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Quality Control of [ 13534-97-9 ]

COA NMR CNMR HPLC LC-MS

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Product Citations

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong , et al. JOC,2022,87(2):910-919. DOI: 10.1021/acs.joc.1c01431 PubMed ID: 34983185

Abstract: In this study, we developed a

Purchased from AmBeed: class="">607-35-2 ; class="">578-66-5 ; class="">613-50-3 ; class="">100-19-6 ; class="">579-71-5 ; class="">3034-94-4 ; class="">5683-43-2 ; class="">99-92-3 ; class="">13534-97-9 ; class="">5676-60-8 ; class="">5470-18-8 ; class="">619-45-4 ; class="">553-26-4 ; class="">580-15-4 ; class="">611-34-7 ; class="span_more span_less">619-72-7 ; class="span_more span_less">100-13-0 ; class="span_more span_less">540-37-4 ; class="span_more span_less">1849-25-8 ; class="span_more span_less">4487-59-6 ; class="span_more span_less">555-16-8 ; class="span_more span_less">6298-19-7 ; class="span_more span_less">556-08-1 ; class="span_more span_less">953-26-4 ; class="span_more span_less">54060-30-9 ; class="span_more span_less">62-23-7 ; class="span_more span_less">607-34-1 ; class="span_more span_less">3867-18-3 ; class="span_more span_less">873-74-5 ; class="span_more span_less">3544-24-9 ; class="span_more span_less">94-52-0 ; class="span_more span_less">1520-21-4 ; class="span_more span_less">5470-34-8 ; class="span_more span_less">619-50-1 ; class="span_more span_less">586-39-0 ; class="span_more span_less">934-22-5 ; class="span_more span_less">402-54-0 ; class="span_more span_less">15411-43-5 ; class="span_more span_less">455-14-1 ; class="span_more span_less">17763-80-3 ; class="span_more span_less">3085-54-9 ; class="span_more span_less">1942-30-9 ; class="span_more span_less">1694-20-8 ; class="span_more span_less">6305-66-4 ; class="span_more span_less">41656-75-1 ; class="span_more span_less">6393-17-5 ; class="span_more span_less">4309-66-4 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Product Details of [ 13534-97-9 ]

CAS No. :	13534-97-9	MDL No. :	MFCD01646116
Formula :	C₅H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XTHKRYHULUJQHN-UHFFFAOYSA-N
M.W :	173.01	Pubchem ID :	642811
Synonyms :

Calculated chemistry of [ 13534-97-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.34
TPSA :	38.91 ?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) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.29
Log Po/w (XLOGP3) :	1.2
Log Po/w (WLOGP) :	1.43
Log Po/w (MLOGP) :	0.58
Log Po/w (SILICOS-IT) :	1.41
Consensus Log Po/w :	1.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.22
Solubility :	1.03 mg/ml ; 0.00597 mol/l
Class :	Soluble
Log S (Ali) :	-1.61
Solubility :	4.21 mg/ml ; 0.0243 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.51
Solubility :	0.531 mg/ml ; 0.00307 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.84

Safety of [ 13534-97-9 ]

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 [ 13534-97-9 ]

* 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 [ 13534-97-9 ]
Downstream synthetic route of [ 13534-97-9 ]

