[ CAS No. 24006-92-6 ] {[proInfo.proName]}

Name: 24006-92-6|(4,5-Dichloro-1,2-phenylene)dimethanol|95%
Brand: Ambeed
SKU: A279767
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Quality Control of [ 24006-92-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 24006-92-6 ]

Product Details of [ 24006-92-6 ]

CAS No. :	24006-92-6	MDL No. :	MFCD06656516
Formula :	C₈H₈Cl₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WSCRUXVCUXHCOW-UHFFFAOYSA-N
M.W :	207.05	Pubchem ID :	13096434
Synonyms :

Calculated chemistry of [ 24006-92-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.72
TPSA :	40.46 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) :	-6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	1.41
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	2.8
Consensus Log Po/w :	1.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.25
Solubility :	1.16 mg/ml ; 0.00562 mol/l
Class :	Soluble
Log S (Ali) :	-1.86
Solubility :	2.83 mg/ml ; 0.0137 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.29
Solubility :	0.105 mg/ml ; 0.000507 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 24006-92-6 ]

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

Application In Synthesis of [ 24006-92-6 ]

* 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 [ 24006-92-6 ]

[ 24006-92-6 ] Synthesis Path-Downstream 1~80

1
[ 942-06-3 ]
[ 24006-92-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃;	[000286] To a solution of 5,6-dichloroisobenzofuran-l,3-dione (12.00 g, 55.30 mmol) in THF (300 mL) was added L1AIH4 (3.15 g, 82.95 mmol) carefully at 0 C. The mixture was stirred at rt overnight. It was then quenched with water (13 mL), 15% aqueous NaOH (3.2 mL). After filtration, the filtrate was evaporated to dryness to yield Compound 7A (11.20 g, yield 98%) as a white solid. LCMS: 207 [M+l]+, 1H-NMR (DMSO-d6, 400 MHz) major characteristic peaks: delta (ppm) 4.47 (d, J= 5.6 Hz, 4H), 5.34 (t, J= 5.6 Hz, 2H), 7.57 (s, 2H).
57%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h;Cooling with ice; Reflux;	4,5-Dichlorophthalic anhydride (4.6 g, 21.2 mmol) was added in small portions to LiAIH4 (1M in THF, 31.2 mL, 31.2 mmol) in THF (20 mL) with cooling in an ice bath. When the addition had been complete the mixture was heated at reflux temperature for 5 hours and then cooled and quenched with water (1.7 mL), 15 wt% NaOH (aq) (1.7 mL) and water (4 mL). Filtration and drying over MgSO4, followed by evaporation gave a white solid. Yield = 2.50 g (57%). 1H NMR (400 MHz, d6-DMSO): delta 7.57 (2H, s, ArH), 5.33 (2Eta, t, 3JHH = 5.5 Hz, OH) and 4.49 (4Eta, d, 3JHH = 5.4 Hz, CH2).
52%	With alumane lithium; In tetrahydrofuran; at 0 - 60℃; for 2h;	Into a 100-mL round-bottom flask, was placed a solution of <strong>[942-06-3]5,6-dichloroisobenzofuran-1,3-dione</strong> (1 g, 4.61 mmol, 1.00 equiv) in tetrahydrofuran (40 mL). This was followed by the addition of alumane lithium (440 mg, 12.97 mmol, 2.50 equiv) batchwise at 0 C. The resulting solution was stirred for 2 h at 60 C. The resulting solution was quenched by 40 mL of water at 0 C. The solids were filtered out. The filtrate was extracted with 3×50 mL of ethyl acetate, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). The collected fraction was concentrated under vacuum to give (4,5-dichloro-1,2-phenylene)dimethanol (500 mg, 52%) of the title compound as a white solid. 1H-NMR (DMSO 300 MHz, ppm): delta 7.57 (s, 2H), 4.48 (s, 4H).

