CAS 85909-08-6 1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester (HCID 379000)

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Basic information

CAS: 85909-08-6
Standard SMILES: CC(C)(C)OC(=O)N1CCCC1=O
InChIKey: GJJYYMXBCYYXPQ-UHFFFAOYSA-N
Molecular formula: C9H15NO3
Average molar mass: 185.22 g/mol
Monoisotopic mass: 185.10519334

Names & identifiers

Preferred name: 1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester
IUPAC: tert-butyl 2-oxopyrrolidine-1-carboxylate
English name: 1-(tert-Butoxycarbonyl)-2-pyrrolidinone
Molecular formula: C9H15NO3
Molecular weight: 185.22

Names & synonyms

tert-butyl 2-oxopyrrolidine-1-carboxylateN-Boc-2-pyrrolidinonetert-Butyl 2-oxo-1-pyrrolidinecarboxylate9GS4FVG7EW1,1-dimethylethyl 2-oxo-1-pyrrolidinecarboxylate1-pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester1-(tert-Butoxycarbonyl)-2-oxopyrrolidineUNII-9GS4FVG7EWNSC 662770NSC-662770DTXSID60235235n-tert-butoxycarbonyl-2-oxopyrrolidine

Show more names

N-boc-2-pyrrolidone2-OXO-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTERAIDS143102CAS_85909-08-61-Boc-2-pyrrolidinone1-BOC-Pyrrolidin-2-one1-BOC-2-OXOPYRROLIDINEN-Boc-2-oxopyrrolidine

2-OXOPYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTERN-(TERT-BUTOXYCARBONYL)PYRROLIDIN-2-ONE1-(TERT-BUTOXYCARBONYL)PYRROLIDIN-2-ONEN-(TERT-BUTYLOXYCARBONYL)PYRROLIDIN-2-ONERefChem:77211DTXCID60157726InChI=1/C9H15NO3/c1-9(2,3)13-8(12)10-6-4-5-7(10)11/h4-6H2,1-3H85909-08-6

Database identifiers

Properties

Computed structural properties

XLogP: 1.3
Topological polar surface area: 46.6 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 13
Formal charge: 0
Complexity: 230

Physicochemical properties

Boiling point: 100 · 100-105 °C/0.5 mmHg(lit.)
Density: 1.086 g/mL · 1.086 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.466(lit.)
Flash point: 113 °C · 113 °C
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Chloroform, Methanol
form: Oil
pka: -2.21 · -2.21±0.20(Predicted)
color: Clear Colorless to Brown
InChI: InChI=1S/C9H15NO3/c1-9(2,3)13-8(12)10-6-4-5-7(10)11/h4-6H2,1-3H3
InChIKey: GJJYYMXBCYYXPQ-UHFFFAOYSA-N
SMILES: N1(C(OC(C)(C)C)=O)CCCC1=O
FDA UNII: 9 GS4FVG7EW · 9GS4FVG7EW
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 05-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/30601

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
hs_code: 2933790090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 10 - Combustible liquids
target organs: Respiratory system
Hazard statements: H315-H319-H335
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements

Chemistry & industry

Applications · 2 items

UsesN-Boc-2-pyrrolidinone is a useful synthetic intermediate. It can be used to prepare highly functionalized N-acyl-2-vinylpyrrolidines by a 4-component Ugi reaction (isocyanide, carbonyl compounds, primary amines, carboxylic acids). It can also be used to synthesize the naturally occurring Maillard flavors via catalytic SeO2 oxidation.

General DescriptionThe kinetics of gas-phase elimination of 1-(tert-butoxycarbonyl)-2-pyrrolidinone has been investigated in a static system. The observed rate coefficient has been reported to be log k1(s-1) = (11.54 ± 0.29) -(140.8 ± 2.8)-kJmol-1 (2.303RT)-1.