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Home > Encyclopedia > 2′,4′-Dichloro-5′-fluoroacetophenone

2′,4′-Dichloro-5′-fluoroacetophenone

2′,4′-Dichloro-5′-fluoroacetophenone structure

2′,4′-Dichloro-5′-fluoroacetophenone 

structure
  • CAS No:

    704-10-9

  • Formula:

    C8H5Cl2FO

  • Chemical Name:

    2′,4′-Dichloro-5′-fluoroacetophenone

  • Synonyms:

    Ethanone,1-(2,4-dichloro-5-fluorophenyl)-;Acetophenone,2′,4′-dichloro-5′-fluoro-;1-(2,4-Dichloro-5-fluorophenyl)ethanone;2′,4′-Dichloro-5′-fluoroacetophenone;1-(2,4-Dichloro-5-fluorophenyl)ethan-1-one

  • Categories:

    Pharmaceutical Intermediates  >  Antibacterials

Description

white to light yellow cryst. low melting solid

2′,4′-Dichloro-5′-fluoroacetophenone Basic Attributes

207.02900

207.03

615-113-6

DTXSID80220668

2914700090

Characteristics

17.07000

3

White to pale-yellow Crystal

1.425

35-36 °C

112-115 °C @ Press: 5 Torr

>110ºC

1.546

Safety Information

NONH for all modes of transport

3

R36/37/38

S26-S36

Xi

P261-P305 + P351 + P338

H315-H319-H335

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2′,4′-Dichloro-5′-fluoroacetophenone Use and Manufacturing

Methods of Manufacturing

In a 10001111 four-necked flask, 2, 4-dichlorofluorobenzene was charged15 (^ (0.911111), cooling to 20 ° (: adding aluminum chloride 200. 2g (l.5mol), in the 20 ~ 30 ° CAdd acetyl chloride 78. 5g (l. Omol), 2 ~ 3h plus finished.Slowly heat up to 40 ° C and incubate for 30 min, then slowly heat up to 70 ° C and incubate for 1 ~ 2h, then slowly heat up to 110 ° C, 110 ± 2 ° CHeat 3 ~ 4h, cooling, add 500g 5percent hydrochloric acid, hydrolysis at 80 ~ 90 ° C 2 ~ 3h, after washing to neutral, there areThe phase of the product was recrystallized from the second distillation to obtain 168 g of 2, 4-dichloro-5-fluoroacetophenone in an amount of 99.8percent. The yield was 89.3percentTo a warm solution of 1, 3-dichloro-4-fluorobenzene at 70° C. (175.0 gm), anhydrous aluminum chloride was added in small portion with stirring (260.0 g). Then acetic anhydride was added in small portion with stirring (125 mL) followed by an additional amount of aluminum chloride (159.0 g). The temperature was slowly raised to 120° C. with stirring for 25 hours. The thick reaction mixture was cooled and poured into 400 cc of concentrated hydrochloric acid containing ice. The oil was extracted with methylene chloride, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 165.0 g of oil (2).

Uses

Used as a pharmaceutical intermediate, it is the third-generation broad-spectrum high-efficiency quinolone antibacterial agent ciprofloxacin; the main intermediate of anthoxacin

Computed Properties

Molecular Weight:207.03
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:205.9701483
Monoisotopic Mass:205.9701483
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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