Dicyclohexyl disulfide

HCID 17356

Basic information

CAS
2550-40-5
Standard SMILES
C1CCC(SSC2CCCCC2)CC1
InChIKey
ODHAQPXNQDBHSH-UHFFFAOYSA-N
Molecular formula
C12H22S2
Average molar mass
230.4 g/mol
Monoisotopic mass
230.11629305

Names & identifiers

Preferred name
Dicyclohexyl disulfide
IUPAC
(cyclohexyldisulfanyl)cyclohexane
English name
Cyclohexyl disulfide
Molecular formula
C12H22S2
Molecular weight
230.43

Names & synonyms

DICYCLOHEXYL DISULFIDECyclohexyl disulfideDisulfide, dicyclohexyl(Cyclohexyldisulfanyl)cyclohexaneDicyclohexyl disulphideBis(cyclohexyl)disulfideBis(cyclohexyl) disulfideFEMA No. 3448DicyclohexyldisulphideDTXSID4047628HSDB 5886EINECS 219-851-6
Show more names
FEMA 34481,2-dicyclohexyldisulfaneDicyclohexyl Disulfide (DCDS)CYCLOHEXYLDISULPHIDEDicyclohxyldisulfideDICYLCOHEXYLDISULFIDEDisulfide,dicyclohexyl
UNII-6G1A0K504Q6G1A0K504QCyclohexyl disulfide (6CI,7CI,8CI)DTXCID2027628DICYCLOHEXYL DISULFIDE [FHFI]DICYCLOHEXYL DISULFIDE [HSDB]RefChem:133235ODHAQPXNQDBHSH-UHFFFAOYSA-N

Database identifiers

CAS
2550-40-5
PubChem CID
17356
DTXSID
DTXSID4047628
ChEMBL
CHEMBL3188833
ChEBI
CHEBI:166589
UNII
6G1A0K504Q
EC Number
219-851-6
Nikkaji
J23.487G

Properties

Computed structural properties

XLogP
4.5
Topological polar surface area
50.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
14

Experimental & physicochemical properties

Density1.042-1.049
Solubility · 2 items

insoluble in water; slightly soluble in alcohol; soluble in fat

(in ethanol)

Boiling Point · 2 items

162.00 to 163.00 °C. @ 6.00 mm Hg

162-163 °C (6 mm Hg)

Vapor Pressure0.000554 [mmHg]
Refractive Index1.543-1.553
Physical DescriptionColorless to yellow liquid with an unpleasant odor; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
127 · 127-130 °C
Boiling point
162 · 162-163 °C6 mm Hg(lit.)
Density
1.046 g/mL · 1.046 g/mL at 25 °C(lit.)
FEMA
3448 · 3448 | DICYCLOHEXYL DISULFIDE
refractive index
20 · n20/D 1.545(lit.)
FLAVIS Number
12.028 · 12.028 | Dicyclohexyl disulfide

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.8% (1 of 130) of reports.

Warning

H315 (99.2%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (99.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (99.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 130 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 130 reports by companies.;There are 6 notifications provided by 129 of 130 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 3 items

Chemical: Disulfide, dicyclohexyl

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Disulfide, dicyclohexyl: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses diarrhea in oral lethal-dose study of rats; [RTECS] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (99.2%);Eye Irrit. 2 (99.2%);STOT SE 3 (99.2%)
Standard Transportation Number49 601 32; Hazardous substance, liquid (or) solid, nos

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7.3X10+4(SRC), determined from an estimated log Kow of 6.41(2,SRC) and a regression-derived equation(3), indicates that dicyclohexyl disulfide is expected to be immobile in soil(SRC). Volatilization of dicyclohexyl disulfide from moist soil surfaces may be important(SRC) given an estimated Henry's Law constant of 4.0X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, volatilization from moist soil surfaces is expected to be attenuated by adsorption to organic matter(SRC). Dicyclohexyl disulfide is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 5.5X10-4 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available for dicyclohexyl disulfide(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7.3X10+4(SRC), determined from an estimated log Kow of 6.41(2,SRC) and a regression-derived equation(3), indicates that dicyclohexyl disulfide is expected to adsorb to suspended solids and sediment in water(SRC). Dicyclohexyl disulfide is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.0X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 4.8 hours and 6.1 days, respectively(3,SRC). However, adsorption to suspended solids and sediment in the water column is expected to attenuate this process(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 2.3 days ignoring adsorption(5); when considering maximum adsorption, the volatilization half-life increases to approximately 23 years(5). According to a classification scheme(6), an estimated BCF of 4.4X10+4(3,SRC), from an estimated log Kow(2,SRC), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Biodegradation data were not available for dicyclohexyl disulfide(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dicyclohexyl disulfide, which has an estimated vapor pressure of 5.5X10-4 mm Hg at 25 °C(2,SRC), is expected to exist solely as a will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dicyclohexyl disulfide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.4 hours(3,SRC). Particulate-phase dicyclohexyl disulfide may be physically removed from the air by wet and dry deposition(SRC).

