Product Name

  • Name

    2-Cyanopyrimidine

  • EINECS 604-202-5
  • CAS No. 14080-23-0
  • Article Data24
  • CAS DataBase
  • Density 1.22 g/cm3
  • Solubility
  • Melting Point 40-44 °C(lit.)
  • Formula C5H3N3
  • Boiling Point 250.7 °C at 760 mmHg
  • Molecular Weight 105.099
  • Flash Point 97.2 °C
  • Transport Information
  • Appearance crystalline solid
  • Safety 26-36/37/39-45-16
  • Risk Codes 22-37/38-41-43-34-11
  • Molecular Structure Molecular Structure of 14080-23-0 (2-Cyanopyrimidine)
  • Hazard Symbols HarmfulXn,CorrosiveC,FlammableF
  • Synonyms 2-Pyrimidinecarbonitrile;2-cyanpyrimidine;
  • PSA 49.57000
  • LogP 0.34828

Synthetic route

tetraethylammoniumcyanide
13435-20-6

tetraethylammoniumcyanide

N,N,N-trimethylpyrimidin-2-aminium chloride
14395-12-1

N,N,N-trimethylpyrimidin-2-aminium chloride

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;93%
In dichloromethane for 0.5h; Ambient temperature;84%
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

sodium cyanide
143-33-9

sodium cyanide

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In dimethyl sulfoxide; isopropyl alcohol at 30 - 35℃; for 5h;93%
In N,N-dimethyl-formamide at 60 - 70℃; for 24h;49%
With trimethylamine In N,N-dimethyl-formamide at 25℃; for 66h; Product distribution; Thermodynamic data; ΔH, E(a); var. catalysts, solvents and times;95 % Chromat.
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

dicyanozinc
557-21-1

dicyanozinc

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With racemic 2-di-tert-butylphosphino-1,1'-binaphthyl; palladium(II) trifluoroacetate; zinc In N,N-dimethyl acetamide at 80℃; for 6h;86.6%
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

sodium cyanide
773837-37-9

sodium cyanide

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In water; dimethyl sulfoxide82%
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

potassium cyanide
151-50-8

potassium cyanide

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; water In dimethyl sulfoxide at 20℃; for 48h;80%
With tetraethylammonium acetate In water; N,N-dimethyl-formamide at 90℃; for 48h;27%
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

potassium cyanide

potassium cyanide

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With 3-quinuclidinol In dimethyl sulfoxide at 70℃; for 2.5h;71%
With 1,4-diaza-bicyclo[2.2.2]octane In water; dimethyl sulfoxide at 20℃; for 48h;65%
With 1,4-diaza-bicyclo[2.2.2]octane In dimethyl sulfoxide at 20℃; for 48h;
pyrimidine-2-diazonium o-benzenedisulfonimide

pyrimidine-2-diazonium o-benzenedisulfonimide

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
In acetonitrile at 22℃; for 1h; Sandmeyer Reaction;69%
pyrimidin-2-carbaldehyde oxime
39232-40-1

pyrimidin-2-carbaldehyde oxime

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With Burgess Reagent In dichloromethane at 25℃; for 2h; Dehydration;63%
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

trimethylamine
75-50-3

trimethylamine

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With benzene Erwaermen des Reaktionsprodukts mit KCN in Gegenwart von Acetamid;
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With sodium sulfite Erhitzen des Reaktionsprodukts mit KCN im Vakuum;
With 1,4-diaza-bicyclo[2.2.2]octane; sodium hydroxide In water; dimethyl sulfoxide
In water; dimethyl sulfoxide
pyrimidine-2-carboxamide
88511-48-2

pyrimidine-2-carboxamide

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With trichlorophosphate
pyrimidine N-oxide
17043-94-6

pyrimidine N-oxide

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

A

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

B

Pyrimidine-4-carbonitrile
42839-04-3

Pyrimidine-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In acetonitrile for 0.17h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
...Expand
potassium cyanide
151-50-8

potassium cyanide

N,N,N-trimethylpyrimidin-2-aminium chloride
14395-12-1

N,N,N-trimethylpyrimidin-2-aminium chloride

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With tetramethlyammonium chloride In dichloromethane; water at 25℃; for 2h; Yield given;
5-bromo-pyrimidine-2-carboxylic acid amide
38275-60-4

