CAS 105832-38-0 2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (HCID 9857522)

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Basic information

CAS: 105832-38-0
Standard SMILES: CN(C)C(ON1C(=O)CCC1=O)=[N+](C)C.F[B-](F)(F)F
InChIKey: YEBLHMRPZHNTEK-UHFFFAOYSA-N
Molecular formula: C9H16BF4N3O3
Average molar mass: 301.05 g/mol
Monoisotopic mass: 301.12208465

Names & identifiers

Preferred name: 2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate
IUPAC: [dimethylamino-(2,5-dioxopyrrolidin-1-yl)oxymethylidene]-dimethylazanium tetrafluoroborate
English name: TSTU
Molecular formula: C9H16BF4N3O3
Molecular weight: 301.05

Names & synonyms

105832-38-02-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateRefChem:452120629-651-4TSTUo-(n-succinimidyl)-1,1,3,3-tetramethyluronium tetrafluoroborateMFCD00077875N,N,N',N'-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate105882-38-0O-(N-Succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2-succinimido-1,1,3,3-tetramethyluronium tetrafluoroborate[dimethylamino-(2,5-dioxopyrrolidin-1-yl)oxymethylidene]-dimethylazanium;tetrafluoroborate

Show more names

O-(N-succinimidyl)-N,N,N',N'-tetramethyl uronium bf4O-(N-SucciniMidyl)-1,1,3,3-tetraMethyl uraniuM tetrafluoroborateTSTU, N-{(Dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene}-N-methylmethylaminium tetrafluoroborateHONSTUTSTU 25 GTSTU USP/EP/BP

[dimethylamino-(2,5-dioxopyrrolidin-1-yl)oxy-methylene]-dimethyl-ammonium tetrafluoroborateo-(n-succinimidyl)-n,n,n',n'-tetramethyl-uronium tetrafluoroborateC9H16BF4N3O32-succinimido-1,1,3,3-tetra-methyluronium tetrafluoroborateSCHEMBL26220SCHEMBL131101orb2939193DTXSID00431911

Properties

Computed structural properties

Topological polar surface area: 52.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 8
Rotatable bonds: 3
Heavy atoms: 20
Formal charge: 0
Complexity: 309

Physicochemical properties

Melting point: 198 · 198-201 °C(lit.)
Density: 1.41 g/cm · 1.41 g/cm
storage temp.: 2 · 2-8°C
solubility: 0.1 g/mL, · acetonitrile: 0.1 g/mL, clear
form: Crystalline Powder or Needles
color: White to off-white
Sensitive: Moisture Sensitive
Major Application: peptide synthesis
InChI: InChI=1S/C9H16N3O3.BF4/c1-10(2)9(11(3)4)15-12-7(13)5-6-8(12)14;2-1(3,4)5/h5-6H2,1-4H3;/q+1;-1
InChIKey: BVYYWTQJMFGHLU-UHFFFAOYSA-M
SMILES: [B+3]([F-])([F-])([F-])[F-].O(N1C(CCC1=O)=O)/C(=[N+](\C)/C)/N(C)C
CAS DataBase Reference: 105832 · 105832-38-0(CAS DataBase Reference)
UNSPSC Code: 12352107 · 12352107
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (14.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 55 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (14.5%)

Safety data

F: 8-10-21
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
ridadr: 1759
hs_code: 29280000
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-37/39
hazard_class: 8
Storage Class: 11 - Combustible Solids
packing_group: III
Hazard statements: H315-H319
Hazard Classifications: Skin Sens. 1A
Precautionary statements: P302+P352-P305+P351+P338

Chemistry & industry

Applications · 4 items

Usespeptide coupling reagent converts carboxylates to N-succinimidyl active esters

UsesReagent for the clean in-situ formation of N-succinimidyl active esters

UsesTSTU is used as a peptide coupling reagent in solvent systems.

General DescriptionN,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate is commonly used for the conversion of carboxylic acid into the corresponding N-hydroxysuccinimidyl (NHS) ester.