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Methyl triflate

HCID 9526
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Basic information

CAS
333-27-7
Standard SMILES
COS(=O)(=O)C(F)(F)F
InChIKey
OIRDBPQYVWXNSJ-UHFFFAOYSA-N
Molecular formula
C2H3F3O3S
Average molar mass
164.11 g/mol
Monoisotopic mass
163.97549962

Overview

Methyl trifluoromethane sulfonate is a brown liquid. Insoluble in water. (NTP, 1992) This material is a very reactive methylating agent, also known as methyl triflate.

Names & identifiers

Preferred name
Methyl triflate
IUPAC
methyl trifluoromethanesulfonate
English name
Methyl trifluoromethanesulfonate
Molecular formula
C2H3F3O3S
Molecular weight
164.1

Names & synonyms

Methyl trifluoromethanesulfonate333-27-7Methyl triflateMethyl trifluoromethanesulphonateMethanesulfonic acid, trifluoro-, methyl esterDTXSID60492727B25Z22EPVNSC-270679DTXCID1029128Trifluoromethanesulfonic acid, methyl esterRefChem:158046206-371-7
Show more names
TfOMeMethyl trifluoromethanesulfateMethyl trifluoroMethanesulfonaMethyl trifluoromethanesulfotemethyltrifluoromethanesulfinateMETHYL TRIFLUROMETHANESULFONATE
Trifluoromethanesulfonic Acid Methyl EsterMethyl trifluoromethane sulfonateC2H3F3O3SMeOTfMFCD00000409methyl-13c trifluoromethanesulfonatetrifluoro-methanesulfonic acid methyl esterMethanesulfonic acid, 1,1,1-trifluoro-, methyl ester

Database identifiers

CAS
333-27-7
PubChem CID
9526
DTXSID
DTXSID6049272
ChEMBL
CHEMBL3185488
UNII
7B25Z22EPV
EC Number
206-371-7
Nikkaji
J193.765K

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
51.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
9
Formal charge
0
Complexity
172

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Sulfur Compounds
SpringerMaterials PropertiesSchoenflies notation
Density · 2 items

1.45 at 68 °F (NTP, 1992) - Denser than water; will sink

1.45 @25 °C

SolubilityInsoluble (NTP, 1992)
Flash Point101 °F (NTP, 1992)
Boiling Point201 to 210 °F at 760 mmHg (NTP, 1992)
Physical Description · 2 items

Methyl trifluoromethane sulfonate is a brown liquid. Insoluble in water. (NTP, 1992) This material is a very reactive methylating agent, also known as methyl triflate.

Brown liquid; [CAMEO] Clear light yellow liquid; [Sigma-Aldrich MSDS]

Physicochemical properties

Boiling point
94 · 94-99 °C(lit.)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Methanesulfonic acid, trifluoro-, methyl ester

Methyl trifluoromethanesulphonate: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelFlammable Liquid Corrosive
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)
Hazards SummaryCauses burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Sigma-Aldrich MSDS] See Trifluoromethanesulfonic acid. See Ethyl methanesulfonate.
Reactive GroupSulfonates, Phosphonates, and Thiophosphonates, Organic
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 item

METHYL TRIFLUOROMETHANE SULFONATE is sensitive to heat. (NTP, 1992). Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Chemistry & industry

Uses & manufacturing

UsesUsed as a reagent for the methylation of sugars; [NTP]
General Manufacturing InformationMethanesulfonic acid, 1,1,1-trifluoro-, methyl ester: ACTIVE

Applications

UsesMethyl trifluoromethanesulfonate is used as a powerful methylating reagent in chemistry. Further, it is used in the conversion of amines to methyl ammonium triflates. In addition, it is also used in Suzuki reaction.

General DescriptionMethyl trifluoromethane sulfonate is a brown liquid. Insoluble in water. (NTP, 1992) This material is a very reactive methylating agent, also known as methyl triflate.

