[ CAS No. 13692-15-4 ] {[proInfo.proName]}

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Quality Control of [ 13692-15-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13692-15-4 ]

SDS Specification

Alternatived Products of [ 13692-15-4 ]

Product Details of [ 13692-15-4 ]

CAS No. :	13692-15-4	MDL No. :	MFCD00022330
Formula :	C₈H₆Cl₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	189.04	Pubchem ID :	-
Synonyms :

Safety of [ 13692-15-4 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P240-P241-P242-P243-P260-P264-P271-P272-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501	UN#:	1993
Hazard Statements:	H225-H315-H319-H335-H373-H317	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 13692-15-4 ]

* 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 [ 13692-15-4 ]
Downstream synthetic route of [ 13692-15-4 ]

[ 13692-15-4 ] Synthesis Path-Upstream 1~3

1
[ 288-32-4 ]
[ 13692-15-4 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere Stage #2: at 60℃; Inert atmosphere	To a mixture of sodium hydride (0.080 g, 2 mmol) in 5 mL of DMF was added imidazole (0.136 g, 2 mmol) dissolved in 2 mL of DMF. The solution was stirred for 30 min under nitrogen atmosphere at room temperature before the addition of 2- (2,4-dichlorophenyl) oxirane 2 (0.378 g, 2 mmol) dissolved in 2 mL of DMF. After, the reaction mixture was stirred at 60 °C for 22 h, TLC indicated the disappearance of the starting material. Then the solution was brought to room temperature with continuous stirring for 20 min, before DMF was removed with extractions using distilled water and AcOEt. The resulting solution was dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure. The crude extract was then purified by flash chromatography on silica eluting with ethyl acetate/hexane 2/8 to afford the white solid 3 (0.293 g, 57percent). Rf: 0.32 (EtOAc/Hex 2/8). m.p. 124e126 C. 1H NMR: (300 MHz,DMSO-D6) d 7.59 (d, J 1.9 Hz, 1H, NeCHeN), 7.52e7.40 (m, 3H),7.05 (s, 1H, CH), 6.84 (s, 1H, CHeN), 6.07 (d, J 4.4 Hz, 1H, OH), 5.08(m, 1H), 4.18 (dd, J 14.2, 3.4 Hz, 1H, NeCH2), 4.04 (dd, J 14.1,7.1 Hz, 1H, NeCH2). 13C NMR: (75.4 MHz, DMSO-D6) d 138.61 (C),137.68 (C),132.69 (CeCl),131.75 (CeCl),129.33 (C),128.36 (C),127.91(C),127.40 (C), 119.96 (C), 68.65 (CHeOH), 51.58 (CH2) ppm.MS [EI]m/z (percent): 257 (M), 239 (2), 221 (56), 175 (58), 147 (13), 113 (8), 108(54), 82 (100), 69 (81), 54 (39), 52 (8).

Reference： [1] Organic Preparations and Procedures International, 1992, vol. 24, # 3, p. 342 - 345
[2] European Journal of Medicinal Chemistry, 2015, vol. 97, p. 275 - 279

2
[ 13692-15-4 ]
[ 22916-47-8 ]

Reference： [1] Organic Preparations and Procedures International, 1992, vol. 24, # 3, p. 342 - 345

3
[ 13692-15-4 ]
[ 1475-13-4 ]

Reference： [1] Synthetic Communications, 2010, vol. 40, # 14, p. 2108 - 2112

[ 13692-15-4 ] Synthesis Path-Downstream 1~5

1
[ 288-32-4 ]
[ 13692-15-4 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
57%		To a mixture of sodium hydride (0.080 g, 2 mmol) in 5 mL of DMF was added imidazole (0.136 g, 2 mmol) dissolved in 2 mL of DMF. The solution was stirred for 30 min under nitrogen atmosphere at room temperature before the addition of 2- (2,4-dichlorophenyl) oxirane 2 (0.378 g, 2 mmol) dissolved in 2 mL of DMF. After, the reaction mixture was stirred at 60 C for 22 h, TLC indicated the disappearance of the starting material. Then the solution was brought to room temperature with continuous stirring for 20 min, before DMF was removed with extractions using distilled water and AcOEt. The resulting solution was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude extract was then purified by flash chromatography on silica eluting with ethyl acetate/hexane 2/8 to afford the white solid 3 (0.293 g, 57%). Rf: 0.32 (EtOAc/Hex 2/8). m.p. 124e126 C. 1H NMR: (300 MHz,DMSO-D6) d 7.59 (d, J 1.9 Hz, 1H, NeCHeN), 7.52e7.40 (m, 3H),7.05 (s, 1H, CH), 6.84 (s, 1H, CHeN), 6.07 (d, J 4.4 Hz, 1H, OH), 5.08(m, 1H), 4.18 (dd, J 14.2, 3.4 Hz, 1H, NeCH2), 4.04 (dd, J 14.1,7.1 Hz, 1H, NeCH2). 13C NMR: (75.4 MHz, DMSO-D6) d 138.61 (C),137.68 (C),132.69 (CeCl),131.75 (CeCl),129.33 (C),128.36 (C),127.91(C),127.40 (C), 119.96 (C), 68.65 (CHeOH), 51.58 (CH2) ppm.MS [EI]m/z (%): 257 (M), 239 (2), 221 (56), 175 (58), 147 (13), 113 (8), 108(54), 82 (100), 69 (81), 54 (39), 52 (8).

