[ CAS No. 75449-26-2 ]

Name: 75449-26-2|[2,2'-Bipyridine]-3,3'-diamine|98%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 75449-26-2 ]

CAS No. :	75449-26-2	MDL No. :	MFCD00137932
Formula :	C₁₀H₁₀N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LSSHHQCMLSBUMT-UHFFFAOYSA-N
M.W :	186.21	Pubchem ID :	3577122
Synonyms :

Safety of [ 75449-26-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 75449-26-2 ]

* 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 [ 75449-26-2 ]
Downstream synthetic route of [ 75449-26-2 ]

[ 75449-26-2 ] Synthesis Path-Upstream 1~2

1
[ 75449-26-2 ]
[ 105166-53-8 ]

Reference： [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1985, vol. 33, # 9-10, p. 401 - 409

2
[ 75449-26-2 ]
[ 653-05-4 ]
[ 105166-53-8 ]

Reference： [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1985, vol. 33, # 9-10, p. 401 - 409

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Precautionary Statements-General
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P101	If medical advice is needed,have product container or label at hand.
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P211	Do not spray on an open flame or other ignition source.
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.
P243	Take precautionary measures against static discharge.
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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.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
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.
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
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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; for 16h;
95%	With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 8h;
95%	With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 8h;

95%	With palladium 10% on activated carbon; hydrogen In ethanol at 20℃;
95%	With hydrogen; palladium In ethanol at 20℃;
88%	With hydrogenchloride; tin In water at 120℃; for 1.5h; Cooling; Inert atmosphere;	10.b To a solution of 700 ml of hydrochloric acid (37%) in 800 ml of ice water are added 72 g (0.292 mol) of 3,3'-dinitro-2,2'-bipyridine and 249.0 g (2.029 mol) of Sn powder (exothermic, wait until cooled down). The green suspension is slowly heated to 120°C under nitrogen. After 1.5 hours TLC (CH2CI2) analysis showes that all starting material has been consumed. The reaction mixture is cooled to room temperature and filtered. The residue is suspended in 1000 ml of water : ethyl acetate 1 :1 , then 400 ml of NaOH (2N) are added (pH = 10). To the thick green-yellow mixture are added 250 ml of ethyl acetate, then the mixture is stirred for 30 minutes. After filtration (slow) the filtrate is stored during the weekend and shows after that time a nice phase separation. The phases are separated and the water phase is extracted 3 times with 250 ml of ethyl acetate each. The organic phase is washed with 250 ml of a puffer solution of pH 7 and 250 ml of brine, dried over Na2S04, filtered and evaporated to yield 51.7 g (88 %) of yellow crystals of 3,3'-diamino-2,2'- bipyridine. (0552) 1H NMR (400 MHz, CDCb): δ 7.98 (dxd,Ji=3.6Hz,J2=2.0Hz,2H); 7.06-7.01 (m,4H); 6.28 (
86%	With hydrogenchloride; tin(ll) chloride In water for 0.5h; Heating;
47%	With hydrogenchloride; tin(ll) chloride In ethanol Ambient temperature;
	With hydrogenchloride; tin(ll) chloride In water for 0.5h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
95.2%	With hydrogenchloride In water for 0.5h; Heating;
1.7 g	With hydrogenchloride In water for 1h; Reflux; Inert atmosphere; Schlenk technique;

Yield	Reaction Conditions	Operation in experiment
	With 4 A molecular sieve In toluene
	In toluene for 120h; Reflux; Dean-Stark; Inert atmosphere;

[ CAS No. 75449-26-2 ]

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Application In Synthesis of [ 75449-26-2 ]

[ 75449-26-2 ] Synthesis Path-Upstream 1~2

[ 75449-26-2 ] Synthesis Path-Downstream 1~68

Precautionary Statements-General

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Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76.6 percent / activated copper bronze / dimethylformamide / 4 h / 110 °C 2: 95.2 percent / HCl / H₂O / 0.5 h / Heating
	Multi-step reaction with 3 steps 1: 48 h / Inert atmosphere; Schlenk technique 2: copper / N,N-dimethyl-formamide / 3 h / 130 °C / Inert atmosphere; Schlenk technique 3: hydrogenchloride / water / 1 h / Reflux; Inert atmosphere; Schlenk technique

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76.6 percent / activated copper bronze / dimethylformamide / 4 h / 110 °C 2: 95.2 percent / HCl / H₂O / 0.5 h / Heating
	Multi-step reaction with 2 steps 1: copper / N,N-dimethyl-formamide / 3 h / 130 °C / Inert atmosphere; Schlenk technique 2: hydrogenchloride / water / 1 h / Reflux; Inert atmosphere; Schlenk technique

