6-HYDROXY-2-NAPHTHYL DISULFIDE Property

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

form 

powder to crystal

pka

8.93±0.40(Predicted)

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2908990090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

6-HYDROXY-2-NAPHTHYL DISULFIDE Chemical Properties,Usage,Production

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.