Reference： [1]Organic Preparations and Procedures International,1992,vol. 24,p. 342 - 345
[2]European Journal of Medicinal Chemistry,2015,vol. 97,p. 275 - 279

2
[ 2181-42-2 ]
[ 874-42-0 ]
[ 13692-15-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium hydroxide; In water; acetonitrile; at 60℃; for 3h;Inert atmosphere;	To a stirred solution of trimethylsulfonium iodide (1.224 g, 6 mmol) in acetonitrile (3 mL) at room temperature was added potassium hydroxide (0.464 g, 9 mmol). Then 2,4-dichlorobenzaldehyde 1 (1.05 g, 6 mmol) dissolved in 3 mL of acetonitrile was slowly added, followed by 0.05 mL of distilled water. The solution was stirred for 3 h at 60 C under nitrogen atmosphere, after which time TLC (treated with 0.05 mL of triethylamine) indicated the disappearance of the starting material. Then the solution was brought to room temperature with continuous stirring for 15 min, and the solvent was evaporated under reduced pressure to give the yellow oil 2 (1.054 g, 93%). Rf: 0.62 (EtOAc/Hex 2/8). 1H NMR: (300 MHz, CDCl3) d 7.38 (d, J 1.8 Hz, 1H),7.26e7.16 (m, 2H), 4.17e4.14 (m, 1H, OeCH), 3.19 (dd, J 4.2, 5.6 Hz,1H, OeCH2), 2.65 (dd, J 1.5, 3.3 Hz, 1H, OeCH2) ppm. 13C NMR:(75.4 MHz, CDCl3) d 134.1 (CeCl), 133.9 (C), 133.6 (CeCl), 128.8(C), 127.3 (C), 126.5 (C), 50.6 (OeCH), 49.5 (OeCH2) ppm.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 97,p. 275 - 279
[2]Organic Preparations and Procedures International,1992,vol. 24,p. 342 - 345
[3]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2691 - 2696

3
[ 13692-15-4 ]
[ 22916-47-8 ]

Reference： [1]Organic Preparations and Procedures International,1992,vol. 24,p. 342 - 345

4
[ 13692-15-4 ]
[ 1475-13-4 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 2108 - 2112

5
[ 13692-15-4 ]
[ 6574-98-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With ammonia; iodine In water; acetonitrile at 70℃;
85%	With ammonia; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetonitrile at 70℃;	General procedure for oxidative fragmentation of oxiranes. General procedure: To a stirred solution of IBX (10.0 mmol) in aqueous ammonia (25 mL of a 28-30% solution) was added oxirane (5.0 mmol) in 5 mL of acetonitrile in one portion. The reaction mixture was stirred at 70 °C until complete consumption of starting material as observed on TLC (up to 4 h). After completion of reaction, the reaction mixture was extracted with chloroform (2 × 15 mL). The organic layer was washed with water (2 × 10 mL); bisulfate solution (15 mL) followed by water (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude product. Pure product was obtained after column chromatography (silica gel, mesh size 60-120, eluent ethyl acetate/hexane 05:95).

Reference： [1]Jadhav, Ravindra R.; Akamanchi, Krishnacharya G. [Chemistry Letters, 2013, vol. 42, # 2, p. 162 - 164]
[2]Location in patent: experimental part Deshmukh, Swapnil S.; Huddar, Sameerana N.; Jadhav, Ravindra R.; Akamanchi, Krishnacharya G. [Tetrahedron Letters, 2011, vol. 52, # 35, p. 4533 - 4536]

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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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.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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[ CAS No. 13692-15-4 ] {[proInfo.proName]}

Quality Control of [ 13692-15-4 ]

Related Doc. of [ 13692-15-4 ]

Product Details of [ 13692-15-4 ]

Safety of [ 13692-15-4 ]

Application In Synthesis of [ 13692-15-4 ]

[ 13692-15-4 ] Synthesis Path-Upstream 1~3

[ 13692-15-4 ] Synthesis Path-Downstream 1~5

Precautionary Statements-General

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