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132039

Sigma-Aldrich

1,2,4-Triacetoxybenzene

97%

Synonym(s):

1,2,4-Phenenyl triacetate

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About This Item

Linear Formula:
(CH3CO2)3C6H3
CAS Number:
613-03-6
Molecular Weight:
252.22
EC Number:
210-327-2
MDL number:
MFCD00008700
UNSPSC Code:
12352100
PubChem Substance ID:
24847542
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

98-100 °C (lit.)

functional group

ester

SMILES string

CC(=O)Oc1ccc(OC(C)=O)c(OC(C)=O)c1

InChI

1S/C12H12O6/c1-7(13)16-10-4-5-11(17-8(2)14)12(6-10)18-9(3)15/h4-6H,1-3H3

InChI key

AESFGSJWSUZRGW-UHFFFAOYSA-N

Application

1,2,4-Triacetoxybenzene can be used as a starting material:
  • To prepare aminated hydroxynaphthazarins, echinamines A and B.
  • To synthesize 6,7-dihydroxychromenones, which are further used to prepare various crown ethers.
  • In the total synthesis of natural product santalin Y.

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
STBF2985V
STBF1360V
STBD9386V
STBC1386V
S42138V

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Biomimetic total synthesis of santalin Y
Strych S, et al.
Angewandte Chemie (International Edition in English), 54, 5079-5083 (2015)
Synthesis of Echinamines A and B, the First Aminated Hydroxynaphthazarins Produced by the Sea Urchin Scaphechinus m irabilis and Its Analogues
Pokhilo ND, et al.
Journal of Natural Products, 69, 1125-1129 (2006)
The synthesis of novel crown ethers, part ix, 3-phenyl chromenone-crown ethers
Bulut M and Erk CL
Journal of Heterocyclic Chemistry, 38, 1291-1295 (2001)
Nataly D Pokhilo et al.
Journal of natural products, 69(8), 1125-1129 (2006-08-29)
The first total synthesis of two marine aminated hydroxynaphthazarins, echinamines A (3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone) and B (2-amino-7-ethyl-3,5,6,8-tetrahydroxy-1,4-naphthoquinone), produced by the sea urchin Scaphechinus mirabilis is described. This was achieved from 1,2,4-triacetoxybenzene (13) through a sequence involving double Fries rearrangement of 13, reduction

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