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 83 percent / copper / dimethylformamide / 2 h / 150 °C 2: 47 percent / SnCl₂*2H₂O, conc. HCl / ethanol / Ambient temperature
	Multi-step reaction with 2 steps 1: copper / N,N-dimethyl-formamide / 0.75 h / 150 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 8 h / 20 °C / 760.05 Torr
	Multi-step reaction with 2 steps 1: copper / N,N-dimethyl-formamide / 110 °C / Inert atmosphere 2: tin(ll) chloride; hydrogenchloride / water / 0.5 h / Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 85 percent / ethanol / 1) 4 h, room temperature, 2) 1 h, reflux 2: 1) NaH (80percent) / 1) DMF, 120-130 deg C, 30 min, 2) DMF, 100 deg C, 30 min 3: 99 percent / KOH, TBAB / dimethylsulfoxide / 3 h / 100 °C 4: 97 percent / 10percent HCl / 4 h / Heating
	Multi-step reaction with 3 steps 1: 85 percent / ethanol / 1) 4 h, room temperature, 2) 1 h, reflux 2: 75 percent / KOH, TBAB / dimethylsulfoxide / 100 - 110 °C 3: 97 percent / 10percent HCl / 4 h / Heating
	Multi-step reaction with 4 steps 1: 85 percent / ethanol / 1) 4 h, room temperature, 2) 1 h, reflux 2: 26 percent / KOH, TBAB / dimethylsulfoxide / 10 h / 100 - 110 °C 3: 25 percent / KOH, TBAB / dimethylsulfoxide / 2 h / 100 - 110 °C 4: 97 percent / 10percent HCl / 4 h / Heating

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85 percent / ethanol / 1) 4 h, room temperature, 2) 1 h, reflux 2: 1) NaH (80percent) / 1) DMF, 120-130 deg C, 30 min, 2) DMF, 100 deg C, 30 min 3: 99 percent / KOH, TBAB / dimethylsulfoxide / 3 h / 100 °C
	Multi-step reaction with 2 steps 1: 85 percent / ethanol / 1) 4 h, room temperature, 2) 1 h, reflux 2: 75 percent / KOH, TBAB / dimethylsulfoxide / 100 - 110 °C
	Multi-step reaction with 3 steps 1: 85 percent / ethanol / 1) 4 h, room temperature, 2) 1 h, reflux 2: 26 percent / KOH, TBAB / dimethylsulfoxide / 10 h / 100 - 110 °C 3: 25 percent / KOH, TBAB / dimethylsulfoxide / 2 h / 100 - 110 °C

Yield	Reaction Conditions	Operation in experiment
80%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
80%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
54%	In methanol; toluene for 6h; Reflux;
48%	In dichloromethane for 18h; Reflux; Darkness;
42%	In chloroform for 8h; Reflux;	Synthesis of 1 A suspension of 3,3′-diamino-2,2′-bipyridine (0.10 g,0.54 mmol) and pentacarbonylchlororhenium(I) (0.19 g,0.54 mmol) was allowed to reflux in chloroform (20 mL)for 8 h. After which time the solution was cooled and filteredto give (1) as a pale yellow solid (0.11 g, 42%).17 1HNMR (500 MHz, (CD3)2SO) δH 8.38 (dd, J = 5.0, 1.2 Hz,2H, py), 7.58 (dd, J = 8.5, 1.2 Hz, 2H, py), 7.40 (dd, J = 8.5,5.0 Hz, 2H, py), 6.19 (s, 4H, NH2); 13C (240 MHz,(CD3)2SO) 199.10 (C=O), 191.99 (C=O), 144.0 (py, quaternary),142.35 (py, CH), 139.96, (py, quaternary), 128.30(py, CH), 125.81 (py CH); IR (ATR, νCO) 2017, 1910 and1863 cm-1; ESI-MS: m/z 457 [M-Cl]+.

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 2,2'-bipyridine-3,3'-diamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-butane In tetrahydrofuran; hexane at 35℃; for 4h; Inert atmosphere;
3.5 g	Stage #1: 2,2'-bipyridine-3,3'-diamine With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 1-bromo-butane at 65℃; for 24h; Reflux;	Compound 2 synthetic (R₁ =- C₄ H₉ ): Under the protection of argon, will 2g compound 1 dissolved in tetrahydrofuran, and cooling to the -78 °C, slowly dropping 2.2 times equivalent n-BuLi, in this temperature 2 hours and adding 3 times equivalent Br - C4 H9 , Gradually raising the temperature to 65 °C reflux 24 hours. The restoration of the room temperature, evaporating solvent, column chromatography (methylene chloride: hexane as the mobile phase) purification 3.5g compound 2.