4,4'-Dichlorobenzophenone Chemical Properties

Melting point:

144-146 °C (lit.)

Boiling point:

353 °C (lit.)

Density 

1,45 g/cm³

refractive index 

1.5555 (estimate)

Flash point:

352-354°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in hot acetone.

form 

powder to crystal

color 

White to Light yellow

BRN 

643345

Stability:

Stable. Incompatible with strong oxidizing agents.

InChI

InChI=1S/C13H8Cl2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8H

InChIKey

OKISUZLXOYGIFP-UHFFFAOYSA-N

SMILES

C(C1=CC=C(Cl)C=C1)(C1=CC=C(Cl)C=C1)=O

CAS DataBase Reference

90-98-2(CAS DataBase Reference)

NIST Chemistry Reference

p-Dichlorobenzophenone(90-98-2)

EPA Substance Registry System

Methanone, bis(4-chlorophenyl)- (90-98-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

DJ0525000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29147000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4,4'-Dichlorobenzophenone Usage And Synthesis

Chemical Properties

faintly yellow crystalline powder

Uses

4,4'-Dichlorobenzophenone is used as pharmaceutical intermediates. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuffs. Bisaminonitrile was polymerized with 4,4'-dichlorobenzophenone using NaH as base.

Application

4,4'-Dichlorobenzophenone can be used to synthesize polyether-polyketones, as well as reduce polymer costs. Furthermore, it is a metabolic product resulting from the degredation of DDT.

Preparation

4,4'-Dichlorobenzophenone is prepared by the acylation of chlorobenzene with 4-chlorobenzoyl chloride. The conversion is typically conducted in the presence of an aluminium chloride catalyst in a petroleum ether solvent.
ClC6H5C(O)Cl + C6H5Cl → (ClC6H4)2CO + HCl

Definition

ChEBI: 4-4-Dichlorobenzophenone is a member of benzophenones.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 1201, 1989 DOI: 10.1021/jo00266a039
Tetrahedron Letters, 36, p. 8411, 1995 DOI: 10.1016/0040-4039(95)01802-O

General Description

4,4′-Dichlorobenzophenone (DBP) is a metabolite obtained when one strain of ectomycorrhizal fungi, Xerocomus chrysenteron, degrades 1,1,1-trichloro-2,2-bis(4-chlorophe-nyl) ethane (DDT).

Purification Methods

Recrystallise it from EtOH [Wagner et al. J Am Chem Soc 108 7727 1986]. The semicarbazone has m 192-193o (from H2O). [Beilstein 7 H 420, 7 I 228, 7 II 359, 7 III 2076, 7 IV 1376.]

References

[1] C. VENKATESAN. Liquid Phase Selective Benzoylation of Chlorobenzene to 4,4′-Dichlorobenzophenone over Zeolite H-Beta[J]. Catalysis Letters, 2001, 75 1-2: 119-123. DOI:10.1023/A:1016771719956.
[2] K. YONEYAMA F. M. Reductive metabolism of heptachlor, parathion, 4,4′-dichlorobenzophenone, and carbophenothion by rat liver systems[J]. Pesticide Biochemistry and Physiology, 1981, 15 3: Pages 213-221. DOI:10.1016/0048-3575(81)90003-1.
[3] YI HUANG Jie W. Degradation and mineralization of DDT by the ectomycorrhizal fungi, Xerocomus chrysenteron[J]. Chemosphere, 2013, 92 7: Pages 760-764. DOI:10.1016/j.chemosphere.2013.04.002.
[4] HONGXIN ZHOU. Synthesis and characterization of phthalazinone‐based poly(aryl ether ketone) derived from 4,4′‐dichlorobenzophenone[J]. Polymers for Advanced Technologies, 2012, 23 1: 742-747. DOI:10.1002/PAT.1950.

4,4'-Dichlorobenzophenone(90-98-2)Related Product Information

• Benzophenone imine
• 4-Chlorobenzophenone
• 3,4-Dihydroxybenzophenone
• 4,4'-Dihydroxybenzophenone
• 2,4-Dihydroxybenzophenone
• 2,4-Difluorobenzophenone
• Bis(4-fluorophenyl)-methanone
• Benzophenone oxime
• Benzophenone
• (3,4-Diaminophenyl)phenylmethanone
• 2,2',4,4'-Tetrahydroxybenzophenone
• 4,4'-Dimethylbenzophenone
• 4'-Methylacetophenone
• 4'-Chloropropiophenone
• 4,4'-DICHLORO-3,3'-DINITROBENZOPHENONE
• 2-Amino-2',5-dichlorobenzophenone
• 2-Chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide
• 2,5-Dichlorobenzophenone