[ CAS No. 948573-26-0 ] {[proInfo.proName]}

Name: 948573-26-0|1-Ethyl-1H-pyrazol-4-amine monohydrochloride|95%
Brand: Ambeed
SKU: A871614
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Quality Control of [ 948573-26-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 948573-26-0 ]

SDS Specification

Alternatived Products of [ 948573-26-0 ]

Product Details of [ 948573-26-0 ]

CAS No. :	948573-26-0	MDL No. :	MFCD08461903
Formula :	C₅H₁₀ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QOVXVNPYUBGBDP-UHFFFAOYSA-N
M.W :	147.61	Pubchem ID :	44630890
Synonyms :

Calculated chemistry of [ 948573-26-0 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.67
TPSA :	43.84 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) :	-6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.65
Log Po/w (WLOGP) :	1.3
Log Po/w (MLOGP) :	0.11
Log Po/w (SILICOS-IT) :	-0.05
Consensus Log Po/w :	0.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.51
Solubility :	4.56 mg/ml ; 0.0309 mol/l
Class :	Very soluble
Log S (Ali) :	-1.15
Solubility :	10.5 mg/ml ; 0.0714 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.78
Solubility :	24.4 mg/ml ; 0.166 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 948573-26-0 ]

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

Application In Synthesis of [ 948573-26-0 ]

* 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 [ 948573-26-0 ]

[ 948573-26-0 ] Synthesis Path-Downstream 1~6

1
[ 948573-26-0 ]
[ 952138-25-9 ]
N-(1-ethyl-1H-pyrazol-4-yl)-2-[3-methoxy-5-(1,6-naphthyridin-4-yloxy)pyridin-2-yl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2-hydroxy-pyridine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 20.0h;	Example 9; iV-(l-ethyl-ljHr-pyrazoI-4-yl)-2-[3-methoxy-5-(l,6-naphthyridin-4-yloxy)pyridin- 2-yl]acetamide; l-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.42 g) was added to a stirred mixture of 2-[3-methoxy-5-(l,6-naphthyridin-4-yloxy)pyridin-2-yl]acetic acid (0.225 g), 4-amino-l -ethyl- lT-pyrazole hydrochloride (0.14 g), diisopropylethylamine (0.5 ml), 2-hydroxypyridine iV-oxide (0.16 g) and DMF (2 ml). The resultant mixture was stirred at ambient temperature for 16 hours. A second portion (0.4 g) of 4-amino-l-ethyl- lH-pyrazole hydrochloride was added and the mixture was stirred at ambient temperature for 4 hours. The reaction mixture was purified by reversed-phase preparative HPLC on a Waters 'beta Basic Hypersil' reversed-phase preparative column (5 microns silica, 30 mm diameter, 250 mm length) using decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The material so obtained was triturated under a 19:1 mixture of diethyl ether and ethanol. The resultant product was isolated and dried under vacuum. There was thus obtained the title compound (0.095 g); 1H NMR Spectrum: (DMSOd6) 1.33 (t, 3H), 3.81 (s, 2H), 3.83 (s, 3H), 4.07 (q, 2H), 6.82 (d, IH), 7.42 (s, IH)5 7.62 (d, IH), 7.87 (s, IH), 7.94 (d, IH), 8.19 (d, IH), 8.84 (d, IH), 8.93 (d, IH), 9.74 (s, IH), 10.1 (s, IH); Mass Spectrum: M+H"1" 405.

Reference： [1]Patent: WO2007/113565,2007,A1 .Location in patent: Page/Page column 112

