[ CAS No. 934758-92-6 ] {[proInfo.proName]}

Name: 934758-92-6|5-Chloro-1H-pyrazole|97%
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SKU: A140011
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Quality Control of [ 934758-92-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 934758-92-6 ]

Product Details of [ 934758-92-6 ]

CAS No. :	934758-92-6	MDL No. :	MFCD25980930
Formula :	C₃H₃ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IJPFBRONCJOTTA-UHFFFAOYSA-N
M.W :	102.52	Pubchem ID :	6426710
Synonyms :

Calculated chemistry of [ 934758-92-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	23.6
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.8
Log Po/w (XLOGP3) :	1.18
Log Po/w (WLOGP) :	1.06
Log Po/w (MLOGP) :	0.2
Log Po/w (SILICOS-IT) :	1.91
Consensus Log Po/w :	1.03

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	1.5 mg/ml ; 0.0146 mol/l
Class :	Very soluble
Log S (Ali) :	-1.38
Solubility :	4.29 mg/ml ; 0.0419 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.78
Solubility :	1.72 mg/ml ; 0.0167 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.21

Safety of [ 934758-92-6 ]

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 [ 934758-92-6 ]

* 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.

Upstream synthesis route of [ 934758-92-6 ]
Downstream synthetic route of [ 934758-92-6 ]

[ 934758-92-6 ] Synthesis Path-Upstream 1~4

1
[ 769937-44-2 ]
[ 934758-92-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With trifluoroacetic acid In dichloromethane at 20℃; for 2 h;	5-Chloro-lH-pyrazole.[0500] To a solution of 5-chloro-N,N-dimethyl-lH-pyrazole-l-sulfonamide (30 g, 143 mmol) in dichloromethane (500 mL) was added trifluoroacetic acid (45.7 g, 401 mmol). The reaction mixture was stirred for 2 h at room temperature and quenched by water. The pH of the solution was adjusted to 8 with saturated sodium bicarbonate. The resulting solution was extracted with dichloromethane and concentrated in vacuo to afford 5-chloro-lH-pyrazole as a reddish solid (14 g , 95percent). LCMS (ESI): M+H⁺ = 103.0.

Reference： [1] Patent: WO2015/52226, 2015, A1, . Location in patent: Paragraph 0500
[2] Patent: WO2010/132999, 2010, A1, . Location in patent: Page/Page column 184

2
[ 108128-27-4 ]
[ 934758-92-6 ]

Yield	Reaction Conditions	Operation in experiment
21%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.75 h; Stage #2: With hexachloroethane In tetrahydrofuran at -78 - 15℃; for 1.41667 h; Stage #3: With sodium methylate In methanol at 20℃; for 0.75 h;	5-Chloropyrazole (VDBuLi (1.6M, 3.4 mL, 5.4 mmol) was added under argon to a solution of1-benzenesulfonylpyrazole (750 mg, 3.6 mmol; see Intermediate (V) above) in THF (50 mL) at -78⁰C. The mixture was stirred for 45 min before hexachloro- ethane (1.70 g, 7.2 mmol) was added in one portion. After stirring at -78⁰C for 10 min, the mixture was allowed to warm to 10- 15⁰C over 75 min. The mixture was poured into H₂OZNH₄Cl (1:1, aq, sat, 50 mL). The layers were separated and the aqueous phase was extracted with EtOAc (2 x 50 mL). The combined organic phases were dried (Na₂SO₄) and concentrated. The semi-solid residue was dissolved in MeOH (30 mL) followed by addition of sodium methoxide (30percent in MeOH, 1.6 mL, 7.2 mmol). Stirring at it for 45 min, addition Of NaHCO₃ (sat., aq., 1 mL) followed by extraction, concentration of the extract and purification of the residue by chromatography (1:1 EtOAc/ heptane) gave the title compound as a white solid (Yield: 78 mg, 21percent).

Reference： [1] Patent: WO2007/45868, 2007, A1, . Location in patent: Page/Page column 44

3
[ 1225387-53-0 ]
[ 934758-92-6 ]

Reference： [1] Patent: WO2015/181747, 2015, A1, . Location in patent: Page/Page column 38; 39

4
[ 34045-29-9 ]
[ 934758-92-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3036 - 3048

[ 934758-92-6 ] Synthesis Path-Downstream 1~11

3
[ 934758-92-6 ]
[ 98-09-9 ]
1-benzenesulfonyl-3-chloropyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine; In acetonitrile; at 60℃; for 4h;	1 -Benzenesulfonyl-3 -chloropyrazole (VII)A solution of <strong>[934758-92-6]5-chloropyrazole</strong> (35 mg, 0.34 mmol; see Intermediate (VI) above), benzene sulfonylchloride (0.044 mL5 0.34 mmol), and triethylamine (0.047 mL, 0.34 mmol) in acetonitrile (250 mL) was stirred for 4 h at 600C. The mixture was cooled and concentrated. Purification by chromatography (1:4 EtO Ac/heptane) gave the title compound as colourless needles (Yield: 42 mg, 51%). EPO <DP n="47"/>1H-NMR (DMSO-d6): delta 8.61 (d, IH)5 8.01 (d, 2H)5 7.84 (t, IH)5 7.71 (t, 2H)5 7.79 (d, IH).

