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Diethylaminosulfur trifluoride

CAS No.
38078-09-0
Chemical Name:
Diethylaminosulfur trifluoride
Synonyms
DAST;ET2NSF3;DIETHYLAMINOSULPHUR TRIFLUORIDE;(diethylamino)trifluorosulfur;Diethylamine sulfur trifluoride;amino)suL;fur trifL;38078-09-0;(beta-4)-sulfu;(T-4)-(N-ethyl
CBNumber:
CB5153161
Molecular Formula:
C4H10F3NS
Molecular Weight:
161.19
MDL Number:
MFCD00000363
MOL File:
38078-09-0.mol
MSDS File:
SDS
Modify Date:2022-11-11 11:01:00

Diethylaminosulfur trifluoride Properties

Boiling point 30-32 °C3 mm Hg(lit.)
Density 1.22 g/mL at 25 °C(lit.)
refractive index 1.41-1.416
Flash point 75 °F
storage temp. 2-8°C
form liquid
pka -4.87±0.70(Predicted)
color Colorless to Yellow to Orange
Specific Gravity 1.220
Water Solubility decomposes
Sensitive Moisture Sensitive
Merck 14,3113
BRN 1849066
Exposure limits ACGIH: TWA 2.5 mg/m3
NIOSH: IDLH 250 mg/m3
InChIKey CSJLBAMHHLJAAS-UHFFFAOYSA-N
CAS DataBase Reference 38078-09-0(CAS DataBase Reference)
FDA UNII 78622BV6IJ
NIST Chemistry Reference Diethylaminosulfur trifluoride(38078-09-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS05
Signal word  Danger
Hazard statements  H226-H242-H314
Precautionary statements  P210-P280-P303+P361+P353-P305+P351+P338-P370+P378-P403+P235
Hazard Codes  C,T,F
Risk Statements  10-14-20/21/22-34-5-35-40
Safety Statements  16-26-36/37/39-45
RIDADR  UN 2920 8/PG 1
WGK Germany  3
3-10-21
Hazard Note  Corrosive/Keep Cold
HazardClass  8
PackingGroup  I
HS Code  29309070
NFPA 704
3
3 2
W

Diethylaminosulfur trifluoride price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 235253 (Diethylamino)sulfur trifluoride 38078-09-0 1g $38.9 2022-05-15 Buy
Sigma-Aldrich 235253 (Diethylamino)sulfur trifluoride 38078-09-0 5g $90.5 2022-05-15 Buy
TCI Chemical D1868 (Diethylamino)sulfur Trifluoride [Fluorinating Reagent] >90.0%(T) 38078-09-0 5g $100 2022-04-27 Buy
TCI Chemical D1868 (Diethylamino)sulfur Trifluoride [Fluorinating Reagent] >90.0%(T) 38078-09-0 25g $317 2022-04-27 Buy
Alfa Aesar A11992 Diethylaminosulfur trifluoride, 95% 38078-09-0 5g $87.6 2021-12-16 Buy
Product number Packaging Price Buy
235253 1g $38.9 Buy
235253 5g $90.5 Buy
D1868 5g $100 Buy
D1868 25g $317 Buy
A11992 5g $87.6 Buy

Diethylaminosulfur trifluoride Chemical Properties,Uses,Production

Fluorinating reagents

N,N-Diethylaminosulfur trifluoride (DAST) is the most widely used fluorinating reagent in this class. It has a similar reactivity to sulfur tetrafluoride, but has the advantage that it can be used in glass vessels at atmospheric pressure. Deoxofluorination reactions with N,N-diethylaminosulfur trifluoride are usually run neat or in anhydrous aprotic solvents, most frequently halogenated solvents, at temperatures of 0- 80 °C. Typically, a stoichiometric amount of the reagent is used for aldehydes and a small excess is used for ketones.
Diethylaminosulfur trifluoride
Diethylaminosulfur trifluoride is the most widely used member of this family of reagents, is a pale yellow liquid that reacts violently with water. DAST is readily obtained from commercial sources (e.g. Aldrich or Lancaster) and can also be prepared by the reaction of N,N-di-ethylaminotrimethylsilane with sulfur tetrafluoride, followed by distillation of the crude product under reduced pressure. DAST is known to be thermally unstable, undergoing either explosion or detonation when heated to > 9°ºC.

