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Safety Information

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

132039-100G:
132039-25G:
132039-BULK:
132039-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
STBF2985V
STBF1360V
STBD9386V
STBC1386V
S42138V

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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
Biomimetic total synthesis of santalin Y
Strych S, et al.
Angewandte Chemie (International Edition in English), 54, 5079-5083 (2015)

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