[ 13534-97-9 ] Synthesis Path-Upstream 1~1

1
[ 13534-97-9 ]
[ 915006-52-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With iodine; silver sulfate In ethanol	To a stirred solution of 6-bromo-pyridin-3-ylamine (10.2 g, 0.0580 mol) and Ag₂SO₄(18.1 g, 0.0580 mol) in EtOH (150 mL) was added 12 (7.59 g, 0.0580 mol) and the reaction was allowed to stir overnight. At this time hexane (200 mL) was added and the resultant mixture was filtered through Celite. The solvent was removed in vacuo, dissolved in CHCl₃(200 mL), washed with aqueous saturated Na₂S₂O₃(100 mL), water (1.x.100 mL), and dried (Na₂SO₄). The solvent was concentrated in vacuo and the residue was dissolved in hot EtOAc (100 mL), filtered and treated with hexanes (100 mL). Filtration gave 11.2 g (65percent) of the title compound as a white crystalline material. ¹H-NMR (CDCl₃; 400 MHz): δ 7.10 (d, 1H, J=8.2 Hz), 6.74 (d, 1H, J=8.2 Hz), 4.06 (br s, 2H).
65%	With iodine; silver sulfate In ethanol at 20℃;	To a stirred solution of 6-bromo-pyridin-3-ylamine (10.2 g, 0.0580 mol) and Ag₂SO₄(18.1 g, 0.0580 mol) in EtOH (150 mL) was added I₂(7.59 g, 0.0580 mol) and the reaction was allowed to stir overnight. At this time hexane (200 mL) was added and the resultant mixture was filtered through Celite. The solvent was removed in vacuo, dissolved in CHCl₃(200 mL), washed with aqueous saturated Na₂S₂O₃(100 mL), water (1.x.100 mL), and dried (Na₂SO₄). The solvent was concentrated in vacuo and the residue was dissolved in hot EtOAc (100 mL), filtered and treated with hexanes (100 mL). Filtration gave 11.2 g (65percent) of 6-bromo-2-iodo-pyridin-3-ylamine as a white crystalline material. ¹H-NMR (CDCl₃; 400 MHz): δ 7.10 (d, 1H, J=8.2 Hz), 6.74 (d, 1H, J=8.2 Hz), 4.06 (br s, 2H).
65%	With iodine; silver sulfate In ethanol	Example 51; 5-Cyano- lH-imidazole-2-carboxylic acid [2-(dimethyl-cyclohex- 1 -enyl)-6-( 1 -hydroxy- 1 - methyl-ethyl)-pyridin-3-yl]-amide; a) 6-Bromo-2-iodo-pyridin-3-ylamine; <n="112"/>To a stirred solution of 6-bromo-pyridin-3-ylamine (10.2 g, 0.0580 mol) and Ag₂SO₄ (18.1 g, 0.0580 mol) in EtOH (150 mL) was added I₂ (7.59 g, 0.0580 mol) and the reaction was allowed to stir overnight. At this time hexane (200 mL) was added and the resultant mixture was filtered through Celite. The solvent was removed in vacuo, dissolved in CHCl₃ (200 mL), washed with aqueous saturated Na₂S₂O₃ (100 mL), water (1 x 100 mL), and dried (Na₂SO₄). The solvent was concentrated in vacuo and the residue was dissolved in hot EtOAc (100 mL), filtered and treated with hexanes (100 mL). Filtration gave 11.2 g (65 percent) of the title compound as a white crystalline material. ¹H- NMR (CDCl₃; 400 MHz): δ 7.10 (d, IH, J = 8.2 Hz), 6.74 (d, IH, J = 8.2 Hz), 4.06 (br s, 2H). .

Reference： [1] Patent: US2007/249649, 2007, A1, . Location in patent: Page/Page column 74
[2] Patent: US2007/249608, 2007, A1, . Location in patent: Page/Page column 41
[3] Patent: WO2007/123516, 2007, A1, . Location in patent: Page/Page column 109-110
[4] Patent: WO2009/149820, 2009, A1, . Location in patent: Page/Page column 82-83
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8860 - 8871

[ 13534-97-9 ] Synthesis Path-Downstream 1~11

1
[ 13534-97-9 ]
[ 39856-56-9 ]

