[ CAS No. 58347-49-2 ]

Name: 7-Chloropyrazolo[1,5-a]pyrimidine
Brand: Ambeed
SKU: A115744
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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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Product Details of [ 58347-49-2 ]

CAS No. :	58347-49-2	MDL No. :	MFCD04035684
Formula :	C₆H₄ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	153.57	Pubchem ID :	12281647
Synonyms :

Computed Properties of [ 58347-49-2 ]

TPSA :Topological Polar Surface Area	30.2	H-Bond Acceptor Count :	2
XLogP3 :	1.3	H-Bond Donor Count :	0
SP3 :	0.00	Rotatable Bond Count :	0

Safety of [ 58347-49-2 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 58347-49-2 ]

Upstream synthesis route of [ 58347-49-2 ]
Downstream synthetic route of [ 58347-49-2 ]

[ 58347-49-2 ] Synthesis Path-Upstream 1~4

1
[ 29274-23-5 ]
[ 58347-49-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	at 90℃;	PREPARATION 32 7-Chloropyrazolo[1,5-a]pyrimidine Pyrazolo[1,5-a]pyrimidin-7(4H)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88 mL, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 mL, 0.74 mmols) were mixed and stirred at 90ºC overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuo. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1) to afford the expected compound (83 mg, 71percent). LRMS (m/z): 154 (M+1)⁺ 1H NMR (400 MHz, DMSO-d₆) d ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d, 1 H) 8.52 (d, 1 H)
71%	at 90℃;	Pyrazolo[1 ,5-a]pyrimidin-7(4/-/)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88 mL, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 mL, 0.74 mmols) were mixed and stirred at 90°C overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1 ) to afford the expected compound (83 mg, 71 percent).LRMS (m/z): 154 (M+1 )⁺ ¹H NMR (400 MHz, DMSO-d₆) δ ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d, 1 H) 8.52 (d, 1 H)
71%	at 90℃;	PREPARATION 897-Chloropyrazolo[1 ,5-a]pyrimidinePyrazolo[1 ,5-a]pyrimidin-7(4H)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88ml, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13ml, 0.74 mmols) were mixed and stirred at 90°C overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1 ) to afford the expected compound (83mg, 71 percent).LRMS (m/z): 154 (M+1 )⁺ ¹ H N MR (400 MHz, DMSO-d₆) d ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d , 1 H) 8.52 (d, 1 H)

65%	at 90℃; for 2.50 h;	7-Hydroxypyrazolo[1 ,5-a]pyrimidine (60 g, 444 mmol), phosphorus oxychloride (108 mL, 1.15 mol) and dimethylaniline (10.8 mL, 89 mmol) were added to a 250 mL round- bottomed flask and the contents heated to 90 ⁰C. After 2.5 h, the reaction mixture was allowed to cool and was concentrated. The black residue was poured into a beaker containing crushed ice (600 mL) and the resulting solution kept cold using an ice bath. The aqueous solution was extracted with CH₂CI₂ (3 ^χ 150 mL) and the combined organic phase was washed with brine (100 mL). The organic phase was dried and concentrated to yield the desired crude product, 7-chloropyrazolo[1 ,5-a]pyrimidine, (44.2 g, 65percent) as a red solid. As the crude product was sufficiently pure to use in the subsequent step, a small sample was purified by column chromatography (33-66percent EtOAc/hexane) to yield an analytical sample as a white solid. HPLC 95percent; ¹H NMR (250 MHz, CDCI₃) δ 8.41 (d, J = 4.5 Hz, 1 H), 8.25 (d, J = 2.3 Hz, 1 H)₁ 6.99 (d, J ~ 4.5 Hz, 1 H), 6.84 (d, J = 2.3 Hz, 1 H); ¹³C NMR (62.9 MHz, CDCI₃) δ 150.0, 148.2, 145.4, 139.0, 108.0, 98.7; MS (APCI) 154 [M+Hf.
47%	for 72.00 h;	The compound prepared in preparative example 1 (2.4 g, 17.4 mmol) was stirred in POCl₃(54 mL) and N,N-dimethylaniline (6.7 mL) 3 days. The reaction mixture was concentrated, dissolved in saturated NaHCO₃(2000 mL) and extracted with CH₂Cl₂, dried over Na₂SO₄, filtered and concentrated. The crude product was purified by flash chromatography using a 2.5percent MeOH in CH₂Cl₂solution as eluent (1.3 g, 47percent yield): M+H=154.