5-bromo-pyrimidine-2-carboxylic acid amide

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Raney nickel; ethanol; diethyl ether / Hydrogenation.Reagens 4:wss.Na2CO3
2: POCl3
View Scheme
methyl 5-bromo-2-pyrimidinecarboxylate
89581-38-4

methyl 5-bromo-2-pyrimidinecarboxylate

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol; NH3
2: Raney nickel; ethanol; diethyl ether / Hydrogenation.Reagens 4:wss.Na2CO3
3: POCl3
View Scheme
sodium cyanide
773837-37-9

sodium cyanide

2-bromopyrimidine
4595-60-2

2-bromopyrimidine

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In dimethyl sulfoxide at 20℃; for 1h;
pyrimidine-2-carbothioamide
4537-73-9

pyrimidine-2-carbothioamide

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Conditions
ConditionsYield
With methylene blue; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; Sealed tube; Irradiation;25.7 mg
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

sodium methylate
124-41-4

sodium methylate

methyl ester of imino-pyrimidine acid
57871-18-8

methyl ester of imino-pyrimidine acid

Conditions
ConditionsYield
In methanol at 20℃; for 1h;100%
In methanol
In methanol at 20℃;
In methanol
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

pyrimidine-2-carboxamidine hydrochloride

pyrimidine-2-carboxamidine hydrochloride

Conditions
ConditionsYield
With sodium methylate; ammonium chloride In methanol at 20℃; for 18h;100%
Stage #1: 2-cyanopyrimidine With sodium methylate In methanol for 48h;
Stage #2: With ammonium chloride In methanol for 24h;		84%
Stage #1: 2-cyanopyrimidine With sodium methylate In methanol at 20℃; for 24h;
Stage #2: With ammonium chloride; acetic acid In methanol at 20℃; for 24h;		37.9%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

pyrimidine-2-carboximidohydrazide
1005-03-4

pyrimidine-2-carboximidohydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; for 2h;100%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

pyrimidine-2-carboxamide
88511-48-2

pyrimidine-2-carboxamide

Conditions
ConditionsYield
With manganese(IV) oxide; water In isopropyl alcohol at 100℃; under 5171.62 Torr; for 0.05h; Catalytic behavior; Temperature;99%
With cerium(IV) oxide; water at 30℃; for 3h;92%
With C14H30ClN3PRh; water at 100℃; for 1h; Catalytic behavior; Inert atmosphere; Schlenk technique;89%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

ethanol
64-17-5

ethanol

2-ethoxy pyrimidine
3739-82-0

2-ethoxy pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 2h;98%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

2-isobutoxypyrimidine
10132-13-5

2-isobutoxypyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 2h;98%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

2-[(4-methylbenzyl)oxy]pyrimidine

2-[(4-methylbenzyl)oxy]pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 4h;97%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

2-methylisothiourea sulphate
14527-26-5, 867-44-7

2-methylisothiourea sulphate

2-(methylsulfanyl)pyrimidine
823-09-6

2-(methylsulfanyl)pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 2h;97%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

S-cyclopropylmethylisothiourea hydrobromide
63667-17-4

S-cyclopropylmethylisothiourea hydrobromide

2-[(cyclopropylmethyl)thio]pyrimidine

2-[(cyclopropylmethyl)thio]pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 4h;97%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

benzyl alcohol
100-51-6

benzyl alcohol

2-(benzyloxy)pyrimidine
4214-64-6

2-(benzyloxy)pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 5h; Solvent; Reagent/catalyst; Temperature;96%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

