CAS 228244-04-0 tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate (HCID 6951263)

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Basic information

CAS: 228244-04-0
Standard SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1C#N
InChIKey: MDMSZBHMBCNYNO-QMMMGPOBSA-N
Molecular formula: C10H16N2O2
Average molar mass: 196.25 g/mol
Monoisotopic mass: 196.12117775

Names & identifiers

Preferred name: tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate
IUPAC: tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate
English name: (S)-1-Boc-2-cyanopyrrolidine
Molecular formula: C10H16N2O2
Molecular weight: 196.25

Names & synonyms

tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylateRefChem:891720672-481-0228244-04-0(S)-1-Boc-2-cyanopyrrolidine(S)-tert-butyl 2-cyanopyrrolidine-1-carboxylateMFCD01861224(S)-1-N-BOC-2-CYANO-PYRROLIDINE(S)-(-)-1-Boc-2-pyrrolidinecarbonitrile(S)-(-)-1-BOC-2-CYANOPYRROLIDINE1-PYRROLIDINECARBOXYLIC ACID, 2-CYANO-, 1,1-DIMETHYLETHYL ESTER, (2S)-(S)-1-Boc-2-pyrrolidinecarbonitrile

Show more names

CAS:228244-04-01-BOC-2-CYANO-PYRROLIDINE(S)-1-Boc-2-cyanopiperidine(s)- N-boc-2-cyano-piperidine2-CYANOPYRROLIDINE, N-BOC PROTECTED(S)-N-Boc-pyrrolidine-2-carbonitrile(S)-1-N-Boc-pyrrolidine-2-carbonitrile

tert-butyl (S)-2-cyanopyrrolidine-1-carboxylate(S)-1-(tert-Butoxycarbonyl)-2-cyanopyrrolidineBOC-2(S)-cyanopyrrolidine(S)-1-(tert-Butoxycarbonyl)-2-pyrrolidinecarbonitrileSCHEMBL13570661-N-Boc-2- pyrrolidinonitrileCHEMBL1081012DTXSID10426237

Database identifiers

Properties

Computed structural properties

XLogP: 1.4
Topological polar surface area: 53.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 14
Formal charge: 0
Complexity: 272

Physicochemical properties

Melting point: 33 · 33-36°C
alpha: -105.5 · -105.5 º (c=1, chloroform)
Boiling point: 307.9 · 307.9±35.0 °C(Predicted)
Density: 1.08 · 1.08±0.1 g/cm3(Predicted)
Flash point: 110 °C · >110°C
storage temp.: 2 · Keep in dark place,Inert atmosphere,2-8°C
pka: -4.97 · -4.97±0.40(Predicted)
form: powder to lump
color: White to Orange to Green
optical activity: 20 · [α]20/D 105.5°, c = 1 in chloroform
Water Solubility: Slightly soluble in water.
Sensitive: Moisture & Light Sensitive
InChI: InChI=1S/C10H16N2O2/c1-10(2,3)14-9(13)12-6-4-5-8(12)7-11/h8H,4-6H2,1-3H3/t8-/m0/s1
InChIKey: MDMSZBHMBCNYNO-QMMMGPOBSA-N
SMILES: N1(C(OC(C)(C)C)=O)CCC[C@H]1C#N

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302+H312+H332 (50%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (50%)

Safety data

PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk: 3
ridadr: 3439
hs_code: 29339900
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 26-36/37/39
Storage Class: 10 - Combustible liquids
Hazard statements: H302+H312+H332-H315-H319-H302-H312-H332-H335
Precautionary statements: P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 2 items

Uses(S)-(-)-1-Boc-2-pyrrolidinecarbonitrile is used in synthesis of prolyl oligopeptidase inhibitors and is a reagent that is used in the design of potent and selective inhibitors of DPP-4 that exhibits an attractive pharmacokinetic profile as antidiabetics.

UsesUsed in synthesis of prolyl oligopeptidase inhibitors.