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270253

Sigma-Aldrich

4-Hydroxybenzamide

98%

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About This Item

Linear Formula:
HOC6H4CONH2
CAS Number:
Molecular Weight:
137.14
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

mp

161-162 °C (lit.)

SMILES string

NC(=O)c1ccc(O)cc1

InChI

1S/C7H7NO2/c8-7(10)5-1-3-6(9)4-2-5/h1-4,9H,(H2,8,10)

InChI key

QXSAKPUBHTZHKW-UHFFFAOYSA-N

General description

The standard molar enthalpy of formation of 4-hydroxybenzamide was studied by micro- or macrocombustion calorimetry.

Application

4-Hydroxybenzamide was used in the synthesis of balanol, a potent protein kinase C (PKC) inhibitor.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

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C Emoto et al.
Xenobiotica; the fate of foreign compounds in biological systems, 37(12), 1408-1420 (2007-10-19)
CJ-036878, N-(3-phenethoxybenzyl)-4-hydroxybenzamide, was developed as an antagonist of the N-methyl-D-aspartate receptor NR2B subunit. Two dimeric metabolites, CJ-047710 and CJ-047713, were identified from the incubation mixture with CJ-036878 in human liver microsomes (HLM). The identification of the enzymes involved in the
Y S Lai et al.
Journal of medicinal chemistry, 40(2), 226-235 (1997-01-17)
Balanol is a potent protein kinase C (PKC) inhibitor that is structurally composed of a benzophenone diacid, a 4-hydroxybenzamide, and a perhydroazepine ring. A number of balanol analogs in which the perhydroazepine moiety is replaced have been synthesized and their
Carlos E S Bernardes et al.
The journal of physical chemistry. A, 112(40), 10029-10039 (2008-09-13)
The energetics of the phenolic O-H bond in a series of 2- and 4-HOC 6H 4C(O)Y (Y = H, CH3, CH 2CH=CH2, C[triple bond]CH, CH2F, NH2, NHCH 3, NO2, OH, OCH3, OCN, CN, F, Cl, SH, and SCH3) compounds and
G D Smith et al.
Protein science : a publication of the Protein Society, 5(8), 1502-1511 (1996-08-01)
The structure of a symmetric T3R3f insulin hexamer, complexed with 4-hydroxybenzamide, has been determined using X-ray crystallographic techniques. Data were measured from six crystals grown in microgravity to a resolution of 1.4 A and the structure has been refined including
G D Hartman et al.
Bioorganic & medicinal chemistry letters, 9(6), 863-868 (1999-04-17)
A new series of potent, linearly-minimized, orally active, selective GPIIb/IIIa inhibitors is identified. Thus 15 (L-750,034) achieves interaction via a constrained, non-turned conformation that maintains the proper distance between its charged termini and full sulfonamide exosite interaction. The diminutive stature

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