Reference： [1]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000286
[2]Journal of Organic Chemistry,2019,vol. 84,p. 9826 - 9834
[3]Patent: WO2017/135897,2017,A1 .Location in patent: Page/Page column 41
[4]Patent: US2016/264518,2016,A1 .Location in patent: Paragraph 0930; 0931
[5]Synthetic Communications,1983,vol. 13,p. 639 - 648
[6]Journal of the Chemical Society. Chemical communications,1994,p. 825 - 826
[7]Angewandte Chemie - International Edition,2014,vol. 53,p. 11325 - 11328
Angew. Chem.,

2
[ 56962-08-4 ]
[ 24006-92-6 ]

Yield	Reaction Conditions	Operation in experiment
88%		4,5-Dichlorobenzene-1,2-dimethanol To a slurry of LiAlH4 (1.61 g, 42.54 mmol) in dry THF (75 mL) cooled to -78 C., a solution of dimethyl 4,5-dichlorobenzene-1,2-dicarboxylic acid (5.0 g, 21.27 mmol) in dry THF (25 mL) was added dropwise over a period of 1 h. After slow warming of the system to RT over a period of 2 h the mixture was heated at reflux overnight. The heterogeneous mixture was then cooled to 0 C. and sodium hydroxide solution (15%, 100 mL) cooled to 0 C. was very slowly added. This was followed by addition of ice-cold water (100 mL), and the reaction mixture was diluted with diethyl ether (200 mL) and the organic layer was separated, dried over MgSO4. Removal of solvents gave a white solid which was passed through a pad of silica gel to afford pure product in 88% yield (3.85 g). 1H NMR (500 MHz, CDCl3): delta 7.60 (s, 2H), 4.65 (s, 4H), 4.50 (bs, 2H).
84%	With lithium aluminium tetrahydride; In tetrahydrofuran; at -78℃;Reflux; Inert atmosphere;	In a 1-L three-necked flask were placed LiAlH4 (12.3 g, 0.33 mol) and dry THF (700 mL). A solution of 4,5-dichlorobenzene-1,2-dicarboxylic acid (38.87 g, 0.165 mol) in dry THF (120 mL) was slowly added dropwise at -78 C under Ar. The reaction mixture was warmed up to room temperature, and refluxed overnight. An aqueous solution of NaOH (10%, 100 mL) was added, followed by the addition of water (150 mL) and THF (300 mL). The organic layer was separated. The aqueous layer was extracted with THF three times and the THF layer was combined with the organic layer. The combined organic layer was washed with saturated aqueous NaCl three times and the solvent was evaporated. The white solid was washed with hexane and dichloromethane: 28.8 g, 84% yield. Mp: 92-95 C. 1H NMR data matched published data.22 1H NMR (acetone-d6, 500 MHz): delta (ppm) 7.64 (s, 2H), 4.67 (d, 4H, J=5.8 Hz), 4.46 (br, 2H).
4.41 g (100%)	In tetrahydrofuran; methanol; diethyl ether;	Step A 4,5-dichloro-1,2-di-hydroxymethyl benzene To a stirred solution of borane tetrahydrofuran complex (45 mL of 1.5 M solution in tetrahydrofuran/diethyl ether) cooled to 0 C. under nitrogen was added a solution of 4,5-dichlorophthalic acid (5.013 g; 21.1 mmol) in tetrahydrofuran (35 mL) dropwise over a 20 minute period. At the end of the addition, the mixture was allowed to stir for 2.5 h at 0 C. The mixture was quenched by slow addition of methanol until gas evolution ceased. The mixture was allowed to stir at room temperature for 30 minutes and the solvent removed in vacuo. The residue was taken up into ethyl acetate, washed with saturated sodium bicarbonate solution followed by brine solution. The organic extract was dried (sodium sulfate), filtered and concentrated in vacuo to give 4.41 g (100%) of 4,5-dichloro-1,2-di-hydroxymethyl benzene as a white solid: ES-LRMS calcd for C8H7 Cl2O2 (M+-1) 205, found 205.

Example 70; [4,5-Dichloro-2-(2,4-diaminoquinazolin-5-yloxymethyl)phenyl] methanol hydrochloride; [00224] Step 1; To a suspension of sodium borohydride (454 mg; 12 mmol) in anhydrous THF (20 mL) is added dropwise a solution of 4,5-dichlorophthalic acid (2.35 g; 10 mmol) in THF (20 mL) over 10 minutes. After the gas evolution has ceased, a solution of Iodine (1.27 g; 5 mmol) in THF (20 mL) is added and stirred 1 hour at room temperature. The reaction is quenched with 3M HCl and stirred an additional 1 hour at room temperature. Water is added to dissolve any solids formed and ether is added. The layers are separated and the organics are washed with 3M KOH and brine, then dried over magnesium sulfate. After removing the solvent, the resulting solid is recrystallized from chloroform to give 235 milligrams of (4,5- dichlorophenyl-2-hydroxymethylphenyl) methanol.

