(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine

HCID 736065

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Basic information

CAS: 78342-42-4
Standard SMILES: COC1=N[C@@H](C(C)C)C(OC)=NC1
InChIKey: FCFWEOGTZZPCTO-QMMMGPOBSA-N
Molecular formula: C9H16N2O2
Average molar mass: 184.24 g/mol
Monoisotopic mass: 184.12117775

Names & identifiers

Preferred name: (2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine
IUPAC: (2S)-3,6-dimethoxy-2-propan-2-yl-2,5-dihydropyrazine
English name: (2S)-(+)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
Molecular formula: C9H16N2O2
Molecular weight: 184.24

Names & synonyms

(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazineRefChem:397873680-195-278342-42-4(S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine(S)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine(2S)-(+)-2,5-DIHYDRO-3,6-DIMETHOXY-2-ISOPROPYLPYRAZINE(2s)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazineMFCD00066229(2S)-3,6-dimethoxy-2-(propan-2-yl)-2,5-dihydropyrazine(2S)-3,6-dimethoxy-2-propan-2-yl-2,5-dihydropyrazineCS-0008324

Show more names

SchllkopfBISLACTIMETHERSchllkopf reagentSCHOELLKOPF-HARTWIG-REAGENT(2S)-(+)-2,5-DIHYDRO-3,6-DIMETHOXY-2-ISO(S)-2,5-DIHYDRO-3,6-DIMETHOXY-2-ISOPROPLPYRAZINE(S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazin

(2S)-2,5-Dihydro-3,6-dimethoxy-2-(1-methylethyl)pyrazine(S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine, >=97.0% (GC)Pyrazine, 2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-, (2S)-(2S)-2,5-Dihydro-3,6-dimethoxy-2-(1-methylethyl)pyrazine; (+)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine; (S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine; (S)-Schollkopf Reagent;(S)-2,5-dihydro-3,6-dimethoxy-2-iso-propylpyrazine(S)-2-Isopro(S)-Schollkopf reagentSCHEMBL369237

Database identifiers

CAS: 78342-42-4
PubChem CID: 736065
DTXSID: DTXSID30999695
ChEMBL: CHEMBL169371
EC Number: 680-195-2
Nikkaji: J922.366E

Properties

Computed structural properties

XLogP: 1.4
Topological polar surface area: 43.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 13
Formal charge: 0
Complexity: 234

Physicochemical properties

alpha: 102 · 102 º (c=1%, EtOH)
Boiling point: 245.2 · 245.2±33.0 °C(Predicted)
Density: 1.028 g/mL · 1.028 g/mL at 20 °C (lit.)
storage temp.: 2 · Sealed in dry,2-8°C
solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly)
pka: 3.81 · 3.81±0.60(Predicted)
form: Liquid
color: Clear colorless to pale yellow
optical activity: 20 · [α]20/D +102.0±5°, c = 1% in ethanol
BRN: 3650245 · 3650245
InChI: InChI=1S/C9H16N2O2/c1-6(2)8-9(13-4)10-5-7(11-8)12-3/h6,8H,5H2,1-4H3/t8-/m0/s1
InChIKey: FCFWEOGTZZPCTO-QMMMGPOBSA-N
SMILES: [C@@H]1(C(C)C)N=C(OC)CN=C1OC
CAS DataBase Reference: 78342 · 78342-42-4(CAS DataBase Reference)
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 22 · 22-36/37/38
Safety Statements: 23 · 23-24/25-37/39-26
WGK Germany: 3 · 3
HS Code: 29335995 · 29335995
Storage Class: 12 · 12 - Non Combustible Liquids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

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

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves
wgk: 3
hs_code: 29335995
risk_code: 22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 23-24/25-37/39-26
Storage Class: 12 - Non Combustible Liquids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 1 item

Uses(2S)-(+)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine is a Schllkopf-Hartwig bislactim ether reagent for asymmetric synthesis of amino acids by reaction of the metalated reagent with alkyl halides, aldehydes, ketones, epoxides, and enones, and subsequent hydrolysis of the resulting bislactim ether adduct.