Soil Adsorption/Mobility · 1 item

The Koc of dicyclohexyl disulfide is estimated as approximately 7.3X10+4(SRC), using an log Kow of 6.41(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that dicyclohexyl disulfide is expected to be immobile in soil(SRC).

Environmental Bioconcentration · 1 item

An estimated BCF of 4.4X10+4 was calculated for dicyclohexyl disulfide(SRC), using an estimated log Kow of 6.41(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for dicyclohexyl disulfide is estimated as 4.0X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dicyclohexyl disulfide is expected to volatilize rapidly from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is approximately 4.8 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is approximately 6.1 days(2,SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 2.3 days ignoring adsorption(3); when considering maximum adsorption, the volatilization half-life increases to about 23 years(3). Dicyclohexyl disulfide's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). Dicyclohexyl disulfide is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 5.5X10-4 mm Hg(SRC), determined from a fragment constant method(4).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of dicyclohexyl disulfide with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

Environmental Fate/Exposure Summary · 1 item

Dicyclohexyl disulfide does not appear to have any commercial uses that could result in its release to the environment. If dicyclohexyl disulfide is released to air, an estimated vapor pressure of 5.5X10-4 mm Hg at 25 °C indicates it will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dicyclohexyl disulfide will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 1.4 hours. Particulate-phase dicyclohexyl disulfide will be physically removed from the atmosphere by wet and dry deposition. If released to soil, dicyclohexyl disulfide is expected to be immobile based upon an estimated Koc of 7.3X10+4. Volatilization from moist soil surfaces may occur based upon an estimated Henry's Law constant of 4.0X10-3 atm-cu m/mole. However, adsorption to organic matter is expected to attenuate this process. If released into water, dicyclohexyl disulfide is expected to adsorb to suspended solids and sediment in water based on the estimated Koc. Volatilization from water surfaces may be an important fate process based upon the estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 4.8 hours and 6.1 days, respectively. However, adsorption to suspended solids and sediment in the water column is expected to attenuate this process. An estimated BCF of 4.4X10+4 suggests the potential for bioconcentration in aquatic organisms is very high. Biodegradation data were not available for dicyclohexyl disulfide. (SRC)

Regulatory information

Regulatory Information · 3 items

Chemical: Disulfide, dicyclohexyl

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Disulfide, dicyclohexyl: Does not have an individual approval but may be used under an appropriate group standard

Safety data

wgk
3
tsca
TSCA listed
rtecs
JO1843850
ridadr
3334
hs_code
2930.90.9250
risk_code
36/37/38

Chemistry & industry

Pharmacology

Cellular LocationsMembrane

Uses & manufacturing

Uses · 3 items

Used as synthetic flavor ingredient; [HSDB]

SYNTHETIC FLAVOR INGREDIENT

CHEM INT FOR N-(CYCLOHEXYLTHIO)PHTHALIMIDE (POSSIBLE USE)

U.S. Production · 2 items

(1979) NOT PRODUCED COMMERCIALLY IN U.S.

(1981) NOT PRODUCED COMMERCIALLY IN U.S.

Methods of ManufacturingPROBABLY BY OXIDATION OF CYCLOHEXYLMERCAPTAN WITH IODINE OR HYDROGEN PEROXIDE.
Use Classification · 2 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 4 items

Disulfide, dicyclohexyl: ACTIVE

The flavor of food, pharmaceuticals, and chewing gum may be enhanced by adding a mixture of 1-butoxy-1-ethanol acetate and 2-phenyl-3-carboethoxyfuran and optionally bis(cyclohexyl) disulfide. ...

The grape flavor of reconstituted grape juice or of grape flavoring materials is intensified and made more mellow by incorporating 0.2 ppb to 1000 ppm bis(cyclohexyl) disulfide.

2-Phenyl-3-carbethoxyfuran (I) and/or bis(cyclohexyl) disulfide (II) when added to food, perfume, or tobacco, enhance and otherwise agreeably modify their natural and/or artificial aroma and flavor. For example, addition of 1.5 parts of I and 0.09 parts of II to an artificial grape flavor improved its aroma and taste when evaluated in a sweetened and acidified tasting solution.

Applications

UsesDicyclohexyl disulfide is employed as an edible spices. It is also used in dyes, medicine and organic synthesis. It is also useful as a synthetic flavor ingredient. Further, it is used in the production of n-(cyclohexylthio) phthalimide.

Upstream & downstream products

Suppliers82 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
Hebei baicao biology science and technology co., ltd+86-19131911055 17824879454 · [email protected]
毕佳索(上海毕得医药科技股份有限公司)400-6005915 · [email protected]

Additional notes

DefinitionChEBI: Dicyclohexyl disulfide is an organic disulfide.

Related reactions

2 records

Compound notes

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