| Identification | More | [Name]
N-Chlorophthalimide | [CAS]
3481-09-2 | [Synonyms]
2-chloro-1h-isoindole-1,3(2h)-dione
N-CHLOROPHTHALIMIDE
ncp
phthalimide chloride
Phthalimidoyl chloride
Chlorophtalimide
N-Chlorphthalimid
2-Chloro-2H-isoindole-1,3-dione | [EINECS(EC#)]
222-459-8 | [Molecular Formula]
C8H4ClNO2 | [MDL Number]
MFCD00023027 | [Molecular Weight]
181.58 | [MOL File]
3481-09-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White to pale yellow powder | [Melting point ]
188-198 °C (lit.) | [Boiling point ]
315.1±25.0 °C(Predicted) | [density ]
1.56±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
powder to crystal | [pka]
-3.53±0.20(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C8H4ClNO2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H | [InChIKey]
WDRFYIPWHMGQPN-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C=CC=C2)C(=O)N1Cl | [CAS DataBase Reference]
3481-09-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
1759 | [WGK Germany ]
1
| [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White to pale yellow powder | [Uses]
N-Chlorophthalimide may be employed in the synthesis of:
- α-amino acetal
- α-amino nitro compounds
- vicinal diamine
- α,β-unsaturated vicinal haloamino nitro compound
It may also be used as a chlorination reagent for the synthesis of 3-(methylthio)oxindoles. | [General Description]
N-Chlorophthalimide in anhydrous acetic acid serves as a useful oxidizing reagent for use in various direct titrimetric analyses. N-Chlorophthalimide can be synthesized by reacting phthalimide, t-butyl hypochlorite, water and t-butyl alcohol. It participates in the synthesis of 2-amino-3-benzoyl-α-(methylthio)phenylacetamide. | [Synthesis]
General procedure for the synthesis of N-chlorophthalimide from 3-hydroxy-1H-isoindol-1-one: Anhydrous aluminum trichloride (AlCl3, 1 eq., 10 mmol, 1.36 g) was added to an anhydrous acetonitrile (CH3CN, 100 mL) solution of lead tetraacetate (Pb(OAc)4, 1 eq., 10 mmol, 4.52 g). The mixture was stirred at room temperature for 5 minutes before phthalimide (1 eq., 10 mmol, 1.5 g) was added. The resulting mixture was gently refluxed under nitrogen protection for 20 h and subsequently cooled to room temperature. The solvent was removed by rotary evaporation and the crude product was purified by column chromatography using pure dichloromethane (DCM) as eluent. Yield: 1.32 g, 71% yield.1H NMR (300 MHz, CDCl3): δ 7.94-7.91 (m, 2H), 7.82-7.79 (m, 2H) ppm. | [References]
[1] Synthesis, 2009, # 16, p. 2797 - 2801
[2] Synlett, 2006, # 2, p. 194 - 200
[3] Catalysis Today, 2018, vol. 308, p. 94 - 101
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1302
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 163 |
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