23602-63-3|5-Chloro-2-hydroxy-3-methylbenzaldehyde| Ambeed

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Quality Control of [ 23602-63-3 ] Purity: 97% SDS Specification

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Product Details of [ 23602-63-3 ]

CAS No. :	23602-63-3
Formula :	C₈H₇ClO₂
M.W :	170.59
SMILES Code :	O=CC1=CC(Cl)=CC(C)=C1O
MDL No. :	MFCD00275687
InChI Key :	NSKZAOKQZDLHGO-UHFFFAOYSA-N
Pubchem ID :	2774358

Safety of [ 23602-63-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 23602-63-3 ]

* 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 [ 23602-63-3 ]

[ 23602-63-3 ] Synthesis Path-Downstream 1~35

1
[ 23602-63-3 ]
[ 7651-98-1 ]
[ 52771-74-1 ]

References: [1]Patent: CH572308,1976,A5 .
Chem.Abstr.,1974,vol. 81.
Chem.Abstr.,1974,vol. 81.

2
[ 23602-63-3 ]
[ 18531-95-8 ]
(S)-2,2'-bis(5-chloro-2-hydroxy-3-methylbenzylideneamino)-1,1'-binaphthyl [ No CAS ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 405 - 414.

3
[ 67-66-3 ]
[ 1570-64-5 ]
[ 23602-63-3 ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.

4
[ 23602-63-3 ]
[ 2032-35-1 ]
[ 179728-65-5 ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.

5
[ 50-00-0 ]
[ 1570-64-5 ]
[ 23602-63-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3783 - 3800.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7164 - 7168.

6
[ 23602-63-3 ]
[ 86302-43-4 ]
[ 726191-05-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20℃; for 48.0h;	To the solution of <strong>[23602-63-3]5-chloro-2-hydroxy-3-methylbenzaldehyde</strong> (22.6 g, 0.13 mol) in THF (200 ml) was added tert-butyl (triphenylphosphoranyl) acetate (50g, 0.13 mol) followed by adding DBU (0.3 ML). The reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated under vacuum. To the concentrated residue was added 10% ethyl acetate in hexane (100 ML). Solid was formed in the solution and filtered out. The filtrated was concentrated and chromatographed on silica gel (10% ethyl acetate in hexane) to give 33.4 g (88%) white SOLID. 1H NMR (300 MHz, CDCl3) No. 1. 56 (s, 9H), 2.32 (s, 3H), 6.20 (s, 1H), 6.44 (d, 1H, J = 16. 11 Hz), 7.13 (m, 1H), 7.35 (m, 1H), 8.01 (d, 1H, J = 16.11).

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3783 - 3800.
[2]Patent: WO2004/60376,2004,A1 .Location in patent: Page/Page column 181-182.

7
[ 23602-63-3 ]
[ 726191-06-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3783 - 3800.

8
[ 23602-63-3 ]
ClCH₃C₆H₂OHCH(NHH)CH₂COOC₄H₉ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3783 - 3800.

9
[ 23602-63-3 ]
[ 179728-81-5 ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.

10
[ 23602-63-3 ]
[ 179728-92-8 ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.

11
[ 23602-63-3 ]
[ 179729-30-7 ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.
[2]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.

12
[ 23602-63-3 ]
4-Amino-3-(5-chloro-7-methyl-benzofuran-2-yl)-butyric acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.
[2]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.

13
[ 23602-63-3 ]
4-Amino-3-(5-chloro-7-methyl-benzofuran-2-yl)-butyric acid ethyl ester [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.

14
[ 23602-63-3 ]
[ 179729-15-8 ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 449 - 460.

15
[ 1570-64-5 ]
[ 925-90-6 ]
[ 23602-63-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With N,N,N,N,N,N-hexamethylphosphoric triamide; formaldehyd; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; toluene; at 4 - 20℃; for 52.0h;Heating / reflux;	To the solution of ETHYLMAGNESIUM bromide (400 mL, 1.0 M in THF) was added 4- CHLORO-2-METHYLPHENOL (57 g, 0.4 mol) in 75 mL toluene slowly at 4 C. To the above solution was added tetramethylethylenediamine (45g, 0.39 mol) followed by adding PARAFORMALDEHYDE (30 g) then HMPA (72.1g, 0.4 mol) at room temperature. The reaction mixture was REFLUXED 4 hours then stirred at room temperature for 48 hours. The reaction mixture was quenched with 50% HCI (450 ml). The aqueous solution was extracted with ethyl acetate (4X250ML). Combined organic solution was washed with brine, dried over MGS04 and concentrated under vacuum. Concentrated residue was chromatographed on silica gel (5% ethyl acetate in hexane) to give 40.8 g (60%) OIL. 1H NMR (400 MHz, CECI3) 8 2. 25 (s, 3H), 7.36 (m, 2H), 9.8 (s, 1 H), 11.16 (s, 1 H).