2
[ 948573-26-0 ]
[ 863310-59-2 ]
[ 948573-28-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 2-hydroxy-pyridine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 17 - 25℃; for 16.0h;	The iV-(l-ethylpyrazol-4-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide used as starting material was prepared as follows :- l-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.845 g) was added to a stirred mixture of 2-(4-benzyloxy-2-methoxyphenyl)acetic acid (0.4 g), 1-ethyl- 4-aminopyrazole hydrochloride (0.239 g), 2-hydroxypyridine iV-oxide (0.327 g), diisopropylethylamine (1.03 ml) and DMF (5 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a gradient of 100:0 to 3:7 of methylene chloride and ethyl acetate as eluent. There was thus obtained iV-(l-ethylpyrazol-4-yl)-2-(4-benzyloxy-2-methoxyphenyl)acetamide (0.256 g); 1HNMR: (DMSOd6) 1.31 (t, 3H), 3.44 (s, 2H), 3.73 (s, 3H), 4.04 (q, 2H), 5.09 (s, 2H), 6.53 (m, IH), 6.62 (s, IH), 7.07 (d, IH), 7.33 (m, IH), 7.39 (m, 3H), 7.45 (m, 2H), 7.84 (s, IH), 9.89 (s, IH); Mass Spectrum: M+H+ 366.
	With 2-hydroxy-pyridine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16.0h;	The iV-(l-ethylpyrazol-4-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide used as starting 0 material was prepared as follows :-; l-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.845 g) was added to a stirred mixture of 2-(4-benzyloxy-2-methoxyphenyl)acetic acid (0.4 g), 1-ethyl- 4-aminopyrazole hydrochloride (0.239 g), 2-hydroxypyridine iV-oxide (0.327 g), diisopropylethylamine (1.03 ml) and DMF (5 ml) and the resultant mixture was stirred at S ambient temperature for 16 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a gradient of 100:0 to 3:7 of methylene chloride and ethyl acetate as eluent. There was thus obtained N-(I -ethylpyrazol-4-yl)-2-(4-benzyloxy- 2-methoxyphenyl)acetamide (0.256 g); 1H NMR Spectrum: (DMSOd6) 1.31 (t, 3H), 3.44 (s, 2H)5 3.73 (s, 3H), 4.04 (q, 2H), 5.09 (s, 2H), 6.53 (m, IH), 6.62 (s, IH), 7.07 (d, IH), 7.33 (m, o IH), 7.39 (m, 3H), 7.45 (m, 2H), 7.84 (s, IH), 9.89 (s, IH); Mass Spectrum: M+H+ 366.

Reference： [1]Patent: WO2007/99326,2007,A1 .Location in patent: Page/Page column 173
[2]Patent: WO2007/113565,2007,A1 .Location in patent: Page/Page column 108

3
[ 948573-26-0 ]
[ 1413913-54-8 ]
[ 1569514-16-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In N,N-dimethyl-formamide; toluene; at 140℃; for 0.333333h;Microwave irradiation;	A mixture of 2-bromo-N-ieri-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3- b]pyrazine-7-carboxamide (150 mg, 351 muiotaetaomicron), l-ethyl-lH-pyrazol-4-amine hydrochloride (51.8 mg, 526 muiotaetaomicron), BINAP (10.9 mg, 17.5 muiotaetaomicron), palladium (II) acetate (19.7 mg, 87.7 muiotaetaomicron) and sodium iert-butoxide (101 mg, 1.05 mmol, Eq: 3) in DMF (1 mL) and toluene (500 mu) was heated in a microwave at 140C for 20 min. The reaction mixture was diluted with water then extracted into ethyl acetate (3x). The combined organic extracts were washed with brine then dried over magnesium sulfate. Purification by chromatography (silica, 40-80 % ethyl acetate in hexanes) gave N-ieri-butyl-2-(l-ethyl-lH-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (82 mg, 179 muiotaetaomicron, 51 %) as a yellow gum. (EI/CI) m/z 458.4 [M + H].

Reference： [1]Patent: WO2014/29732,2014,A1 .Location in patent: Page/Page column 55

4
[ 948573-26-0 ]
C₂₀H₂₅ClF₂N₄S [ No CAS ]
C₂₅H₃₃F₂N₇S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With hydrogenchloride; In 1,4-dioxane; isopropyl alcohol; at 140℃; for 2.0h;Microwave irradiation;	Synthesis of compound 1-97. To a solution of compound 115.5 (55 mg, 0.13 mmol, 1.00 equiv) in isopropanol (2 mL) was added 0.05 mL of hydrochloric acid (4 M in dioxane) followed by 1 -ethyl- lH-pyrazol-4-amine hydrochloride (23 mg, 0.16 mmol, 1.21 equiv) at room temperature. Reaction mixture was irradiated in microwave for 2 h at 140 C. Upon completion solvent was removed under vacuum and crude was purified via flash column chromatography. Additional purification was done via trituration with Cf^CVhexanes to give 19.6 mg (30%) of N4-(( lr,4r)-4-(4,4-difluoropiperidin- 1 -yl)cyclohexyl)-N2-( 1 -ethyl- 1 H-pyrazol-4-yl)-6,7-dihydro- 5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine-2,4-diamine, 1-97 as a off-white solid. LCMS (ES, m/z): 502 [M+H]+, 1H NMR (400 MHz, CDC13): delta 7.86 (1H, s), 7.52 (1H, s), 6.56 (1H, s), 4.76 (1H, d), 4.17 (2H, q), 4.08-3.95 (1H, m), 2.93 (4H, brs), 2.76 (4H, brs), 2.62-2.45 (3H, m), 2.31 (2H, d), 2.20-1.92 (6H, m), 1.60-1.45 (5H, m), 1.35-1.18 (4H, m).

