Sulfoxonium, trimethyl-, iodide (1:1)

HCID 74498
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Basic information

CAS
1774-47-6
Standard SMILES
C[S+](C)(C)=O.[I-]
InChIKey
BPLKQGGAXWRFOE-UHFFFAOYSA-M
Molecular formula
C3H9IOS
Average molar mass
220.07 g/mol
Monoisotopic mass
219.94188391

Names & identifiers

Preferred name
Sulfoxonium, trimethyl-, iodide (1:1)
English name
Trimethylsulfoxonium iodide
Molecular formula
C3H9IOS
Molecular weight
220.07

Names & synonyms

Trimethylsulfoxonium iodide1774-47-6Sulfoxonium, trimethyl-, iodide (1:1)S,S,S-Trimethylsulfoxonium iodideTrimethyl sulphoxonium ioidieEINECS 217-204-2NSC 71213Sulfonium, trimethyl-, iodide, oxidetrimethyl sulphoxonium iodideEC 217-204-2RefChem:186625Sulfoxonium, trimethyl, iodide
Show more names
TMSOITrimethylsulfoxoniumTrimethyl sulfoxide iodideTrimethyl sulfoxiderimethylsulfoxonium iodideTrimethylsulfoxonium iodide, 98+%
S,S,STrimethylsulfoxonium iodideSulfonium, trimethyl, iodide, oxideTrimethylsulphoxonium iodideTrimethyloxosulfonium iodideSulfoxonium, trimethyl-, iodideTrimethyloxosulphonium iodideMFCD00011899C3H9IOS

Database identifiers

CAS
1774-47-6
PubChem CID
74498
DTXSID
DTXSID001014581
ChEMBL
CHEMBL283149
EC Number
217-204-2

Properties

Computed structural properties

Topological polar surface area
18.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Sulfur Compounds
Physical DescriptionYellow crystalline powder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
208 · 208-212 °C (dec.) (lit.)
Density
1.7074 · 1.7074 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
2 O: · H2O: 50 mg/mL, clear
form
Crystalline Powder
color
White to light yellow

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 8.5% (4 of 47) of reports.

Warning

H303 (17%): May be harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 08-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/15834

Sulfoxonium, trimethyl-, iodide: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryIntravenous LD50 (mouse) = 180 mg/kg; [RTECS] An irritant; [Alfa Aesar MSDS] See Dimethyl sulfoxide. See Iodine for the TLV of Iodides.
Hazard Classes and CategoriesAcute Tox. 5 (17%)

Safety & protection

Threshold Limit Values (TLV)0.01 [ppm], inhalable fraction and vapor (iodides)

Safety data

F
8
PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
tsca
TSCA listed
rtecs
WS3585000
hs_code
29309070

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationSulfoxonium, trimethyl-, iodide (1:1): ACTIVE
Applications · 3 items

UsesTreatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5

UsesTrimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.

UsesTrimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of epoxides.

Upstream & downstream products

Upstream raw materials

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
宁波君龙新材料有限公司0574 88552216 19032109277 · [email protected]
南京一化生物科技有限公司13429882898; 13429882898

Related reactions

551 records
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Compound notes

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