Methyl 2-aminobenzoate

Methyl 2-aminobenzoate - Names and Identifiers

Name	Methyl anthranilate
Synonyms	Methyl anthranilate Methl-O-Aminobenzoate Methyl 2-Aminobenzoate 2-amino-3-methylbenzoate Anthranilic acid methylester Anthranilic acid methyl ester 2-Aminobenzoic acid methyl ester
CAS	134-20-3
EINECS	205-132-4
InChI	InChI=1/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
InChIKey	VAMXMNNIEUEQDV-UHFFFAOYSA-N

Methyl 2-aminobenzoate - Physico-chemical Properties

Molecular Formula	C8H9NO2
Molar Mass	151.163
Density	1.166g/cm³
Melting Point	24℃
Boling Point	256°C at 760 mmHg
Flash Point	112.9°C
Water Solubility	slightly soluble
Vapor Presure	0.0158mmHg at 25°C
Appearance	Clear yellow-brown Liquid
pKa	pK1:2.23(＋1) (25°C)
PH	7.5-8 (H2O, 20℃)Aqueous solution
Storage Condition	Keep in dark place,Inert atmosphere,Room temperature
Stability	Stable. Combustible. Incompatible with strong oxidizing agents.
Refractive Index	1.565
Physical and Chemical Properties	Appearance: White Crystal Melting Point: 24 ℃ Boiling Point: 256 ℃
Use	For the synthesis of spices, drugs, etc

Methyl 2-aminobenzoate - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection
WGK Germany	1
RTECS	CB3325000
FLUKA BRAND F CODES	21
TSCA	Yes
HS Code	29224995
Toxicity	LD50 orally in rats, mice: 2910, 3900 mg/kg, P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964)

Methyl 2-aminobenzoate - Upstream Downstream Industry

Methyl 2-aminobenzoate - Nature

Open Data Verified Data

colorless to light yellow liquid, with blue fluorescence, with orange flower fruit aroma. Soluble in ethanol, ether and other organic solvents, water-soluble and glycerol.

Last Update：2024-01-02 23:10:35

Methyl 2-aminobenzoate - Preparation Method

Open Data Verified Data

prepared by esterification of anthranilic acid with methanol under acidic conditions and neutralization by alkali. Or by phthalic anhydride by ammonification, degradation, esterification.

Last Update：2022-01-01 10:07:48

Methyl 2-aminobenzoate - Use

Open Data Verified Data

for the preparation of grape, cherry, strawberry, watermelon, citrus and other food flavor and wine flavor. In chewing gum, the usage amount is 2200mg/kg; In candy, 56mg/kg; In pudding, 23mg/kg; In cold drinks, 21mg/kg; In baked food, 20mg/kg; In soft drinks, 16mg/kg; 0.2mg/kg in alcohol.

Last Update：2022-01-01 10:07:48

Methyl 2-aminobenzoate - Security information

category flammable liquids

Toxicity grading poisoning

acute toxicity oral-rat LD50: 2910 mg/kg; Oral-mouse LD50: 3900 mg/kg

stimulation data skin-rabbit 500 mg/24 hours moderate

Flammable hazard characteristics are flammable; combustion produces toxic nitrogen oxide smoke

storage and transportation characteristics warehouse ventilation and low temperature drying

Fire extinguishing agent dry powder, foam, sand, carbon dioxide, mist water

Dangerous Goods Sign Xi

hazard category code 36/37/38

Safety instructions 26-36-37/39

WGK Germany 1

RTECS number CB3325000

F 21

autoignition temperature 986 °F

TSCA Yes

customs code 29224995

toxicity LD50 orally in rats, mice: 2910, 3900 mg/kg, p. m. Jenner et al., food cosmet. Toxicol. 2,327 (1964)

Last Update：2024-04-10 22:29:15

Methyl 2-aminobenzoate - Uses and synthesis methods

background

Since the discovery of methyl anthranilate in neroli oil in 1899, people have successively found anthranilic acid esters in many natural plants such as oranges, lemon jasmine, ylang-ylang, gardenia, etc. The existence of compounds has attracted the attention of the spice industry. Anthranilates are both esters and primary aromatic amines, so they have the dual characteristics of esters and amines. When it is added to flavors containing other aldehydes, it can undergo condensation reaction with aldehydes to produce Sch base (Sch near Base) with more stable properties and stronger aroma.

application

Most Schiff bases have dark colors, but some are light orange and have a strong aroma, which is a good agent in essence. Because such compounds have strong fruit fragrance and flower fragrance, they have been widely used in daily flavor and edible flavor. In edible flavors, it is the main flavor of grape flavor, and can also be used in various berries, melons, honey flavors, citrus, roses, violets and wine flavors. Methyl anthranilate is one of the backbone products of the perfume industry. It can also prepare about 60 kinds of spices; menthyl anthranilate obtained by transesterification with menthol is an effective sunscreen agent.