Reference： [1]Patent: WO2014/194242,2014,A2 .Location in patent: Paragraph 00669; 00676

5
[ 948573-26-0 ]
C₁₆H₂₁ClN₄O₂S [ No CAS ]
N-(1-ethyl-1H-pyrazol-4-yl)-2-methyl-7-(((1r,4r)-4-morpholinocyclohexyl)oxy)thiazolo[5,4-d]pyrimidin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With potassium phosphate; XPhos; In tert-butyl alcohol; at 20℃;Inert atmosphere;	Into a 25 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed intermediate 55.1 (200 mg, 0.54 mmol, 1.00 equiv), potassium phosphate (346 mg, 1.63 mmol, 3.00 equiv), <strong>[948573-26-0]1-ethyl-1H-pyrazol-4-amine hydrochloride</strong> (120 mg, 0.82 mmol, 1.50 equiv), 2-methylpropan-2-ol (5 mL) and Xphos precatalyst (43 mg, 0.05 mmol, 0.10 equiv). The reaction was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum and the crude product was purified using preparative HPLC to furnish 38.1 mg (16%) of compound 1-56 as a pink solid. LCMS (ES, mlz): 444 [M+H] ?H NMR (400 MHz, CDC13): oe 7.553 (s, 1H), 7.903 (s, 1H), 5.1525.227 (m, 1H), 4.1004.184 (m,2H), 3.6743.739 (m, 4H), 2.6812.724 (d, 2H), 2.58O2.61O (t, 4H), 2.2882.325 (d, 3H),2.O652.1O3 (d, 2H), 1.4791.677 (m, 7 H).

Reference： [1]Patent: WO2015/48281,2015,A1 .Location in patent: Paragraph 00519; 00520

6
[ 948573-26-0 ]
5-chloro-2-ethyl-N-[4-(morpholin-4-yl)cyclohexyl]-[1,3 ]thiazolo[5,4-d]pyrimidin-7-amine [ No CAS ]
2-ethyl-N₅-(1-ethyl-1H-pyrazol-4-yl)-N₇-((1r,4r)-4-morpholino-cyclohexyl)thiazolo[5,4-d]pyrimidine-5,7-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In butan-1-ol; at 110℃;	Into a 50 mL round-bottom flask, was placed a solution of intermediate 7.7 (150 mg, 0.39 mmol, 1.00 equiv) in n-butanol (6 mL), and <strong>[948573-26-0]1-ethyl-1H-pyrazol-4-amine hydrochloride</strong> (87 mg, 0.78 mmol, 1.99 equiv). Reaction was stirred overnight at 110 C in an oil bath. Upon completion of the reaction resulting mixture was concentrated under vacuum, and crude purified using flash column chromatography to furnish 180 mg (98%) of compound 1-22 as a yellow solid. LCMS (ES, m/z): 457 [M+H] ?H NMR (400 MHz, DMSO) (5 9.03 (1H, s), 7.85 (1H, s), 7.46 (1H, s), 7.45 (br s, 1H), 4.07 (2H, q), 4.05-3.95 (1H, m), 3.58 (4H, br s), 2.97 (2H, q), 2.50 (4H, s), 2.25-2.16 (1H, m), 2.02-1.85 (4H, m), 1.52-1.42 (2H, m), 1.40-1.29 (8H, m).

Reference： [1]Patent: WO2015/48281,2015,A1 .Location in patent: Paragraph 00393

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Ghs Precautionary Statements

Precautionary Statements-General
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P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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Code	Phrase
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P304	IF INHALED:
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
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P342	If experiencing respiratory symptoms:
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P378
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P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
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.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
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

[ CAS No. 948573-26-0 ] {[proInfo.proName]}

Quality Control of [ 948573-26-0 ]

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[ 948573-26-0 ] Synthesis Path-Downstream 1~6

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Amines

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Pyrazoles

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[ 948573-26-0 ]

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[ 948573-26-0 ]