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Methyl anthranilate structure
Methyl anthranilate structure

Methyl anthranilate

Iupac Name:methyl 2-aminobenzoate
CAS No.: 134-20-3
Molecular Weight:151.165
Modify Date.: 2022-11-05 06:58
Introduction: Methyl anthranilate, also known as MA, methyl 2-amino benzoate or carbo methoxy aniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2. View more+
1. Names and Identifiers
1.1 Name
Methyl anthranilate
1.2 Synonyms

1-aminobenzene-2-carboxylic acid methyl ester 2-AMINOBENZOIC ACID METHYL ESTER 2-methoxycarbonylaniline ANTHRANILIC ACID METHYL ESTER ANTHRANILIC ACID:METHYL ESTER Benzoic acid, 2-amino-, methyl ester Carbomethoxyaniline EINECS 205-132-4 FEMA 2682 Methl-O-Aminobenzoate METHYL 2-AMINOBENZOATE methyl 2-amino-benzoate METHYL 2-ANTHRANILATE Methyl anthanilate methyl anthranlate Methyl anthranylate methyl o-amino-benzoate Methylaminobenzoate MFCD00007710 NEROLI NEROLI OIL, ARTIFICIAL nerolioil,artifical Nevoli oil

1.3 CAS No.
134-20-3
1.4 CID
8635
1.5 EINECS(EC#)
205-132-4
1.6 Molecular Formula
C8H9NO2 (isomer)
1.7 Inchi
InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
1.8 InChkey
VAMXMNNIEUEQDV-UHFFFAOYSA-N
1.9 Canonical Smiles
COC(=O)C1=CC=CC=C1N
1.10 Isomers Smiles
COC(=O)C1=CC=CC=C1N
2. Properties
2.1 Density
1.168
2.1 Melting point
24℃
2.1 Boiling point
75 to 77° F (NTP, 1992)
2.1 Refractive index
1.581-1.584
2.1 Flash Point
220° F (NTP, 1992)
2.1 Precise Quality
151.06300
2.1 PSA
52.32000
2.1 logP
1.63660
2.1 Solubility
alcohol: freely soluble(lit.)
2.2 AnalyticLaboratory Methods
Method: AOAC 950.25, Methyl Anthranilate; in Non-alcoholic Beverages, Colorimetric Method; Analyte: methyl anthranilate;; Matrix: beverages containing <500 mg/l; Detection Level: not provided.
2.3 Appearance
Colourless to pale yellow liquid or crystals with bluish fluorescence; Grape-like or orange aroma
2.4 Storage
Ambient temperatures.
2.5 Chemical Properties
It appears as colorless to pale yellow liquid; it has blue fluorescence with orange blossom aroma. It has a freezing point of 24 °C with a boiling point of 273 ° C and a temperature of 132 ° C (1.87 kPa). It is soluble in ethanol, ether and other organic solvents, slightly soluble in water and glycerol. Rat oral LD50:2910mg/kg, Adl 0~1.5mg/kg (FAO/WHO1994).
2.6 Color/Form
Crystals
Pale-yellow liquid with bluish fluorescence
Colorless to pale yellow liquid or solid
2.7 Decomposition
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
2.8 Odor
Grape-like odor
2.9 PH
7.5-8 (H2O, 20℃)Aqueous solution
2.10 Physical
PHYSICAL DESCRIPTION: Clear colorless to tan liquid with an odor of grapes. Has light blue fluorescence. (NTP, 1992)
2.11 pKa
pK1:2.23(+1) (25°C)
2.12 Water Solubility
slightly soluble
2.13 Spectral Properties
Index of refraction: 1.5810 @ 25 deg C
MAX ABSORPTION (ALCOHOL): 248 & 341 NM (LOG E= 3.7); SADTLER REF NUMBER: 897 (IR, PRISM); 280 (IR, GRATING); 1200 (UV)
IR: 1234 (Coblentz Society Spectral Collection)
UV: 280 (Sadtler Research Laboratories Spectral Collection)
1H-NMR: 1200 (Sadtler Research Laboratories Spectral Collection)
MASS: 4756 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
2.14 Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
2.15 StorageTemp
Keep in dark place,Inert atmosphere,Room temperature
3. Use and Manufacturing
3.1 Definition
ChEBI: A benzoate ester that is the methyl ester of anthranilic acid.
3.2 General Description
Clear colorless to tan liquid with an odor of grapes. Has light blue fluorescence.
3.3 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 1689 companies from 10 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria by 4 of 1689 companies. For more detailed information, please visit ECHA C&L website