Use

Methyl anthranilate orMethyl 2-aminobenzoate naturally exists in essential oils such as citrus, tuberose, jasmine, gardenia, orange blossom, etc. It has strong fruit and flower fragrance. It is one of the backbone products of the spice industry and is widely used in daily and edible flavors. In the edible flavor, it is the main flavor of grape flavor, and can also be used in various berry, melon, honey flavor, citrus, lemon, strawberry and pineapple. About 60 kinds of fragrances can also be prepared from methyl anthranilate. For example, other anthranilate esters prepared by transesterification reaction of methyl anthranilate are one of the commonly used raw materials for flavoring, with a wide range of uses and high value; It reacts with some aldehydes to form Schiff bases with more stable properties and stronger aroma. It is a good fixative in flavors.

Preparation

Using o-nitrotoluene as the starting material:

o-nitrotoluene is oxidized to o-nitrobenzoic acid, which is then ammoniated and converted into o-aminobenzoic acid. Finally, it reacts with methanol and catalyzes esterification with an acidic catalyst to obtain methyl anthranilate

content analysis

accurately weigh about 1.0g of sample and determine it according to method 1 in ester determination method (OT-18). The equivalent factor (e) in the calculation is 75.59.

Toxicity

ADI 0~1.5 mg/kg FAO/WHO,1994).

GRAS(FDA,& sect;182.60,2000).

LD50 2910mg/kg (rat, oral).

use limit

FEMA(mg/kg 1998 revision): baked products 38; Alcohol-free beverage 40; Alcohol-containing beverage 0.2~2.0; Gum sugar 200~1583; Frozen dairy 40; Fruit ice 40; Gel and pudding 20; Hard candy 80~161; Jam and jelly 6; Fudge 80.

Last Update：2024-04-09 21:01:54

Methyl 2-aminobenzoate - Uses and synthesis methods

Use

methyl anthranilate is a food spice allowed by the hygienic standard for the use of food additives in China. it is used to prepare watermelon, citrus, grape, strawberry and other fruit flavor and wine flavor. The usage amount in chewing gum is 2200 mg/kg; 56 mg/kg in candy; 23 mg/kg in pudding; 21 mg/kg in cold drinks; 20 mg/kg in baked food; 16rng/kg in soft drinks; 0.2 mg/kg in alcohol.

this product can be used as an intermediate for pesticides and saccharin. Methyl anthranilate has the sweet fragrance of tower flowers, and has a grape-like fragrance when diluted. It is used for the blending of cheap artificial flower oils. It also uses soap spices or grape flavors. Our GB 2760-86 stipulates that edible spices are allowed to be used. It is mainly used to prepare flavors such as grapes, oranges, roganberries, strawberries and watermelons. Anthranilates can react with aldehydes to form valuable soap-based fragrances, such as hydroxyl aromatic aldehydes and anthranilate. The following spices are obtained by the action of methyl ester. This kind of spice is already commercially available in China, and the trade name is Aurantiol. The oral LD50 was 2910mg/kg in rats and 3900mg/kg in mice.

for organic synthesis

Used to synthesize spices, drugs, etc.

GB 2760 a 1996 stipulates that it is temporarily allowed to use edible spices. It is mainly used to prepare flavors such as grapes, citrus, luogan berries, strawberries and watermelons. It is also a necessary raw material for the preparation of artificial orange oil.

can be used to prepare jasmine, orange blossom, gardenia, narcissus, tuberose, white orchid, ylang ylang and other types of flavors. It is often shared with orange leaf oil in oriental fragrance, heavy floral fragrance, and sweet wood fragrance. In edible flavor, it is not only suitable for grape type, but also for berry, strawberry, watermelon, honey, citrus and other types. It is also available in wine flavors.

Production method

dissolve anthranilic acid in methanol with 5 times the volume, pass hydrogen chloride, saturate and place for 1h, then heat and reflux for 1h, evaporate excess methanol, add sodium hydroxide solution, and make it precipitate by steam distillation or vacuum distillation.

With the participation of sulfuric acid, the o-nitrobenzoic acid and methanol are esterified into methyl o-nitrobenzoate, and then reduced with stannous chloride in ethanol solution, neutralized with alkali, and then distilled by steam.

It is obtained by esterification of sodium o-benzamide formate, sodium hypochlorite, methanol, etc.

Production method

in nature, methyl anthranilate exists in tartar oil, neroli oil, ylang ylang, jasmine oil, tuberose oil, etc. Industrial manufacturing is generally obtained by esterification of anthranilic acid and methanol. The methanol solution of anthranilic acid was heated to 65 ℃, sulfuric acid was added dropwise, and the sulfate of methyl anthranilic acid was formed at 75 ℃. Then neutralize and precipitate methyl anthranilate with sodium hydroxide solution. After extracting with toluene, washing the toluene extract and evaporating toluene, the crude methyl anthranilate was subjected to vacuum distillation in the presence of sodium carbonate, and the finished fraction was cooled to below 12-15 ℃, I .e. methyl anthranilate was precipitated. Another preparation method is to obtain this product by ammonification, degradation and esterification of phthalic anhydride.

