CAS 22509-74-6 N-Carbethoxyphthalimide (HCID 31187)

Names & identifiers

Preferred name: N-Carbethoxyphthalimide
IUPAC: ethyl 1,3-dioxoisoindole-2-carboxylate
English name: N-Carbethoxyphthalimide
Molecular formula: C11H9NO4
Molecular weight: 219.19

Names & synonyms

N-CARBETHOXYPHTHALIMIDE22509-74-6N-CarboethoxyphthalimideN-(Ethoxycarbonyl)phthalimideEthyl N-phthaloylcarbamatePhthalimide-N-carbethoxy2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl esterethyl 1,3-dioxoisoindoline-2-carboxylateN-Karbetoksi-ftalimidNSC 765762-Isoindolinecarboxylic acid, 1,3-dioxo-, ethyl esterDGO9NPX8LS

Show more names

CPIN-ETHOXYCARBONYLPHTHALIMIDEECPTADIN-010NEFKEN'S REAGENTN-CarbethoxyphthaL

N-Karbetoksi-ftalimid [Yugoslavian]EINECS 245-048-5BRN 0196340AI3-52139NEFKENS' REAGENTEthyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylateethyl 1,3-dioxo-2,3-dihydro-1H-isoindole-2-carboxylateNSC-76576

Database identifiers

CAS: 22509-74-6
PubChem CID: 31187
DTXSID: DTXSID7066805
UNII: DGO9NPX8LS
EC Number: 245-048-5
Nikkaji: J26.042H

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 63.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 16
Formal charge: 0
Complexity: 315

Experimental & physicochemical properties

Vapor Pressure0.00000002 [mmHg]

Physical DescriptionLumps or powder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point: 90 · 90-92 °C(lit.)
Boiling point: 360 °C · 360°C (rough estimate)
Density: 1.3219 · 1.3219 (rough estimate)
vapor pressure: 0.003 · 0.003-0.006Pa at 20-25℃
refractive index: 1.495 · 1.4950 (estimate)
storage temp.: 2 · Inert atmosphere,2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Crystalline Powder
pka: -3.02 · -3.02±0.20(Predicted)
color: White
Water Solubility: insoluble
BRN: 196340 · 196340
InChI: 1S/C11H9NO4/c1-2-16-11(15)12-9(13)7-5-3-4-6-8(7)10(12)14/h3-6H,2H2,1H3
InChIKey: VRHAQNTWKSVEEC-UHFFFAOYSA-N
SMILES: CCOC(=O)N1C(=O)c2ccccc2C1=O
LogP: 1.1 at · 1.1 at 20℃ and pH6.6-6.9
CAS DataBase Reference: 22509 · 22509-74-6(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 9 NPX8LS · DGO9NPX8LS
NIST Chemistry Reference: 2 H-isoindole-2-carboxylic · 2H-isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester(22509-74-6)
EPA Substance Registry System: 2 H-Isoindole-2-carboxylic · 2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester (22509-74-6)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 b-P270-P301+P312-P330-P403+P233-P501c · P264b-P270-P301+P312-P330-P403+P233-P501c
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xn
Risk Statements: 22 · 22-36/37/38-20/21/22
Safety Statements: 22 · 22-24/25-36/37/39-26-36
WGK Germany: 3 · 3
RTECS: 3459500 · NR3459500
F: 10 · 10
TSCA: TSCA listed
HazardClass: IRRITANT
HS Code: 29251995 · 29251995
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 1 Skin · Eye Dam. 1Skin Irrit. 2Skin Sens. 1
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H315 (91.7%): Causes skin irritation [Warning Skin corrosion/irritation]；H317 (86.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H318 (86.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 36 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 23-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19227

2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryMay cause irritation; [Alfa Aesar MSDS] See Phthalimide.

Hazard Classes and CategoriesSkin Irrit. 2 (91.7%)；Skin Sens. 1B (86.1%)；Eye Dam. 1 (86.1%)

Regulatory information

Regulatory Information · 2 items

Status: Active Update: 23-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19227

2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F: 10
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
tsca: TSCA listed
rtecs: NR3459500
hs_code: 29251995
risk_code: 22-36/37/38-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 22-24/25-36/37/39-26-36
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H302
REACH Registrations: Active
Hazard Classifications: Eye Dam. 1Skin Irrit. 2Skin Sens. 1
Precautionary statements: P264b-P270-P301+P312-P330-P403+P233-P501c

Chemistry & industry

Uses & manufacturing

General Manufacturing Information2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester: ACTIVE

Applications

UsesN-Carbethoxyphthalimide is used in the synthetic preparation of a novel dual binders as potent, selective, and orally bioavailable tankyrase inhibitors.

Preparation methods

PreparationN-Carbethoxyphthalimide is prepared for: addition of Ethyl Chloroformate to a cold solution of Phthalimide and Triethylamine in DMF; alkylation of potassium phthalimide with ethyl chloroformate.