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527742

Sigma-Aldrich

2-Cyanobenzoic acid

technical grade

Synonym(s):

o-Carboxybenzonitrile, NSC 193443

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About This Item

Linear Formula:
NCC6H4CO2H
CAS Number:
3839-22-3
Molecular Weight:
147.13
MDL number:
MFCD00045796
UNSPSC Code:
12352100
PubChem Substance ID:
24874642
NACRES:
NA.22

grade

technical grade

form

solid

mp

212 °C (lit.)

functional group

carboxylic acid
nitrile

SMILES string

OC(=O)c1ccccc1C#N

InChI

1S/C8H5NO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4H,(H,10,11)

InChI key

DTNSDCJFTHMDAK-UHFFFAOYSA-N

General description

2-Cyanobenzoic acid can be prepared from phthalic anhydride.[1] Mass spectrophotometry, NMR, IR are extremely useful techniques to determine the ring-chain tautomeric equilibrium of 2-cyanobenzoic acid in all three phases.[2] The standard (p° = 0.1MPa) molar enthalpy of formation of 2-cyanobenzoic acid is -(150.7 ± 2.0) kJ.mol-1.[3]

Application

2-Cyanobenzoic acid may be used to synthesize phthalamidine.[4]
Reactant involved in the synthesis of:
  • T-box riboswitch antiterminator RNA-binding oxazolidinone derivatives
  • Benzoate modified β-cyclodextrin derivatives
  • Pyrrolo[1,2-f]triazines for use as JAK2 inhibitors

Reactant involved in:
  • Decarboxylation
  • Decarboxylative halogenation
  • Protodecarboxylation

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.

PDSCL

Deleterious substance

JAN Code

527742-BULK:
527742-VAR:
527742-5G:4548173166308
527742-1G:4548173166292

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Certificates of Analysis (COA)

Lot/Batch Number
0000117215
BGBB6262V
BGBB6130V
BGBB4528V
BGBB0303

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Experimental Study of Tautomeric Equilibria of 2-Cyanobenzoic Acids in Gas, Solution and Solid Phase.
Iglesias DA, et al.
Journal of Applied Solution Chemistry and Modeling, 1(2), 113-113 (2012)
The Study of Novel Synthetic Method of 2-Cyanobenzo.
Yang YS, et al.
Guangzhou Chemical Industry/ Guangzhou Huagong, 22, 016-016 (2011)
Standard molar enthalpies of formation of 2-, 3-and 4-cyanobenzoic acids.
da Silva MAVR, et al.
The Journal of Chemical Thermodynamics, 40(8), 1226-1231 (2008)
Studies on the syntheses of heterocyclic compounds. CCIV. Ring contraction in the catalytic hydrogenation of 3-oximino-4-oxoisocarbostyril.
Kametani T, et al.
Chemical & Pharmaceutical Bulletin, 15(12), 1916-1921 (1967)

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