Product Name

  • Name

    Mitotan

  • EINECS 200-166-6
  • CAS No. 53-19-0
  • Article Data12
  • CAS DataBase
  • Density 1.372 g/cm3
  • Solubility <0.1 g/100 mL at 24℃
  • Melting Point 77-78 °C(lit.)
  • Formula C14H10Cl4
  • Boiling Point 398.9 °C at 760 mmHg
  • Molecular Weight 320.045
  • Flash Point 194.2 °C
  • Transport Information
  • Appearance Crystalline Solid
  • Safety 36/37
  • Risk Codes 40
  • Molecular Structure Molecular Structure of 53-19-0 (Mitotan)
  • Hazard Symbols HarmfulXn
  • Synonyms 1,1-Dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane;1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane;1-(o-Chlorophenyl)-1-(p-chlorophenyl)-2,2-dichloroethane;2,4'-Dichlorodiphenyldichloroethane;2-(p-Chlorophenyl)-2-(o-chlorophenyl)-1,1-dichloroethane;CB 313;Chloditan;Chlodithane;Lysodren;Mitotane;NSC 38721;Opeprim;o,p'-DDD;o,p'-Dichlorodiphenyldichloroethane;o,p'-TDE;
  • PSA 0.00000
  • LogP 5.92900

Synthetic route

2,2‐dichloro‐1‐(2‐chlorophenyl)ethan‐1‐one
24123-67-9

2,2‐dichloro‐1‐(2‐chlorophenyl)ethan‐1‐one

chlorobenzene
108-90-7

chlorobenzene

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
Stage #1: 2,2‐dichloro‐1‐(2‐chlorophenyl)ethan‐1‐one With sodium tetrahydroborate In methanol at 20℃; for 0.333333h; Schlenk technique; Inert atmosphere;
Stage #2: chlorobenzene With sulfuric acid at 20℃; for 0.166667h;		89%
2,2-dichloro-1-(2-chlorophenyl)ethanol
27683-60-9

2,2-dichloro-1-(2-chlorophenyl)ethanol

chlorobenzene
108-90-7

chlorobenzene

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
With sulfuric acid at 35℃; for 6h;71%
With sulfuric acid at 30 - 60℃;
With sulfuric acid; sulfur trioxide
o,p'-DDT
789-02-6

o,p'-DDT

A

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

B

1-(4-chlorophenyl)-1-phenylethane
60617-89-2

1-(4-chlorophenyl)-1-phenylethane

C

1-(o-chlorophenyl)-1-(p-chlorophenyl)ethane
77008-62-9

1-(o-chlorophenyl)-1-(p-chlorophenyl)ethane

D

1-(2-chloro-phenyl)-1-phenyl-ethane
76690-79-4

1-(2-chloro-phenyl)-1-phenyl-ethane

Conditions
ConditionsYield
With hydrogen; triethylamine; palladium on activated charcoal In methanol at 20℃; for 0.166667h;A 25%
B n/a
C 42%
D n/a
...Expand
p,p'-DDT
50-29-3

p,p'-DDT

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

o,p'-DDT
789-02-6

o,p'-DDT

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
With aluminium amalgam In ethanol
o,p'-DDT
789-02-6

o,p'-DDT

A

1-chloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane
13312-58-8

1-chloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane

B

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
With sodium tetrahydroborate In dimethyl sulfoxide
sulfuric acid
7664-93-9

sulfuric acid

2,2-dichloro-1-(2-chlorophenyl)ethanol
27683-60-9

2,2-dichloro-1-(2-chlorophenyl)ethanol

chlorobenzene
108-90-7

chlorobenzene

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
at 30 - 60℃;
...Expand
2-chlorophenylmagnesium bromide
36692-27-0

2-chlorophenylmagnesium bromide

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether
2: concentrated H2SO4 / 30 - 60 °C
View Scheme
chlorobenzene
108-90-7

chlorobenzene

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2SO4
View Scheme
Multi-step reaction with 2 steps
1: H2SO4
View Scheme
2,2,2-trichloro-1-(2-chloro-phenyl)-ethanol
10291-39-1

