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536652

Sigma-Aldrich

(S)-(−)-2-(Boc-amino)-1,4-butanediol

97%

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About This Item

Linear Formula:
HOCH2CH2CH[NHCO2C(CH3)3]CH2OH
CAS Number:
128427-10-1
Molecular Weight:
205.25
MDL number:
MFCD03093946
UNSPSC Code:
12352108
PubChem Substance ID:
24878173
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D −8°, c = 1 in chloroform

mp

65-69 °C (lit.)

functional group

amine
hydroxyl

SMILES string

CC(C)(C)OC(=O)N[C@H](CO)CCO

InChI

1S/C9H19NO4/c1-9(2,3)14-8(13)10-7(6-12)4-5-11/h7,11-12H,4-6H2,1-3H3,(H,10,13)/t7-/m0/s1

InChI key

KLRRFBSWOIUAHZ-ZETCQYMHSA-N

Application

(S)-(−)-2-(Boc-amino)-1,4-butanediol can be used as a reactant to synthesize:
  • Thiourea-based organocatalysts for asymmetric Michael addition reactions of nitroalkenes to α-nitrocyclohexanone.
  • Bis-copper (II) complex based catalysts for enantioselective Michael reactions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBV7927V
MKBK4207V
MKBH8537V
05623HJ
08410JH

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Asymmetric Michael additions of α-nitrocyclohexanone to aryl nitroalkenes catalyzed by natural amino acid-derived bifunctional thioureas
Jo?rres M, et al.
Organic Letters, 14(17), 4518-4521 (2012)
Copper (II) in organic synthesis. XI. Evaluation of the ligand architecture on the efficiency of a copper (II) catalyst for enantioselective Michael reactions
Desimoni G, et al.
Tetrahedron, 51(14), 4131-4144 (1995)

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