[ CAS No. 19539-50-5 ] {[proInfo.proName]}

Name: 19539-50-5|Furo[2,3-c]pyridine|96%
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SKU: A279212
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Structure of 19539-50-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 19539-50-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 19539-50-5 ]

SDS Specification

Alternatived Products of [ 19539-50-5 ]

Product Details of [ 19539-50-5 ]

CAS No. :	19539-50-5	MDL No. :	MFCD09955599
Formula :	C₇H₅NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZYXBIOIYWUIXSM-UHFFFAOYSA-N
M.W :	119.12	Pubchem ID :	12826108
Synonyms :

Safety of [ 19539-50-5 ]

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 [ 19539-50-5 ]

* 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 [ 19539-50-5 ]
Downstream synthetic route of [ 19539-50-5 ]

[ 19539-50-5 ] Synthesis Path-Upstream 1~22

1
[ 19539-50-5 ]
[ 10128-71-9 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 725 - 736
[2] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 725 - 736

2
[ 1219102-40-5 ]
[ 19539-50-5 ]

Yield	Reaction Conditions	Operation in experiment
43.3%	Stage #1: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine; trimethylsilylacetylene In tetrahydrofuran at 20℃; for 24 h; Inert atmosphere Stage #2: With potassium fluoride In methanol at 20℃; for 48 h;	To a solution of 198.1 (16.0g, 74.06mmol, l .Oeq), Trimethylsilylacetylene (9.43g, 96.78mmol, 1.3eq) and triethylamine (112.2g, 1110.9mmol, 15eq) in tetrahydrofuran (1.6L). The reaction mixture was degassed for 10 min. under argon atmosphere. The [l, l'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.6g, 2.22mmol, 0.03eq) and copper iodide (0.843g, 4.44mmol, 0.06eq) was added, again reaction mixture was degassed for 10 min. under argon atmosphere. The reaction was stirred at room temperature for 24h. After completion of reaction, reaction mixture was filtered and residue was concentrated under vacuum. The residue was diluted with methanol (2.2L) and potassium fluoride was added into reaction mixture. The reaction mixture was stirred at room temperature for 48h. After completion of reaction, reaction mixture was filtered through bed of celite and washed with ethyl acetate. Combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography using 10percent ethyl acetate in hexane to obtain pure 1.2 (3.82g, 43.30percent). MS(ES): m/z 120.12 [M+H]⁺

Reference： [1] Patent: WO2018/71794, 2018, A1, . Location in patent: Paragraph 00915; 00917

3
[ 84400-99-7 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1207 - 1209

4
[ 106531-53-7 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 549 - 552

5
[ 1334308-13-2 ]
[ 19539-50-5 ]

Reference： [1] Heterocycles, 2011, vol. 83, # 8, p. 1889 - 1896

6
[ 109-72-8 ]
[ 1219101-85-5 ]
[ 1219102-00-7 ]
[ 19539-50-5 ]

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 7, p. 2227 - 2235

7
[ 181526-20-5 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 2, p. 493 - 499

8
[ 10128-71-9 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 549 - 552

9
[ 18343-02-7 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 549 - 552

10
[ 106531-50-4 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 549 - 552

11
[ 106531-51-5 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 549 - 552

12
[ 18342-97-7 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 549 - 552

13
[ 84400-98-6 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1207 - 1209

14
[ 289473-47-8 ]
[ 19539-50-5 ]

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 7, p. 2227 - 2235

15
[ 1228187-59-4 ]
[ 19539-50-5 ]

Reference： [1] Heterocycles, 2011, vol. 83, # 8, p. 1889 - 1896

16
[ 1228187-72-1 ]
[ 19539-50-5 ]

Reference： [1] Heterocycles, 2011, vol. 83, # 8, p. 1889 - 1896

17
[ 1334308-12-1 ]
[ 19539-50-5 ]

Reference： [1] Heterocycles, 2011, vol. 83, # 8, p. 1889 - 1896

18
[ 34259-86-4 ]
[ 19539-50-5 ]

Reference： [1] Heterocycles, 2011, vol. 83, # 8, p. 1889 - 1896

19
[ 161417-28-3 ]
[ 19539-50-5 ]

Reference： [1] Patent: WO2018/71794, 2018, A1,

20
[ 108-24-7 ]
[ 193605-32-2 ]
[ 19539-50-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 941 - 952

21
[ 92404-66-5 ]
[ 19539-50-5 ]
[ 142503-06-8 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 413 - 422

22
[ 19539-50-5 ]
[ 112372-15-3 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 373 - 376