Reference： [1]Patent: WO2007/45868,2007,A1 .Location in patent: Page/Page column 44-45

4
[ 108128-27-4 ]
[ 934758-92-6 ]

Yield	Reaction Conditions	Operation in experiment
21%		5-Chloropyrazole (VDBuLi (1.6M, 3.4 mL, 5.4 mmol) was added under argon to a solution of1-benzenesulfonylpyrazole (750 mg, 3.6 mmol; see Intermediate (V) above) in THF (50 mL) at -780C. The mixture was stirred for 45 min before hexachloro- ethane (1.70 g, 7.2 mmol) was added in one portion. After stirring at -780C for 10 min, the mixture was allowed to warm to 10- 150C over 75 min. The mixture was poured into H2OZNH4Cl (1:1, aq, sat, 50 mL). The layers were separated and the aqueous phase was extracted with EtOAc (2 x 50 mL). The combined organic phases were dried (Na2SO4) and concentrated. The semi-solid residue was dissolved in MeOH (30 mL) followed by addition of sodium methoxide (30% in MeOH, 1.6 mL, 7.2 mmol). Stirring at it for 45 min, addition Of NaHCO3 (sat., aq., 1 mL) followed by extraction, concentration of the extract and purification of the residue by chromatography (1:1 EtOAc/ heptane) gave the title compound as a white solid (Yield: 78 mg, 21%).

Reference： [1]Patent: WO2007/45868,2007,A1 .Location in patent: Page/Page column 44

5
[ 50-00-0 ]
[ 934758-92-6 ]
[ 1256562-08-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 20 - 45℃;	5-chloro-lH-pyrazole (50.8 mmol) was dissolved in ethanol (55 mL). A solution of formalin (15.2 g, 508 mmol, 37%) was added at room temperature, and the mixture was heated at 450C overnight. The reaction mixture was evaporated and dried under vacuum, and the residue was triturated in methanol. The solid was filtered and rinsed with methanol. The filtrate was evaporated, and crude (5-chloro-lH-pyrazol-l- yl)methanol was obtained and used in the next step without further purification.

Reference： [1]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 184

6
[ 769937-44-2 ]
[ 934758-92-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 2h;	5-Chloro-lH-pyrazole.[0500] To a solution of 5-chloro-N,N-dimethyl-lH-pyrazole-l-sulfonamide (30 g, 143 mmol) in dichloromethane (500 mL) was added trifluoroacetic acid (45.7 g, 401 mmol). The reaction mixture was stirred for 2 h at room temperature and quenched by water. The pH of the solution was adjusted to 8 with saturated sodium bicarbonate. The resulting solution was extracted with dichloromethane and concentrated in vacuo to afford 5-chloro-lH-pyrazole as a reddish solid (14 g , 95%). LCMS (ESI): M+H+ = 103.0.
	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 48h;	5-chloro-N,N-dimethyl-lH-pyrazole-l -sulfonamide (8.9 g, 50.8 mmol) was dissolved in anhydrous dichloromethane (40 mL), TFA (80 mL, 1016 mmol) was added at 00C, and the mixture was stirred at room temperature for 2 days. The mixture was partially evaporated, hexane was added, and the solid was filtered and then rinsed with hexane. The filtrate was evaporated, and the crude 5-chloro-lH-pyrazole was used in the next step without further purification

Reference： [1]Patent: WO2015/52226,2015,A1 .Location in patent: Paragraph 0500
[2]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 184

7
[ 34045-29-9 ]
[ 934758-92-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3036 - 3048

8
[ 934758-92-6 ]
[ 1369959-11-4 ]

Yield	Reaction Conditions	Operation in experiment
6.2%	With nitric acid; acetic anhydride; acetic acid; at 0 - 20℃;	Fuming nitric acid (14.00 ml, 329 mmol) was added at 0 C over a period of 10 min to a solution of <strong>[934758-92-6]5-chloro-1H-pyrazole</strong> (10.0 g, 97.5 mmol) in acetic acid (14.0 ml, 245 mmol). The resulting mixture was stirred at 0 C for 2 h, then acetic anhydride (33.0 ml, 349 mmol) was added and the reaction mixture was stirred at rt. Progress of the reaction was monitored by TLC and LCMS and when starting material was deemed completely consumed (after 4h), the reaction mixture was poured into ice-water (70 mL) and basified with Na2C03 (60 g) and extracted with EtOAc (3 x 100 mL). The combined organic layers were washed with aqueous saturated sodium bicarbonate (100 mL) and brine (50 mL), dried over Na2S04 and concentrated. The afforded solid was washed with n-pentane which gave the title compound (7.0 g, 6.2%) as a solid. MS (ES+) 147.93 [M+H]+.