2-phenylethanol
60-12-8

2-phenylethanol

2-phenethoxypyrimidine

2-phenethoxypyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 3h;96%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

Cyclopropylmethanol
2516-33-8

Cyclopropylmethanol

2-(cyclopropylmethoxy)pyrimidine

2-(cyclopropylmethoxy)pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 5h;96%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

C6H12N2S*BrH

C6H12N2S*BrH

2-[(cyclobutylmethyl)thio]pyrimidine

2-[(cyclobutylmethyl)thio]pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 4h;96%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

2-pent-4-enyl-isothiourea; hydrobromide

2-pent-4-enyl-isothiourea; hydrobromide

2-(pent-4-en-1-ylthio)pyrimidine

2-(pent-4-en-1-ylthio)pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 4h;96%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

2-(1H-tetrazol-5-yl)pyrimidine
13600-33-4

2-(1H-tetrazol-5-yl)pyrimidine

Conditions
ConditionsYield
With sodium azide; betaine; zinc(II) chloride In water at 20℃; for 20h;95%
With sodium azide; water; zinc(II) chloride at 25℃; for 24h; Micellar solution;88%
With sodium azide; zinc(II) chloride In water at 25℃; for 24h;88%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

2-aminomethylpyrimidine
75985-45-4

2-aminomethylpyrimidine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol under 760.051 Torr; for 12h; Inert atmosphere;95%
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 3h;44%
With hydrogen; Pd-C; ammonia In ethanol
pyrrolidine
123-75-1

pyrrolidine

2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

2-(pyrrolidine-1-yl)pyrimidine
192197-34-5

2-(pyrrolidine-1-yl)pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 5h;95%

2-Cyanopyrimidine Chemical Properties

Molecular Structure of 2-Cyanopyrimidine (CAS NO. 14080-23-0):

IUPAC Name: Pyrimidine-2-carbonitrile 
Molecular Formula: C5H3N3
Molecular Weight: 105.09742 g/mol
XLogP3: -0.3
H-Bond Donor: 0
H-Bond Acceptor: 3
Canonical SMILES: C1=CN=C(N=C1)C#N
InChI: InChI=1S/C5H3N3/c6-4-5-7-2-1-3-8-5/h1-3H
InChIKey: IIHQNAXFIODVDU-UHFFFAOYSA-N
Index of Refraction: 1.54
Molar Refractivity: 26.91 cm3
Molar Volume: 85.7 cm3
Surface Tension: 65.8 dyne/cm
Density: 1.22 g/cm3
Flash Point: 97.2 °C
Enthalpy of Vaporization: 48.79 kJ/mol
Boiling Point: 250.7 °C at 760 mmHg
Vapour Pressure: 0.0214 mmHg at 25 °C
Melting Point: 40-44 °C(lit.)

2-Cyanopyrimidine Safety Profile

Safety Information of 2-Cyanopyrimidine (CAS NO. 14080-23-0):
Hazard Codes: Xn Harmful,C Corrosive ,F Highly
Hazard Note: Harmful
Risk Statements: 22-37/38-41-43-34-11
R22:Harmful if swallowed
R37/38:Irritating to respiratory system and skin
R41:Risk of serious damage to the eyes
R43:May cause sensitization by skin contact
R34:Causes burns
R11:Highly flammable
Safety Statements: 26-36/37/39-45-16
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S16:Keep away from sources of ignition
RIDADR: 3276
WGK Germany: 3
HazardClass: IRRITANT

2-Cyanopyrimidine Specification

  2-Cyanopyrimidine with cas registry number of 14080-23-0 is also known as 2-Pyrimidinecarbonitrile ; pyrimidine-2-carbonitrile ; 646830_ALDRICH ; MolPort-000-153-735 ; ZINC02531032 ; ALBB-006249 ; STK503786 ; CID2757979 ; HC210003 .  2-Cyanopyrimidine can be used as pharmaceutical intermediate.

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