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9062 - 9065
[2]Synthesis,1994,p. 1035 - 1036
[3]Patent: US2011/130594,2011,A1 .Location in patent: Page/Page column 6
[4]Journal of the American Chemical Society,2003,vol. 125,p. 10190 - 10191
[5]Tetrahedron,2016,vol. 72,p. 4918 - 4924
[6]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 975 - 979
[7]Patent: US2002/82260,2002,A1
[8]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4
[9]Journal of Organic Chemistry,2014,vol. 79,p. 11592 - 11608
[10]ChemCatChem,2015,vol. 7,p. 865 - 871
[11]Organic Letters,2015,vol. 17,p. 4220 - 4223
[12]Patent: WO2008/151211,2008,A1
[13]Patent: WO2005/123724,2005,A1 .Location in patent: Page/Page column 54

3
[ 24006-92-6 ]
[ 21903-56-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogen bromide; at 90℃;	[000287] A suspension of Compound 7A (4.80 g, 23.2 mmol) in cone. HBr (100 mL) was stirred at 90 C overnight. The mixture was diluted with ethyl acetate (100 mL) and petroleum ether (100 mL), washed with water and brine, concentrated, and then purified by silica chromatography on silica gel (ethyl acetate in petroleum ether, 8% v/v) to give Compound 7B (5.20 g, yield 68%) as a light yellow solid. LCMS: 333 [M+l]+, 1H-NMR (CDCI3, 400 MHz) major characteristic peaks: delta (ppm) 4.55 (s, 4H), 7.47 (s, 2H).
50%	With phosphorus tribromide; In dichloromethane; at 20℃;	Into a 100-mL round-bottom flask, was placed a solution of <strong>[24006-92-6](4,5-dichloro-1,2-phenylene)dimethanol</strong> (500 mg, 2.41 mmol, 1.00 equiv) in dichloromethane (50 mL) and tribromophosphane (1.30 g, 4.80 mmol, 2.00 equiv). The resulting solution was stirred overnight at room temperature. The mixture was poured into 50 mL of water/ice. The resulting solution was extracted with 3×100 mL of ethyl acetate, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). The collected fraction was concentrated under vacuum to give 1,2-bis(bromomethyl)-4,5-dichlorobenzene (400 mg, 50%) as off-white oil. 1H-NMR (CDCl3, 4001411z, ppm): delta 7.48 (s, 2H), 4.57 (s, 4H).
	With hydrogen bromide; In water; for 6h;Heating / reflux;	EXAMPLE 252; 1 ,2-Bis-( bromomethyl)-4,5-dichlorobenzene (252) :A mixture of 4,5-dichloro-l,2-bis(hydroxymethyl)benzene (251, 32.87g, 158.75 mmol) and 48% aqueous hydrobromic acid (16OmL) is heated at reflux temperature for 6h. The reaction is cooled and extracted with diethyl ether (I x 45OmL + 2 x 20OmL). The combined organic extracts are backwashed with water (1 x 20OmL) and with brine (1 x 20OmL). The organic layer is separated, dried over MgSO4, filtered and concentrated in vacuo on a rotary evaporator to afford a light yellow solid that is dissolved in heptane-0.5% EtOAc by heating and placed atop a column of silica gel (7.2cm x 23cm) prepared in heptane-0.5% EtOAc and flash chromatographed taking 50OmL fractions and eluting with heptane-0.5% EtOAc (1.6L), and heptane-1% EtOAc (4L). The product containing fractions (5-14) are combined and concentrated in vacuo on a rotary evaporator to give l,2-bis-(bromomethyl)-4,5- dichlorobenzene (252, 50.0Ig) as a colorless liquid. [L. A. Levy, Synth. Commun., L3, 639- 648 (1983)]1H NMR (CDCl3, 300MHz): delta 4.55 (s, 2H), 7.46 (s, IH) EI-MS m/z 330,332,334,336202 <n="204"/>Anal. Calcd. for C8H6Br2Cl2: C, 28.87;H, 1.82. Found: C, 28.84;H, 1.68

