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Benzoic acid, 2-amino-, butyl ester

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Name

Benzoic acid, 2-amino-, butyl ester

EINECS 231-816-7
CAS No. 7756-96-9 Density 1.078 g/cm3
PSA 52.32000 LogP 2.80690
Solubility Insoluble in water Melting Point <0 °C
Formula C11H15NO2 Boiling Point 297.1 °C at 760 mmHg
Molecular Weight 193.246 Flash Point 153.2 °C
Transport Information DG1527000 Appearance dark brown liquid
Safety 26 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 7756-96-9 (BUTYL ANTHRANILATE) Hazard Symbols HarmfulXn
Synonyms

Anthranilicacid, butyl ester (6CI,7CI,8CI);2-Aminobenzoic acid butyl ester;Butylanthranilate;Butyl o-aminobenzoate;NSC 406509;

Article Data 18

Benzoic acid, 2-amino-, butyl ester Synthetic route

64001-48-5

2-(sulfinylamino)benzoyl chloride

71-36-3

butan-1-ol

7756-96-9

n-butyl anthranilate

Conditions
ConditionsYield
for 1h;99.4%
118-48-9

isatoic anhydride

71-36-3

butan-1-ol

7756-96-9

n-butyl anthranilate

Conditions
ConditionsYield
With sodium hydroxide at 85℃;78%
With sodium hydride In mineral oil for 2h; Reflux; Inert atmosphere;56%
With sodium Heating;40.3%
552-89-6

2-nitro-benzaldehyde

71-36-3

butan-1-ol

7756-96-9

n-butyl anthranilate

Conditions
ConditionsYield
With dmap; ethyl 2-cyanoacetate at 20℃; for 5h; chemoselective reaction;70%
612-25-9

2-Nitrobenzyl alcohol

71-36-3

butan-1-ol

7756-96-9

n-butyl anthranilate

Conditions
ConditionsYield
With caesium carbonate at 100℃; for 16h; Inert atmosphere; Schlenk technique;48%
118-92-3

anthranilic acid

71-36-3

butan-1-ol

7756-96-9

n-butyl anthranilate

Conditions
ConditionsYield
With thionyl chloride for 2h; Heating;39%
With sulfuric acid Reflux;29.13%
With phosphate buffer; Porcine Pancreas Lipase In hexane; chloroform for 72h; pH=7.0;4.5%
Stage #1: anthranilic acid; butan-1-ol With sulfuric acid for 2h; Reflux;
Stage #2: With ammonium hydroxide In water
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
134-20-3

2-carbomethoxyaniline

71-36-3

butan-1-ol

7756-96-9

n-butyl anthranilate

Conditions
ConditionsYield
With hydrogenchloride

mesityl(3-(pentafluoro-λ6-sulfanyl)phenyl)iodonium trifluoromethanesulfonate

7756-96-9

n-butyl anthranilate

butyl 2-((3-(pentafluoro-λ6-sulfanyl)phenyl)amino)benzoate

Conditions
ConditionsYield
With copper In 1-methyl-pyrrolidin-2-one at 80℃; for 12h; Inert atmosphere;97%
7756-96-9

n-butyl anthranilate

693-13-0

diisopropyl-carbodiimide

14333-75-6

3-isopropyl-2-(isopropylamino)quinazolin-4(3H)-one

Conditions
ConditionsYield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 100℃; for 12h; Schlenk technique; Inert atmosphere;93%
7756-96-9

n-butyl anthranilate

1415326-10-1

n-butyl 2-azidobenzoate

Conditions
ConditionsYield
Stage #1: n-butyl anthranilate With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.666667h;
Stage #2: With sodium azide In water for 0.5h;
75%
Stage #1: n-butyl anthranilate With hydrogenchloride; sodium nitrite In water; acetone at 0℃;
Stage #2: With sodium azide; sodium acetate In water; acetone at 5℃;
18698-97-0

ortho-bromophenylacetic acid

7756-96-9

n-butyl anthranilate

1345540-38-6

n-butyl 2-(2-(2-bromophenyl)acetamido)benzoate

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;74%

Benzoic acid, 2-amino-, butyl ester Specification

The IUPAC name of Benzoic acid, 2-amino-, butyl ester is butyl 2-aminobenzoate. With the CAS registry number 7756-96-9, it is also named as Butyl anthranilate. The product's categories are A-B; Alphabetical Listings; Flavors and Fragrances. It is dark brown liquid which is insoluble in water. And it will hydrolyze under high and low pH conditions. In addition, this chemical is probably combustible, stable and sensitive to air and light. Furthermore, this chemical should be avoided direct sunshine.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.63; (4)ACD/LogD (pH 7.4): 3.63; (5)ACD/BCF (pH 5.5): 339.5; (6)ACD/BCF (pH 7.4): 339.51; (7)ACD/KOC (pH 5.5): 2255.19; (8)ACD/KOC (pH 7.4): 2255.22; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.539; (13)Molar Refractivity: 56.16 cm3; (14)Molar Volume: 179.1 cm3; (15)Polarizability: 22.26×10-24 cm3; (16)Surface Tension: 42.4 dyne/cm; (17)Enthalpy of Vaporization: 53.69 kJ/mol; (18)Vapour Pressure: 0.00138 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Tautomer Count: 4; (21)Exact Mass: 193.110279; (22)MonoIsotopic Mass: 193.110279; (23)Topological Polar Surface Area: 52.3; (24)Heavy Atom Count: 14; (25)Complexity: 182.

Preparation of Benzoic acid, 2-amino-, butyl ester: It can be obtained by 2-amino-benzoic acid and butan-1-ol. This reaction needs reagent porcine pancreas lipase and aq. phosphate buffer and solvent CHCl3 and hexane at PH of 7.0. The reaction time is 72 hours. The yield is 4.5%.

Uses of Benzoic acid, 2-amino-, butyl ester: Microscale Can be used in jasmine, orange blossom, grape, longan, etc. And it can react with phosphorochloridous acid dibutyl ester to get dibutyl [o-(butoxycarbonyl)phenyl]phosphoramidite. This reaction needs reagent triethylamine and solvent acetonitrile at ambient temperature. The reaction time is 2 hours. The yield is 71 %. 

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 

People can use the following data to convert to the molecule structure.
1. Smiles: c1(C(OCCCC)=O)c(cccc1)N
2. InChI: InChI=1/C11H15NO2/c1-2-3-8-14-11(13)9-6-4-5-7-10(9)12/h4-7H,2-3,8,12H2,1H3

The following are the toxicity data which has been tested. 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 13, Pg. 727, 1975.
rat LD50 oral > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 13, Pg. 727, 1975.

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