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Isatoic Anhydride

HCID 8359
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
118-48-9
Standard SMILES
O=c1[nH]c2ccccc2c(=O)o1
InChIKey
TXJUTRJFNRYTHH-UHFFFAOYSA-N
Molecular formula
C8H5NO3
Average molar mass
163.13 g/mol
Monoisotopic mass
163.02694302

Overview

structure given in first source

Names & identifiers

Preferred name
Isatoic Anhydride
IUPAC
1H-3,1-benzoxazine-2,4-dione
English name
Isatoic Anhydride
Molecular formula
C8H5NO3
Molecular weight
163.13

Names & synonyms

Isatoic anhydride118-48-92H-3,1-Benzoxazine-2,4(1H)-dioneISATOIC ACID ANHYDRIDE4H-3,1-Benzoxazine-2,4(1H)-dioneN-Carboxyanthranilic anhydrideDTXSID60269553,1-Benzoxazine-2,4(1H)-dioneAnthranilic acid, N-carboxy-, cyclic anhydrideBenzoic acid, 2-(carboxyamino)-, cyclic anhydrideR8TFA74Y4U2,4-dihydro-1H-3,1-benzoxazine-2,4-dione
Show more names
1H-BENZO[D][1,3]OXAZINE-2,4-DIONEIsatoic2-(carboxyamino)-benzoicacicyclicanhydrideBENZOXAZINEDIONE4H-3Isatoic Ac4(1H)-dione
1,2-dihydro-3,1-benzoxazine-2,4-dioneNSC-295551h-benz(d)(1,3)oxazine-2,4-dioneNSC-104662DTXCID9069552,4-dioxo-1,2-dihydro-4h-3,1-benzoxazineRefChem:791499204-255-0

Database identifiers

CAS
118-48-9
PubChem CID
8359
DTXSID
DTXSID6026955
ChEMBL
CHEMBL1235999、CHEMBL346059
UNII
R8TFA74Y4U
EC Number
204-255-0
Nikkaji
J5.526C

Properties

Computed structural propertiesFilling in

XLogP
1
Topological polar surface area
55.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
12
Formal charge
0
Complexity
226

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials PropertiesChemical shift
Color/Form · 2 items

PRISM FROM ALC OR GLACIAL ACETIC ACID; CRYSTALS FROM ALCOHOL OR DIOXANE

TAN POWDER

SolubilityMISCIBLE IN WATER, HOT ALC, AND ACETONE; INSOL IN ETHER, BENZENE, AND CHLOROFORM
Melting Point243 °C WITH DECOMPOSITION
Physical Description · 2 items

Dry Powder

Tan solid; [Hawley] Grey powder; [MSDSonline]

Physicochemical properties

Melting point
233 °C · 233 °C (dec.) (lit.)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 5.2% (11 of 210) of reports.

Warning

H317 (94.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Hazard information

Regulatory Information · 5 items

Chemical: 2H-3,1-Benzoxazine-2,4(1H)-dione

2H-3,1-Benzoxazine-2,4(1H)-dione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-3,1-Benzoxazine-2,4(1H)-dione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 25-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18515

Isatoic anhydride: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn eye irritant; May cause skin sensitization; [eChemPortal: ESIS] Danger of skin sensitization; [MAK] An irritant; May cause skin sensitization; [MSDSonline] See ACID ANHYDRIDES.
Hazard Classes and Categories · 3 items

Skin Sens. 1 (94.8%)

Eye irritation - category 2

Eye Irrit. 2

Toxicology

Adverse Effects

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationEndogenous substances and drugs that inhibit or block the activity of BETA-LACTAMASES.

Uses & manufacturing

Uses · 4 items

Used to make polymer curing agents, anthranilic esters, heterocyclic compounds, benzyne, saccharin, methyl anthranilate, and pesticides; Also used as a corrosion inhibitor in engine lubricants and as a modifier of natural and synthetic polymers and resins; [HSDB]

Plastic Composites Manufacturing [Category: Industry]

INTERMEDIATE FOR POLYMER CURING AGENTS, ANTHRANILIC ESTERS, HETEROCYCLIC COMPD, & BENZYNE

CHEM INT FOR SACCHARIN, METHYL ANTHRANILATE, PESTICIDES (EG, GUTHION); CORROSION INHIBITOR IN ENGINE LUBRICANTS; MODIFIER OF NATURAL & SYNTHETIC POLYMERS & RESINS

U.S. Exports · 2 items

(1977) No Data

(1979) No Data

U.S. Imports · 2 items

(1977) No Data

(1979) No Data

U.S. Production · 3 items

2023: 100,000 - <250,000 lb

(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Industry UsesIntermediate
Methods of ManufacturingPASSING PHOSGENE INTO A SOLUTION OF ANTHRANILIC ACID IN AQUEOUS HYDROCHLORIC ACID
Formulations/PreparationsGRADE: TECHNICAL, 96% MIN
General Manufacturing Information · 3 items

Not Known or Reasonably Ascertainable

2H-3,1-Benzoxazine-2,4(1H)-dione: ACTIVE

A BICYLIC MOLECULE COMPOSED OF A BENZENE RING ATTACHED @ ORTHO & META POSITIONS TO HETEROCYCLIC RING. IT FORMS USEFUL ANTHRANILIC ACID DERIVATIVES BY REACTION WITH HYDROGEN.