Of the 9 notification(s) provided by 1685 of 1689 companies with hazard statement code(s):

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P280, P305+P351+P338, P33, and P313
3.4 Methods of Manufacturing
Methyl anthranilate; is prepared by esterification of anthranilic acid; with methanol; or by reaction of isatoic anhydride; with methanol;.
3.5 Usage
Methyl anthranilate acts as a bird repellent. It is food-grade and can be used to protect corn, sunflowers, rice, fruit, and golf courses. Dimethyl anthranilate (DMA) has a similar effect. It is also used for the flavor of grape Kool Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), gums, and drugs. Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery . It is also used to produce Schiff's Bases with aldehydes, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol - produced by combining methyl anthranilate and hydroxyl citronellal.
4. Safety and Handling
4.1 Symbol
GHS07
4.1 Hazard Codes
Xi
4.1 Signal Word
Warning
4.1 Risk Statements
R36/37/38
4.1 Safety Statements
S26;S37/39
4.1 Exposure Standards and Regulations
Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Methyl anthranilate is included on this list.
Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, withn the meaning of section 409 of the Act. Methyl anthranilate is included on this list.
Sunscreen active ingredients. The active ingredient of the product consists of any of the following, within the concentration specified for each ingredient, and the finished product provides a minimum SPF value of not less than 2 as measured by the testing procedures established in subpart D of this part: ... (h) Methyl anthranilate up to 5 percent.
4.2 Octanol/Water Partition Coefficient
log Kow = 1.88
4.3 Fire Hazard
Methyl anthranilate is combustible.
4.4 Other Preventative Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
4.5 Hazard Declaration
H315-H319-H335
4.5 Cleanup Methods
Contain the spill to prevent a large discharge to surface streams or storm sewers. Since landfill operations will not accept liquid waste, allow to dry if possible before collecting for disposal. An absorbent material would aid in cleaning up a liquid spill. If liquid cleanup is necessary, collect in drums, buckets, or other containers.
4.6 DisposalMethods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
4.7 RIDADR
100kg
4.7 Fire Fighting Procedures
Extinguishing Media: Dry chemical, foam. ...Water may be used to cool closed containers to prevent pressure build-up and/or explosion when exposed to extreme heat.
4.8 Safety Profile
Moderately toxic byingestion. Experimental reproductiveeffects. A skin irritant. See also ESTERS.Combustible liquid. When heated todecomposition it emits toxic fumes of NOx.
4.9 Caution Statement
P261-P305 + P351 + P338
4.9 Formulations/Preparations
Grades: Technical; FCC.
USEPA/OPP Pesticide Code 128725; Trade Names: Bird Shield Repellant Concentrate (26.4%), Rejex-It AG-145 (14.5%), Rejex-It AG-36 (14.5%), Rejex-It MA (98.5%), Rejex-It TP-40 (40%).
4.10 WGK Germany
1
4.10 RTECS
CB3325000
4.10 Protective Equipment and Clothing
Prolonged inhalation may lead to respiratory tract irritation. ...Prolonged or repeated /skin or eye/ contact may result in mechanical irritation.
4.11 Report

The Methyl anthranilate, with its CAS registry number 134-20-3, has the IUPAC name of methyl 2-aminobenzoate. For being a kind of colorless to light yellow liquid with a smell of orange blossom, it is slightly soluble in water while soluble in ethanol, diethyl ether and other organic solvents, and it is stable but incompatible with strong oxidizing agents. Besides, its product categories are including Carboxylicester; Benzene derivatives; Aromatic Esters; pharmacetical.

The physical properties of this chemical are as below: (1)ACD/LogP: 2.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.04; (4)ACD/LogD (pH 7.4): 2.04; (5)ACD/BCF (pH 5.5): 20.85; (6)ACD/BCF (pH 7.4): 20.86; (7)ACD/KOC (pH 5.5): 306.06; (8)ACD/KOC (pH 7.4): 306.21; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 52.32; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 42.26 cm3; (15)Molar Volume: 129.6 cm3; (16)Polarizability: 16.75×10-24 cm3; (17)Surface Tension: 46.2 dyne/cm; (18)Density: 1.166 g/cm3; (19)Flash Point: 112.9 °C; (20)Enthalpy of Vaporization: 49.35 kJ/mol; (21)Boiling Point: 256 °C at 760 mmHg; (22)Vapour Pressure: 0.0158 mmHg at 25°C; (23)Exact Mass: 151.063329; (24)MonoIsotopic Mass: 151.063329; (25)Topological Polar Surface Area: 52.3; (26)Heavy Atom Count: 11; (27)Complexity: 147.

