J u m p t o c o n t e n t
M a i n m e n u
M a i n m e n u
N a v i g a t i o n
● M a i n p a g e ● C o n t e n t s ● C u r r e n t e v e n t s ● R a n d o m a r t i c l e ● A b o u t W i k i p e d i a ● C o n t a c t u s ● D o n a t e
C o n t r i b u t e
● H e l p ● L e a r n t o e d i t ● C o m m u n i t y p o r t a l ● R e c e n t c h a n g e s ● U p l o a d f i l e
S e a r c h
Search
A p p e a r a n c e
● C r e a t e a c c o u n t ● L o g i n
P e r s o n a l t o o l s
● C r e a t e a c c o u n t ● L o g i n
P a g e s f o r l o g g e d o u t e d i t o r s l e a r n m o r e ● C o n t r i b u t i o n s ● T a l k
( T o p )
1 P r e p a r a t i o n
2 U s e s
3 R e a c t i v i t y
4 N a t u r a l o c c u r r e n c e
5 S a f e t y
6 R e f e r e n c e s
T o g g l e R e f e r e n c e s s u b s e c t i o n
6 . 1 G e n e r a l r e a d i n g
T o g g l e t h e t a b l e o f c o n t e n t s
P h t h a l i m i d e
2 3 l a n g u a g e s
● ا ل ع ر ب ي ة ● ت ۆ ر ک ج ه ● C a t a l à ● Č e š t i n a ● D e u t s c h ● E s p a ñ o l ● E s p e r a n t o ● E u s k a r a ● ف ا ر س ی ● F r a n ç a i s ● B a h a s a I n d o n e s i a ● I t a l i a n o ● M a g y a r ● N e d e r l a n d s ● P o l s k i ● P o r t u g u ê s ● R o m â n ă ● Р у с с к и й ● С р п с к и / s r p s k i ● S r p s k o h r v a t s k i / с р п с к о х р в а т с к и ● S u o m i ● S v e n s k a ● 中 文
E d i t l i n k s
● A r t i c l e ● T a l k
E n g l i s h
● R e a d ● E d i t ● V i e w h i s t o r y
T o o l s
T o o l s
A c t i o n s
● R e a d ● E d i t ● V i e w h i s t o r y
G e n e r a l
● W h a t l i n k s h e r e ● R e l a t e d c h a n g e s ● U p l o a d f i l e ● S p e c i a l p a g e s ● P e r m a n e n t l i n k ● P a g e i n f o r m a t i o n ● C i t e t h i s p a g e ● G e t s h o r t e n e d U R L ● D o w n l o a d Q R c o d e ● W i k i d a t a i t e m
P r i n t / e x p o r t
● D o w n l o a d a s P D F ● P r i n t a b l e v e r s i o n
I n o t h e r p r o j e c t s
● W i k i m e d i a C o m m o n s
A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
( R e d i r e c t e d f r o m P h t h a l i m i d e f u n g i c i d e )
Phthalimide
Names
Preferred IUPAC name
1 H 2 H
Other names
1,3-dioxoisoindoline
Identifiers
CAS Number
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.458
PubChem CID
UNII
CompTox Dashboard (EPA )
InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5 )8(11 )9-7/h1-4H,(H,9,10,11) Y
Key: XKJCHHZQLQNZHY-UHFFFAOYSA-N Y
InChI=1/C8H5NO2/c10-7-5-3-1-2-4-6(5 )8(11 )9-7/h1-4H,(H,9,10,11)
Key: XKJCHHZQLQNZHY-UHFFFAOYAS
Properties[1]
Chemical formula
C 8 H 5 N O 2
Molar mass
−1
Appearance
White solid
Melting point
238 °C (460 °F; 511 K )
Boiling point
336 °C (637 °F; 609 K ) sublimes
Solubility in water
<0.1 g/100 ml (19.5 °C)
Acidity (p K a 8.3
Basicity (p K b 5.7
Magnetic susceptibility (χ)
× 10 −6 cm 3
Related compounds
Related Amides
Maleimide
Related compounds
Phthalic anhydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Phthalimide is the organic compound with the formula C6 H 4 CO )2 imide derivative of phthalic anhydride . It is a sublimable white solid that is slightly soluble in water but more so upon addition of base . It is used as a precursor to other organic compounds as a masked source of ammonia .[2]
Preparation
[ edit ]
Phthalimide can be prepared by heating phthalic anhydride with alcoholic ammonia giving 95–97% yield. Alternatively, it may be prepared by treating the anhydride with ammonium carbonate or urea . It can also be produced by ammoxidation of o [2]
Uses
[ edit ]
Phthalimide is used as a precursor to anthranilic acid , a precursor to azo dyes and saccharin .[2]
Alkyl phthalimides are useful precursors to amines in chemical synthesis, especially in peptide synthesis where they are used "to block both hydrogens and avoid racemization of the substrates".[3]
C 6 H 4 CO )2 6 H 4 CO )2 2 O
The amine is commonly liberated using hydrazine:
C 6 H 4 CO )2 2 H 4 6 H 4 CO )2 N 2 H 2 2
Dimethylamine can also be used.[4]
Some examples of phthalimide drugs include thalidomide , amphotalide , taltrimide , talmetoprim , and apremilast . With a trichloromethylthio substituent, a phthalimide-derived fungicide is Folpet .
Reactivity
[ edit ]
It forms salts upon treatment with bases such as sodium hydroxide. The high acidity of the imido N-H is the result of the pair of flanking electrophilic carbonyl groups. Potassium phthalimide , made by reacting phthalimide with potassium carbonate in water at 100 °C or with potassium hydroxide in absolute ethanol,[5] Gabriel synthesis of primary amines, such as glycine .
Natural occurrence
[ edit ]
Kladnoite is a natural mineral analog of phthalimide.[6] coal fire sites.
Safety
[ edit ]
Phthalimide has low acute toxicity with LD 50 [2]
References
[ edit ]
^ a b c d Lorz, Peter M.; Towae, Friedrich K.; Enke, Walter; Jäckh, Rudolf; Bhargava, Naresh; Hillesheim, Wolfgang. "Phthalic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry doi :10.1002/14356007.a20_181.pub2 . ISBN 978-3527306732
^ "Phthalimides" . Retrieved 2013-02-07 .
^ "Deprotection – removal of amine protecting groups (phthalimide and dimethylaminosulphonyl)" . Archived from the original on 2014-12-03. Retrieved 2013-02-07 .
^ Salzberg, P. L.; Supniewski, J. V. "β-Bromoethylphthalimide". Organic Syntheses 7 doi :10.15227/orgsyn.007.0008 Collected Volumes , vol. 1, p. 119
^ "Kladnoite" . mindat.org. Retrieved 15 November 2011 .
General reading
[ edit ]
Finar, Ivor Lionel (1973). Organic Chemistry . Vol. 1 (6th ed.). London: Longman. ISBN 0-582-44221-4
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Phthalimide&oldid=1148795944#Uses " C a t e g o r y : ● P h t h a l i m i d e s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a ● A r t i c l e s w i t h o u t K E G G s o u r c e ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 8 A p r i l 2 0 2 3 , a t 1 1 : 1 9 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