Production method

phthalic anhydride is added into ammonia water at 0 ℃, and the solution is completed within 1~2min. when the temperature rises to 48~50 ℃, sodium hydroxide solution at 5 ℃ is added, the temperature is controlled below 70 ℃, and the reaction solution remains alkaline. Ammonia was discharged at 60~65 ℃ for 10h to obtain sodium orthoformyl carbamobenzoate solution. Cool it to -12 ℃, add methanol at -10 ℃, add sodium hypochlorite solution at -10 ℃ under stirring, and maintain the reaction below 0 ℃ for 1h. Then the temperature is raised to about 20°C and tested with potassium iodide starch solution until it is colorless. Heat to 45 ℃ to dissolve it, transfer to the sedimentation tank and stand for 8h, separate out the mother liquor, take the oil layer and filter it, then stand for stratification to obtain methyl anthranilate with a yield of more than 90%.

Heat the methanol solution of anthranilic acid to 65°C, add sulfuric acid dropwise, and react at 75°C to produce sulfate of methyl anthranilic acid. After neutralization with sodium hydroxide, methyl anthranilate is precipitated, extracted with toluene, washed the toluene extract, and evaporated to remove toluene, and finally distilled under reduced pressure in the presence of sodium carbonate to obtain the finished product.

Last Update：2024-04-09 21:01:54

Methyl 2-aminobenzoate - Nature

melting point	24°C (lit.)
boiling point	256°C (lit.)
density	1.168 g/mL at 25°C (lit.)
Vapor pressure	1mm Hg ( 20 °C)
refractive index	n20/D 1.582(lit.)
FEMA	2682 \| METHYL ANTHRANILATE
flash point	220 °F
storage conditions	Keep in dark place,Inert atmosphere,Room temperature
solubility	alcohol: freely soluble(lit.)
acidity coefficient (pKa)	pK1:2.23(+1) (25°C)
morphology	Liquid
color	Clear yellow-brown
Odor	grape odor
PH value	7.5-8 (H2O, 20℃)Aqueous solution
explosion limit value (explosive limit)	1.4-7.8%(V)
water solubility	slightly soluble
sensitivity	Air Sensitive
JECFA Number	1534
Merck	14,6020
BRN	606965
stability	Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey	VAMXMNNIEUEQDV-UHFFFAOYSA-N
NIST chemical information	Benzoic acid, 2-amino-, methyl ester(134-20-3)
EPA chemical information	Methyl anthranilate (134-20-3)

Last Update：2024-04-09 19:04:55

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Methyl 2-aminobenzoate

Methyl anthranilate

CAS: 134-20-3

Molecular Formula: C8H9NO2

Methyl 2-aminobenzoate - Names and Identifiers

Methyl 2-aminobenzoate - Physico-chemical Properties

Methyl 2-aminobenzoate - Risk and Safety

Methyl 2-aminobenzoate - Upstream Downstream Industry

Methyl 2-aminobenzoate - Nature

Open Data Verified Data

Methyl 2-aminobenzoate - Preparation Method

Open Data Verified Data

Methyl 2-aminobenzoate - Use

Open Data Verified Data

Methyl 2-aminobenzoate - Security information

Methyl 2-aminobenzoate - Uses and synthesis methods

background

application

Use

Preparation

content analysis

Toxicity

use limit

Methyl 2-aminobenzoate - Uses and synthesis methods

Use

Production method

Production method

Production method

Methyl 2-aminobenzoate - Nature

Supplier List

Methyl 2-aminobenzoate Request for Quotation

Methyl anthranilate

CAS: 134-20-3

Molecular Formula: C8H9NO2

Methyl 2-aminobenzoate - Names and Identifiers

Methyl 2-aminobenzoate - Physico-chemical Properties

Methyl 2-aminobenzoate - Risk and Safety

Methyl 2-aminobenzoate - Upstream Downstream Industry

Methyl 2-aminobenzoate - Nature

Open Data Verified Data

Methyl 2-aminobenzoate - Preparation Method

Open Data Verified Data

Methyl 2-aminobenzoate - Use

Open Data Verified Data

Methyl 2-aminobenzoate - Security information

Methyl 2-aminobenzoate - Uses and synthesis methods

background

application

Use

Preparation

content analysis

Toxicity

use limit

Methyl 2-aminobenzoate - Uses and synthesis methods

Use

Production method

Production method

Production method

Methyl 2-aminobenzoate - Nature

Supplier List

Methyl 2-aminobenzoate