Related reactions

359 records
New reaction record
HRID 6692 reaction equation
HRID 6692As reactantuspto-grants-2006_08
HRID 14359 reaction equation
HRID 14359As reactantuspto-grants-2010_06
HRID 19442 reaction equation
HRID 19442As reactantuspto-grants-2010_06
HRID 26644 reaction equation
HRID 26644As reactantuspto-grants-1979_04
HRID 30400 reaction equation
HRID 30400As reactantuspto-grants-2008_09
HRID 30402 reaction equation
HRID 30402As reactantuspto-grants-2008_09
HRID 30404 reaction equation
HRID 30404As reactantuspto-grants-2008_09
HRID 36055 reaction equation
HRID 36055As reactantuspto-grants-1995_05
Page 1 of 45

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Boiling point
290.19 °C · 290.19°C (rough estimate)
bulk density
600 kg/m3 · 600kg/m3
Density
1 · 1,52 g/cm3
vapor density
5.6 · 5.6 (vs air)
refractive index
1.551 · 1.5510 (estimate)
Flash point
308 °C · 308 °C
storage temp.
30 °C · Store below +30°C.
solubility
0.3 g/l · 0.3g/l
pka
11.06 · 11.06±0.20(Predicted)
form
Powder
color
Beige to brown
Water Solubility
decomposes
Sensitive
Moisture Sensitive
BRN
136786 · 136786
InChI
1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11)
InChIKey
TXJUTRJFNRYTHH-UHFFFAOYSA-N
SMILES
O=C1Nc2ccccc2C(=O)O1
LogP
0.978 · 0.978 (est)
CAS DataBase Reference
118 · 118-48-9(CAS DataBase Reference)
EWG's Food Scores
1 · 1-2
FDA UNII
8 TFA74Y4U · R8TFA74Y4U
NIST Chemistry Reference
Isatoic anhydride(118-48-9)
EPA Substance Registry System
2 H-3,1-Benzoxazine-2,4 · 2H-3,1-Benzoxazine-2,4(1H)-dione (118-48-9)
UNSPSC Code
12352115 · 12352115
NACRES
23 · NA.23
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
317 · H317-H319
Precautionary statements
261 · P261-P264-P272-P280-P302+P352-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36-43
Safety Statements
24 · 24-26-37
WGK Germany
1 · 1
RTECS
3100000 · DM3100000
F
3 · 3
Autoignition Temperature
600 °C · >600 °C
TSCA
TSCA listed
HS Code
29349990 · 29349990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Sens. 1
Hazardous Substances Data
118 · 118-48-9(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: > 6400 mg/kg LD50 dermal Rabbit > 2000 mg/kg
REACH Registrations
Active
Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
Non-Human Toxicity ExcerptsTESTED FOR ANTIFERTILITY EFFECTS IN MICE AFTER ORAL ADMIN FOR 21 DAYS, WITH MALES INTRODUCED @ END OF 1ST WK, & AFTER INJECTIONS TWICE DAILY FOR 5 DAYS. EFFECTIVE IN DECR NUMBER OF MICE WITH LITTERS @ LEAST 50%.

Safety data

F
3
PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
DM3100000
hs_code
29349990
Toxicity
LD50 orally in Rabbit: > 6400 mg/kg LD50 dermal Rabbit > 2000 mg/kg
risk_code
36-43
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
24-26-37
Storage Class
11 - Combustible Solids
Hazard statements
H317-H319
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2Skin Sens. 1
Autoignition Temperature
>600 °C
Precautionary statements
P261-P264-P272-P280-P302+P352-P305+P351+P338
Hazardous Substances Data
118-48-9(Hazardous Substances Data)

Applications

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

Preparation methods · 1 item

PreparationPhosphorus 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%.

Upstream & downstream products

Upstream raw materials

Anthranilic acid2-(Carboxyamino)benzoic acid2-Methoxy-6-(MethylaMino)benzoic acid2-Azidobenzoic acidBenzene, 1-bromo-2-isocyano- (9CI)Boc-2-abz-OHTRYPTANTHRINIndole-3-carboxaldehydePhthalamic acidIsatin2-IodoanilineIndoleDiphosgene

Downstream products

5-Bromoisatoic anhydrideIsobutyl anthranilate4-Nitrophenyl anthranilate1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxylic acid ethyl ester

Additional notes

DefinitionA 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.