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100-70-9

Basic Information
CAS No.: 100-70-9
Name: 2-Cyanopyridine
Article Data: 212
Cas Database
Molecular Structure:
Molecular Structure of 100-70-9 (2-Cyanopyridine)
Formula: C6H4N2
Molecular Weight: 104.111
Synonyms: 2-Cyano pyridine;Picolinonitrile(6CI,8CI);2-Azabenzonitrile;2-Pyridinenitrile;2-Pyridylcyanide;2-Pyridylnitrile;NSC 59697;Picolinic acid nitrile;a-Cyanopyridine;
EINECS: 202-880-3
Density: 1.12 g/cm3
Melting Point: 26-28 °C
Boiling Point: 225.5 °C at 760 mmHg
Flash Point: 89.4 °C
Solubility: immiscible with water
Appearance: white to brown low melting crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38-20/21/22
Safety: 26-24/25
Transport Information: UN 3276
PSA: 36.68000
LogP: 0.95328
Synthetic route
109-04-6

2-bromo-pyridine

potassium ferrocyanide

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; copper(l) iodide In toluene at 160℃; for 16h; Product distribution / selectivity;100%
With 1-methyl-1H-imidazole; copper(l) iodide at 140℃; for 16h; Product distribution / selectivity;100%
With 1,3-bis-(diphenylphosphino)propane; sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 130℃; for 16h; Product distribution / selectivity;30%
1121-60-4

pyridine-2-carbaldehyde

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; trimethylsilylazide In acetonitrile at 25℃; for 0.00138889h; Schmidt Reaction; Flow reactor;99%
Stage #1: pyridine-2-carbaldehyde With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: With potassium hydrogen difluoride; 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate In water at 20℃; for 3h;
96%
With ammonium acetate; phenyltrimethylammonium tribromide In dichloromethane at 20℃; for 17h; Reagent/catalyst; Solvent; Time;95%
355023-81-3

t-butyl α-anti-(methoxycarbonyl)oximino-α-(2-pyridyl)acetate

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃; for 6h;99%

t-butyl α-anti-{[(S)-α-methylbenzyl]carbamoyl}oximino-α-(2-pyridyl)acetate

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃; for 36h;99%
5029-67-4

2-iodopyridine

773837-37-9

sodium cyanide

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;99%
109-04-6

2-bromo-pyridine

75-86-5

2-hydroxy-2-methylpropanenitrile

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine With copper(l) iodide; 1,10-Phenanthroline; potassium iodide In N,N-dimethyl-formamide at 110℃; for 6h;
Stage #2: 2-hydroxy-2-methylpropanenitrile With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 48h;
98%
With 1-Butylimidazole; copper(l) iodide; sodium carbonate In o-xylene at 150℃; for 21h; Inert atmosphere; Pressure tube;91%
873-69-8

2-pyridinealdoxime

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 3h;97%
With trichloro(trifluoromethanesulfonato)titanium(IV) at 80℃; for 10h; Dehydration;95%
With thionyl chloride; polyvinylpyrrolidone In dichloromethane at 20℃; for 0.25h; Dehydration;93%
109-04-6

2-bromo-pyridine

151-50-8

potassium cyanide

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tributyltin chloride; tris(dibenzylideneacetone)dipalladium (0) In acetonitrile at 80℃; for 17h;96%
109-06-8

α-picoline

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With ammonia; water; oxygen; V*0.5Sn*7.5Ti*xO at 400℃; for 0.000130556h; Oxidation;95%
With cobalt(II) 5,10,15,20-tetraphenylporphyrin; ammonia; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate at 300℃; for 12h; Temperature;95.7%
With ammonium hydroxide at 370℃; Temperature; Flow reactor;86%
109-06-8

α-picoline

A

110-86-1

pyridine

B

100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With air; ammonia; water; vanadia; titanium(IV) oxide; tin(IV) oxide at 380℃; for 0.000105556h; Product distribution; var. reagents ratios, temp. and contact time;A 3%
B 95%
With air; ammonia; water; vanadia; titanium(IV) oxide; tin(IV) oxide at 380℃; for 0.000105556h;A 3%
B 95%
With air; water; vanadia at 380℃; for 0.000508333h;A 86%
B 3.2%
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    Product Name: 2-Cyanopyridine Synonyms: 2-pyridinecarboxylicacid,nitrile;2-Pyridyl nitrile;2-pyridylnitrile;CYANOPYRIDINE(2-);AKOS BBS-00004280;2-CYANOPYRIDINE;2-PYRIDINECARBONITRILE;2-PICOLINONITRILE CAS: 100-70-9 MF: C6H4N2 MW: 104.1

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Specification

The 2-Cyanopyridine is an organic compound with the formula C6H4N2. The IUPAC name of this chemical is pyridine-2-carbonitrile. With the CAS registry number 100-70-9 and EINECS 202-880-3, it is also named as 2-Pyridinecarboxylic acid, nitrile. The product's categories are Pyridine; Pyridines Derivates. It is white to brown low melting crystalline solid which is immiscible with water. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.51; (4)ACD/LogD (pH 7.4): 0.51; (5)ACD/BCF (pH 5.5): 1.44; (6)ACD/BCF (pH 7.4): 1.44; (7)ACD/KOC (pH 5.5): 45.22; (8)ACD/KOC (pH 7.4): 45.22; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 36.68 Å2; (13)Index of Refraction: 1.539; (14)Molar Refractivity: 29.11 cm3; (15)Molar Volume: 92.8 cm3; (16)Surface Tension: 51.4 dyne/cm; (17)Enthalpy of Vaporization: 46.2 kJ/mol; (18)Vapour Pressure: 0.0861 mmHg at 25°C; (19)Exact Mass: 104.037448; (20)MonoIsotopic Mass: 104.037448; (21)Topological Polar Surface Area: 36.7; (22)Heavy Atom Count: 8; (23)Complexity: 111.

Preparation of 2-Cyanopyridine: It can be obtained by pyridine-2-carbaldehyde oxime. This reaction which is a kind of dehydration needs reagent TiCl3(OTf) at temperature of 80 °C. The reaction time is 10 hours. The yield is 95%.

Uses of 2-Cyanopyridine: It is used as intermediate in pharmaceutical, dye and other industries. It also can react with S-Methylcysteinol to get (R)-(-)-4,5-dihydro-4-(methylsulfanylmethyl)-2-(2-pyridyl)oxazole. This reaction needs reagent ZnCl2 and solvent chlorobenzene at temperature of 135 °C. The reaction time is 16 hours. The yield is 36%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
1. SMILES:N#Cc1ncccc1
2. InChI:InChI=1/C6H4N2/c7-5-6-3-1-2-4-8-6/h1-4H
3. InChIKey:FFNVQNRYTPFDDP-UHFFFAOYAF