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Details

Stereochemistry ACHIRAL
Molecular Formula C4H10F3NS
Molecular Weight 161.189
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIETHYLAMINOSULFUR TRIFLUORIDE

SMILES

CCN(CC)S(F)(F)F

InChI

InChIKey=CSJLBAMHHLJAAS-UHFFFAOYSA-N
InChI=1S/C4H10F3NS/c1-3-8(4-2)9(5,6)7/h3-4H2,1-2H3

HIDE SMILES / InChI
Molecular Formula C4H10F3NS
Molecular Weight 161.189
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Diethylaminosulfur trifluoride (DAST) has proven itself to be an extremely popular reagent for nucleophilic fluorination, due to its ease of handling and versatility. It has regularly been employed in a myriad selective fluorinations of alcohols, alkenols, carbohydrates, ketones, sulfides, epoxides, thioethers, and cyanohydrins. In addition some novel organic cyclizations are possible when DAST is employed as a reagent.

Originator

Von Halasz, S.P.|Glemser, O.
1
Sources: S. P. von Halasz and O. Glemser, Chem. Ber., 104, 1247 (1971).
Curator's Comment: reference retrieved from http://orgsyn.org/demo.aspx?prep=cv6p0440

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Enantioselective synthesis of β-fluoroamines from β-amino alcohols: application to the synthesis of LY503430.
2010-10-15
Aminodifluorosulfinium salts: selective fluorination reagents with enhanced thermal stability and ease of handling.
2010-05-21
First principles insight into the alpha-glucan structures of starch: their synthesis, conformation, and hydration.
2010-04-14
Synthesis and anti-HIV-1 activity of 1-substiuted 6-(3-cyanobenzoyl) and [(3-cyanophenyl)fluoromethyl]-5-ethyl-uracils.
2009-09
DAST-mediated regioselective anomeric group migration in saccharides.
2009-06-05
Synthesis of 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) protected N-methyl amino acids by reduction of Bsmoc-5-oxazoli-dinones and their use in peptide synthesis.
2009
Fluorination reactions in microreactors.
2008-07-14
Brassinosteroids: synthesis and activity of some fluoro analogues.
2008-07-10
Fluorination of triptolide and its analogues and their cytotoxicity.
2008-04-01
1H,13C, 19F NMR, and ESI mass spectral characterization of two geminal difluorosteroids.
2008-04
Synthesis and antimicrobial activity of 7-fluoro-3-aminosteroids.
2007-09-15
Application of solid-phase chemistry for the synthesis of 3'-fluoro-3'-deoxythymidine.
2007
4'-Fluorinated carbocyclic nucleosides: synthesis and inhibitory activity against S-adenosyl-L-homocysteine hydrolase.
2006-08-15
Rearrangement of homoallylic alcohols induced by DAST.
2006-05-11
Synthesis of fluorinated analogs of myristic acid as potential inhibitors of Egyptian armyworm (Spodoptera littoralis) delta11 desaturase.
2003-08
Synthesis of 2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine.
2003-01-23
Electrophilic fluorinating reagent mediated synthesis of fluorinated alpha-keto Ethers, benzil, and 6,6'-dialkoxy-2,2'-bipyridines.
2002-09-06
Synthesis of 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (FddA) via a purine 3'-deoxynucleoside.
2001-11-02
Synthetic explorations towards 3-deoxy-3-fluoro derivatives of D-perosamine.
2001-08-30
Patents

Patents

04837327
1
04933365
1
04957934
1
04997941
2
05153200
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:22:16 GMT 2025
Edited
by admin
on Mon Mar 31 21:22:16 GMT 2025
Record UNII
78622BV6IJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(T-4)-(N-ETHYLETHANAMINATO)TRIFLUOROSULFUR
Preferred Name English
DIETHYLAMINOSULFUR TRIFLUORIDE
MI  
Systematic Name English
DAST
Common Name English
DIETHYLAMINOSULFATE TRIFLUORIDE
Systematic Name English
(N,N-DIETHYLAMINO)SULFUR TRIFLUORIDE
Systematic Name English
DAST (FLUORINATING AGENT)
Common Name English
(DIETHYLAMINO)TRIFLUOROSULFUR
Systematic Name English
(DIETHYLAMINO)SULFUR TRIFLUORIDE
Systematic Name English
(DIETHYLAMINO)SULPHUR TRIFLUORIDE
Systematic Name English
DIETHYLAMINOSULFUR TRIFLUORIDE [MI]
Common Name English
TRIFLUORO(DIETHYLAMINO)SULFUR
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID20191484
Created by admin on Mon Mar 31 21:22:16 GMT 2025 , Edited by admin on Mon Mar 31 21:22:16 GMT 2025
PRIMARY
MERCK INDEX
m4394
Created by admin on Mon Mar 31 21:22:16 GMT 2025 , Edited by admin on Mon Mar 31 21:22:16 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
253-771-2
Created by admin on Mon Mar 31 21:22:16 GMT 2025 , Edited by admin on Mon Mar 31 21:22:16 GMT 2025
PRIMARY
FDA UNII
78622BV6IJ
Created by admin on Mon Mar 31 21:22:16 GMT 2025 , Edited by admin on Mon Mar 31 21:22:16 GMT 2025
PRIMARY
CAS
38078-09-0
Created by admin on Mon Mar 31 21:22:16 GMT 2025 , Edited by admin on Mon Mar 31 21:22:16 GMT 2025
PRIMARY
WIKIPEDIA
DIETHYLAMINOSULFUR TRIFLUORIDE
Created by admin on Mon Mar 31 21:22:16 GMT 2025 , Edited by admin on Mon Mar 31 21:22:16 GMT 2025
PRIMARY
PUBCHEM
123472
Created by admin on Mon Mar 31 21:22:16 GMT 2025 , Edited by admin on Mon Mar 31 21:22:16 GMT 2025
PRIMARY
NIH
NCATS
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