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Sigma-Aldrich

Methyl 2-aminobenzoate

ReagentPlus®, ≥99%

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Synonym(s):
Methyl anthranilate
Linear Formula:
2-(H2N)C6H4CO2CH3
CAS Number:
134-20-3
Molecular Weight:
151.16
Beilstein:
606965
EC Number:
205-132-4
MDL number:
MFCD00007710
UNSPSC Code:
12352100
PubChem Substance ID:
24854171
NACRES:
NA.22

vapor pressure

1 mmHg ( 20 °C)

Quality Level

100

product line

ReagentPlus®

Assay

≥99%

form

liquid

autoignition temp.

986 °F

refractive index

n20/D 1.582 (lit.)

bp

256 °C (lit.)

mp

24 °C (lit.)

solubility

alcohol: freely soluble(lit.)
diethyl ether: freely soluble(lit.)
water: slightly soluble(lit.)

density

1.168 g/mL at 25 °C (lit.)

SMILES string

COC(=O)c1ccccc1N

InChI

1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3

InChI key

VAMXMNNIEUEQDV-UHFFFAOYSA-N

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General description

Methyl 2-aminobenzoate reacts with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulphide at 140°C to yield 1,2-dihydro-2-(p-methoxyphenyl)-4H-3,1,2-benzothiazaphosphorin-4-thione-2-sulfide and dimethyl-4-methoxyphenylphosphonotrithioate.

Application

Methyl 2-aminobenzoate has been used in the synthesis of novel 4-chloro-2-mercaptobenzenesulfonamide derivatives.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

WGK

WGK 1

Flash Point(F)

262.4 °F

Flash Point(C)

128 °C

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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Studies on organophosphorus compounds-XXXVI: simple new routes to phosphorins from 2-hydroxy-, 2-mercapto-, and 2-aminobenzoic acids and their derivatives.
El-Barbary AA and Lawesson S-O.
Tetrahedron, 37(15), 2641-2646 (1981)
M Galtayries et al.
Luminescence : the journal of biological and chemical luminescence, 15(6), 363-369 (2000-12-13)
A sensitive and fast approach for the determination of methyl anthranilate in grape must and honey samples, using time-resolved luminescence measurements, has been reported for the first time. The method involves the alkaline hydrolysis of the ester to anthranilic acid
S Richard et al.
Physiology & behavior, 70(5), 521-525 (2000-12-09)
Methyl anthranilate (MeA) has been widely used as a taste aversant for domestic chicks in the one-trial passive avoidance learning (PAL) task. However, MeA has a strong smell that may be aversive to chicks. Therefore, odourless denatonium benzoate (DB) has
Tanya Pankiw
Journal of medical entomology, 46(4), 782-788 (2009-08-04)
Human victims of a massive number of stings have been steadily increasing since the invasion of Africanized honey bees (Apis mellifera) to the United States in 1990. Multiple honey bee stings may result in venom toxicity, leading to renal failure
Leslie Hammack et al.
Journal of chemical ecology, 30(9), 1809-1825 (2004-12-14)
We used field assays to study attraction of feral northern and western corn rootworm beetles (Diabrotica barberi and D. virgifera virgifera) to a series of mostly nitrogenous and benzenoid synthetic compounds allied with host plant and floral aromas. Vaporization rates
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