Synthesis
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Isatoic Anhydride

Synthesis
Product Name
Isatoic Anhydride
CAS No.
118-48-9
Chemical Name
Isatoic Anhydride
Synonyms
1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;Isatoic;2-(carboxyamino)-benzoicacicyclicanhydride;BENZOXAZINEDIONE;4H-3,1-Benzoxazine-2,4(1H)-dione;1,2-Dihydro-3,1-benzoxazine-2,4-dione;4H-3;Isatoic Ac;4(1H)-dione;1-Benzoxazine-2
CBNumber
CB9238051
Molecular Formula
C8H5NO3
Formula Weight
163.13
MOL File
118-48-9.mol
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Isatoic Anhydride Property

Melting point:
233 °C (dec.) (lit.)
Boiling point:
290.19°C (rough estimate)
Density 
1,52 g/cm3
vapor density 
5.6 (vs air)
refractive index 
1.5510 (estimate)
Flash point:
308 °C
storage temp. 
Store below +30°C.
solubility 
0.3g/l
form 
Powder
pka
11.06±0.20(Predicted)
color 
Beige to brown
Water Solubility 
decomposes
Sensitive 
Moisture Sensitive
BRN 
136786
LogP
0.978 (est)
CAS DataBase Reference
118-48-9(CAS DataBase Reference)
NIST Chemistry Reference
Isatoic anhydride(118-48-9)
EPA Substance Registry System
2H-3,1-Benzoxazine-2,4(1H)-dione (118-48-9)
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Safety

Hazard Codes 
Xi
Risk Statements 
36-43
Safety Statements 
24-26-37
WGK Germany 
1
RTECS 
DM3100000
F 
3
Autoignition Temperature
>600 °C
TSCA 
Yes
HS Code 
29349990
Hazardous Substances Data
118-48-9(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 6400 mg/kg LD50 dermal Rabbit > 2000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
I12808
Product name
Isatoic anhydride
Purity
96%
Packaging
100g
Price
$42.8
Updated
2024/03/01
Sigma-Aldrich
Product number
I12808
Product name
Isatoic anhydride
Purity
96%
Packaging
500g
Price
$149
Updated
2024/03/01
Sigma-Aldrich
Product number
8.04784
Product name
Isatoic anhydride
Purity
for synthesis
Packaging
100g
Price
$73.2
Updated
2024/03/01
Sigma-Aldrich
Product number
8.04784
Product name
Isatoic anhydride
Purity
for synthesis
Packaging
500g
Price
$461
Updated
2023/01/07
TCI Chemical
Product number
I0081
Product name
Isatoic Anhydride
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$60
Updated
2024/03/01
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Isatoic Anhydride Chemical Properties,Usage,Production

Synthesis

Isatoic Anhydride is synthesized from indole (9a) by stirring in a 4:1 mixture of  DMF/H2O for 16 h at room temperature. 
1 H NMR (DMSO-d6): δ11.73 (s, br., 1H),  7.92 (d, J = 7.8 Hz, 1H), 7.74 (t, J = 7.8 Hz, 1H), 7.26 (t, J = 7.8 Hz, 1H), 7.16 (d,  J = 7.8 Hz, 1H).

Chemical Properties

BEIGE TO BROWN POWDER

Uses

Isatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.

Definition

A bicyclic molecule composed of a benzene ring attached at the oand mpositions to a heterocyclic ring. It forms useful anthranilic acid derivatives by reaction with hydrogen.

Preparation

Phosphorus tribromide (0.035 mol) was added to a solution of N-carbethoxy- or N-carbobenzoxy-anthranilic acid (0.1 mol;prepared by coupling anthranilic acid with the corresponding carbalkoxy chloride in the usual way) in anhydrous diethyl ether (100 mL). After 24 h at room temperature, isatoic anhydride had separated as a microcrystalline product. It was collected by filtration, washed with dry diethyl ether, and recrystallized from ethanol. Yield ca. 90%.

Flammability and Explosibility

Non flammable

Purification Methods

Recrystallise it from EtOH or 95% EtOH (30mL/g) or dioxane (10mL/g) and dry it in a vacuum. [Wagner & Fegley Org Synth Coll Vol III 488 1955, Ben-Ishai & Katchalski J Am Chem Soc 74 3688 1952, UV: Zentmyer & Wagner J Org Chem 14 967 1949, Beilstein 27 II 299, 27III/IV 3330.]

