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Methyl 2-(methylamino)benzoate

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Methyl 2-(methylamino)benzoate Basic information

Product Name:
Methyl 2-(methylamino)benzoate
Synonyms:
  • METHYL 2-(N-METHYLAMINO)BENZOATE
  • METHYL 2-METHYLAMINOBENZOATE
  • METHYL O-(METHYLAMINO)BENZOATE
  • METHYL N-METHYLANTHRANILATE
  • METHYL METHYLANTHRANILATE
  • FEMA 2718
  • DIMETHYL ANTHRANILATE
  • 2-METHYLAMINOBENZOIC ACID METHYL ESTER
CAS:
85-91-6
MF:
C9H11NO2
MW:
165.19
EINECS:
201-642-6
Product Categories:
  • Building Blocks
  • C8 to C9
  • pharmacetical
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • Aromatic Esters
  • C8 to C9
  • Carbonyl Compounds
  • Esters
Mol File:
85-91-6.mol
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Methyl 2-(methylamino)benzoate Chemical Properties

Melting point:
17-19 °C(lit.)
Boiling point:
256 °C(lit.)
Density 
1.126 g/mL at 25 °C(lit.)
FEMA 
2718 | METHYL N-METHYLANTHRANILATE
refractive index 
n20/D 1.579(lit.)
Flash point:
>230 °F
storage temp. 
2-8°C
solubility 
Miscible in all proportions with ethanol 96%, DMSO and diethyl ether.
pka
2.80±0.10(Predicted)
form 
neat
PH
7-8 (H2O, 20℃)
JECFA Number
1545
BRN 
607217
CAS DataBase Reference
85-91-6(CAS DataBase Reference)
NIST Chemistry Reference
Benzoic acid,o-(methylamino)-, methyl ester(85-91-6)
EPA Substance Registry System
Methyl N-methyl anthranilate (85-91-6)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-36/37/39-22
WGK Germany 
1
RTECS 
CB3500000
TSCA 
Yes
Hazardous Substances Data
85-91-6(Hazardous Substances Data)

MSDS

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Methyl 2-(methylamino)benzoate Usage And Synthesis

Description

Methyl n-methylanthranilate has an orange and mandarin peel-like odor with a musty, grape-like flavor. It is somewhat more berry-like than grape. May be prepared by methylation of methyl anthranilate or esterification of N-methylanthranilic acid.

Chemical Properties

Methyl-n-methylanthranilate has an orange and mandarin peel-like odor and a musty, grape-like flavor; somewhat more berry-like than grape.

Chemical Properties

Methyl N-Methylanthranilate is the main component of petitgrain oils from mandarin leaves and is also found in mandarin oil. It is a pale yellow, fluorescent liquid with a delicate mandarin odor. The ester can be prepared by methylation ofmethyl anthranilate. It is used in soap and cosmetic perfumes as well as in aromas, particularly for mandarin flavors.

Occurrence

Reported found in mandarin essential oil and mandarin leaves essential oil (50 to 76.5%); also reported in the oil from bulbs of Kaempferia ethelae L., in orange petitgrain, and in the oil from hyacinth flowers. Also reported found in starfruit, orange peel oil and grapefruit juice.

Uses

It is used as a flavorant in a wide range of foods (particularly flour and sugar confections).

Production Methods

Methyl N-methanthranilate is a component of mandarin and mandarin tree leaf essential oil. It is also found in oil from bulbs of Kaempferia ethelae L., hyacinth flowers, and orange petitgrain . It is synthesized by methylation of methyl anthranilate or esterification ofN-methylanthranilic acid.

Preparation

By methylation of methyl anthranilate or esterification of N-methylanthranillic acid.

Taste threshold values

Taste characteristics at 10 ppm: fruity grape skin, anthranilate-like with a woody and floral nuance

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 3373, 1984 DOI: 10.1021/jo00192a024

Toxicity evaluation

The acute oral LD50 value in rats was reported as 3.7 ml/kg (Levenstein, 1974). The acute oral LD50 in female rats was reported to be between 2.25 g/kg (no deaths) and 3.38 g/kg (100% deaths) (Gaunt, Sharratt, Grasso & Wright, 1970). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Levenstein, 1974). The LC 50 for larvae of Tribolium destructor was found to be 0-1151 mg/cm3 (Vasechko, Kuznetsov, Smelyanets & Guznenok, 1970).

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.

Methyl 2-(methylamino)benzoate Preparation Products And Raw materials

Raw materials

Methyl 2-(methylamino)benzoateSupplier

Abmole Bioscience Inc. Gold
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021-50967598-
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J & K SCIENTIFIC LTD.
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010-82848833- ;010-82848833-
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jkinfo@jkchemical.com;market6@jkchemical.com
3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801
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3bsc@sina.com
Alfa Aesar
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400-610-6006; 021-67582000
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saleschina@alfa-asia.com
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Email
Sales-CN@TCIchemicals.com