Phthalimide

Short description: Organic Compound

Phthalimide

Names
Preferred IUPAC name

1H-Isoindole-1,3(2H)-dione

Other names

1,3-dioxoisoindoline
Phthalimidoyl (deprotonated)

Identifiers

CAS Number

* 85-41-6 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:38817 Y

ChEMBL |

* ChEMBL277294 Y

ChemSpider |

* 6550 Y

PubChem CID

* 6809

UNII |

* 1J6PQ7YI80 Y

InChI

* 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

SMILES

* O=C2c1ccccc1C(=O)N2

Properties[1]

Chemical formula

| C8H5NO2
Molar mass | 147.133 g·mol−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 (pKa)  | 8.3
Basicity (pKb)  | 5.7

Magnetic susceptibility (χ)

| −78.4×10−6 cm3/mol
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).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Phthalimide is the organic compound with the formula C6H4(CO)2NH. It is the 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]

## Contents

* 1 Preparation
* 2 Uses
* 3 Reactivity
* 4 Natural occurrence
* 5 Safety
* 6 References
* 6.1 General reading

## Preparation

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-xylene.[2]

## Uses

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] Alkyl halides can be converted to the N-alkylphthalimide:

C6H4(CO)2NH + RX + NaOH → C6H4(CO)2NR + NaX + H2O

The amine is commonly liberated using hydrazine:

C6H4(CO)2NR + N2H4 → C6H4(CO)2N2H2 \+ RNH2

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

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] is used in the Gabriel synthesis of primary amines, such as glycine.

## Natural occurrence

Kladnoite is a natural mineral analog of phthalimide.[6] It is very rarely found among a few burning coal fire sites.

## Safety

Phthalimide has low acute toxicity with -1">50 (rat, oral) of greater than 5,000 mg/kg.[2]

## References

1. ↑ "Phthalimide". Chemicalland21. http://www.chemicalland21.com/specialtychem/finechem/PHTHALIMIDE.htm. Retrieved 15 November 2011.
2. ↑ 2.0 2.1 2.2 2.3 Lorz, Peter M.; Towae, Friedrich K.; Enke, Walter; Jäckh, Rudolf; Bhargava, Naresh; Hillesheim, Wolfgang. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_181.pub2.
3. ↑ "Phthalimides". https://www.organic-chemistry.org/protectivegroups/amino/phthalimides.htm. Retrieved 2013-02-07.
4. ↑ "Deprotection – removal of amine protecting groups (phthalimide and dimethylaminosulphonyl)". Archived from the original on 2014-12-03. https://archive.today/20141203032450/http://scientificupdate.co.uk/process-chemistry-information/item/deprotection-removal-of-amine-protecting-groups-phthalimide-and-dimethylaminosulphonyl.html. Retrieved 2013-02-07.
5. ↑ Salzberg, P. L.; Supniewski, J. V.. "β-Bromoethylphthalimide". Organic Syntheses 7: 8. doi:10.15227/orgsyn.007.0008. ;  Collective Volume, 1, pp. 119
6. ↑ "Kladnoite". mindat.org. http://www.mindat.org/min-2222.html. Retrieved 15 November 2011.

### General reading

* Vollhardt, K. Peter C.; Schore, Neil Eric (2002). Organic Chemistry: Structure and Function (4th ed.). New York: W. H. Freeman. ISBN 978-0-7167-4374-3. https://archive.org/details/organicchemistry00voll_0.
* Finar, Ivor Lionel (1973). Organic Chemistry. 1 (6th ed.). London: Longman. ISBN 0-582-44221-4.

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*[CID]: Compound ID