[ CAS No. 141-30-0 ] {[proInfo.proName]}

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2D 3D

Structure of 141-30-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 141-30-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 141-30-0 ]

SDS Specification

Alternatived Products of [ 141-30-0 ]

Product Details of [ 141-30-0 ]

CAS No. :	141-30-0	MDL No. :	MFCD00006466
Formula :	C₄H₂Cl₂N₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	GUSWJGOYDXFJSI-UHFFFAOYSA-N
M.W :	148.98	Pubchem ID :	67331
Synonyms :

Calculated chemistry of [ 141-30-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.05
TPSA :	25.78 ?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) :	-6.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	0.7
Log Po/w (WLOGP) :	1.78
Log Po/w (MLOGP) :	1.21
Log Po/w (SILICOS-IT) :	2.34
Consensus Log Po/w :	1.55

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.76
Solubility :	2.59 mg/ml ; 0.0174 mol/l
Class :	Very soluble
Log S (Ali) :	-0.82
Solubility :	22.6 mg/ml ; 0.152 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.203 mg/ml ; 0.00136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 141-30-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P305+P351+P338	UN#:
Hazard Statements:	H302-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 141-30-0 ]

* 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.

Upstream synthesis route of [ 141-30-0 ]
Downstream synthetic route of [ 141-30-0 ]

[ 141-30-0 ] Synthesis Path-Upstream 1~5

1
[ 141-30-0 ]
[ 33097-39-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2015, vol. 51, # 5, p. 1404 - 1409
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2720 - 2725

2
[ 141-30-0 ]
[ 33097-38-0 ]
[ 33097-39-1 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 35, p. 6763 - 6767
[2] Tetrahedron, 2001, vol. 57, # 4, p. 739 - 750
[3] Chemistry Letters, 1993, # 3, p. 509 - 512

3
[ 141-30-0 ]
[ 75-98-9 ]
[ 22808-29-3 ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: With ammonium peroxydisulfate; sulfuric acid; silver nitrate In water at 70℃; for 1 h;	Synthesis of Compound J.1. A flask was charged with 3,6-dichloropyridazine (1.49 g, 0.01 mol, 1.0 equiv), silver nitrate (0.17 g, 0.001 mol, 0.1 equiv), water (30 mL), pivalic acid (3.57 g, 0.035 mol, 3.5 equiv), and sulfuric acid (1.6 mL, 0.03 mol, 3.0 equiv). The mixture was heated to 70° C. and a solution of ammonium persulfate (2.28 g, 0.01 mol, 1.0 equiv) in water (10 mL) was added dropwise over ten minutes. The reaction was stirred at 70° C. for one hour and then cooled to RT. The reaction mixture was poured into ice water and then adjusted to pH 8 with aqueous ammonium hydroxide. The aqueous mixture was extracted with CH₂Cl₂(2.x.250 mL). The combined organic extracts were filtered through a cotton plug, washed with aqueous 1 N NaOH (70 mL), dried over anhydrous MgSO₄and concentrated under reduced pressure. Purification by flash column chromatography (20percent EtOAc/hexanes) afforded the title compound (1.32 g, 64percent) as a white solid. ¹H NMR: (CDCl₃, 400 MHz) δ: 7.5 (s, 1H), 1.5 (s, 9H); R_f=0.5 (80percent EtOAc/hexanes).
64%	With ammonium peroxydisulfate; sulfuric acid; silver nitrate In water at 70℃; for 1 h;	A flask was charged with 3,6-dichloropyridazine (1.49 g, 0.01 mol, 1.0 equiv), silver nitrate (0.17 g, 0.001 mol, 0.1 equiv), water (30 mL), pivalic acid (3.57 g, 0.035 mol, 3.5 equiv), and sulfuric acid (1.6 mL, 0.03 mol, 3.0 equiv). The mixture was heated to 70° C. and a solution of ammonium persulfate (2.28 g, 0.01 mol, 1.0 equiv) in water (10 mL) was added dropwise over ten minutes. The reaction was stirred at 70° C. for one hr and then cooled to RT. The reaction mixture was poured into ice water and then adjusted to pH 8 with aqueous ammonium hydroxide. The aqueous mixture was extracted with CH₂Cl₂(2.x.250 mL). The combined organic extracts were filtered through a cotton plug, washed with aqueous 1 N NaOH (70 mL), dried over anhydrous MgSO₄and concentrated under reduced pressure. Purification by flash column chromatography (20percent EtOAc/hexanes) afforded the title compound (1.32 g, 64percent) as a white solid. ¹H NMR: (CDCl₃, 400 MHz) δ: 7.5 (s, 1 H), 1.5 (s, 9 H); R_f=0.5 (80percent EtOAc/hexanes).

