| Identification | More | [Name]
4-Chloro-isatoic anhydride | [CAS]
40928-13-0 | [Synonyms]
4-CHLORO-ISATOIC ANHYDRIDE
6-CHLOROISATOIC ANHYDRIDE
7-CHLORO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
7-CHLOROISATOIC ANHYDRIDE
AURORA KA-6696
4-CHLOROISATONIC ANHYDRIDE
7-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione, 7-Chloroisatoic anhydride
7-chloro-2H-3,1-benzoxazine-2,4(1H)-dione | [Molecular Formula]
C8H4ClNO3 | [MDL Number]
MFCD00090431 | [Molecular Weight]
197.58 | [MOL File]
40928-13-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
255-259 °C | [density ]
1.540±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
soluble in Dimethylformamide | [form ]
powder to crystal | [pka]
9.95±0.20(Predicted) | [color ]
White to Light yellow | [InChI]
1S/C8H4ClNO3/c9-4-1-2-5-6(3-4)10-8(12)13-7(5)11/h1-3H,(H,10,12) | [InChIKey]
QRUPDIJQZCABTC-UHFFFAOYSA-N | [SMILES]
Clc1ccc2C(=O)OC(=O)Nc2c1 | [CAS DataBase Reference]
40928-13-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
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 .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
2934999090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 26, p. 613, 1961 DOI: 10.1021/jo01061a618 | [Synthesis]
General procedure for the synthesis of 7-chloro-1H-benzo[d][1,3]oxazine-2,4-dione from triphosgene and 2-amino-4-chlorobenzoic acid:
1. Preparation of Intermediate G: To a stirred solution of 2-amino-4-chlorobenzoic acid (10 g, 0.058 mol) in acetonitrile (60 mL), a solution of pyridine (9.4 mL, 0.117 mol, 2 eq.) and triphosgene (17.3 g, 0.058 mol, 1 eq.) in dichloromethane (85 mL, 0.7 M) was slowly added.
2. Treatment of the reaction mixture: the resulting orange reaction solution was heated at 50 °C for 2 h and subsequently cooled to room temperature.
3. Separation and purification: the reaction solution was diluted with water (50 mL) to separate the organic and aqueous layers. The aqueous layer was extracted with dichloromethane (3 x 50 mL) and the combined organic layers were washed once with brine (50 mL) and dried with anhydrous magnesium sulfate. 4. Purification of products: The reaction solution was heated at 50 °C for 2 h and subsequently cooled to room temperature.
4. Purification of product: The solvent was removed by distillation under reduced pressure to give a yellow solid. The solid was recrystallized from hexane to give 7-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (9.1 g, 74% yield) as a yellow solid.
1H NMR (acetone-d6, 500 MHz): δ (ppm) 7.13-7.14 (1H, s), 7.28-7.30 (1H, d, J = 8.5 Hz), 7.90-7.92 (1H, d, J = 8.6 Hz), 11.84 (1H, bs). | [References]
[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6928 - 6937
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2311 - 2319
[3] Patent: US9126978, 2015, B2. Location in patent: Page/Page column 57; 58
[4] European Journal of Medicinal Chemistry, 1994, vol. 29, # 12, p. 925 - 940
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2295 - 2299 |
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