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2,4-Dichloro-5-fluoropyrimidine

2,4-Dichloro-5-fluoropyrimidine structure

CAS No:
2927-71-1
Formula:
C4HCl2FN2
Chemical Name:
2,4-Dichloro-5-fluoropyrimidine
Synonyms:
Pyrimidine,2,4-dichloro-5-fluoro-;2,4-Dichloro-5-fluoropyrimidine;NSC 70442;5-Fluoro-2,4-dichloropyrimidine;2,6-Dichloro-5-fluoropyrimidine
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

2,4-Dichloro-5-fluoropyrimidine is Yellow to Orange Crystalline Solid

2,4-Dichloro-5-fluoropyrimidine Basic Attributes

Molecular Weight：

166.97

Exact Mass：

166.97

EC Number：

249-616-3

NSC Number：

70442

DSSTox ID：

DTXSID00290702

HScode：

2933599090

Characteristics

PSA：

25.8

XLogP3：

2.2

Appearance：

White to pale brown Powder or Crystalline Powder or Low Melting Solid

Density：

1.6±0.1 g/cm3

Melting Point：

38-39 °C

Boiling Point：

74-80 °C @ Press: 16 Torr

Flash Point：

223 °F

Refractive Index：

1.532

Storage Conditions：

-20°C Freezer, Under Inert Atmosphere

Safety Information

Packing level：

Ⅲ

Hazard category：

Transport codes：

3261

wgk germany：

hazard class code：

36/37/38-34-22

safety instructions：

26-36-37/39-45-36/37/39

Marks：

Xi,C

Hazard note：

Irritant

Precautionary statement(s)：

P280-P305 + P351 + P338-P310

Hazard Statements：

H302-H314

GHS Classification：

|Danger|H302 (84.91%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, and P501|Aggregated GHS information provided by 53 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2,4-Dichloro-5-fluoropyrimidine Use and Manufacturing

Methods of Manufacturing

5-fluoropyrimidine-2, 4-diol (525 kg, 1.00 mol eq) is mixed with phosphorous oxychloride (1545 kg, 2.50 mol eq) and heated to about 100° C. with stirring under a nitrogen atmosphere. N, N-dimethylaniline (980 kg, 2.00 mol eq) is then added over a period of about 9 hours and the resulting mixture stirred at about 100° C. for up to 4 hours. After the input of 5-fluoropyrimidine-2, 4-diol (formula 11) 11.2g (86.1m) and phosphorus oxychloride (POCl3) 38.9g (253.8m) to the reactor and heated to 95 °C, 20.7g N, N-dimethylamine (DMA) was added dropwise for 1 hour and the temperature was raised to 120 °C, this mixture was stirred for 3 hours. Cooling the temperature to 0 °C, and the dropwise addition of 3N HCl solution in 1500ml below 10 °C. After the addition was complete, filtered and stirred for 3 hours at 10 °C and dried to give 2, 4-dichloro-5-fluoropyrimidine (chemical formula 9) 13.2g (79.1mmol) (yield: 92percent).11.1 g (85.3 mmol) of 5-fluorouracil (Formula 10) and 39.4 g (257.0 mmol) of phosphorus oxychloride (POCl3) were added to the reactor, and the temperature was raised to 95 °C. N, N-Dimethylamine was added dropwise for 1 hour, the temperature was raised to 120 °C, and the mixture was stirred for 3 hours. The temperature was cooled to 0 °C and 1500 ml of 3N HCl aqueous solution was added dropwise at 10 °C or lower. After completion of the dropwise addition, the mixture was stirred at 10 °C for 3 hours, filtered and dried to obtain 13.4 g (80.3 mmol) of 2, 4-dichloro-5-fluoropyrimidine (formula 9) (yield: 94percent)

Uses

Used in the synthesis of two glucuronic derivatives of 5-fluorouracil as neoplasm inhibitors.

Computed Properties

Molecular Weight:166.97
XLogP3:2.2
Hydrogen Bond Acceptor Count:3
Exact Mass:165.9500816
Monoisotopic Mass:165.9500816
Topological Polar Surface Area:25.8
Heavy Atom Count:9
Complexity:103
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of 2,4-Dichloro-5-fluoropyrimidine

Description
Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
Latest News
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2,4-Dichloro-5-fluoropyrimidine

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