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3036 - 3048
[2]Patent: WO2018/226150,2018,A1 .Location in patent: Page/Page column 52

9
[ 934758-92-6 ]
5-chloro-1-nitro-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With nitric acid; acetic anhydride; acetic acid; at 20℃;	To a solution of 5-chloro-lH-pyrazole (14 g, 136 mmol) in acetic acid/acetic anhydride (36 ml .792 ml . ) was added fuming nitric acid (36 mL). The resulting solution was stirred overnight at room temperature, and then diluted with water (500 mL). The solids were collected by filtration to afford 5- chloro-1 -nitro- lH-pyrazole as a yellow solid (7 g, 35%).
6.2%		Fuming nitric acid (14.00 ml, 329 mmol) was added at 0 'C over a period of 10 min to a solution of 5-chloro-1 H-pyrazole (10.0 g, 97.5 mmol) in acetic acid (14.0 ml, 245 mmol). The resulting mixture was stirred at 0 'C for 2 h, then acetic anhydride (33.0 ml, 349 mmol) was added and the reaction mixture was stirred at rt. Progress of the reaction was monitored by TLC and LCMS and when starting material was deemed completely consumed (after 4h), the reaction mixture was poured into ice-water (70 mL) and basified with Na2C03 (60 g) and extracted with EtOAc (3 x 100 mL). The combined organic layers were washed with aqueous saturated sodium bicarbonate (100 mL) and brine (50 mL), dried over Na2S04 and concentrated. The afforded solid was washed with n-pentane which gave the title compound (7.0 g, 6.2%) as a solid. MS (ES+) 147.93 [M+H]+.
		To a soution of 5-choro-1H-pyrazoe (3.88 g, 35.2 mmoD in AcOH (5.10 m, 89 mmoD was added at 0C dropwise 90% aqueous HNO3 (5.10 m, 35.2 mmo) and the reaction mixture was stirred at 0C for 2h. Ac20 (12.92 mL 137 mmo) was then added dropwise. The mixture was stirred at RT for 4h, The mixture was poured nto ce-water and AcOEt and Na2003 (33.6 g, 317 mmo) were added. The organic phase was separated and the aqueous phase was extracted with AcOEt, The combined organic ayers were washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4 and concentrated to afford 5-choro-1-nitro-1H-pyrazoe. M/z = 146/148 [M-Hj-. Rt = 0.71 mm (UPLC Method E32), 1H NMR (400 MHz, DMSO-d6): 6 ppm: 8.91 (d, IH), 6.90 (d, IH).

Reference： [1]Patent: WO2015/52226,2015,A1 .Location in patent: Paragraph 0501
[2]Patent: WO2018/141749,2018,A1 .Location in patent: Page/Page column 41-42
[3]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 38; 39

10
[ 1225387-53-0 ]
[ 934758-92-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; copper(l) chloride; isopentyl nitrite; In water; acetonitrile; at 0 - 20℃; for 180h;Inert atmosphere;	To a souUon of 1H-pyrazo-5-amne (23.6 g, 284 mmo) n CH3CN (1 L) under a nitrogen atmosphere were added HC (140 m, 1420 mmo, 32%) and copper chorde (56.3 g, 568 mmo) at 0C, sopenty ntrte (80 mL 568 mmo) was added at 0C and the mixture was stirred at 0C for 2 days. sopenty nitrite (20 m, 0.5 eq) was added and the mixture was stirred at RT for another 5.5 days. The reaction mixture was sowy poured into ammonium hydroxide (1 L, 25%) and extracted with AcOEt. The organic phase was separated and the aqueous phase was extracted with AcOEt. The combined organic ayers were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by sWca ge co?umn chromatography (hexane / TBME from 1:0 to 4:6) to afford 5-choro-1H-pyrazoe. Mz = 103/105 [M+H]+, Rt = 0.48 mm (UPLC Method B2), 1H NMR (600 MHz, DMSO-d6) : 6 ppm: 1300 (bs, IH), 7.79 (t, IH), 6.29 (t, IH), isoarny acoho :4.28 (t, IH), 3.41 (q, 2H), 1.30 (q, 2H), 0.85 (d, 6H).

Reference： [1]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 38; 39

11
[ 934758-92-6 ]
[ 168077-38-1 ]
[ 1032964-34-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5277 - 5283

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Chloroalkane Synthesis with SOCI2 • Convert Haloalkanes into Alcohols by SN2 • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Halogenation of Alkenes • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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