When you are dealing with this chemical, you should be very careful. For being irritating to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
?
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: COC(=O)C1=CC=CC=C1N
(2)InChI: InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
(3)InChIKey: VAMXMNNIEUEQDV-UHFFFAOYSA-N?

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 2780mg/kg (2780mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
mouse LD50 oral 3900mg/kg (3900mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rabbit LD50 skin > 5gm/kg (5000mg/kg) ? Food and Cosmetics Toxicology. Vol. 12, Pg. 935, 1974.
rat LD50 oral 2910mg/kg (2910mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

4.12 Skin, Eye, and Respiratory Irritations
Prolonged inhalation may lead to respiratory tract irritation. ...Prolonged or repeated /skin or eye/ contact may result in mechanical irritation.
4.13 Sensitive
Air Sensitive
4.14 Specification

The Methyl anthranilate, with its CAS registry number 134-20-3, has the IUPAC name of methyl 2-aminobenzoate. For being a kind of colorless to light yellow liquid with a smell of orange blossom, it is slightly soluble in water while soluble in ethanol, diethyl ether and other organic solvents, and it is stable but incompatible with strong oxidizing agents. Besides, its product categories are including Carboxylicester; Benzene derivatives; Aromatic Esters; pharmacetical.

The physical properties of this chemical are as below: (1)ACD/LogP: 2.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.04; (4)ACD/LogD (pH 7.4): 2.04; (5)ACD/BCF (pH 5.5): 20.85; (6)ACD/BCF (pH 7.4): 20.86; (7)ACD/KOC (pH 5.5): 306.06; (8)ACD/KOC (pH 7.4): 306.21; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 52.32; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 42.26 cm3; (15)Molar Volume: 129.6 cm3; (16)Polarizability: 16.75×10-24 cm3; (17)Surface Tension: 46.2 dyne/cm; (18)Density: 1.166 g/cm3; (19)Flash Point: 112.9 °C; (20)Enthalpy of Vaporization: 49.35 kJ/mol; (21)Boiling Point: 256 °C at 760 mmHg; (22)Vapour Pressure: 0.0158 mmHg at 25°C; (23)Exact Mass: 151.063329; (24)MonoIsotopic Mass: 151.063329; (25)Topological Polar Surface Area: 52.3; (26)Heavy Atom Count: 11; (27)Complexity: 147.

When you are dealing with this chemical, you should be very careful. For being irritating to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
?
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: COC(=O)C1=CC=CC=C1N
(2)InChI: InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
(3)InChIKey: VAMXMNNIEUEQDV-UHFFFAOYSA-N?

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 2780mg/kg (2780mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
mouse LD50 oral 3900mg/kg (3900mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rabbit LD50 skin > 5gm/kg (5000mg/kg) ? Food and Cosmetics Toxicology. Vol. 12, Pg. 935, 1974.
rat LD50 oral 2910mg/kg (2910mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

4.15 Toxicity
ORL-RAT LD50 2910 mg kg-1, ORL-MUS LD50 3900 mg kg-1
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H319 Causes serious eye irritation