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 9826 - 9834
[2]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000287
[3]Patent: US2016/264518,2016,A1 .Location in patent: Paragraph 0930; 0932
[4]Synthetic Communications,1983,vol. 13,p. 639 - 648
[5]Journal of the Chemical Society. Chemical communications,1994,p. 825 - 826
[6]Journal of Organic Chemistry,2014,vol. 79,p. 11592 - 11608
[7]Patent: WO2008/151211,2008,A1 .Location in patent: Page/Page column 201-203

4
[ 24006-92-6 ]
[ 18162-48-6 ]
[ 130217-48-0 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14836 - 14837
[2]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 975 - 979

5
[ 24006-92-6 ]
[ 13209-33-1 ]

Yield	Reaction Conditions	Operation in experiment
78%		4,5-Dichlorobenzene-1,2-dicarbaldehyde To a dry 500 mL three-necked flask equipped with a thermometer and a dropping funnel, was added a solution of dry CH2Cl2 (60 mL) and oxalyl chloride (2.7 mL, 34.35 mmol) under Ar. The stirred solution was cooled to -78 C. and a solution of DMSO (4.24 mL, 59.67 mmol) in CH2Cl2 (10 mL) was added dropwise. The solution was stirred for 3-5 min. and <strong>[24006-92-6]4,5-dichlorobenzene-1,2-dimethanol</strong> (2.0 g, 9.71 mmol) dissolved in CH2Cl2-DMSO mixture (25 mL) was added dropwise. The reaction was allowed to continue for 0.5 h and then triethylamine (24 mL, 0.18 mol) was slowly added at -78 C. the reaction mixture was allowed to stir for 10 min. and then slowly warmed to RT. Ice-cold water (50 mL) was added to the reaction mixture and the aqueous layer extracted with CH2Cl2 (2×50 mL) and then dried over CaCl2. Removal of solvent gave the yellow solids of 4,5-dichlorobenzene-1,2-dicarbaldehyde in 78% yield (1.53 g). 1H NMR (500 MHz, CDCl3): delta 10.46 (s, 2H), 8.05 (s, 2H). 13C NMR (125.68 MHz, CDCl3): delta 189.92, 139.07, 135.32, 133.08.
50%		In a 500-mL three-necked flask were placed dry dichloromethane (100 mL) and oxalyl chloride (10 mL, 0.116 mol). A mixture of dry dichloromethane (25 mL) and dry DMSO (13.6 mL) was slowly added at -78 C under Ar with stirring. After the mixture was stirred for 5 min, a solution of 8 (12.4 g, 59.8 mmol) in dry DMSO (15 mL) and dry dichloromethane (15 mL) was slowly added and the mixture was stirred for 30 min. Dry triethylamine (125 mL) was then added slowly and stirring was continued for 10 min. The mixture was then warmed up to room temperature and stirred overnight. The reaction was quenched by adding water, and the organic layer was collected. The aqueous layer was washed with dichloromethane three times, and the dichloromethane solution was combined with the organic layer. The organic solvents were evaporated and the residue was subjected to silica gel chromatography using ethyl acetate:hexane (30:70) as eluant: 6.1g, 50% yield. White powder, mp: 134-135 C. 1H NMR data matched published data.22 1H NMR (CDCl3, 500 MHz): delta (ppm)=10.49 (s, 2H), 8.11 (s, 2H).
	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; acetone; at 80℃; for 3.5h;	General procedure: To a suspension of IBX (5.4 mmol) in ethyl acetate (75 ml) was added a solution of the suitable diol19 (1.8 mmol) in acetone (5 ml). The reaction mixture was heated at 80 C for 3.5 h, cooled and filtered, and the filtered solid was washed with acetone (2×5 ml). The combined filtrate and washings were evaporated under reduced pressure and purified by distillation, giving the desired dialdehydes in 66-80% yields.

