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Merck
CN

344648

Triethylamine trihydrofluoride

97%

Synonym(s):

Hydrogen fluoride triethylamine, TREAT-HF

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About This Item

Linear Formula:
(C2H5)3N · 3HF
CAS Number:
73602-61-6
Molecular Weight:
161.21
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24861270
EC Number:
277-550-5
Beilstein/REAXYS Number:
5522945
MDL number:
MFCD00043294

Key Documents

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InChI key

IKGLACJFEHSFNN-UHFFFAOYSA-N

InChI

1S/C6H15N.3FH/c1-4-7(5-2)6-3;;;/h4-6H2,1-3H3;3*1H

SMILES string

F[H].F[H].F[H].CCN(CC)CC

assay

97%

refractive index

n20/D 1.3915 (lit.)

bp

70 °C/15 mmHg (lit.)

density

0.989 g/mL at 25 °C (lit.)

functional group

amine

Quality Level

300

General description

Triethylamine trihydrofluoride (TREAT-HF) is a mild and selective reagent for the fluorination of a wide variety of compounds.

Application

Mild and selective reagent that has been used in the fluorination of a wide variety of compounds. For a review, see Aldrichimica Acta.
TREAT-HF can be used in the synthesis of:
  • Vicinal difluorides from epoxides.
  • 3-fluoroazetidines.
  • 9-(2,3-dideoxy-2-fluoro-β-d-threo-pentofuranosyl)adenine (FddA).
  • Multivicinal hexafluoroalkanes.
  • Aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1A

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

190.4 °F - closed cup

flash_point_c

88 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT3123
SHBS4321
SHBS3626
SHBP0256
SHBM8698

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Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines
Hende E, et al.
Organic & Biomolecular Chemistry, 8(11), 2509-2512 (2010)
Willem Van Brabandt et al.
The Journal of organic chemistry, 71(18), 7100-7102 (2006-08-26)
N-(Alkylidene or 1-arylmethylidene)-2-propenylamines were regiospecifically functionalized to novel N-(alkylidene or 1-arylmethylidene)-3-bromo-2-fluoropropylamines, which were proven to be excellent precursors for 3-fluoroazetidines.
Saira Ashraf et al.
RNA biology, 16(10), 1377-1385 (2019-06-27)
N6-methyladenine is the most common covalent modification in cellular RNA species, with demonstrated functional consequences. At the molecular level this methylation could alter local RNA structure, and/or modulate the binding of specific proteins. We have previously shown that trans-Hoogsteen-sugar (sheared)
Effect of Partially Fluorinated N-Alkyl-Substituted Piperidine-2-carboxamides on Pharmacologically Relevant Properties
Vorberg R, et al.
ChemMedChem, 11(19), 2216-2239 (2016)
Synthesis and structure of stereoisomeric multivicinal hexafluoroalkanes
Hunter L, et al.
Angewandte Chemie (International ed. in English), 48(30), 5457-5460 (2009)
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