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Usage
It is applied as a flavoring agent. Food companies use artificial MA in their candy and chewing gum to give them their grape flavor. Beverage companies have been adding it to the carbonated water and sugar in their soft drinks for the same reason.
8.1 Merck
14,6020
8.2 BRN
606965
8.3 Description
Methyl anthranilate, also known as MA, methyl 2-amino benzoate or carbo methoxy aniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2.
8.4 Chemical Properties
Methyl anthranilate has a characteristic orange-flower odor and a slightly bitter, pungent taste. May be prepared by heating anthranilic acid and methyl alcohol in the presence of sulfuric acid and subsequent distillation.
8.5 Chemical Properties
Methyl Anthranilate occurs in a large number of blossom essential oils (e.g., neroli, ylang-ylang, and jasmine oils), grapes, and citrus oils. It occurs as white crystals (mp 24–25°C), or a yellowish liquid, that show blue fluorescence and have an orange blossom odor. Methyl anthranilate is prepared by esterification of anthranilic acid with methanol or by reaction of isatoic anhydride with methanol.
It is used in a large number of blossom fragrances. However, its use in perfumes for soaps and cosmetics is limited because it causes discoloration. It is used in flavor compositions (e.g., in grape and citrus flavors).
8.6 Occurrence
Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes or hybrids thereof, and in bergamot, black locust, champaca , gardenia, jasmine, lemon, mandarin, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate.It is also secreted by the musk glands of foxes and dogs, and lends a "sickly sweetness" to the smell of rotting flesh.
8.7 Uses
Methyl anthranilate acts as a bird repellent. It is food-grade and can be used to protect corn, sunflowers, rice, fruit, and golf courses. Dimethyl anthranilate (DMA) has a similar effect. It is also used for the flavor of grape Kool Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), gums, and drugs.
Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery . It is also used to produce Schiff's Bases with aldehydes, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol - produced by combining methyl anthranilate and hydroxyl citronellal.
8.8 Definition
ChEBI: Methyl anthranilate is a benzoate ester that is the methyl ester of anthranilic acid. It has a role as a metabolite and a flavouring agent. It derives from an anthranilic acid.
8.9 Preparation
By heating anthranilic acid and methyl alcohol in the presence of sulfuric acid and subsequent distillation.
8.10 Synthesis Reference(s)
Tetrahedron Letters, 33, p. 3599, 1992 DOI: 10.1016/S0040-4039(00)92512-7
8.11 General Description
Clear colorless to tan liquid with an odor of grapes. Has light blue fluorescence.
8.12 Air & Water Reactions
Methyl anthranilate is sensitive to air and light. Slightly water soluble .
8.13 Reactivity Profile
An amine and ester. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
8.14 Fire Hazard
Methyl anthranilate is combustible.
8.15 Safety Profile
Moderately toxic by ingestion. Experimental reproductive effects. A skin irritant. See also ESTERS. Combustible liquid. When heated to decomposition it emits toxic fumes of NOx.
8.16 Toxicology
Methyl anthranilate is a colorless liquid that has a sweet, fruity, grape-like flavor. It is found in the essential oils of orange, lemon, and jasmine and has been widely used to create imitation Concord grape flavor. Table 10.8 shows the acute toxicity of methyl anthranilate. Methyl anthranilate promotes some allergic reactions on human skin, which has led to it being prohibited for use in cosmetic products.
8.17 Metabolism
It is probable that this ester is hydrolysed and the anthranilate is excreted mostly as oaminobenzoyl glucuronide (Charconnet-Harding, Dalgliesh & Neuberger, 1953).
8.18 Toxicity evaluation
Even though MA is palatable to humans, it is an irritant to birds. The bird-repellent properties of MA and related compounds were discovered in the late 1950s (25). The mode of action is via the trigeminal nerve. Thus, all avian species tested so far perceive MA as an irritant, not as a taste repellent per se.
9. Computational chemical data
  • Molecular Weight: 151.165g/mol
  • Molecular Formula: C8H9NO2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 151.063328530
  • Monoisotopic Mass: 151.063328530
  • Complexity: 147
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 52.3
  • Heavy Atom Count: 11
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccByMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgAQAAAADAiBmAIyyIBABACIAiTSSACCAAAkAgAIiAEAbMgIJjqAtZmAMYBm0AEI6ceYyCCOAAAAAAACAAAAAAAAAAQAAAAAAAAAAA==
10. Question & Answer
  • Because of the hazards posed by the UV lamp, this is not a good gift for a child. Also, look up the wavelength spectrum for absorbtion of UV by methyl anthranilate and make sure the spectrum overlaps the spectrum for emission by the lamp. If they don’t overlap, i.e. the light emitted by the lamp i...
  • When methyl anthranilate is added to sulfuric acid a white precipitate forms. I am assuming this is an insoluble salt produced in the acid base reaction, where the lone pair on the nitrogen will accept a proton. My question is, does sulfuric acid lose both protons in the reaction, so that there are...
  • Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid manufactured through chemical synthesis, available as clear to pale yellow liquid (graph 1). Its chemical formula is C8H9NO2. It has a fruity grape smell, and one of its key uses i...
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