Reference： [1]Patent: US2011/130594,2011,A1 .Location in patent: Page/Page column 6
[2]Journal of the American Chemical Society,2012,vol. 134,p. 9062 - 9065
[3]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4
[4]Journal of the American Chemical Society,2003,vol. 125,p. 10190 - 10191
[5]Tetrahedron,2016,vol. 72,p. 4918 - 4924
[6]Synthesis,1994,p. 1035 - 1036
[7]Tetrahedron,2011,vol. 67,p. 5582 - 5589

6
[ 24006-92-6 ]
2,3-dichloro-5,10-dihydro-6,9-dioxa-7,8-dithia-benzocyclooctene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 6659 - 6661

7
[ 24006-92-6 ]
[ 606927-22-4 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 10190 - 10191

8
[ 24006-92-6 ]
6,13-dihydro-2,3,9,10-tetrachloropentacene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 10190 - 10191

9
[ 24006-92-6 ]
2,3,9,10-tetrachloropentacene-6,13-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 10190 - 10191
[2]Patent: US2011/130594,2011,A1

10
[ 24006-92-6 ]
[ 87743-19-9 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1994,p. 825 - 826
[2]Synthetic Communications,1983,vol. 13,p. 639 - 648

11
[ 24006-92-6 ]
5,6-Dichloro-benzo[c]thiophene [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1994,p. 825 - 826

12
[ 24006-92-6 ]
[ 164732-13-2 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1994,p. 825 - 826

13
[ 24006-92-6 ]
[ 34588-40-4 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 639 - 648

14
[ 24006-92-6 ]
[ 87743-20-2 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 639 - 648

15
[ 24006-92-6 ]
[ 87743-22-4 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 639 - 648

16
[ 24006-92-6 ]
[ 87743-26-8 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 639 - 648

17
[ 24006-92-6 ]
[ 87743-25-7 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 639 - 648

18
[ 24006-92-6 ]
[ 87743-21-3 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 639 - 648

19
[ 24006-92-6 ]
[ 87743-23-5 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 639 - 648

20
[ 24006-92-6 ]
[ 87743-24-6 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 639 - 648

21
[ 24006-92-6 ]
[ 130217-38-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 975 - 979

22
[ 24006-92-6 ]
[ 130217-40-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 975 - 979

23
[ 24006-92-6 ]
[ 130217-36-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 975 - 979

24
[ 24006-92-6 ]
[ 130217-45-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 975 - 979

25
[ 24006-92-6 ]
[ 130217-42-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 975 - 979

26
[ 24006-92-6 ]
[ 149-73-5 ]
[ 872181-18-5 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2; The previous alcohol (235 mg; 1.13 mmol) and camphorsulfonic acid (5.3 mg; 2 mol%) are dissolved in dichloromethane with trimethylorthoformate (0.5 mL; 4.54 mmol). The reaction is stirred at room temperature overnight, then cooled to-78 C (dry ice/acetone) while diisobutylaluminum hydride (1M in hexane; 11.35 mL; 11.35 mmol) is added dropwise over 30 minutes. The temperature is maintained at -78 C for 30 minutes, the allowed to 0 C for 15 minutes. The reaction is neutralized with 3M KOH and stirred with ether for 2 hours. The aqueous layer is extracted with fresh ether. All organics are combined and dried over magnesium sulfate, then concentrated to give 271 milligrams of (4,5-dichloro-2-methoxy- methoxymethylphenyl) methanol.

Reference： [1]Patent: WO2005/123724,2005,A1 .Location in patent: Page/Page column 54

27
[ 1074-86-8 ]
4,5-dichloro-2-tetrahydropyranyloxy benzylchloride [ No CAS ]
[ 24006-92-6 ]
[ 280134-99-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tetrahydrofuran;	This compound was prepared from 4-formylindole and 4,5-dichloro-2-tetrahydropyranyloxy benzylchloride [prep. from 1,2-dihydroxymethyl-4,5-dichloro benzene acc. W. Y. Lee et al. J. Org. Chem. 57, 1992, 4074-4079] following the general procedure for alkylation of indoles. After treatment of the product with 1N HCl in THF, 4-formyl-1-(4,5-dichloro-2-hydroxymethylbenzyl)-indole was obtained. 1H NMR (CDCl3): delta 4.65 (s, 2H), 5.45 (s, 2H), 6.81 (s, 1H), 7.26 (s, 1H), 7.27 (d, J=3.4 H8 Hz, 1H), 7.32 (d, J=7.9 Hz, 1H), 7.36 (d, J=3.8 Hz, 1H), 7.51 (d, J=6.8 Hz, 1H), 7.52 (s, 1H), 7.66 (d, J=7.2 Hz, 1H), 10.25 (s, 1H).

