[ 49619-82-1 ]
[ 5720-07-0 ]
[ 1621-58-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010
[2]Chemical Communications,2015,vol. 51,p. 925 - 928

19
[ 49619-82-1 ]
[ 13922-41-3 ]
3-(naphthalen-1-yl)-4H-chromen-4-one [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010

20
[ 49619-82-1 ]
[ 7330-48-5 ]
[ 574-12-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010

21
[ 49619-82-1 ]
[ 120185-90-2 ]
2',4',6'-trimethylisoflavone [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010

22
[ 49619-82-1 ]
[ 24067-17-2 ]
[ 120185-88-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010

23
[ 49619-82-1 ]
[ 108-91-8 ]
[ 87744-30-7 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3435 - 3438

24
[ 49619-82-1 ]
[ 108-03-2 ]
[ 140473-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20℃;	The compound 1, 8 - diazabicyclo eleven carbon -7 - ene (DBU) (0.457 g, 3 mmol) is dissolved in acetonitrile (5 ml) in the, the use of the dropping funnel and added compound 3 - bromo - 4H - [...] -4 - ketone (0.224 g, 1 mmol) and nitro-propane (0.098 g, 1.1 mmol) of acetonitrile in the mixed solution. Reaction at room temperature, to the reaction solution after the reaction is complete concentrating under reduced pressure, the concentrate through silica gel column chromatography (DCM:MeOH=100:3) purification, get intermediate 3-hydroxy-2-[1-(hydroxyimino)propyl]-4H-chromen-4-one(18).

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 993 - 996
[2]Patent: CN109438471,2019,A .Location in patent: Paragraph 0204; 0205

25
[ 49619-82-1 ]
[ 96982-67-1 ]
[ 120185-88-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010

26
[ 49619-82-1 ]
[ 109-73-9 ]
[ 87744-28-3 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3435 - 3438

27
[ 49619-82-1 ]
[ 292638-85-8 ]
[ 115237-36-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2597 - 2604

28
[ 49619-82-1 ]
[ 105-56-6 ]
[ 140483-30-3 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 997 - 1000

29
[ 49619-82-1 ]
[ 100-46-9 ]
[ 87744-29-4 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3435 - 3438

30
[ 49619-82-1 ]
[ 105-53-3 ]
[ 140483-29-0 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 997 - 1000

31
[ 49619-82-1 ]
[ 2274-42-2 ]
[ 140483-32-5 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 997 - 1000

32
[ 49619-82-1 ]
[ 98-80-6 ]
[ 574-12-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrabutylammomium bromide; sodium carbonate; In water; at 100℃; for 1h;Green chemistry;	General procedure: A mixture of the corresponding bromochromone1(0.50 mmol), the corresponding boronic acid2(0.60 mmol), Na2CO3(0.50 mmol) andPdSILP(0.05% mmol of Pd) in H2O was stirred under ohmic heating at 100 C for 1 h. The catalyst was filtered-off and the filtrate was extracted with Et2O (3 × 10 mL). The combined extracts were dried over Na2SO4and evaporated under reduced pressure affording products3. The physical data of known isoflavones3a-fwere comparable to those of the literature [34,35,36,37,38]. The physical data of the new isoflavones3g-jare shown below.

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010
[2]Organic Letters,2009,vol. 11,p. 4010 - 4013
[3]Tetrahedron,2007,vol. 63,p. 9642 - 9651
[4]Molecules,2020,vol. 25
[5]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 3008 - 3010
[6]Tetrahedron,2006,vol. 62,p. 3395 - 3401
[7]Chemical Communications,2015,vol. 51,p. 925 - 928

33
[ 49619-82-1 ]
[ 87744-31-8 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3435 - 3438

34
[ 35572-23-7 ]
[ 49619-82-1 ]

Reference： [1]Synthesis,1981,p. 719 - 721

35
[ 118-93-4 ]
[ 4637-24-5 ]
[ 49619-82-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2597 - 2604

36
[ 58264-73-6 ]
[ 49619-82-1 ]

Reference： [1]Synthesis,1981,p. 33 - 34

37
[ 675-10-5 ]
[ 49619-82-1 ]
2-(2'-hydroxybenzoyl)-4H-furo<3,2-c>-6-methylpyran-4-one [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 639 - 640

38
[ 49619-82-1 ]
[ 81016-39-9 ]
5-(2'-hydroxybenoyl)-2-thiomethyl-3-nitro-1-phenyl-pyrrole [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 639 - 640

39
[ 49619-82-1 ]
[ 168127-08-0 ]
5-(2'-hydroxybenoyl)-1-methyl-2-thiomethyl-3-nitro-pyrrole [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 639 - 640

40
[ 288-32-4 ]
[ 49619-82-1 ]
[ 99875-03-3 ]

Reference： [1]Heterocycles,1996,vol. 43,p. 2503 - 2511

41
[ 49619-82-1 ]
[ 1165952-91-9 ]
C₁₅H₁₃BrO₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7904 - 7905

44
[ 110-89-4 ]
[ 49619-82-1 ]
[ 1084-62-4 ]
[ 40302-79-2 ]
3-iodo-2-piperidino-4H-1-benzopyran-4-one [ No CAS ]

Reference： [1]Heterocycles,2001,vol. 55,p. 881 - 888

45
[ 110-89-4 ]
[ 49619-82-1 ]
2-piperidinomethylene-3(2H)-benzofuranone [ No CAS ]

Reference： [1]Heterocycles,2001,vol. 55,p. 881 - 888

46
[ 49619-82-1 ]
[ 17933-03-8 ]
3-(m-tolyl)-4H-chromen-4-one [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 3395 - 3401

47
[ 49619-82-1 ]
[ 32316-92-0 ]
3-(naphthalen-2-yl)-4H-chromen-4-one [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 3395 - 3401
[2]Organic Letters,2009,vol. 11,p. 4010 - 4013

48
[ 49619-82-1 ]
[ 1826-67-1 ]
3-bromo-2-vinylchroman-4-one [ No CAS ]
3-bromo-2-vinylchroman-4-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1531 - 1536

49
[ 49619-82-1 ]
[ 94839-07-3 ]
[ 36136-89-7 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 9642 - 9651

50
[ 292638-84-7 ]
[ 49619-82-1 ]
2-(α-styryl)-4-chromone [ No CAS ]
[ 115237-37-1 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 9642 - 9651

51
[ 109-01-3 ]
[ 49619-82-1 ]
C₉H₅O₂N(CH₂)4NCH₃ [ No CAS ]