Upstream & downstream products

Upstream raw materials

Trifluoromethanesulfonic acidMethanolThionyl chlorideDimethyl sulfate

Downstream products

7,10-Dimethoxy-10-DAB IIIN-Methylaniline hydrochloride5-Methoxy-3,4-dihydro-1(2H)-isoquinolinone4-Difluoromethoxyphenylboronic acid pinacol ester3-Methylphenyl isothiocyanate

Related reactions

245 records
New reaction record
HRID 7222 reaction equation
HRID 7222As productuspto-grants-2006_08
HRID 22242 reaction equation
HRID 22242As reactantuspto-grants-1995_06
HRID 31510 reaction equation
HRID 31510As reactantuspto-grants-2008_09
HRID 43293 reaction equation
HRID 43293As reactantuspto-grants-2013_09
HRID 43294 reaction equation
HRID 43294As reactantuspto-grants-2013_09
HRID 43295 reaction equation
HRID 43295As reactantuspto-grants-2013_09
HRID 43296 reaction equation
HRID 43296As reactantuspto-grants-2013_09
HRID 46582 reaction equation
HRID 46582As reactantuspto-grants-1979_11
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Density
1.45 g/mL · 1.45 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.326(lit.)
Flash point
101 °F · 101 °F
storage temp.
2 · 2-8°C
solubility
Chloroform (Sparingly), Ethyl Acetate (Slightly)
form
Liquid
Specific Gravity
1.45 · 1.450
color
Clear colorless to yellow
Sensitive
Air Sensitive
BRN
774772 · 774772
Stability
Hygroscopic, Moisture Sensitive, Volatile
InChI
InChI=1S/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3
InChIKey
OIRDBPQYVWXNSJ-UHFFFAOYSA-N
SMILES
C(F)(F)(F)S(OC)(=O)=O
CAS DataBase Reference
333 · 333-27-7(CAS DataBase Reference)
FDA UNII
7 B25Z22EPV · 7B25Z22EPV
EPA Substance Registry System
Methyl trifluoromethanesulfonate (333-27-7)
UNSPSC Code
41116105 · 41116105
NACRES
22 · NA.22
Symbol(GHS)
2 · GHS02,GHS05,GHS06
Signal word
Danger
Hazard statements
226 · H226-H301+H311-H314-H330
Precautionary statements
210 · P210-P233-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazard Codes
C,T
Risk Statements
10 · 10-34-20/21/22
Safety Statements
26 · 26-36/37/39-45-16
RIDADR
2920 · UN 2920 8/PG 2
WGK Germany
3 · 3
F
10 · 10
Hazard Note
Highly Toxic/Corrosive
TSCA
TSCA listed
HazardClass
3.2 · 3.2
PackingGroup
III
HS Code
29049020 · 29049020
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
1 InhalationAcute · Acute Tox. 1 InhalationAcute Tox. 3 DermalAcute Tox. 3 OralEye Dam. 1Flam. Liq. 3Skin Corr. 1B
Limited Quantities
1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Air and Water ReactionsHighly flammable. Insoluble in water.
Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety & protection

Fire FightingFires involving this material should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Protective Action Criteria (PAC) · 3 items

22 [mg/m3]

240 [mg/m3]

1400 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (NTP, 1992)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Safety data

F
10
wgk
3
tsca
TSCA listed
ridadr
UN 2920 8/PG 2
hs_code
29049020
risk_code
10-34-20/21/22
Signal word
Danger
Symbol(GHS)
GHS02,GHS05,GHS06
hazard_code
C,T
hazard_note
Highly Toxic/Corrosive
safety_code
26-36/37/39-45-16
hazard_class
3.2
Storage Class
3 - Flammable liquids
packing_group
III
Hazard statements
H226-H301+H311-H314-H330
Limited Quantities
1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications
Acute Tox. 1 InhalationAcute Tox. 3 DermalAcute Tox. 3 OralEye Dam. 1Flam. Liq. 3Skin Corr. 1B
Precautionary statements
P210-P233-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
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