[ CAS No. 102645-33-0 ] {[proInfo.proName]}

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Quality Control of [ 102645-33-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 102645-33-0 ]

SDS Specification

Alternatived Products of [ 102645-33-0 ]

Product Details of [ 102645-33-0 ]

CAS No. :	102645-33-0	MDL No. :	MFCD06410679
Formula :	C₆H₃Cl₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UIPSRNHDSBVXHY-UHFFFAOYSA-N
M.W :	176.00	Pubchem ID :	2762993
Synonyms :

Calculated chemistry of [ 102645-33-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.64
TPSA :	29.96 ?2

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) :	-6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.47
Log Po/w (XLOGP3) :	1.9
Log Po/w (WLOGP) :	2.2
Log Po/w (MLOGP) :	1.0
Log Po/w (SILICOS-IT) :	2.79
Consensus Log Po/w :	1.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.51
Solubility :	0.549 mg/ml ; 0.00312 mol/l
Class :	Soluble
Log S (Ali) :	-2.15
Solubility :	1.24 mg/ml ; 0.00705 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.2
Solubility :	0.111 mg/ml ; 0.000628 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 102645-33-0 ]

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

Application In Synthesis of [ 102645-33-0 ]

* 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 [ 102645-33-0 ]

[ 102645-33-0 ] Synthesis Path-Downstream 1~12

1
[ 102645-33-0 ]
[ 108-24-7 ]
[ 862170-49-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 20℃; for 20h;	Intermediate 9: (2. 5-Dichloro-4-pyridinvl) methanedivl diacetate; Concentrated sulfuric acid (3 drops) was added to a suspension of 2, 5-dichloro-4- pyridinecarbaldehyde (Intermediate 8,4. 0g) in acetic anhydride (25ml) and the mixture was stirred at room temperature for 20h. The acetic anhydride was removed under vacuum to give the title compound as a pale brown oil. LC-MS: Rt 2.94min, MH+ 278

Reference： [1]Patent: WO2005/73232,2005,A1 .Location in patent: Page/Page column 35

2
[ 16110-09-1 ]
[ 68-12-2 ]
[ 102645-33-0 ]

Yield	Reaction Conditions	Operation in experiment
56%		2,5-dichloropyridine-4-carbaldehvde A solution of 2,5-dichloropyridine (27.0 g, 180 mmol) in THF (65 mL) was added via cannula to a cooled solution of LDA (100 mL of a 1 .8 M solution, 180 mmol) in THF (80 mL) at -78 C. The mixture was stirred at -78 C for 30 mins, then a solution of DMF (21.1 mL, 271 mmol) in THF (25 mL) was added slowly via syringe. The reaction was stirred at -78 C for 3 hours and was then warmed to R.T. gradually. The solution was poured into a mixture of ice (800 mL) and cone. HCI (150 mL) and stirred for 20 mins before being basified with NaOH (3.0 M) to pH 9-10, and extracted with Et20 (2 x 500 mL). The combined organic layers were dried over MgS04 and concentrated to give the crude product as pale yellow solid. This solid was suspended in n-hexane with trace EtOAc and boiled for 5 mins. The liquors were decanted and stripped to yield a yellow solid which was purified by Biotage flash chromatography (65i, loaded in DCM / EtOAc, eluted with heptane - 20 % EtOAc / heptane over 8 CV, then holding for 5 CV) to afford the title compound (17.9 g, 56 %) as a pale yellow solid, 1H NMR (400 MHz, DMSO-d6) delta 7.85 (s, 1 H) 8.76 (s, 1 H) 10.22 (s, 1 H).
	With n-butyllithium;	2,5-Dichloropyridine-4-carboxaldehyde was prepared from 2.5-dichloropyridine using the procedure described in Eur. J. Org. Chem. 2001, 1371-1376 (E. Marzi, A. Bigi, M. Schlosser ) and converted to 2-(2,5-dichloro-pyridin-3-yl)-lH- benzoimidazole using the method in route 1 step 4. This was aminated as described for compound 34 and the aminopyridine converted to compound 38 using the method in route 1 step 1
		Intermediate 8: 2, 5-Dichloro-4-pyridinecarbaldehyde; Diisopropylamine (7. 5ml) was dissolved in THF (47ml) and the solution was cooled to -35C. n-Butyl lithium (1.6M in hexanes, 44ml) was added slowly maintaining the temperature below-30C. After the addition the reaction mixture was cooled to-75C and a solution of 2, 5-dichloropyridine (8.9g) in THF (27ml) was added dropwise. The mixture was stirred at-75C for a further 30min and a solution of DMF (7. Oml) in THF (14ml) was added dropwise. The reaction mixture was stirred at-75C for 1.5h then allowed to warm to 10C over 2.5h. The solution was poured onto a mixture of ice (500ml) and concentrated hydrochloric acid (45ml) and stirred for 15min. The mixture was basified to pH8 with sodium hydroxide (2N), extracted with ether (x3) and the combined organic extracts were washed with brine, dried (magnesium sulfate) and reduced to dryness under vacuum. The resulting oil was applied to a silica column (50g) and eluted with cyclohexane/ethyl acetate (100: 0 to 80: 20) The product obtained was recrystallised from cyclohexane to give the title compound as beige needles (6.65g). NMR: [8H d6-DMSO] 10.20 (1H, s), 8.75 (1H, s), 7.83 (1H, s)

Reference： [1]Patent: WO2011/27249,2011,A2 .Location in patent: Page/Page column 58
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6578 - 6581
[3]Patent: WO2006/50506,2006,A1 .Location in patent: Page/Page column 132
[4]Patent: WO2005/73232,2005,A1 .Location in patent: Page/Page column 34

Yield	Reaction Conditions	Operation in experiment
		The organic solutions were combined, washed with saturated NaCl solution, dried and evaporated to dryness to give about 22 g of 2,5-dichloro-4-pyridinecarboxaldehyde.

4
[ 102645-33-0 ]
2,5-dichloro-4-pyridinecarboxaldehyde oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22.8 g (85%)	With hydrogenchloride; hydroxylamine hydrochloride; In isopropyl alcohol;	This aldehyde was dissolved in 100 ml of 2-propanol, mixed with 13.8 g of hydroxylamine hydrochloride and 20 drops of concentrated HCl and heated on a steambath for 1 hour. The mixture was then poured onto 200 g of ice, stirred well and filtered leaving a solid residue. The solid was vacuum dried to give 22.8 g (85%) of the desired <strong>[102645-33-0]2,5-dichloro-4-pyridinecarboxaldehyde</strong> oxime STR6 m.p. 173-174 C.

Reference： [1]Patent: US4558134,1985,A

5
[ 102645-33-0 ]
[ 102645-34-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6578 - 6581

6
[ 102645-33-0 ]
[ 4760-34-3 ]
[ 1269771-37-0 ]