Preparation

This preparation of diethylaminosulfur trifluoride is an adaptation of a procedure first described by von Halasz and Glemser.The same procedure can also be used to prepare other dialkylaminosulfur trifluorides by the substitution of the diethylaminotrimethylsilane with other dialkylaminotrimethylsilanes.
preparation of diethylaminosulfur trifluoride
A solution of 96 g (0.66 mole) of diethylaminotrimethylsilane in 100 ml trichlorofluoromethane was added dropwise to a solution of 40 ml (measured at -78°, 0.72 mole) of sulfur tetrafluoride in 200 ml of trichlorofluoromethane at -65° to -60°. The reaction mixture was warmed to room temperature and then distilled to give 88.86 g (84% yield) of diethylaminosulfur trifluoride as a pale yellow liquid, bp 46°-47° (10 mm).

Reactions

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.
Fluorodeoxygenation was achieved using DAST in a preparatively simple synthesis of 5,5-difluoropipecolic acid from glutamic acid.

1,2,2-Trifluorostyrenes can be synthesized using a sequential reaction on the parent a-(trifluoromethyl)phenylethanol with DAST, followed by dehydrohalogenation with lithium bis(trimethylsilyl)amide (LHMDS). This method achieves the trifluorostyrene without requirement of palladium coupling.

DAST was recently used to obtain fluorinated analogues of 3,6-dibromocarbazole piperazine derivatives of 2-propanol (Scheme 7). A series of these analogues are described as the first small and potent modulators of the cytochrome c release triggered by Bid-induced Bax activation in a mitochondrial assay.

Precautions

diethylaminosulfur trifluoride (DAST) reacts violently with water, it is volatile, and is reported to be explosive when heated owing to its calorimetry profile and its rapid dismutation to SF4 and (Et2N)2SF2. Furthermore, its decomposition products are themselves highly reactive and will etch laboratory glassware. Accordingly, DAST must be used with extreme caution, and samples are recommended not to be heated above 90 °C.

Chemical Properties

Pale yellow liquid. Soluble in most non-polar organic solvents, commonly used in CH2Cl2, CHCl3 and CCl4.

Uses

Diethylaminosulfur Trifluoride is a very useful Nucleophilic fluorinating agent in chemical synthesis. It is also used as a reagent in the preparation of 2-thiazolines from (1,2)-thioam ido-alcohols.

Application

Diethylaminosulfur trifluoride (DAST) is used as a precursor to prepare 2,6-dimethoxybenzoyl fluoride and 2-thiazolines. It is a useful fluorinating agent used for a variety of compounds including alcohols, thioethers, alkenols and cyanohydrins. It also serves as a catalyst for Friedel-Crafts allylation reaction using tertiary cyclopropyl silyl ethers and in the rearrangement of homoallylic alcohols to unsaturated aldehydes. It plays an important role for gem difluorination of ketopipecolinic acids.

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View Lastest Price from Diethylaminosulfur trifluoride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Diethylaminosulfur trifluoride pictures 2022-12-08 Diethylaminosulfur trifluoride
38078-09-0
US $0.00 / KG 1KG 99% 500000kg Hebei Guanlang Biotechnology Co., Ltd.
Diethylaminosulfur trifluoride pictures 2022-10-10 Diethylaminosulfur trifluoride
38078-09-0
US $0.00-0.00 / kg 1kg 98% 1Ton Henan Aochuang Chemical Co.,Ltd.
Diethylaminosulfur trifluoride  pictures 2022-08-18 Diethylaminosulfur trifluoride
38078-09-0
US $1.10 / g 1g 99.00% 100 Tons Min Dideu Industries Group Limited
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