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[ 19539-50-5 ]

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Ghs Precautionary Statements

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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
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P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
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P391	Collect spillage. Hazardous to the aquatic environment
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
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H221	Flammable gas
H222	Extremely flammable aerosol
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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
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H252	Self-heating in large quantities; may catch fire
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H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
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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
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H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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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

Yield	Reaction Conditions	Operation in experiment
		A mixture of <strong>[19539-50-5]furo[2,3-c]-pyridine</strong> (918 mg, 7.7 mmol) in dry THF (45 mL) was cooled to -78 C. A solution of n-butyllithium in hexane (4.6 ml, c = 2.5 M, 1 1 .6 mmol) was added and the resulting mixture stirred for 1 h at -78 C. Tributyltin chloride (3.1 mL, 1 1 .6 mmol) was added at -78 C. The cooling bath was removed and the reaction mixture was stirred at room temperature for 2 h.Methanol was added and the solvent evaporated. Aminophase-silica-gel chromatography gave 1 .9 g of crude 2-(tributylstannyl)<strong>[19539-50-5]furo[2,3-c]pyridine</strong> which was used without further purification.
		A mixture of <strong>[19539-50-5]furo[2,3-c]-pyridine</strong> (918 mg, 7.7 mmoi) in anhydrous THF (45 mL) was cooled to -78C. A solution of n-butyllithium in hexane (4.6 ml, c = 2.5 M, 11.6 mmoi) was added and the resulting mixture was stirred for 1 h at -78C. Tributyltin chloride (3.1 mL, 11.6 mmoi) was added at -78C. The cooling bath was removed and the reaction mixture was stirred at room temperature for 2 h. Methanol was added and the solvent was evaporated. Aminophase-silica-gel chromatography gave 1.9 g of crude 2-(tributylstannyl)<strong>[19539-50-5]furo[2,3-c]pyridine</strong> which was used without further purification. To a stirred solution of crude 2-(tributylstannyl)<strong>[19539-50-5]furo[2,3-c]pyridine</strong> (1.9 g) in THF (20 mL) in an inert atmosphere was added 3-bromo-6-chloro-imidazo[1 ,2- fajpyridazine (676 mg, 2.9 mmol), copper (I) iodide (55 mg, 0.29 mmol) bis(triphenylphosphine) palladium(ll)chloride (102 mg, 0.145 mmol) and triphenylphosphine (38 mg, 0.145 mmol). The mixture was heated to reflux for 2 h. The solvent was removed in vaccuum. The residue was dissolved in a mixture of dichloromethane and methanol, filtered through an aminophase-silica-gel column and the solvent was removed in vaccuum. Silicagel chromatography gave a solid that was triturated with a mixture of ethyl acetate and hexane to give 343 mg of the title compound, which was used without further purification. 1H-NMR (300MHz, CHLOROFORM-d): delta [ppm]= 7.24 (d, 1 H), 7.62 (d, 1H), 7.71 (s, 1H), 8.07 (d, 1 H), 8.43 (s, 1H), 8.48 (d, 1 H), 8.95 (s, 1H). LCMS (Method 3): Rt = 0.63 min; MS (ESIpos) m/z = 271 [M+H]+.
		A mixture of <strong>[19539-50-5]furo[2,3-c]pyridine</strong> (918 mg, 7.7 mmol) in dry THF (45 mL) was cooled to -78C. A solution of n-butyllithium in hexane (4.6 mL, c = 2.5 M, 11.6 mmol) was added and the resulting mixture was stirred for 1 h at -78 C. Tributyltin chloride (3.1 mL, 11.6 mmol) was added at -78 C. The cooling bath was removed and the reaction mixture was stirred at room temperature for 2 h. Methanol was added and the solvent was evaporated. Aminophase-silica-gel chromatography gave 1.9 g of crude 2-(tributylstannyl)<strong>[19539-50-5]furo[2,3-c]pyridine</strong> which was used without further purification.

[ CAS No. 19539-50-5 ] {[proInfo.proName]}

Quality Control of [ 19539-50-5 ]

Related Doc. of [ 19539-50-5 ]

Product Details of [ 19539-50-5 ]

Safety of [ 19539-50-5 ]

Application In Synthesis of [ 19539-50-5 ]

[ 19539-50-5 ] Synthesis Path-Upstream 1~22

[ 19539-50-5 ] Synthesis Path-Downstream 1~88

Related Parent Nucleus of [ 19539-50-5 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Parent Nucleus of
[ 19539-50-5 ]