2,2,2-trichloro-1-(2-chloro-phenyl)-ethanol

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Al-Hg, iPrOH
2: SO3/H2SO4
View Scheme
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nBuLi
2: SO3/H2SO4
View Scheme
2-chlorophenylacetylene
873-31-4

2-chlorophenylacetylene

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydrogensulfate monohydrate; water; lithium chloride / acetonitrile / 24 h / 20 °C / Schlenk technique
2.1: sodium tetrahydroborate / methanol / 0.33 h / 20 °C / Schlenk technique; Inert atmosphere
2.2: 0.17 h / 20 °C
View Scheme
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

1-Chloro-2-o-chlorophenyl-2-p'-chlorophenylethylene
14835-94-0

1-Chloro-2-o-chlorophenyl-2-p'-chlorophenylethylene

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 80 - 90℃; for 2h;78%
With potassium hydroxide In 1,4-dioxane
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

o-Chlorophenyl-1-p'-chlorophenylmethane
52094-02-7

o-Chlorophenyl-1-p'-chlorophenylmethane

Conditions
ConditionsYield
With potassium hydroxide In ethylene glycol for 6h; Heating;68%
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

C14H9Cl3
120189-90-4

C14H9Cl3

Conditions
ConditionsYield
With hexacarbonyl molybdenum In various solvent(s) at 145℃; for 3h;90 % Chromat.
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloro-2-iodoethane

1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloro-2-iodoethane

Conditions
ConditionsYield
With N-iodo-succinimide; lithium diisopropyl amide 1.) THF, ether, -78 deg C, 50 min, 2.) THF, ether, 15 min; Multistep reaction;
sulfuric acid
7664-93-9

sulfuric acid

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

nitric acid
7697-37-2

nitric acid

2.2-dichloro-1-<2-chloro-3.5-dinitro-phenyl>-1-<4-chloro-3.5-dinitro-phenyl>-ethane (?)

2.2-dichloro-1-<2-chloro-3.5-dinitro-phenyl>-1-<4-chloro-3.5-dinitro-phenyl>-ethane (?)

Conditions
ConditionsYield
auf dem Dampfbad;
...Expand
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

nitric acid
7697-37-2

nitric acid

2.2-dichloro-1-<4-chloro-3-nitro-phenyl>-1-<6-chloro-3-nitro-phenyl>-ethane (?)

2.2-dichloro-1-<4-chloro-3-nitro-phenyl>-1-<6-chloro-3-nitro-phenyl>-ethane (?)

Conditions
ConditionsYield
at 50℃;
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

ethanolic KOH

ethanolic KOH

1-Chloro-2-o-chlorophenyl-2-p'-chlorophenylethylene
14835-94-0

1-Chloro-2-o-chlorophenyl-2-p'-chlorophenylethylene

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

2,4'-dichlorobenzophenone
85-29-0

2,4'-dichlorobenzophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / KOH / ethanol / 2 h / 80 - 90 °C
2: 54 percent / CrO3 / acetic acid / 1.5 h / 100 °C
View Scheme
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

1-(o-chlorophenyl)-1-(p-chlorophenyl)ethane
77008-62-9

1-(o-chlorophenyl)-1-(p-chlorophenyl)ethane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / KOH / ethanol / 2 h / 80 - 90 °C
2: 54 percent / CrO3 / acetic acid / 1.5 h / 100 °C
3: 65 percent / diethyl ether / 1 h / Heating
4: 80 percent / H2 / 5percent Pd/C / ethanol / 0.5 h
View Scheme
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

1-o-Chlorophenyl-1-p'-chlorophenylethylene
39274-24-3

1-o-Chlorophenyl-1-p'-chlorophenylethylene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / KOH / ethanol / 2 h / 80 - 90 °C
2: 54 percent / CrO3 / acetic acid / 1.5 h / 100 °C
3: 65 percent / diethyl ether / 1 h / Heating
View Scheme
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

1,2-Dichloro-2-o-chlorophenyl-2-p'-chlorophenylethane
90284-72-3

1,2-Dichloro-2-o-chlorophenyl-2-p'-chlorophenylethane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / KOH / ethanol / 2 h / 80 - 90 °C
2: 54 percent / CrO3 / acetic acid / 1.5 h / 100 °C
3: 65 percent / diethyl ether / 1 h / Heating
4: 76 percent / Cl2 / CCl4 / 24 h
View Scheme
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