Yield	Reaction Conditions	Operation in experiment
5.2 g (40%)	With formaldehyd; aqueous KOH; HCO2H; In dichloromethane; water; Petroleum ether;	(1) Synthesis of 2-bromo-5-dimethylaminopyridine 2-bromo-5-aminopyridine (11.7 g, 67.6 mmol) was added portionwise to HCO2H (20 ml) at 0 C. Formaldehyde (37% in water, 17 ml, 210 mmol) was then added and the mixture heated to reflux for hours. The reaction was then cooled to room temperature and an aqueous KOH solution (1N, ml) was added. The mixture was extracted with Et2O (3100 ml) and the combined extract was dried over MgSO4, filtered and evaporated to dryness. The residual oil was purified by flash chromatography on silica (CH2Cl2). The yellowish solid was dissolved in the minimum volume of CH2Cl2, petroleum ether (150 ml) was added and the solution was stand in the fridge overnight. The white crystalline solid was filtered and washed with small portion of cold petroleum ether to afford 5.2 g (40%) of the desired compound as white crystalline solid. 1H-NMR (CDCl3, 298K, 200 MHz, delta ppm) delta 2.96 (s, 6H), 6.87 (dd, J=2.59 Hz, 1H), 7.25 (d, J=9 Hz, 1H), 7.84 (d, J=2.5 Hz, 1H).

Reference： [1]Patent: US2009/200920,2009,A1

2
[ 13534-97-9 ]
[ 882521-96-2 ]
[ 120-07-0 ]
[ 160539-04-8 ]

Reference： [1]Synthesis,2010,p. 85 - 90

3
[ 13534-97-9 ]
[ 5720-07-0 ]
[ 52057-98-4 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux;	General procedure: To 0.329 g (1.5 mmol) 4-iodoaniline, 1.8 mmol ArB(OH)2, 0.318 g (3 mmol) Na2CO3 and 75 mg (0.075 mmol) PdCl2(PPh3)2, 15 mL of a blended solution of dioxane and water (v/v = 3/1) was added under N2 atmosphere. Then the reaction was heated to reflux and monitored by TLC. Upon cooling, the reaction mixture was dilute with sat. NH4Cl solution, then extracted with EA (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography to afford different 4-aminobiphenyl derivatives. According to the reductive amination procedure, the 4-aminobiphenyl derivative was further treated with salicylaldehyde and to afford the corresponding compound 5&6.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3057 - 3061

4
[ 13534-97-9 ]
[ 145349-76-4 ]
2-(((6-(4-(ethylthio)phenyl)pyridin-3-yl)amino)methyl)phenol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3057 - 3061

5
[ 13534-97-9 ]
[ 145349-76-4 ]
C₁₃H₁₄N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux;	General procedure: To 0.329 g (1.5 mmol) 4-iodoaniline, 1.8 mmol ArB(OH)2, 0.318 g (3 mmol) Na2CO3 and 75 mg (0.075 mmol) PdCl2(PPh3)2, 15 mL of a blended solution of dioxane and water (v/v = 3/1) was added under N2 atmosphere. Then the reaction was heated to reflux and monitored by TLC. Upon cooling, the reaction mixture was dilute with sat. NH4Cl solution, then extracted with EA (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography to afford different 4-aminobiphenyl derivatives. According to the reductive amination procedure, the 4-aminobiphenyl derivative was further treated with salicylaldehyde and to afford the corresponding compound 5&6.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3057 - 3061

6
[ 13534-97-9 ]
[ 74-88-4 ]
[ 39856-56-9 ]

Yield	Reaction Conditions	Operation in experiment
72%		To a solution of 6- bromopyridin-3 -amine (300 mg, 1.73 mmol) in tetrahydrofuran (30 ml) was added 1 M solution of lithium bis(trimethylsilyl)amide (3.46 mL, 3.46 mmol) in tetrahydrofuran over 5 min at - 78 C under nitrogen atmosphere. After stirring for 30 min at -78 C, iodomethane (566 mg, 3.99 mmol) was added. The resulting mixture was stirred for 1 hour at ambient temperature and then quenched by the addition of saturated aqueous solution of ammonium chloride (50 mL). The resulting mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic layers was washed with brine (2 x 50 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluted with 1-10% ethyl acetate in petroleum ether to afford 6-bromo- N,N-dimethylpyridin-3 -amine as a light yellow solid: MS (ESI, m/z): 201.0, 203.0 [M + 1]+.