Reference： [1] Patent: US2009/5359, 2009, A1, . Location in patent: Page/Page column 39
[2] Patent: US2009/36419, 2009, A1, . Location in patent: Page/Page column 84
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7089 - 7092
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 20, p. 6030 - 6033

4
[ 141-30-0 ]
[ 22808-29-3 ]

Reference： [1] Patent: US4628088, 1986, A,

5
[ 141-30-0 ]
[ 7664-93-9 ]
[ 75-98-9 ]
[ 22808-29-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With silver nitrate In hexane; water	a 3,6-Dichloro-4-(1,1-dimethylethyl)pyridazine Concentrated sulphuric acid (53.6 ml, 1.0 mol) was added carefully to a stirred suspension of 3,6-dichloropyridazine (50.0 g, 0.34 mol) in water (1.25 l). This mixture was then heated to 70° C. (internal temperature) before the addition of trimethylacetic acid (47.5 ml, 0.41 mol). A solution of silver nitrate (11.4 g, 0.07 mol) in water (20 ml) was then added over approximately one minute. This caused the reaction mixture to become milky in appearance. A solution of ammonium persulphate (230 g, 1.0 mol) in water (0.63 l) was then added over 20-30 minutes. The internal temperature rose to approximately 85° C. During the addition the product formed as a sticky precipitate. Upon complete addition the reaction was stirred for an additional 10 minutes, then allowed to cool to room temperature. The mixture was then poured onto ice and basified with concentrated aqueous ammonia, with the addition of more ice as required to keep the temperature below 10° C. The aqueous was extracted with dichloromethane (3*300 ml). The combined extracts were dried (MgSO₄), filtered and evaporated to give 55.8 g of crude product as an oil. This was purified by silica gel chromatography using 0-15percent ethyl acetate in hexane as eluent to give 37.31 g (53percent) of the desired compound. Data for the title compound: ¹H NMR (360 MHz, d₆-DMSO) δ1.50 (9H, s), 7.48 (1H, s); MS (ES⁺) m/e 205 [MH]⁺, 207 [MH]⁺.

Reference： [1] Patent: US6630471, 2003, B1,

[ 141-30-0 ] Synthesis Path-Downstream 1~4

1
[ 141-30-0 ]
[ 50595-15-8 ]
2-(3-pyrazinyloxy)acetic acid trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid;palladium; In N-methyl-acetamide; ethanol; dichloromethane; ethyl acetate; mineral oil;	A stirred suspension of 88 mg (2.2 mmol) sodium hydride (60percent dispersion in mineral oil) in 5 ml of dry dimethylformamide at -5° C. under nitrogen was treated with 264 mg (2 mmol) tert-butylglycolate. After 10 minutes 298 mg (2 mmol) of 3,6-dichloropyridazine (Aldrich D7, 320-0) was added and the solution was allowed to warm to room temperature and was stirred overnight. The volatiles were evaporated under reduced pressure and the residue was chromatographed on silica eluding with ethyl acetate/hexane (1:2) to give 210 mg of a gum that was dissolved in 20 ml of ethanol and treated with 10percent palladium on carbon (Fluka) and hydrogenated under a hydrogen atmosphere overnight. The catalyst was removed by filtration and the volatiles were evaporated under reduced pressure to give a gum that was chromatographed on silica eluding with ethyl acetate/hexane (1:2) followed by ethyl acetate to give 50 mg of a gum [M+H+MeCN]+252. The gum was dissolved in 2 ml of dichloromethane and treated with 1 ml of trifluoroacetic acid. After 10 minutes the volatiles were evaporated and the residue triturated with toluene and re-evaportated to give a gum that was further triturated with petroleum ether bp 40-60° C. to give 2-(3-pyrazinyloxy)acetic acid trifluoroacetate.

