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Sigma-Aldrich

Methyl 2-isocyanatobenzoate

97%

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About This Item

Linear Formula:
OCNC6H4CO2CH3
CAS Number:
1793-07-3
Molecular Weight:
177.16
MDL number:
MFCD00013848
UNSPSC Code:
12352100
PubChem Substance ID:
24867555
NACRES:
NA.22

Assay

97%

form

solid

bp

101 °C/2 mmHg (lit.)

mp

45-49 °C (lit.)

SMILES string

COC(=O)c1ccccc1N=C=O

InChI

1S/C9H7NO3/c1-13-9(12)7-4-2-3-5-8(7)10-6-11/h2-5H,1H3

InChI key

ATFKBWNEVZUSKC-UHFFFAOYSA-N

Application

Methyl 2-isocyanatobenzoate may be used for the following syntheses:
  • 3H-quinazolin-4-ones
  • A1120, a high affinity (Ki = 8.3nM) non-retinoid ligand for the Retinol-binding protein
  • trans- and cis-N-phenyl-N′-(4-phenoxy)cyclohexylureas

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - 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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chemistry of 4H-3, 1-Benzoxazin-4-ones.
El-Mekabaty A.
International Journal of Modern Organic Chemistry, 2(2), 81-121 (2013)
Alexander V Lygin et al.
Organic letters, 11(2), 389-392 (2008-12-23)
ortho-Lithiophenyl isocyanide has been generated from ortho-bromophenyl isocyanide and successfully employed toward the synthesis of 2-substituted phenyl isocyanides as well as 2,3-disubstituted 3H-quinazoline-4-ones and 3H-quinazolin-4-thiones.
Alykhan Motani et al.
The Journal of biological chemistry, 284(12), 7673-7680 (2009-01-17)
Retinol-binding protein 4 (RBP4) transports retinol from the liver to extrahepatic tissues, and RBP4 lowering is reported to improve insulin sensitivity in mice. We have identified A1120, a high affinity (K(i) = 8.3 nm) non-retinoid ligand for RBP4, which disrupts
Ting Chen et al.
Journal of medicinal chemistry, 56(23), 9457-9470 (2013-11-23)
Heme-regulated inhibitor kinase (HRI), a eukaryotic translation initiation factor 2 alpha (eIF2α) kinase, plays critical roles in cell proliferation, differentiation, and adaptation to cytoplasmic stress. HRI is also a critical modifier of hemoglobin disorders such as β-thalassemia. We previously identified

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