A

(R)-(+)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane

(R)-(+)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane

B

(S)-(-)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane

(S)-(-)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane

Conditions
ConditionsYield
With Daicel Chiralcel OJ-H column Resolution of racemate;
1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
53-19-0

1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane

1-chloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane
13312-58-8

1-chloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane

Conditions
ConditionsYield
With triethylsilane; {Rh(H)[SiMe2(o-C6H4SMe)](PPh3)2}[BArF4] In neat (no solvent) at 80℃; for 72h; Inert atmosphere; Schlenk technique;

Mitotan Consensus Reports

NCI Carcinogenesis Studies (ipr); Equivocal Evidence: mouse, rat CANCAR    Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.

Mitotan Specification

The Chlodithane is an organic compound with the formula C14H10Cl4. The IUPAC name of this chemical is 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene. With the CAS registry number 53-19-0, it is also named as Benzene, 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)-. The product's categories are Organics; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a crystalline solid, which should be stored in a closed dark and dry place. It is used to treat pituitary-dependent Cushing's syndrome in canines. The medication is used in the controlled destruction of adrenal tissue, leading to a decrease in cortisol production.

Physical properties about Chlodithane are: (1)ACD/LogP: 5.39; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.39; (4)ACD/LogD (pH 7.4): 5.39; (5)ACD/BCF (pH 5.5): 7332.84; (6)ACD/BCF (pH 7.4): 7332.84; (7)ACD/KOC (pH 5.5): 20340.07; (8)ACD/KOC (pH 7.4): 20340.07; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.599; (11)Molar Refractivity: 79.65 cm3; (12)Molar Volume: 233.1 cm3; (13)Polarizability: 31.57×10-24cm3; (14)Surface Tension: 44.6 dyne/cm; (15)Density: 1.372 g/cm3; (16)Flash Point: 194.2 °C; (17)Enthalpy of Vaporization: 62.42 kJ/mol; (18)Boiling Point: 398.9 °C at 760 mmHg; (19)Vapour Pressure: 3.28E-06 mmHg at 25°C.

Preparation: this chemical can be prepared by chlorobenzene and 2,2-dichloro-1-(2-chloro-phenyl)-ethanol. This reaction will need reagent concentrated H2SO4. The reaction temperature is 30 - 60 °C. The yield is about 78%.



Uses of Chlodithane: it can be used to produce (2-chloro-phenyl)-(4-chloro-phenyl)-methane by heating. It will need reagent KOH and solvent ethane-1,2-diol with reaction time of 6 hours. The yield is about 68%.

When you are using this chemical, please be cautious about it as the following:
It has limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1ccccc1C(c2ccc(Cl)cc2)C(Cl)Cl
(2)InChI: InChI=1/C14H10Cl4/c15-10-7-5-9(6-8-10)13(14(17)18)11-3-1-2-4-12(11)16/h1-8,13-14H
(3)InChIKey: JWBOIMRXGHLCPP-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C14H10Cl4/c15-10-7-5-9(6-8-10)13(14(17)18)11-3-1-2-4-12(11)16/h1-8,13-14H
(5)Std. InChIKey: JWBOIMRXGHLCPP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral > 5gm/kg (5000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 309, 1984.
man TDLo oral 17gm/kg/35W (17000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Cancer Vol. 42, Pg. 2177, 1978.
mouse LD50 oral > 4gm/kg (4000mg/kg)   Pharmaceutical Chemistry Journal Vol. 11, Pg. 1298, 1977.
rat LD50 oral > 5gm/kg (5000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 309, 1984.
women TDLo oral 800mg/kg/4D (800mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Cancer Vol. 42, Pg. 2177, 1978.
women TDLo oral 11gm/kg/15W (11000mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BLOOD: NORMOCYTIC ANEMIA

BLOOD: PIGMENTED OR NUCLEATED RED BLLOD CELLS		 Cancer Vol. 42, Pg. 2177, 1978.
women TDLo oral 14gm/kg/22W (14000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING		 Cancer Vol. 42, Pg. 2177, 1978.

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