Reference： [1] Patent: EP2518071, 2012, A1. Location in patent: Page/Page column 38
[2] Patent: WO2012/146667, 2012, A1. Location in patent: Page/Page column 90
[3] Patent: WO2012/146666, 2012, A1. Location in patent: Page/Page column 160
[4] Patent: WO2007/17678, 2007, A1. Location in patent: Page/Page column 44
[5] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 610 - 613
[6] Patent: US2007/82901, 2007, A1. Location in patent: Page/Page column 21
[7] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527

2
[ 57489-79-9 ]
[ 58347-49-2 ]

Reference： [1] Patent: US2012/122838, 2012, A1. Location in patent: Page/Page column 80

3
[ 29274-18-8 ]
[ 58347-49-2 ]

Reference： [1] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527

4
[ 197367-75-2 ]
[ 58347-49-2 ]

Reference： [1] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527

[ 58347-49-2 ] Synthesis Path-Downstream 1~10

2
[ 58347-49-2 ]
N-{pyrazolo[1,5-a]pyrimidin-7-yl}-N-({5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophen-2-yl}methyl)pyrazin-2-amine [ No CAS ]

Reference： [1]Patent: WO2019/166824,2019,A1

3
[ 5049-61-6 ]
[ 58347-49-2 ]
C₁₀H₈N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 40h;Inert atmosphere;	Under Ar(g), to a mixture of pyrazin-2-amine (1) (209mg, 2.2mmol), 7- chloropyrazolo[1 ,5-a]pyrimidine (2) (307mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13ml_). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt. EtOAc (15ml_), H20 (10ml_) and brine (5mL) were added to the reaction mixture. The organic phase was separated and the aqueous phase was extracted with EtOAc (15ml_). The organic layers were combined and Pd-scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (34mg, 8%).

Reference： [1]Patent: WO2019/166824,2019,A1.Location in patent: Page/Page column 80; 81

4
[ 58347-49-2 ]
7-chloro-3-fluoro-pyrazolo[1,5-a]pyrimidine [ No CAS ]
3,7-dichloropyrazolo[1,5-a]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Selectfluor; In acetonitrile; at 20℃; for 16h;Inert atmosphere;	7-Chloro-3-fluoro-pyrazolo[l,5-a]pyrimidine and 3,7-dichloropyrazolo[l,5- ajpyrimidine:

Reference： [1]Patent: WO2018/213632,2018,A1.Location in patent: Paragraph 0256; 0407

5
6-bromo-3-fluoro-2-(fluoromethyl)pyridine [ No CAS ]
[ 58347-49-2 ]
7-(5-fluoro-6-(fluoromethyl)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With tetrakis(triphenylphosphine) palladium(0); hexamethyldistannane; In 1,4-dioxane; at 130℃; for 1.5h;Inert atmosphere; Microwave irradiation;	A solution 7-chloropyrazolo[1,5-ajpyrimidine (75 mg, 0.488 mmol), 6- bromo-3 -fluoro-2-(fluoromethyl)pyridine (102 mg, 0.488 mmol), tetrakis(triphenylphosphine)palladium (0) (28.2 mg, 0.024 mmol) and hexamethylditin (0.101 mL, 0.488 mmol) in 1,4-dioxane (2 mL) was purged withnitrogen gas for 2 mm and irradiated at 130 C in a microwave for 90 mm. The reaction mixture was concentrated under reduced pressure. Water (10 mL) was added and the solution was extracted with ethyl acetate (2x10 mL). The organic layer was separated, washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purifiedby silica gel column chromatography (ethyl acetate in hexanes) to afford 7-(5-fluoro-6-(fluoromethyl)pyridin-2-yl)pyrazolo [1,5 -aj pyrimidine (72 mg, 0.120 mmol, 25% yield) as a yellow solid. LCMS (ESI) m/e 247.0 [(M+H) , calcd for C12H9F2N4 247.11; LC/MS retention time (Method C): tR = 0.79 mm.

Reference： [1]Patent: WO2017/59080,2017,A1.Location in patent: Page/Page column 82

6
(S)-tert-butyl (1-(2,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate [ No CAS ]
[ 58347-49-2 ]
(S)-1-(2,5-difluoro-4-(pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2017/59080,2017,A1

7
(S)-tert-butyl (1-(2,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate [ No CAS ]
[ 58347-49-2 ]
(S)-tert-butyl (1-(2,5-difluoro-4-(pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; potassium bromide; In 1,4-dioxane; at 88℃; for 2h;Inert atmosphere;	A solution of 7-chloropyrazolo[1,5-ajpyrimidine (25 mg, 0.163 mmol), (8)-tert-butyl (1 -(2,5 -difluoro-4-(4,4,5 ,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (prepared as described in Example 285) (76 mg,0.163 mmol), C52CO3 (106 mg, 0.326 mmol), and KBr (19.37 mg, 0.163 mmol) in1,4-dioxane (10 mL) was purged with nitrogen gas for 30 mi PdC12 (dppf)-CH2C12 adduct (13.29 mg, 0.016 mmol) was added to the reaction mixture and the solutionwas purged with nitrogen gas again for 10 mm. The reaction mixture was heated in a microwave at 88 C for 2 h. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (30 mL) and water (30 mL). The biphasic mixture was filtered through diatomaceous earth (Diatomaceous earth) and the bed was washed with ethyl acetate (50 mL). The ethyl acetate layer was separated, driedover Na2SO4, filtered, and concentrated under reduced pressure to afford (8)-tert- butyl (1 -(2,5 -difluoro-4-(pyrazolo [1,5 -ajpyrimidin-7-yl)phenoxy)-2,4- dimethylpentan-2-yl)carbamate (40 mg, 0.087 mmol, 53% yield) as a brown solid which was carried forward without further purification. LCMS (ESI) m/e 461.2 [(M+H), calcd for C24H31F2N403 461.21; LC/MS retention time (Method Al): tR =2.73 mm.

