[ CAS No. 4996-21-8 ] {[proInfo.proName]}

Name: 4996-21-8|4-Chlorophenylglyoxal hydrate|97%
Brand: Ambeed
SKU: A145220
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Quality Control of [ 4996-21-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4996-21-8 ]

SDS Specification

Alternatived Products of [ 4996-21-8 ]

Product Details of [ 4996-21-8 ]

CAS No. :	4996-21-8	MDL No. :	MFCD08272327
Formula :	C₈H₇ClO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JTOCXCVDVKZPEB-UHFFFAOYSA-N
M.W :	186.59	Pubchem ID :	15556731
Synonyms :

Calculated chemistry of [ 4996-21-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.89
TPSA :	43.37 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) :	-6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.25
Log Po/w (XLOGP3) :	1.99
Log Po/w (WLOGP) :	1.66
Log Po/w (MLOGP) :	0.47
Log Po/w (SILICOS-IT) :	2.48
Consensus Log Po/w :	1.57

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.49
Solubility :	0.606 mg/ml ; 0.00325 mol/l
Class :	Soluble
Log S (Ali) :	-2.53
Solubility :	0.554 mg/ml ; 0.00297 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.9
Solubility :	0.233 mg/ml ; 0.00125 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.19

Safety of [ 4996-21-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4996-21-8 ]

* 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.

Upstream synthesis route of [ 4996-21-8 ]
Downstream synthetic route of [ 4996-21-8 ]

[ 4996-21-8 ] Synthesis Path-Upstream 1~3

1
[ 536-38-9 ]
[ 4996-21-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With water; hydrogen bromide In dimethyl sulfoxide at 80℃; for 5 h;	A solution of 4'-chloro-2-bromoacetophenone (25. 0 g, 107 MMOL), water (1. 92 mL, 107 mmol) and 47percent HYDROBROMIC ACID (0. 20 ML) IN DIMETHYLSULFOXIDE (160 mL) was stirred at 80°C for 5 h. After the reaction mixture was poured into water, the precipitate was filtered, washed with diethylether and dried, affording 4 -CHLORO-2, 2-DIHYDROXYACETOPHENONE (14. 0 G, percent). 1H NMR (300MHZ, CDCL3), No. 5. 92 (1H, S), 7. 45-7. 52 (2H, M), 8. 05-8. 20 (2H, M).

Reference： [1] Patent: WO2004/85408, 2004, A1, . Location in patent: Page 276

2
[ 99-91-2 ]
[ 4996-21-8 ]

Reference： [1] ACS Combinatorial Science, 2013, vol. 15, # 5, p. 261 - 266
[2] Tetrahedron Asymmetry, 2010, vol. 21, # 18, p. 2244 - 2248
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 3124 - 3153
[4] Chemistry of Heterocyclic Compounds, 2018, vol. 54, # 1, p. 51 - 57[5] Khim. Geterotsikl. Soedin., 2018, vol. 54, # 1, p. 51 - 57,7
[6] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4036 - 4038
[7] Synlett, 2013, vol. 24, # 8, p. 977 - 980
[8] Journal of Sulfur Chemistry, 2013, vol. 34, # 5, p. 464 - 473
[9] Journal of the American Chemical Society, 2013, vol. 135, # 45, p. 16849 - 16852
[10] Journal of the Chinese Chemical Society, 2013, vol. 60, # 11, p. 1323 - 1327
[11] Journal of the Iranian Chemical Society, 2014, vol. 11, # 4, p. 963 - 968
[12] Turkish Journal of Chemistry, 2015, vol. 39, # 2, p. 244 - 254
[13] RSC Advances, 2015, vol. 5, # 65, p. 52852 - 52865
[14] RSC Advances, 2015, vol. 5, # 64, p. 51501 - 51507
[15] Journal of Sulfur Chemistry, 2014, vol. 35, # 6, p. 700 - 710
[16] Australian Journal of Chemistry, 2015, vol. 68, # 10, p. 1529 - 1534
[17] Tetrahedron Letters, 2016, vol. 57, # 1, p. 103 - 104
[18] Chemical Communications, 2017, vol. 53, # 22, p. 3232 - 3235
[19] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 8, p. 1660 - 1664
[20] Chemical Communications, 2017, vol. 53, # 69, p. 9640 - 9643
[21] Journal of Molecular Structure, 2018, vol. 1152, p. 44 - 52
[22] Tetrahedron, 2017, vol. 73, # 47, p. 6587 - 6596
[23] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3163 - 3168
[24] Research on Chemical Intermediates, 2017, vol. 43, # 7, p. 3925 - 3937
[25] Australian Journal of Chemistry, 2017, vol. 70, # 6, p. 660 - 668
[26] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 1, p. 149 - 153
[27] Heterocyclic Communications, 2018, vol. 24, # 1, p. 37 - 41
[28] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 4, p. 951 - 956
[29] Tetrahedron Letters, 2018, vol. 59, # 31, p. 2970 - 2974
[30] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6998 - 7003

3
[ 4998-15-6 ]
[ 4996-21-8 ]

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4036 - 4038
[2] Turkish Journal of Chemistry, 2015, vol. 39, # 2, p. 244 - 254
[3] Research on Chemical Intermediates, 2017, vol. 43, # 7, p. 3925 - 3937
[4] Australian Journal of Chemistry, 2015, vol. 68, # 10, p. 1529 - 1534

[ 4996-21-8 ] Synthesis Path-Downstream 1~81

1
[ 536-38-9 ]
[ 4996-21-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With water; hydrogen bromide; In dimethyl sulfoxide; at 80℃; for 5h;	A solution of 4'-chloro-2-bromoacetophenone (25. 0 g, 107 MMOL), water (1. 92 mL, 107 mmol) and 47% HYDROBROMIC ACID (0. 20 ML) IN DIMETHYLSULFOXIDE (160 mL) was stirred at 80C for 5 h. After the reaction mixture was poured into water, the precipitate was filtered, washed with diethylether and dried, affording 4 -CHLORO-2, 2-DIHYDROXYACETOPHENONE (14. 0 G, %). 1H NMR (300MHZ, CDCL3), No. 5. 92 (1H, S), 7. 45-7. 52 (2H, M), 8. 05-8. 20 (2H, M).

