2-Amino-4,6-dichloropyrimidine Chemical Properties

Melting point:

219-222 °C (lit.)

Boiling point:

219-222°C

Density 

1.6662 (rough estimate)

refractive index 

1.6300 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

0.14±0.10(Predicted)

form 

Liquid

color 

Clear colorless to light yellow

Water Solubility 

Insoluble in water, soluble in acetone, two monomer (VCM) and thermal toluene.

BRN 

118454

InChI

InChI=1S/C4H3Cl2N3/c5-2-1-3(6)9-4(7)8-2/h1H,(H2,7,8,9)

InChIKey

JPZOAVGMSDSWSW-UHFFFAOYSA-N

SMILES

C1(N)=NC(Cl)=CC(Cl)=N1

CAS DataBase Reference

56-05-3(CAS DataBase Reference)

EPA Substance Registry System

2-Pyrimidinamine, 4,6-dichloro- (56-05-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

RTECS 

UV6260485

F 

10

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29335995

MSDS

• Language:English Provider:2-Amino-4,6-dichloropyrimidine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Amino-4,6-dichloropyrimidine Usage And Synthesis

Chemical Properties

LIGHT BROWN CRYSTALLINE POWDER

Uses

Microwave-assisted synthesis of pyrazolo [3, 4-d] pyrimidines from 2-amino-4, 6-dichloropyrimidine-5-carbaldehyde is under solvent-free conditions. A series of 6-alkynyl-2,4-diaminopyrimidine derivatives bearing various substituents at alkynyl moiety was prepared by the Sonogashira cross-coupling reaction of 2,4-diamino-6-iodopyrimidine using Pd(PPh3)2Cl2 as catalyst.

Synthesis

The general procedure for the synthesis of 2-amino-4,6-dichloropyrimidine from 2-amino-4,6-dihydroxypyrimidine is as follows: in a four-necked flask equipped with a reflux condenser, 510 g of 2-amino-4,6-dihydroxypyrimidine (98% purity, 4 mol) and 1428 g of phosphorus triclosan (99% purity) were added, heated and stirred. 810 g of triethylamine (99% purity) was slowly added dropwise at 40 to 45 °C through a constant pressure dropping funnel. After the dropwise addition, the reaction temperature was raised to 85 to 90 °C and maintained at this temperature for 2 hours. The progress of the reaction was monitored by high performance liquid chromatography (HPLC) and the reaction was considered complete when the amount of 2-amino-4,6-dihydroxypyrimidine was less than 1%. Subsequently, 3000 g of toluene was added to the reaction mixture, cooled to 0-10°C, and 3000 g of ice-water mixture was added for low temperature hydrolysis. The mixture was then warmed to room temperature and left to stratify. The aqueous layer was extracted twice with 400 g of toluene, and the organic phases were combined and washed sequentially with aqueous sodium carbonate and water until neutral. The organic phase was concentrated and 1800 g of toluene was recovered to give 2668 g of highly concentrated toluene solution. The product was analyzed by HPLC, the purity was 96.8%, the content was 22.58% (external standard method), and the yield of crude product was 92%.

References

[1] Patent: CN108395409, 2018, A. Location in patent: Paragraph 0046-0047; 0050
[2] Organic Letters, 2009, vol. 11, # 1, p. 61 - 64
[3] Chemical Communications, 2017, vol. 53, # 18, p. 2689 - 2692
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 47, p. 10087 - 10094
[5] Tetrahedron Letters, 2015, vol. 56, # 10, p. 1179 - 1182

2-Amino-4,6-dichloropyrimidine(56-05-3)Related Product Information

• EC 2.6.1.2
• Glucosamine
• ALTRENOGEST
• Aminopyrine
• 4,6-Dichloropyrimidine
• 4,6-Diaminopyrimidine
• Acetaminophen
• 2',4'-Dichloroacetophenone
• 3-Aminophenol
• Dichloroethane
• 2-Aminopyrimidine
• Glycine
• 6-Aminocaproic acid
• 2-Amino-4-chloropyrimidine
• 1,2-Dichloro-4-(chloromethyl)benzene
• Tris(hydroxymethyl)aminomethane
• 2-Amino-4-chloro-6-methoxypyrimidine
• 2-Amino-4,6-dimethylpyrimidine