References: [1]Patent: WO2004/60376,2004,A1 .Location in patent: Page/Page column 181.

16
[ 23602-63-3 ]
[ 1539-42-0 ]
[ 1105704-31-1 ]

References: [1]New Journal of Chemistry,2008,vol. 32,p. 2279 - 2291.

17
[ 1159568-13-4 ]
[ 23602-63-3 ]
[ 1159567-88-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 47 6-[4-(5-Chloro-2-hydroxy-3-methyl-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one 6-[4-(5-Chloro-2-hydroxy-3-methyl-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one was prepared using Procedure B from 6-piperazin-1-yl-3H-pyrimidin-4-one (Intermediate 4) and <strong>[23602-63-3]5-chloro-2-hydroxy-3-methylbenzaldehyde</strong> (available from Alfa Aesar, Ward Hill, Mass., USA). 1H NMR (400 MHz, CDCl3) δ 2.19 (s, 3H), 2.58-2.63 (m, 4H), 3.48-3.67 (m, 6H), 5.40 (s, 1H), 6.80-6.81 (m, 1H), 7.03-7.04 (m, 1H), 7.85 (s, 1H), 10.60 (br s, 1H), 12.45 (br s, 1H). Mass spectrum (ES) MH+=335.

References: [1]Patent: US2009/149466,2009,A1 .

18
[ 23602-63-3 ]
[ 1210749-61-3 ]

References: [1]Synlett,2009,p. 3378 - 3382.

19
[ 23602-63-3 ]
[ 74-88-4 ]
[ 82129-11-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetra(n-butyl)ammonium hydroxide; sodium hydroxide; In water; at 20℃; for 3.0h;	Stepi : <strong>[23602-63-3]5-chloro-2-hydroxy-3-methylbenzaldehyde</strong> [23602-63-3] was suspended in 5ml of dichloromethane and 5 ml of water. 1.47 ml (4.4 mmol, 3 eq.) of sodium hydroxide 1 N and 1.52 g (2.94 mmol, 2 eq.) of tetrabutyl ammonium hydroxide 50%, then iodomethane (457 μl, 5 eq.) were added to the solution. The mixture was stirred 3h at room temperature. The reaction mixture was extracted 3 times with dichloromethane, the combined organic layers were washed with brine, dried with anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane) to give 100 mg (yield 93%) of 5-chloro-2-methoxy-3-methylbenzaldehyde

References: [1]Patent: WO2010/66847,2010,A1 .Location in patent: Page/Page column 71-72.

20
[ 25597-16-4 ]
[ 23602-63-3 ]
C₁₄H₁₂ClF₃O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7164 - 7168.
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1162 - 1166.

21
[ 16400-32-1 ]
[ 23602-63-3 ]
[ 1344713-68-3 ]

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 9076 - 9080.

22
[ 23602-63-3 ]
(Z)-5-chloro-1-methyl-2-(pent-2-yn-1-yloxy)-3-styrylbenzene [ No CAS ]
(E)-5-chloro-1-methyl-2-(pent-2-yn-1-yloxy)-3-styrylbenzene [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 9076 - 9080.

23
[ 23602-63-3 ]
(Z)-5-chloro-1-methyl-2-(pent-2-yn-1-yloxy)-3-(α-deuterostyryl)benzene [ No CAS ]
(E)-5-chloro-1-methyl-2-(pent-2-yn-1-yloxy)-3-(α-deuterostyryl)benzene [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 9076 - 9080.

24
[ 42726-73-8 ]
[ 23602-63-3 ]
tert-butyl 6-chloro-8-methyl-2-oxo-2H-chromene-3-carboxylate [ No CAS ]