Reference： [1]Patent: WO2004/85408,2004,A1 .Location in patent: Page 276

2
[ 99-91-2 ]
[ 4996-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	With selenium(IV) oxide; water; In 1,4-dioxane;Reflux;	General procedure: Melting points were determined with an electrothermal 9100 apparatus. Fourier transform infrared (FT-IR) spectra were recorded on a Unicam/Mattson 8700 spectrometer. 1H and 13C NMR spectrawere recorded on a Bruker 400 spectrometer in CDCl3. The chemicals used in this work were purchased from Fluka and Merck and were used without further purification. Arylglyoxal hydrates were prepared by the oxidation of acetophenones using SeO2 in refluxing dioxane in the presence of water as done in the Riley et al. (47) method.
	With selenium(IV) oxide; In 1,4-dioxane; water; for 6h;Reflux;	General procedure: The arylglyoxals were prepared according to reported procedure with some improvements [42]. To a solution of SeO2 (25 mmol) in dioxane (30 mL) containing H2O (1 mL) was added an aryl methyl ketone (25 mmol). The solution was heated under reflux conditions for 6 h. Then the hot solution was decanted to remove the precipitated selenium. Distillation of dioxane was resulted a yellow liquid. Subsequently recrystallization of the liquid in hot H2O obtained the corresponding arylglyoxals 1a-1c.
	With selenium(IV) oxide; water;	All the utilized aryl glyoxals were prepared by the SeO2-oxidation of the related aryl methyl ketones on the basis of the reported procedure and used as their monohydrates.

With selenium(IV) oxide; water; In 1,4-dioxane; at 80℃; for 7h;Inert atmosphere;

General procedure: To a solution of selenium dioxide (220 mg, 2 mmol) in 1,4-dioxane (1 mL) and H2O(2 drops) was added acetophenone 1a (120 mg, 1 mmol). The reaction mixture wasstirred and refluxed for 7 h (monitored by TLC, Vethyl acetate/VPE = 1/4). After cooling to r.t.,5 mL of dichloromethane was added to the reaction mixture, then filtered on celite,washed the celite with dichloromethane (3×5 mL). The combined solution wasconcentrated under reduced pressure, the residue was purified by columnchromatography on silica gel eluting with ethyl acetate/PE (V /V = 1/10) to give 121 mgof 2a, yield 80%. Compounds 2b~2m were synthesized followed the same procedure,yield 61~82%.

Reference： [1]ACS Combinatorial Science,2013,vol. 15,p. 261 - 266
[2]Tetrahedron Asymmetry,2010,vol. 21,p. 2244 - 2248
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 3124 - 3153
[4]Chemistry of Heterocyclic Compounds,2018,vol. 54,p. 51 - 57
Khim. Geterotsikl. Soedin.,2018,vol. 54,p. 51 - 57,7
[5]Tetrahedron Letters,2011,vol. 52,p. 4036 - 4038
[6]Synlett,2013,vol. 24,p. 977 - 980
[7]Journal of Sulfur Chemistry,2013,vol. 34,p. 464 - 473
[8]Journal of the American Chemical Society,2013,vol. 135,p. 16849 - 16852
[9]Journal of the Chinese Chemical Society,2013,vol. 60,p. 1323 - 1327
[10]Turkish Journal of Chemistry,2015,vol. 39,p. 244 - 254
[11]RSC Advances,2015,vol. 5,p. 52852 - 52865
[12]RSC Advances,2015,vol. 5,p. 51501 - 51507
[13]Journal of Sulfur Chemistry,2014,vol. 35,p. 700 - 710
[14]Australian Journal of Chemistry,2015,vol. 68,p. 1529 - 1534
[15]Tetrahedron Letters,2016,vol. 57,p. 103 - 104
[16]Chemical Communications,2017,vol. 53,p. 3232 - 3235
[17]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1660 - 1664
[18]Chemical Communications,2017,vol. 53,p. 9640 - 9643
[19]Journal of Molecular Structure,2018,vol. 1152,p. 44 - 52
[20]Tetrahedron,2017,vol. 73,p. 6587 - 6596
[21]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 3163 - 3168
[22]Research on Chemical Intermediates,2017,vol. 43,p. 3925 - 3937
[23]Australian Journal of Chemistry,2017,vol. 70,p. 660 - 668
[24]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 149 - 153
[25]Heterocyclic Communications,2018,vol. 24,p. 37 - 41
[26]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 951 - 956
[27]Tetrahedron Letters,2018,vol. 59,p. 2970 - 2974
[28]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6998 - 7003
[29]Heterocyclic Communications,2018,vol. 24,p. 297 - 302
[30]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 2772 - 2778
[31]Journal of Organic Chemistry,2020,vol. 85,p. 8405 - 8414

3
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