91678
N-(4-Hydroxybutyl)trifluoroacetamide
≥98.0% (GC)
Synonym(s):
4-(Trifluoroacetamido)-1-butanol
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About This Item
Empirical Formula (Hill Notation):
C6H10F3NO2
CAS Number:
Molecular Weight:
185.14
UNSPSC Code:
12352202
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
6644043
Assay:
≥98.0% (GC)
Form:
liquid
InChI
1S/C6H10F3NO2/c7-6(8,9)5(12)10-3-1-2-4-11/h11H,1-4H2,(H,10,12)
SMILES string
O=C(NCCCCO)C(F)(F)F
InChI key
LZUDPIMZEXACCH-UHFFFAOYSA-N
assay
≥98.0% (GC)
form
liquid
reaction suitability
reagent type: cross-linking reagent
refractive index
n20/D 1.413
density
1.262 g/mL at 20 °C (lit.)
functional group
hydroxyl
Other Notes
Building block to introduce a 4-aminobutyl residue in a daunomycinone giving optimal intercalation with DNA; Protecting group in phosphodiesters; cleavage occurs by cyclo-de-esterification
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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A. Wilk et al.
The Journal of Organic Chemistry, 62, 6712-6712 (1997)
Zoltán Dienes et al.
The Journal of organic chemistry, 61(20), 6958-6970 (1996-10-04)
The BF(3).Et(2)O-promoted Diels-Alder addition of 1-acetylvinyl RADO(Et)-ate (RADO(Et)-ate = 3-ethyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate) to 1-(dimethoxymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane led to one major monoadduct that added to 1,2-didehydrobenzene and was converted into (-)-4-demethoxy-7-deoxydaunomycinone and (2R)-12-acetoxy-2-acetyl-5-(bromomethyl)-1,2,3,4-tetrahydronaphthacen-2-yl RADO(Et)-ate. The latter compound was used to construct (8R)-8-acetyl-6,8-dihydroxy-11-[[(3'-[(aminopropyl)oxy]-, -4'-[(aminobutyl)oxy], and -5'-[(aminopentyl)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione
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