Reference： [1]Patent: US6613942,2003,B1

28
diethyl ether ether [ No CAS ]
[ 75-18-3 ]
[ 24006-92-6 ]
[ 21903-56-0 ]

Yield	Reaction Conditions	Operation in experiment
	In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane;	EXAMPLE 80 1,2-Bis(bromomethyl)-4,5-dichlorobenzene A 2.53 g portion of N-bromosuccinimde is added to 40 mL methylene chloride and 5 mL diethyl ether ether. The solution is cooled to 0 C. and 1.25 mL methyl sulfide is slowly added via a syringe. A yellow solid is formed. Following complete addition of the methyl sulfide, the reaction mixture is cooled to -20 C. To this is added 0.736 g of <strong>[24006-92-6]4,5-dichloro-1,2-benzenedimethanol</strong>. The reaction mixture is warmed to 0 C. and stirred for 3 hours, followed by quenching with 30 mL of ice water. A further 30 mL of methylene chloride is added and the layers are separated. The organic layer is washed with 20 mL brine, and dried over magnesium sulfate. Purification by silica gel chromatography (2:1 ethyl acetate/hexane) provides 0.40 g of the desired product as a white solid. mp 55-56 C. MS (Hi res): m/z Calcd for C8 H6 Cl2 Br2 2 329.8214 Found 329.8215

Reference： [1]Patent: US5387685,1995,A

29
borane-methyl sulfide [ No CAS ]
[ 56962-08-4 ]
[ 24006-92-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 79 4,5-Dichloro-1,2-benzenedimethanol A 1.24 g portion of 4,5-dichlorophthalic acid is dissolved in 40 mL anhydrous tetahydrofuran and the solution is cooled to 0 C. To this solution is slowly added 4 mL of borane-methyl sulfide. The reaction flask is first warmed to room temperature, then heated to reflux for 12 hours. The product mixture is cooled to 0 C., then slowly quenched with 50 mL methyl alcohol. Following removal of the solvent, the residue is partitioned between 40 mL water, and 100 mL 1:1 ethyl acetate tetrahydrofuran. The organic layer is washed with 30 mL brine, then dried over magnesium sulfate. Purification by silica gel chromatography (2:1 ethyl acetate/hexane) affords 1.01 g of the desired product as a white solid, m.p. 128-136 C. MS(Hi res): m/z Calcd for C8 H8 Cl2 O2 205.9901 Found 205.9872

Reference： [1]Patent: US5387685,1995,A

30
[ 106727-86-0 ]
[ 24006-92-6 ]

Yield	Reaction Conditions	Operation in experiment
		4,5-Dichloro- 1 ,2-bis( hydr oxymethvDbenzene (251):A solution of dimethyl 4,5-dichlorophthalate A5 (98.86g, 375.78 mmol) in tetrahydrofuran (15OmL) is added dropwise over Ih to a mechanically stirred suspension of LAH (20.8g,201 <n="203"/>548.1 mmol) in tetrahydrofuran (1.5L). During the addition, the reaction is cooled in an ice- water bath. When the addition is completed, the reaction is stirred overnight at RT. The excess LAH is decomposed by cautious addition of water (2OmL), 10% aqueous NaOH (4OmL) and water (2OmL). The solids are removed by filtration through a celite pad and washed with tetrahydrofuran. The combined filtrate and wash is concentrated in vacuo on a rotary evaporator to afford crude 251 as white solid that is purified by crystallization from acetone (150mL)-heptane (15OmL). The crystals are collected by filtration, washed with heptane and dried to give 4,5-dichloro-l,2-bis(hydroxymethyl)benzene (37.2g). The combined filtrate and wash afforded a second crop of 251 (18.8g, 24.1%). [L. A. Levy, Synth. Commun., U, 639- 648 (1983); O. Farooq, Synthesis, 1035-1036 (1994)]1H NMR (DMSO-d6, 300MHz): delta 4.49 (d, 2H), 5.32 (t, IH), 7.57 (s, IH) EI-MS m/z 209,207Anal. Calcd. for C8H8Cl2O2: C, 46.41;H, 3.89. Found: C, 46.50;H, 3.83

