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107743

Sigma-Aldrich

5-Norbornen-2-yl acetate, mixture of endo and exo

98%

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About This Item

Empirical Formula (Hill Notation):
C9H12O2
CAS Number:
6143-29-9
Molecular Weight:
152.19
EC Number:
228-144-1
MDL number:
MFCD00167565
UNSPSC Code:
12352100
PubChem Substance ID:
24846777
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.47 (lit.)

bp

73-76 °C/14 mmHg (lit.)

density

1.044 g/mL at 25 °C (lit.)

SMILES string

CC(=O)OC1C[C@H]2C[C@@H]1C=C2

InChI

1S/C9H12O2/c1-6(10)11-9-5-7-2-3-8(9)4-7/h2-3,7-9H,4-5H2,1H3/t7-,8+,9?/m1/s1

InChI key

DRWRVXAXXGJZIO-WGTSGOJVSA-N

Application

5-Norbornen-2-yl acetate (mixture of endo and exo) was used to study the ring opening metathesis polymerization of norbornene catalysed by dinuclear complex Cp*2Os2Br4 (Cp*=pentamethylcyclopentadienyl) and related compounds.

Biochem/physiol Actions

5-Norbornen-2-yl acetate undergoes copolymerisation with ethylene by nickel catalyst system to form high molecular weight functionalized polyethylene bearing ester functionalities. -Norbornen-2-yl acetate is the starting reagent for synthesis of urea condensation products from a-dicarbonyl compounds using Bi (OTf)3 catalyst.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ0977
STBF8352V
STBF2522V
S78958V
S86623

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A Weissfloch et al.
Bioorganic & medicinal chemistry, 2(6), 493-500 (1994-06-01)
A practical integrated process, combining an enzymatic resolution step with a few chemical transformations, is described for the synthesis of (1R, 4R)- and (2S, 4S)-bicyclo[2.2.1]heptan-2,5-diones 1 of high enantiomeric purity, starting from a standard mixture of (+/-)-endo- and exo-2-acetoxy-5-norbornene.
Ring-opening metathesis polymerization of norbornene by Cp* 2Os2Br4 and related compounds.
Brumaghim JL and Girolami GS.
Organometallics, 18(10), 1923-1929 (1999)
Ethylene homopolymerization and copolymerization with functionalized 5-norbornen-2-yl monomers by a novel nickel catalyst system.
Diamanti SJ, et al.
Macromolecules, 36(26), 9731-9735 (2003)
Bi (OTf)3-a mild catalyst for the synthesis of difficult to obtain C-alkyl substituted glycolurils.
Wu F, et al.
Tetrahedron, 69(47), 9957-9965 (2013)

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