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Sigma-Aldrich

2-(Benzoyloxymethyl)benzoic acid

≥98.0% (T)

Synonym(s):

2-(Hydroxymethyl)benzoic acid benzoate

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About This Item

Empirical Formula (Hill Notation):
C15H12O4
CAS Number:
58249-83-5
Molecular Weight:
256.25
Beilstein/REAXYS Number:
2131052
EC Number:
261-185-3
MDL number:
MFCD00077655
UNSPSC Code:
12352108
PubChem Substance ID:
57647050
NACRES:
NA.22

assay

≥98.0% (T)

mp

126-129 °C

application(s)

peptide synthesis

functional group

carboxylic acid
ester
phenyl

SMILES string

OC(=O)c1ccccc1COC(=O)c2ccccc2

InChI

1S/C15H12O4/c16-14(17)13-9-5-4-8-12(13)10-19-15(18)11-6-2-1-3-7-11/h1-9H,10H2,(H,16,17)

InChI key

QDENBWUYSUBCID-UHFFFAOYSA-N

Application

2-(Benzoyloxymethyl)benzoic acid can be used to synthesize:
  • 2-(Benzoyloxymethyl)benzoyl chloride (BMBC) by reacting with oxalyl chloride. BMBC intermediate is utilized for the preparation of dimethyl 2-(benzoyloxymethyl)benzoylphosphonate by treating with trimethyl phosphite.[1]
  • 2-Benzoyloxymethylbenzoic acid 4-nitrophenyl ester by reaction with 4-nitrophenol via 2-benzoyloxymethylbenzoyl chloride formation.[2]
  • 2-[2-(Benzoyloxymethyl)benzamido]acetamide by treating with glycinamide and followed by addition of PCl3.[2]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBG3673V
1355231
011861/2
011861/1
11861/2

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Cyclisation reactions of 2-substituted benzoylphosphonates with trialkyl phosphites via nucleophilic attack on a carbonyl-containing ortho substituent
Cheong Y-K, et al.
Tetrahedron, 64(10), 2329-2338 (2008)
2-Acyloxymethylbenzoic acids. Novel amine protective functions providing amides with the lability of esters
Cain BF
The Journal of Organic Chemistry, 41(11), 2029-2031 (1976)

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