CAS 3385-94-2 Disilathiane, 1,1,1,3,3,3-hexamethyl- (HCID 76920)

Names & identifiers

Preferred name: Disilathiane, 1,1,1,3,3,3-hexamethyl-
IUPAC: trimethyl(trimethylsilylsulfanyl)silane
English name: BIS(TRIMETHYLSILYL) SULFIDE
Molecular formula: C6H18SSi2
Molecular weight: 178.44

Names & synonyms

3385-94-2Bis(trimethylsilyl) sulfideHexamethyldisilathianeDisilathiane, hexamethyl-Disilthiane, hexamethyl-Disilathiane, 1,1,1,3,3,3-hexamethyl-EINECS 222-201-4NSC 252160DTXSID2063006RefChem:589178DTXCID0038756222-201-4

Show more names

HexamethyldisilthianDK269athianehexamethyl-disilathianDisilthiane,hexamethyl-Hexamethyldisilylthiane

Bis(trimethylsilyl)sulfideHexamethyldisilthianetrimethyl(trimethylsilylsulfanyl)silane1,1,1,3,3,3-HexamethyldisilathianeMFCD00014851AZ6L5QJY5HNSC-252160Thiobis(trimethylsilane)

Database identifiers

CAS: 3385-94-2
PubChem CID: 76920
DTXSID: DTXSID2063006
UNII: AZ6L5QJY5H
EC Number: 222-201-4
Nikkaji: J205.475B

Properties

Computed structural properties

Topological polar surface area: 25.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 2
Heavy atoms: 9
Formal charge: 0
Complexity: 76

Experimental & physicochemical properties

Kovats Retention Index993

Physicochemical properties

Boiling point: 164 °C · 164 °C(lit.)
Density: 0.846 g/mL · 0.846 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.4586(lit.)
Flash point: 79 °F · 79 °F
storage temp.: Flammables area
solubility: Miscible with terahydrofuran and toluene.
form: Liquid
Specific Gravity: 0.851 · 0.851
color: Colorless
Water Solubility: Soluble in tetrahydrofuran and toluene. Hydrolyzes in water.
Hydrolytic Sensitivity: 7 · 7: reacts slowly with moisture/water
Sensitive: Air Sensitive
BRN: 1740046 · 1740046
Stability: store cold
InChI: 1S/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3
InChIKey: RLECCBFNWDXKPK-UHFFFAOYSA-N
SMILES: C[Si](C)(C)S[Si](C)(C)C
CAS DataBase Reference: 3385 · 3385-94-2(CAS DataBase Reference)
FDA UNII: 6 L5QJY5H · AZ6L5QJY5H
EPA Substance Registry System: Disilathiane, hexamethyl- (3385-94-2)
UNSPSC Code: 12352103 · 12352103
NACRES: 23 · NA.23
Symbol(GHS): 2 · GHS02,GHS06
Signal word: Danger
Hazard statements: 226 · H226-H301+H311+H331
Precautionary statements: 210 · P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: T
Risk Statements: 10 · 10-23/24/25
Safety Statements: 36 · 36/37/39-45
RIDADR: 1993 · UN 1993 3/PG 3
WGK Germany: 3 · 3
F: 10 · 10-13-21
TSCA: TSCA listed
HazardClass: 3 · 3
PackingGroup: II
HS Code: 29319090 · 29319090
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 3

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H226 (97.8%): Flammable liquid and vapor [Warning Flammable liquids]；H301 (84.8%): Toxic if swallowed [Danger Acute toxicity, oral]；H311 (84.8%): Toxic in contact with skin [Danger Acute toxicity, dermal]；H315 (13%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (13%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H331 (84.8%): Toxic if inhaled [Danger Acute toxicity, inhalation]；H335 (13%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；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

Hazard Classes and CategoriesFlam. Liq. 3 (97.8%)；Acute Tox. 3 (84.8%)；Acute Tox. 3 (84.8%)；Skin Irrit. 2 (13%)；Eye Irrit. 2 (13%)；Acute Tox. 3 (84.8%)；STOT SE 3 (13%)

Safety data

F: 10-13-21
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 1993 3/PG 3
hs_code: 29319090
risk_code: 10-23/24/25
Signal word: Danger
Symbol(GHS): GHS02,GHS06
hazard_code: T
safety_code: 36/37/39-45
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: II
Hazard statements: H226-H301+H311+H331
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 3
Precautionary statements: P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationDisilathiane, 1,1,1,3,3,3-hexamethyl-: ACTIVE

Applications · 3 items

UsesBis(trimethylsilyl)sulfide is used as a silylating agent in the synthesis of pseudohalides, trifluoroacetate and tetramethylsilyl halides. It is used in the transformation of oxides and chlorides into corresponding sulfides. It is also used in the preparation of dimethyltrisulfane as well as thiones from aldehydes and ketones. Further, it is used as a reducing agent to reduce aromatic nitro compounds to amines.

UsesHexamethyldisilathiane may be used in the bis-O-demethylation of dimethoxy aromatic compounds. It may also be used as a sulfur source in the following conversion: Amides and lactams to their corresponding sulfur analogs.Allyl alcohols to diallyl sulfides. Transition metal halides to metal sulfides.Aryl iodides to diaryl sulfides.

UsesBis(trimethylsilyl) sulfide (TMS2S) is used to reduce aromatic nitro groups to amines and the oxides of sulfur, selenium, and tellurium. Conditions for nitro group reduction (eq 1) are forcing; however, yields are good. Reactions of TMS2S with primary aliphatic nitro groups result in the formation of the thiohydroxamic acids (eq 2) which can be isolated or carried further to the nitrile. Secondary alkyl nitro derivatives provide oximes. Sulfoxides are reduced to sulfides, selenoxides to selenides, and telluroxides to tellurides. Conditions are mild and work well on both the aliphatic and aromatic oxides.