Reference： [1]Patent: US6472404,2002,B1

2
[ 141-30-0 ]
[ 894807-98-8 ]
[ 1022151-61-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 100℃; for 4h;	Example 9: 6-[6-(l/-r-Pyrazol-4-yl)-[l,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl]- quinoline (compound 39); Step 1 : 3-Chloro-6- [ 1 -(2-trimethy Isilanyl-ethoxymethyl)-li7-py razol-4-yl] -py ridazine; [0365] A mixture of 3,6-dichloropyridazine (505 mg, 3.4 mmol), 4-(4,4,5,5-tetramethyl- [l,3,2]dioxaborolan-2-yl)-l-(2-trimethylsilanyl-ethoxymethyl)-l//-pyrazole (l g, 3.1 mmol) and K2CO3 (1.3 g, 9.3 mmol) in 10 mL of dioxane and 4 mL of H2O was degassed with nitrogen. To this mixture was added dichloro[ 1 , 1 '-bis(diphenylphosphino)ferrocene] palladium(II) dichloromethane adduct (45 mg, 0.06 mmol) and the resulting mixture was bubbled with nitrogen for another 15 min. The reaction mixture was heated at 1000C for 4h, then after cooling to room temperature the aqueous phase was removed via pipette. The organic phase was concentrated onto silica gel and purified by flash column chromatography eluting with hexanes:ethyl acetate 100:0 to 60:40 returning title compound as a white solid (640 mg, 2.06 mmol, 66% yield): 1H NMR(CDCl3) delta 0.02 (9H, s), 0.96 (2H, t), 3.64 (2H, t), 5.52 (2H, s), 7.52 (IH, d), 7.62 (IH, d), 8.10 (IH, s), 8.34 (IH, s); MS (m/z) 311 [M+H+]+.

Reference： [1]Patent: WO2008/51808,2008,A2 .Location in patent: Page/Page column 104

3
[ 141-30-0 ]
[ 5271-27-2 ]
[ 1094259-06-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 180℃; for 0.5h;microwave irradiation;	A mixture of 3,6-dichloropyridazine (845mg) and <strong>[5271-27-2]1-methyl-3-phenylpiperazine</strong> (1g) in N- methyl-2-pyrrolidone (5ml) and Hunig's base (2.5ml) was heated in the microwave at18O0C for thirty minutes.The reaction mixture was diluted with ethyl acetate (60ml) and washed with water (3 x30ml) then evaporated.The reaction mixture was loaded onto a Biotage Si 40+M column and purified using the Biotage SP4 eluting with 0 to 5percent methanol/dichloromethane over 10CV to afford the title compound (204mg) as a brown solidWeight of brown solid = 204mgMS (ES) Ci5H1735CIN4 requires 288; found 289 [M+H]+

Reference： [1]Patent: WO2009/50227,2009,A1 .Location in patent: Page/Page column 61

4
[ 141-30-0 ]
[ 1151802-22-0 ]
[ 1440965-10-5 ]

Yield	Reaction Conditions	Operation in experiment
407 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 20 - 90℃;Inert atmosphere;	3-Chloro-6-(l-cyclopropy -lH-pyrazol-4-yl)pyridazine To a 100 mL round bottom flask is added the above solid (6.64 g, 28.4 mol), 3,6-dichoropyridazine (8.46 g, 56.8 mmol), Pd(dppf)Cl2 (1.04 g, 1.42 mol) potassium phosphate (18.1 g, 85.2 mmol), water (5 mL), and 1,4-dioxane (50 g) at room temperature under nitrogen. The reaction mixture is stirred at 90 °C overnight. After cooled to 30 °C, water (20 mL) is added. The aqueous phase is isolated and extracted with ethyl acetate (3 X 30 mL). The combined organic phases are concentrated and the residue is purified on a silica gel flash chromatography to provide a yellow solid (4.07 g, 65percent yield). (MS: [M+l] 222)

Reference： [1]Patent: WO2014/32498,2014,A1 .Location in patent: Page/Page column 19

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

Related Functional Groups of
[ 141-30-0 ]

Chlorides

[ 856847-77-3 ]

3-Chloropyridazine hydrochloride

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3,6-Dichloro-4,5-dimethylpyridazine

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3-Chloro-6-(chloromethyl)pyridazine hydrochloride

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3,4,6-Trichloropyridazine

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[ 141-30-0 ]

Pyridazines

[ 856847-77-3 ]

3-Chloropyridazine hydrochloride

Similarity: 1.00

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3,6-Dichloro-4,5-dimethylpyridazine

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6-Chloropyridazin-4-amine

Similarity: 0.72

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3-Chloro-6-(chloromethyl)pyridazine hydrochloride

Similarity: 0.72

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3,4,6-Trichloropyridazine

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H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 141-30-0 ] {[proInfo.proName]}

Quality Control of [ 141-30-0 ]

Related Doc. of [ 141-30-0 ]

Product Details of [ 141-30-0 ]

Calculated chemistry of [ 141-30-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 141-30-0 ]

Application In Synthesis of [ 141-30-0 ]

[ 141-30-0 ] Synthesis Path-Upstream 1~5

[ 141-30-0 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 141-30-0 ]

Chlorides

Related Parent Nucleus of [ 141-30-0 ]

Pyridazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

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[ 141-30-0 ]

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[ 141-30-0 ]