Isatoic Anhydride Preparation Products And Raw materials

Raw materials

Anthranilic acid

Preparation Products

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View Lastest Price from Isatoic Anhydride manufacturers

Hebei Duling International Trade Co. LTD
Product
ISATOIC ANHYDRIDE 118-48-9
Price
US $20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000 tons
Release date
2022-12-07
Hebei Yanxi Chemical Co., Ltd.
Product
Isatoic Anhydride 118-48-9
Price
US $25.00-10.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-11-16
Hebei Guanlang Biotechnology Co., Ltd.
Product
Isatoic Anhydride 118-48-9
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2023-02-09

118-48-9, Isatoic AnhydrideRelated Search:

6-METHYL ISATINIC ANHYDRIDE N-methylisatoic anhydride 4-NITRO-ISATOIC ANHYDRIDE Isatoic Anhydride 5-Bromoisatoic anhydride 6-CHLOROISATIN 3-[2-(Diethylamino)ethyl]-2H-1,3-benzoxazine-2,4(3H)-dione 5-Fluoroisatonic anhydride 6-Fluoroisatoic anhydride 4-Chloro-isatoic anhydride 2 H-1,3-BENZOXAZINE-2,4(3 H)-DIONE 6-Chloro-4H-3,1-benzoxazine-2(1H),4-dione,6-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione,6-chloro-4h-3,1-benzoxazine-2,4(1h)-dione 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE 1-Benzyl-2H-3,1-benzoxazine-2,4(1H)-dione 6-Hydroxy-2H-3,1-benzoxazine-2,4(1H)-dione 4-CARBOXYLIC-ISATOIC ANHYDRIDE 6,8-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione N-ALLYLISATOIC ANHYDRIDE

  • 1,2-Dihydro-3,1-benzoxazine-2,4-dione
  • 2-(carboxyamino)-benzoicacicyclicanhydride
  • 2,4-Dioxo-1,2-dihydro-4H-3,1-benzoxazine
  • 4H-3,1-Benzoxazin-2,4-(1H)-dion
  • 4H-3,1-Benzoxazin-2,4(1H)-dion
  • Anthranilic acid, N-carboxy-, cyclic anhydride
  • Benzoic acid, 2-(carboxyamino)-, cyclic anhydride
  • Benzoicacid,2-(carboxyamino)-,cyclicanhydride
  • Isato acid anhydride
  • 4H-3,1-Benzoxazine-2,4(1H)-dione
  • 1,2-dihydro-4h-3,1-benzoxazine-2,4-dione
  • 1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2,4-DIONE
  • 3,1-BENZOXAZINE-2,4(1H)-DIONE
  • 2H-3,1-BENZOXAZINE-2,4(1H)-DIONE
  • 1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
  • LABOTEST-BB LT00053651
  • ISATOLC ANHYDRIDE
  • ISATOIC ANHYDRIDE
  • BENZOXAZINEDIONE
  • ANTHRANILIC ACID N-CARBOXYLIC ACID ANHYDRIDE
  • TIMTEC-BB SBB003928
  • N-CARBOXYANTHRANILIC ACID CYCLIC ANHYDRIDE
  • 2H-3,1-benzoxazine-2,4(1H)-dio
  • N-carboxyanthranilic acid anhydride
  • 1,4-Dihydro-2H-3,1-benzoxazine-2,4-dione
  • Isatoic anhydride,98%
  • Isatoic anhydride, 98% 100GR
  • 3,1-Benzoxazine-2,4(1H)-dione, Anthranilic acid N-carboxylic acid anhydride
  • 1H-3,1-Benzoxazine-2,4-dione
  • Isatoic
  • Isatoic acid anhydride
  • isatoicacidanhydride
  • Isatonicanhydride
  • Isatosαureanhydrid
  • n-carboxy-anthranilicacicyclicanhydride
  • N-Carboxyanthranilicanbydride
  • n-carboxyanthranilicanhydride
  • 1H-Benz[d][1,3]oxazine-2,4-dione
  • 2-(CarboxyaMino)benzoic Acid Cyclic Anhydride
  • Isatoic Ac
  • ISATOIC ANHYDRIDE FOR SYNTHESIS
  • Isatoic anhydrate
  • 1H-3,1-benzoxazine-2,4-quinone
  • 1-Benzoxazine-2
  • 4(1H)-dione
  • 4H-3
  • IsatoicAnhydride&gt
  • Isatin anhydride
  • Isatoic anhydride, 97%,
  • Isatoic anhydride (6CI)
  • Isatioc anhydride
  • 118-48-9
  • C6H4C2HNO3
  • CC6H4NHCOO
  • C8H5NO3
  • Organic Building Blocks
  • Building Blocks
  • Carbonyl Compounds