Reference： [1]Patent: WO2008/151211,2008,A1 .Location in patent: Page/Page column 201-202

31
[ 24006-92-6 ]
[ 1309592-07-1 ]

Reference： [1]Patent: US2011/130594,2011,A1

32
[ 24006-92-6 ]
[ 1258851-05-6 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 5582 - 5589

33
[ 24006-92-6 ]
[ 1316054-11-1 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 5582 - 5589

34
[ 24006-92-6 ]
[ 1379772-55-0 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9062 - 9065

35
[ 24006-92-6 ]
[ 1379772-67-4 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9062 - 9065

36
[ 24006-92-6 ]
[ 24006-91-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With Iron(III) nitrate nonahydrate; 9-azabicyclo<3.3.1>nonane-N-oxyl; In acetonitrile; at 20℃; for 20h;	Fe(NO3)3·9H2O (40.4 mg, 10 mol%) and ABNO (7 mg, 5 mol%) were used in this order.<strong>[24006-92-6]4,5-dichloro-1,2-benzenedimethanol</strong> (207 mg, 1 mmol) was added to a 10 ml reaction tube.Then, 2 ml of acetonitrile was added as a solvent, and the reaction was exposed at room temperature, and then the degree of reaction was checked by GC-MS.After 20 hours of reaction, the internal standard n-dodecane was added after completion of the reaction, and the product was quantitatively analyzed by GC.The conversion of <strong>[24006-92-6]4,5-dichloro-1,2-benzenedimethanol</strong> was 86%, and the product yield was 85%.

Reference： [1]ChemCatChem,2014,vol. 6,p. 109 - 112
[2]Patent: CN106831675,2017,A .Location in patent: Paragraph 0024; 0025
[3]ChemCatChem,2015,vol. 7,p. 865 - 871
[4]European Journal of Organic Chemistry,2013,p. 2445 - 2452

37
[ 24006-92-6 ]
[ 847946-04-7 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4
[2]Organic Letters,2015,vol. 17,p. 4220 - 4223

38
[ 24006-92-6 ]
C₂₉H₂₈Cl₄N₄O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4

39
[ 24006-92-6 ]
C₂₈H₂₈Cl₄N₄O₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4

40
[ 24006-92-6 ]
C₃₂H₂₈Cl₄N₄O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4

41
[ 24006-92-6 ]
C₃₀H₂₆Cl₄N₄O₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4

42
[ 24006-92-6 ]
C₃₀H₃₂Cl₄N₄O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4

43
[ 24006-92-6 ]
14-butyl-4,5,11,12-tetrachloro-13b,14-dihydropyrimido[2,1-a:4,3-a']diphthalazin-15(6bH)-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4

44
[ 24006-92-6 ]
C₂₅H₂₄Cl₄N₄O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13576 - 13579
Angew. Chem.,2013,vol. 125,p. 13821 - 13824,4

45
[ 24006-92-6 ]
[ 24006-91-5 ]
[ 13209-33-1 ]

Yield	Reaction Conditions	Operation in experiment
70%; 28%	With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid; In nitromethane; at 30℃; for 10h;Green chemistry;	General procedure: In a typical experiment, a round bottom flask containing 4-6mL of acetonitrile/water mixture (1:1) was charged with 0.5-1.0mmol of the diol, 5mol% of TetMe-IA, and oxone (2equiv). The resulting mixture was stirred at rt for benzylic diols and at 45C for aliphatic diols. At the end of the reaction, as judged from TLC analysis, little water was added to dissolve the inorganic salts, and the organic matter was extracted with EtOAc at least two times. The combined extract was dried over anhydrous Na2SO4, concentrated in vacuo to obtain the crude product, which was subjected to silica-gel column chromatography using ethyl acetate/pet ether to isolate the pure product.

Reference： [1]Tetrahedron,2014,vol. 70,p. 2286 - 2293

46
[ 24006-92-6 ]
C₁₅H₁₆Cl₂O₄ [ No CAS ]