CAS 145100-51-2 N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-trifluoromethanesulfonylmethanesulfonamide (HCID 388544)

Substructure search Find similar structures

Basic information

CAS: 145100-51-2
Standard SMILES: O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F
InChIKey: TUFGVZMNGTYAQD-UHFFFAOYSA-N
Molecular formula: C7H3ClF6N2O4S2
Average molar mass: 392.7 g/mol
Monoisotopic mass: 391.9126956

Names & identifiers

Preferred name: N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-trifluoromethanesulfonylmethanesulfonamide
IUPAC: N-(5-chloro-2-pyridinyl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide
English name: 2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE
Molecular formula: C7H3ClF6N2O4S2
Molecular weight: 392.68

Names & synonyms

N-(5-Chloro-2-pyridyl)triflimideN-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-trifluoromethanesulfonylmethanesulfonamideRefChem:828151629-110-2145100-51-22-[N,N-Bis(Trifluoromethylsulphonyl)amino]-5-chloropyridine2-[N,N-Bis(trifluoromethanesulfonyl)amino]-5-chloropyridineN-(5-Chloro-2-pyridyl)bis(trifluoromethanesulfonimide)Comins' Reagent2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridineMFCD00191833N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide

Show more names

CominsN,N-BIS(TRIFLUOROMETHYLSULFONYL)-5-CHLORO-2-PYRIDYLAMINEN-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-Comins'reagent

Comins Triflating ReagentMethanesulfonamide, N-(5-chloro-2-pyridinyl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]-NSC683533NSC-683533WS933U9U66N-(5-chloro-2-pyridyl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamideN-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamideN,N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridinamine

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 101 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 12
Rotatable bonds: 3
Heavy atoms: 22
Formal charge: 0
Complexity: 561

Physicochemical properties

Melting point: 45 · 45-47 °C(lit.)
Boiling point: 77 · 77-90°C/0.2mmHg
Density: 1.892 · 1.892±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: Benzene (Slightly)
form: Solid
pka: -7.71 · -7.71±0.10(Predicted)
color: yellow
Water Solubility: Reacts with water.
Sensitive: Moisture Sensitive
BRN: 5833971 · 5833971
Stability: Moisture Sensitive, Unstable in DMSO Solution
InChI: InChI=1S/C7H3ClF6N2O4S2/c8-4-1-2-5(15-3-4)16(21(17,18)6(9,10)11)22(19,20)7(12,13)14/h1-3H
InChIKey: TUFGVZMNGTYAQD-UHFFFAOYSA-N
SMILES: C(F)(F)(F)S(N(C1=NC=C(Cl)C=C1)S(C(F)(F)F)(=O)=O)(=O)=O
CAS DataBase Reference: 145100 · 145100-51-2(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (10%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (10%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (10%): Harmful if inhaled [Warning Acute toxicity, inhalation]；H335 (98%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 8 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 CategoriesAcute Tox. 4 (10%)；Acute Tox. 4 (10%)；Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；Acute Tox. 4 (10%)；STOT SE 3 (98%)

Safety data

F: 9
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29350090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi

Chemistry & industry

Applications · 2 items

Uses2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine provides good yields of vinyl triflates from the corresponding ketone enolates or dienolates. It is used in the total synthesis of (-)-porantheridine and the trans decahydroquinoline alkaloid (+)-219A. It is also used as a reactant for Suzuki-Miyaura cross coupling, synthesis of nicotinic acetylcholine receptor-selective ligands, enantioselective desymmetrizing palladium catalyzed carbonylation reactions, synthesis of high affinity niacin receptor GPR109A agonists and in preparation of heteroaromatics.

UsesReactant for: Suzuki-Miyaura cross coupling Synthesis of nicotinic acetylcholine receptor-selective ligands Enantioselective desymmetrizing palladium catalyzed carbonylation reactions Synthesis of high affinity niacin receptor GPR109A agonists Preparation of heteroaromatics