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37286

Sigma-Aldrich

(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine

≥97.0% (GC)

Synonym(s):

(R)-Schollkopf Reagent, (R)-2,5-Dimethoxy-3-isopropyl-3,6-dihydropyrazine

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About This Item

Empirical Formula (Hill Notation):
C9H16N2O2
CAS Number:
109838-85-9
Molecular Weight:
184.24
Beilstein:
3542790
MDL number:
MFCD00040565
UNSPSC Code:
12352005
PubChem Substance ID:
57649714
NACRES:
NA.22
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Quality Level

100

Assay

≥97.0% (GC)

form

liquid

optical activity

[α]20/D −102±5°, c = 1% in ethanol

density

1.028 g/mL at 20 °C (lit.)

SMILES string

COC1=N[C@H](C(C)C)C(OC)=NC1

InChI

1S/C9H16N2O2/c1-6(2)8-9(13-4)10-5-7(11-8)12-3/h6,8H,5H2,1-4H3/t8-/m1/s1

InChI key

FCFWEOGTZZPCTO-MRVPVSSYSA-N

Application

(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine may be used as a chiral auxiliary in the stereoselective synthesis of α-amino acids[1], α-amino-β-hydroxy acids[2] and α-amino-γ-hydroxy acids.[3]

Other Notes

Chiral auxiliary for the synthesis of α-amino acids[4]

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3425
BCBT9708
BCBN2998V
BCBN2999V
BCBF1407V

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Synthesis of conformationally restricted serine derivatives through ruthenium (II)-catalyzed ring closing metathesis.
Hammer K and Undheim K.
Tetrahedron, 53(16), 5925-5936 (1997)
Ru (II)-catalyzed ring closing metathesis in stereoselective syntheses of constrained homoserine analogues.
Hammer K, et al.
Tetrahedron, 54(36), 10837-10850 (1998)
U. Schollkopf et al.
Synthesis, 861-861 (1982)
Ruthenium (II) in ring closing metathesis for the stereoselective preparation of cyclic 1-amino-1-carboxylic acids.
Hammer K and Undheim K.
Tetrahedron, 53(6), 2309-2322 (1997)

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