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236454

Sigma-Aldrich

Methyl 2-aminobenzoate

ReagentPlus®, ≥99%

Synonym(s):

Methyl anthranilate

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About This Item

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.)

functional group

ester

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

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

262.4 °F - closed cup

Flash Point(C)

128 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3796
MKCK3934
MKBV9370V
MKBN4660V
MKBK8185V

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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)
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
Marie E Gibbs et al.
Brain research bulletin, 76(3), 198-207 (2008-05-24)
A one-trial learning task, where chicks learn that a bead of a particular shape and/or colour has a bitter taste (because it has been coated in 100% methyl anthranilate, MeA) and subsequently avoids it on test, has been widely used
Jihong Wang et al.
The Plant journal : for cell and molecular biology, 44(4), 606-619 (2005-11-03)
The biosynthesis of methyl anthranilate, the volatile compound responsible for the distinctive 'foxy' aroma and flavor of the Washington Concord grape (Vitis labrusca), involves an alcohol acyltransferase that catalyzes the formation of methyl anthranilate from anthraniloyl-coenzyme A (CoA) and methanol.
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
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