Reference： [1]Patent: WO2017/59080,2017,A1.Location in patent: Page/Page column 275

8
5-bromo-2-fluoronicotinonitrile [ No CAS ]
[ 58347-49-2 ]
2-fluoro-5-(pyrazolo[1,5-a]pyrimidin-7-yl)nicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With tetrakis(triphenylphosphine) palladium(0); hexamethyldistannane; In 1,4-dioxane; at 150℃; for 2h;Inert atmosphere; Microwave irradiation;	A solution of 7-chloropyrazolo[l,5-ajpyrimidine (0.1 g, 0.651 mmol), 5- bromo-2-fluoronicotinonitrile (prepared as described in Example 487) (0.131 g, 0.651 mmol) and 1,1,1,2,2,2-hexamethyldistannane (0.213 g, 0.651 mmol) in 1,4- dioxane (2 mL) was purged with nitrogen gas forlO mm. Pd (Ph3P)4 (0.075 g, 0.065mmol) was added to the reaction mixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated in a microwave at 150 C forh. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (20 mL) and water (20 mL). The biphasic mixture was filtered through diatomaceous earth (Diatomaceous earth) and the bed was washed withethyl acetate (25 mL). The ethyl acetate layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a brown colored solid. The solid was purified by silica gel chromatography (0-40% EtOAc in pet ether) to afford 2-fluoro-5 -(pyrazolo [1,5 -aj pyrimidin-7-yl)nicotinonitrile (0.032 g, 0.134 mmol, 21% yield) as a light-yellow color solid. LCMS (ESI) m/e 239.0 [(M), calcdfor C12H6FN5 239.11; LC/MS retention time (Method Al): tR = 2.33 mm.

Reference： [1]Patent: WO2017/59080,2017,A1.Location in patent: Page/Page column 273

9
(S)-tert-butyl (1-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate [ No CAS ]
[ 58347-49-2 ]
(S)-tert-butyl (1-(2-chloro-4-(pyrazolo[1,5-a] pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; potassium bromide; In 1,4-dioxane; water; at 80℃; for 12h;Inert atmosphere;	A solution of 7-chloropyrazolo[1,5-ajpyrimidine (0.05 g, 0.326 mmol), (8)-tert-butyl (1 -(2-chloro-4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (prepared as described in Example 260, Part A and B) (0.152 g, 0.326 mmol), C52CO3 (0.212 g, 0.65 1 mmol), and KBr (0.039 g, 0.326 mmol) in 1,4-dioxane (10 mL) and water (1 mL) was purged with nitrogen gas for 30 mi PdC12 (dppf)-CH2C12 adduct (0.027 g, 0.033 mmol) was added to the reactionmixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated at 80 C for 12 h. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (30 mL) and water (30 mL). The biphasic mixture was filtered through diatomaceous earth. The diatomaceous earth was washed with ethyl acetate (50 mL). The organic layer wasseparated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford cmde product as a brown solid which was purified by silica-gel column chromatography (pet ether/ethyl acetate) to afford (5)-tert-butyl (1 -(2-chloro-4- (pyrazolo [1,5 -aj pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (0.08 g, 0.174 mmol, 54% yield) as an off-white solid. LCMS (ESI) m/e 459.2 [(M+H) ,calcd for C24H32C1N403 459.21; LC/MS retention time (Method Al): tR = 3.28 mm.

Reference： [1]Patent: WO2017/59080,2017,A1.Location in patent: Page/Page column 225

10
(S)-tert-butyl (2,4-dimethyl-1-((7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-4-yl)oxy)pentan-2-yl)carbamate [ No CAS ]
[ 58347-49-2 ]
(S)-2,4-dimethyl-1-((7-(pyrazolo[1,5-a]pyrimidin-7-yl)benzo[d]thiazol-4-yl)oxy)pentan-2-amine trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2017/59080,2017,A1

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Ghs Precautionary Statements

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P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *1-2 Days	Global Stock *3-4 Days	Quantity
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Purity	Size	Price	VIP Price	USA Stock *1-2 Days	Global Stock *3-4 Days	Quantity
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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. 58347-49-2 ]

Quality Control of [ 58347-49-2 ]

Related Doc. of [ 58347-49-2 ]

Product Details of [ 58347-49-2 ]

Computed Properties of [ 58347-49-2 ]

Safety of [ 58347-49-2 ]

Application In Synthesis of [ 58347-49-2 ]

[ 58347-49-2 ] Synthesis Path-Upstream 1~4

[ 58347-49-2 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 58347-49-2 ]

Chlorides

Related Parent Nucleus of [ 58347-49-2 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 58347-49-2 ]

Related Parent Nucleus of
[ 58347-49-2 ]