bis(2-methoxyethyl)(trifluoro-$l^{4}-sulfanyl)amine

• ChemBase ID: 9793
• Molecular Formular: C6H14F3NO2S
• Molecular Mass: 221.2410696
• Monoisotopic Mass: 221.06973435
• SMILES: N(S(F)(F)F)(CCOC)CCOC
• Canonical SMILES: COCCN(S(F)(F)F)CCOC
• InChI: InChI=1S/C6H14F3NO2S/c1-11-5-3-10(4-6-12-2)13(7,8)9/h3-6H2,1-2H3
• InChIKey: APOYTRAZFJURPB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2-methoxyethyl)(trifluoro-$l^{4}-sulfanyl)amine; bis(2-methoxyethyl)(trifluoro-λ^4-sulfanyl)amine
• IUPAC Traditional name: bis(2-methoxyethyl)(trifluoro-$l^{4}-sulfanyl)amine; bis(2-methoxyethyl)(trifluoro-λ^4-sulfanyl)amine
• Synonyms: Bis(2-methoxyethyl)aminosulfur trifluoride; Bis(2-methoxyethyl)aminosulfur trifluoride solution; Deoxo-Fluor® solution; Bis(2-methoxyethyl)aminosulfur trifluoride; Deoxo-Fluor®; Bis(2-methoxyethyl)aminosulphur trifluoride (50% solution in toluene); Deoxo-Fluor; Bis(2-methoxyethyl)aminosulphur trifluoride (50% solution in THF); 双(2-甲氧基乙基)氨基三氟化硫 溶液; Deoxo-Fluor® 溶液; 双(2-甲氧基乙基)氨基三氟化硫

Database IDs

• CAS Number: 202289-38-1
• MDL Number: MFCD01321415
• PubChem SID: 24889983; 24889985; 24872877; 160973100
• PubChem CID: 2734690

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.20042366
• LogD (pH = 7.4): 0.20042366
• Log P: 0.20042366
• Molar Refractivity: 46.2401 cm^3
• Polarizability: 17.993706 Å^3
• Polar Surface Area: 21.7 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: clear yellow liquid
• Boiling Point: >80°C(dec); >80(dec.)°C
• Flash Point: <10 °C; <50 °F
• Density: 1.03-1.05 g/mL at 20 °C; 1.2; 1.2 g/mL at 25 °C(lit.)

Safety Information

• Storage Warning: KEEP COLD, CORROSIVE, WATER REACTIVE; Toxic/Corrosive/Flammable/Moisture Sensitive/Store under Argon/Keep Cold; Toxic/Corrosive/Highly Flammable/Moisture Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 3286
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-14-19-23/25-29-35-37; 14-23/25-29-35; 63-11-14-23/25-29-35-48/20-65
• Safety Statements: 16-26-36/37/39-45; 16-26-36/37/39-45-62; 23-26-36/37/39-43-45
• TSCA Listed: false
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H261-H301 + H331-H304-H314-H336-H361d-H373; H225-H261-H301 + H331-H314-H335; H261-H301-H314-H331
• GHS Precautionary statements: P210-P231 + P232-P261-P280-P301 + P310-P422; P231 + P232-P261-P280-P301 + P310-P305 + P351 + P338-P422
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3286 3/PG 2; UN REST
• Supplemental Hazard Statements: Contact with water liberates toxic gas., May form explosive peroxides., Reacts violently with water.; Contact with water liberates toxic gas., Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Concentration: ~50% in toluene (NMR); 50% in THF
• Linear Formula: (CH3OCH2CH2)2NSF3
• Empirical Formula (Hill Notation): C6H14F3NO2S

DETAILS

Apollo Scientific Ltd - PC6001

Deoxo-FluorR (Registered trademark of Air Products), 50% solution in THF. Stable alternative to DAST.

Apollo Scientific Ltd - PC5471

Deoxo-FluorR (Registered trademark of Air Products), 50% solution in Toluene. Stable alternative to DAST.

Sigma Aldrich - 94324

Other Notes
Fluorinating agent with high thermal stability 7,8,9,10
Application
Reactant for:
• Fluorination reactions1
• Preparation of fluorinated catechols via Umpolung based nucleophilic deoxyfluorination2
• Preparation of imidazole derivatives as CXCR3 antagonists3
• Ring expansion reactions4
• Synthesis of acyl azides from carboxylic acids5
• Aldehydes or ketones from carboxylic acids and Grignard reagents via in situ generation of Weinreb amides6
Legal Information
Deoxo-Fluor is a registered trademark of Air Products & Chemicals, Inc.

Sigma Aldrich - 494119

Other Notes
For a review of recent work on nucleophilic fluorination of organic compounds with Deoxo-Fluor® and DAST, see Synthesis, 2002, 17, 2561.1
One flask conversion of carboxylic acids to amides via the intermediacy of acyl fluorides.
Packaging
5, 25, 100 g in poly bottle
Legal Information
Deoxo-Fluor is a registered trademark of Air Products & Chemicals, Inc.

Sigma Aldrich - 94327

Other Notes
Fluorinating agent with high thermal stability7,8,9
Packaging
10, 50 mL in PFA/FEP bottle
Application
Reactant for:
• Fluorination reactions1
• Preparation of fluorinated catechols via Umpolung based nucleophilic deoxyfluorination2
• Preparation of imidazole derivatives as CXCR3 antagonists3
• Ring expansion reactions4
• Synthesis of acyl azides from carboxylic acids5
• Aldehydes or ketones from carboxylic acids and Grignard reagents via in situ generation of Weinreb amides6
Legal Information
Deoxo-Fluor is a registered trademark of Air Products & Chemicals, Inc.