6-HYDROXY-2-NAPHTHYL DISULFIDE Chemical Properties

Melting point:

226 °C

Boiling point:

597.5±25.0 °C(Predicted)

Density 

1.46±0.1 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

<26.28mg/ml in DMSO

pka

8.93±0.40(Predicted)

form 

powder to crystal

color 

White to Brown

Merck 

14,2840

CAS DataBase Reference

6088-51-3(CAS DataBase Reference)

EPA Substance Registry System

2-Naphthalenol, 6,6'-dithiobis- (6088-51-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2908990090

MSDS

• Language:English Provider:SigmaAldrich

6-HYDROXY-2-NAPHTHYL DISULFIDE Usage And Synthesis

Description

DDD, 1,1-dichloro-2,2-bis-(4-chlorophenyl) ethane, also known as TDE, is a metabolite of DDT, which found use in agriculture. As with DDT, the p,p -isomer is insecticidal and the o,p -isomer is an impurity.

Uses

For determination of protein-bound sulfhydryl groups.

Purification Methods

It crystallises as leaflets from AcOH and is slightly soluble in EtOH, and AcOH, but is soluble in *C6H6 and in alkalis to give a yellow solution. [Zincke & Dereser Chem Ber 51 352 1918.] The acetoxy derivative has m 198-200o (from AcOH or dioxane/MeOH), and the diacetyl derivative has m 167-168o (from AcOH). A small amount of impure disulfide can be purified by dissolving it in a small volume of Me2CO and adding a large volume of toluene, filter rapidly and concentrate to one-third of its volume. The hot toluene solution is filtered rapidly from any tarry residue, and crystals separate on cooling. Recrystallisation from hot acetic acid gives crystals with m 220-223o [Barrett & Seligman Science 116 323 1952]. [Beilstein 6 I 481.]

Toxicity evaluation

Animal Studies. DDD is less acutely toxic than DDT (29), with an oral LD₅₀ of 3400 to 4000 mg/kg in the rat and a dermal LD₅₀ ca. 1200 mg/kg in the rabbit. In a 2-year chronic dietary study in the rat, a LOEL of 100 ppm (5 mg/kg/day) was quoted for tissue damage, similar to that produced by DDT.
Human Studies. Most of the studies conducted in humans have used the o,p -isomer of DDD. This has been used as a drug, with medical and veterinary uses, for the treatment of Cushing’s syndrome and adrenal carcinoma, under the generic name of mitotane. After oral ingestion, o,p’-DDD binds to lung and adrenal tissue. Its toxicity to the adrenal appears to be species-dependent, however, causing gross atrophy in the dog and reducing corticosteroid production without pathological effects in other mammals, including humans.

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