2,4-Dichloro-5-pyrimidinecarbonyl chloride

2,4-Dichloro-5-pyrimidinecarbonyl chloride Property

Boiling point:

83 °C(Press: 0.05 Torr)

Density 

1.645 g/mL at 25 °C

refractive index 

n20/D1.586

Flash point:

93℃

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

liquid

pka

-5.08±0.29(Predicted)

color 

Clear, colourless

InChI

InChI=1S/C5HCl3N2O/c6-3-2(4(7)11)1-9-5(8)10-3/h1H

InChIKey

DZTIFMWYYHCREC-UHFFFAOYSA-N

SMILES

C(Cl)(C1=CN=C(Cl)N=C1Cl)=O

CAS DataBase Reference

2972-52-3(CAS DataBase Reference)

Safety

Hazard Codes 

C,Xi

Risk Statements 

20/21/22-34

Safety Statements 

6-7/9-24/25-26-36/37/39-51

RIDADR 

3265

WGK Germany 

3

HazardClass 

IRRITANT, CORROSIVE

PackingGroup 

Ⅲ

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

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

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

2,4-Dichloro-5-pyrimidinecarbonyl chloride Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2,4-dichloro-5-pyrimidinecarbonyl chloride from uracil-5-carboxylic acid is as follows: 9.1 Preparation of 2,4-dihydroxypyrimidine-5-carbonyl chloride In a 250 mL round bottom flask, 10.0 g (64.0 mmol) of 2,4-dihydroxypyrimidine-5-carboxylic acid was dissolved in 46 mL (500.0 mmol) of phosphorus oxychloride (POCl3) under nitrogen protection. The reaction mixture was cooled to 0°C via an ice bath, followed by the batch addition of 47.7 g (230 mmol) phosphorus pentachloride (PCl5). The reaction solution was heated and stirred at reflux for 16 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in 100 mL of toluene and ground, followed by filtration. After this operation was repeated three times, the filtrate was evaporated under reduced pressure to give 13.5 g (64.0 mmol) of the yellow oily product 2,4-dichloro-5-pyrimidinecarbonyl chloride, which was used directly in the next step of the reaction. Yield = 100%.

References

[1] Patent: US2011/251194, 2011, A1. Location in patent: Page/Page column 21
[2] Patent: US2010/222319, 2010, A1. Location in patent: Page/Page column 18
[3] Patent: WO2015/21149, 2015, A1. Location in patent: Page/Page column 56; 57
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2746 - 2763
[5] Patent: WO2015/48662, 2015, A2. Location in patent: Page/Page column 55