5-Bromopyrimidine-2-carbonitrile

5-Bromopyrimidine-2-carbonitrile Property

Boiling point:

317.7±34.0 °C(Predicted)

Density 

1.86±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

pka

-4.65±0.22(Predicted)

form 

Solid

color 

White to yellow

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C5H2BrN3/c6-4-2-8-5(1-7)9-3-4/h2-3H

InChIKey

VPQICCOHFSGBMA-UHFFFAOYSA-N

SMILES

C1(C#N)=NC=C(Br)C=N1

CAS DataBase Reference

38275-57-9(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn,N

Risk Statements 

20/21/22-37/38-41-50

Safety Statements 

26-36/37-39-61

RIDADR 

3077

Hazard Note 

Irritant

TSCA 

No

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

5-Bromopyrimidine-2-carbonitrile Chemical Properties,Usage,Production

Chemical Properties

Light yellow crystalline/powder

Uses

5-Bromo-2-cyanopyrimidine is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Preparation

5-Bromopyrimidine-2-carbonitrile is a pharmaceutical intermediate that can be obtained by reacting 5-bromo-2-chloropyrimidine with potassium nitride. It can also be obtained as follow: 5-Bromo-2-chloropyrimidine (7.51 g, 38.83 mmol), dissolved in DMSO (20 mL), is added to a mixture of NaCN (1.9 g, 38.83 mmol) and l,4-diazabicyclo[2,2,2]octane (0.87 g, 7.77 mmol) in DMSO (10 mL) and water (20 mL). The mixture is stirred overnight, and then water (100 mL) is added. The mixture is extracted with ether (3x100 mL). The combined organic layer is dried (Na2SO4), filtered, and concentrated in vacuo to afford 5-Bromopyrimidine-2-carbonitrile as a solid.

Synthesis

General procedure for the synthesis of 5-bromo-2-cyanopyrimidine from sodium cyanide and 5-bromo-2-chloropyrimidine: 1. In a reaction flask, 5-bromo-2-chloropyrimidine (10 g, 51.8 mmol) was dissolved in dimethyl sulfoxide (26 mL). 2. a mixture of sodium cyanide (2.59 g, 51.8 mmol) and triethylenediamine (1.2 g, 10.4 mmol) in dimethyl sulfoxide (14 mL) and water (28 mL) was added sequentially to the above solution. 3. The reaction mixture was stirred at room temperature for 18 hours. 4. Upon completion of the reaction, the mixture was diluted with water (130 mL) and extracted with ether (3 x 150 mL). 5. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a light yellow solid. 6. The resulting solid was purified by recrystallization from hot dichloromethane to afford the target product 5-bromo-2-cyanopyrimidine. Yield: 99% (9.4 g). 1H NMR (CDCl3, 400 MHz) δ: 8.84 (s, 2H).

References

[1] Patent: WO2005/28452, 2005, A1. Location in patent: Page/Page column 87
[2] Patent: WO2008/121670, 2008, A1. Location in patent: Page/Page column 93-94
[3] Patent: WO2008/57336, 2008, A2. Location in patent: Page/Page column 44
[4] Patent: WO2004/56369, 2004, A1. Location in patent: Page/Page column 20