Reference： [1]Patent: WO2015/188368,2015,A1 .Location in patent: Page/Page column 54
[2]European Journal of Organic Chemistry,2020

7
[ 13534-97-9 ]
[ 50-00-0 ]
[ 39856-56-9 ]

Yield	Reaction Conditions	Operation in experiment
0.43 g	With formic acid; at 90℃; for 16h;	Step a. To a solution of 6-bromopyridin-3 -amine (CAS Number 97-65-4) (1 g, 5.78 mmol) in formic acid (5 ml) was added para-formaldehyde (1.5 g, 1.5 eq w/w) at rt. The reaction mixture was heated at 90C for 16 hr. The resulting reaction mixture was poured into ice cold water, basified using solid sodium carbonate and extracted using EtOAc (30ml x 3). The organic layer was combined and dried over Na2S04 concentrated under reduced pressure. The obtained residue was purified using column chromatography (20% EtOAc in hexane) yielding 6-bromo-N, N-dimethylpyridin-3 -amine (0.43 g, 2.160 mmol). LCMS: Method C, 1.77 min, MS: ES+ 201.14. NMR (400 MHz, DMSO-d6) delta ppm 8.31-8.32 (d, 1 H), 7.84-7.85 (d, 1 H), 7.33-7.35 (d, 1 H), 2.91 (s, 6 H).

Reference： [1]Patent: WO2017/9650,2017,A1 .Location in patent: Page/Page column 87

8
[ 110-91-8 ]
[ 13534-97-9 ]
[ 52023-68-4 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2809 - 2812

9
[ 13534-97-9 ]
[ 1022641-52-6 ]

Reference： [1]Patent: WO2017/207813,2017,A1

10
[ 13534-97-9 ]
[ 160539-04-8 ]

Reference： [1]Patent: EP3498694,2019,A1

11
[ 13534-97-9 ]
[ 17997-47-6 ]
[ 160539-04-8 ]

Yield	Reaction Conditions	Operation in experiment
43.5%	With tetrakis(triphenylphosphine) palladium(0); In toluene; at 130℃; for 48h;Inert atmosphere;	Method B: To a solution of 55 6-bromopyridin-3-amine (50 mg, 0.29 mmol) in 1.5 mL of dry 63 toluene at room temperature, was added 64 2-(tributylstannyl)pyridine (0.013 mL, 0.35 mmol) dropwise under N2 atmosphere following by the addition of 65 tetrakis(triphenylphosphine)palladium (40.2 mg, 0.03 mmol). The reaction mixture was degassed with nitrogen and was stirred at 130c for two days. The reaction was cooled to room temperature. Next, the mixture was taken up with NaOH 2M and separated with ethyl acetate (x2). The organic layer was washed with brine, was dried with Na2SO4 and the solvent was removed under vacuum. The crude was purified by CombiFlash chromatography column (DCM/DCM:MeOH 20%) to afforded the desired compound (21.6 mg, 43.5 %). 1H-NMR (400 MHz, DMSO-d6): δ = 8.54 (d, 1 H), 8.17 (d, 1 H), 8.08 (d, 1 H), 8.01 (d, 1 H), 7.80 (td, 1 H), 7.25 (m, 1 H), 7.01 (dd, 1 H), 5.65 (s, 2H). HPLC-MS: Rt 2.746; m/z 172.0 (MH+).

Reference： [1]Patent: EP3498694,2019,A1 .Location in patent: Paragraph 0144

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Technical Information

? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

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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.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
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

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

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[ CAS No. 13534-97-9 ] {[proInfo.proName]}

Quality Control of [ 13534-97-9 ]

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[ 13534-97-9 ] Synthesis Path-Upstream 1~1

[ 13534-97-9 ] Synthesis Path-Downstream 1~11

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Bromides

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Pyridines

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[ 13534-97-9 ]

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[ 13534-97-9 ]