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2,2'-Dipicolylamine
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Name

2,2'-Dipicolylamine

 EINECS 216-266-8
CAS No. 1539-42-0 Density 1.118 g/cm3
PSA 37.81000 LogP 2.15730
Solubility N/A Melting Point N/A
Formula C12H13N3 Boiling Point 322.159 °C at 760 mmHg
Molecular Weight 199.255 Flash Point 148.637 °C
Transport Information N/A Appearance N/A
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 1539-42-0 (2,2'-DIPICOLYLAMINE) Hazard Symbols IrritantXi
Synonyms

Di(2-pyridylmethyl)amine;Di-2-picolylamine;N,N-Bis(2-pyridylmethyl)amine;N,N-Bis[(pyridin-2-yl)methyl]amine;N,N-Di-2-picolylamine;NSC 176070;Pyridine,2,2'-(iminodimethylene)di- (7CI,8CI);Bis(2-picolyl)amine;Bis(2-pyridinylmethyl)amine;Bis(2-pyridylmethyl)amine;1-(Pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine;1-Pyridin-2-yl-N-(pyridin-2-ylmethyl)methanamine;

Article Data 70

2,2'-Dipicolylamine Synthetic route

100-70-9

2-Cyanopyridine

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In ethanol for 72h; Molecular sieve;99.7%
With sodium tetrahydroborate; La0.5Ca0.5CoO3 In methanol at 40℃; under 760.051 Torr; for 0.583333h; chemoselective reaction;85%
With hydrogen; palladium on activated charcoal In ethanol; water for 9h; Ambient temperature;
1121-60-4

pyridine-2-carbaldehyde

3731-51-9

(2-aminomethylpyridine)

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
Stage #1: pyridine-2-carbaldehyde; 2-(Aminomethyl)pyridine In methanol at 20℃; for 10h;
Stage #2: With methanol; sodium tetrahydroborate at 20℃;		95%
Stage #1: pyridine-2-carbaldehyde; 2-(Aminomethyl)pyridine In methanol at 20℃; for 1h;
Stage #2: With methanol; sodium tetrahydroborate at 0 - 20℃;		95%
Stage #1: pyridine-2-carbaldehyde; 2-(Aminomethyl)pyridine In ethanol at 0℃; for 4h;
Stage #2: With sodium tetrahydroborate at 0 - 20℃; for 12h;
Stage #3: With hydrogenchloride In water for 1h;		89%
117053-67-5

N,N-di(2-picolyl)-4-methylbenzenesulfonamide

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 2h;94%
3731-51-9

(2-aminomethylpyridine)

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With 5 % Pd/TiO2 at 30℃; for 24h; Inert atmosphere; UV-irradiation;85%
With bis(dichloro[η5-pentamethylcyclopentadienyl]iridium) at 170℃; for 18h; Neat (no solvent);79%
Multi-step reaction with 2 steps
1: Zn powder / acetic acid
View Scheme
1206455-31-3

C18H16N4O4S

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With potassium carbonate; thiophenol In N,N-dimethyl-formamide74%
With potassium carbonate; thiophenol In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;
119715-60-5

(E)-1-(pyridine-2-yl)-N-(pyridine-2-ylmethylene)methaneamine

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol; acetic acid; acetonitrile at 20℃; for 18h;73%
With sodium tetrahydroborate
3731-51-9

(2-aminomethylpyridine)

2038-57-5

3-Phenylpropan-1-amine

A

1539-42-0

bis[(2-pyridyl)methyl]amine

B

137649-90-2

N-(3-phenylpropyl)-2-pyridinemethanamine

Conditions
ConditionsYield
With 1-(3-amino-2,4-dihydroxyphenyl)-1-ethanone In methanol at 20℃; for 4h; Inert atmosphere; Electrochemical reaction; chemoselective reaction;A 4%
B 61%
586-98-1

2-Hydroxymethylpyridine

3731-51-9

(2-aminomethylpyridine)

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With Ru3(2-(2-hydroxoethyl)pyridine)2(CO)8; potassium tert-butylate In toluene at 110℃; Molecular sieve; Inert atmosphere;41%
100-70-9

2-Cyanopyridine

A

586-98-1

2-Hydroxymethylpyridine

B

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; water; hydrogen; silica gel; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In hexane at 100℃; under 10343.2 Torr; for 48h; Autoclave; Green chemistry; chemoselective reaction;A 8%
B n/a
119715-60-5

N-(2-pyridylmethyl)-2-pyridylmethanimine

1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 3h;
With sodium tetrahydroborate In methanol for 0.25h; microwave irradiation;
With zinc In acetic acid

2,2'-Dipicolylamine Specification

The 2-Pyridinemethanamine,N-(2-pyridinylmethyl)-, with the CAS registry number 1539-42-0, is also known as Bis(2-pyridinylmethyl)amine. It belongs to the product categories of Heterocyclic Compounds; Heterocyclic Building Blocks; Pyridines. Its EINECS number is 216-266-8. This chemical's molecular formula is C12H13N3 and molecular weight is 298.34. What's more, its systematic name is 1-pyridin-2-yl-N-(pyridin-2-ylmethyl)methanamine. It should be sealed and stored in a cool and dry place. What's more, it should be ensured that the workshop is well ventilated or equipped with exhaust devices.

Physical properties of 2-Pyridinemethanamine,N-(2-pyridinylmethyl)- are: (1)ACD/LogP: 0.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.01; (4)ACD/LogD (pH 7.4): 0.43; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.24; (7)ACD/KOC (pH 5.5): 14.79; (8)ACD/KOC (pH 7.4): 40.28; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 29.02 Å2; (13)Index of Refraction: 1.589; (14)Molar Refractivity: 60.06 cm3; (15)Molar Volume: 178.2 cm3; (16)Polarizability: 23.81×10-24cm3; (17)Surface Tension: 49.3 dyne/cm; (18)Density: 1.118 g/cm3; (19)Flash Point: 148.6 °C; (20)Enthalpy of Vaporization: 56.4 kJ/mol; (21)Boiling Point: 322.2 °C at 760 mmHg; (22)Vapour Pressure: 0.000284 mmHg at 25°C.

Preparation of 2-Pyridinemethanamine,N-(2-pyridinylmethyl)-: this chemical can be prepared by N-Tosyl-bis(2-pyridylmethyl)amin at the temperature of 100 °C. This reaction will need reagent conc. H2SO4 with the reaction time of 2 hours. The yield is about 94%.

2-Pyridinemethanamine,N-(2-pyridinylmethyl)- can be prepared by N-Tosyl-bis(2-pyridylmethyl)amin at the temperature of 100 °C

Uses of 2-Pyridinemethanamine,N-(2-pyridinylmethyl)-: it can be used to produce 3-(bis-pyridin-2-ylmethyl-amino)-propionic acid at the temperature of 80 °C. It will need reagent triethylamine and solvent ethanol with the reaction time of 18 hours. The yield is about 43%.

2-Pyridinemethanamine,N-(2-pyridinylmethyl)- can be used to produce 3-(bis-pyridin-2-ylmethyl-amino)-propionic acid at the temperature of 80 °C

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=NC(=C1)CNCC2=CC=CC=N2
(2)InChI: InChI=1S/C12H13N3/c1-3-7-14-11(5-1)9-13-10-12-6-2-4-8-15-12/h1-8,13H,9-10H2
(3)InChIKey: KXZQYLBVMZGIKC-UHFFFAOYSA-N

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