Product Name

  • Name

    BUTYL ANTHRANILATE

  • EINECS 231-816-7
  • CAS No. 7756-96-9
  • Article Data18
  • CAS DataBase
  • Density 1.078 g/cm3
  • 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;
  • PSA 52.32000
  • LogP 2.80690

Synthetic route

2-(sulfinylamino)benzoyl chloride
64001-48-5

2-(sulfinylamino)benzoyl chloride

butan-1-ol
71-36-3

butan-1-ol

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

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

isatoic anhydride

butan-1-ol
71-36-3

butan-1-ol

n-butyl anthranilate
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%
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

butan-1-ol
71-36-3

butan-1-ol

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

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

2-Nitrobenzyl alcohol

butan-1-ol
71-36-3

butan-1-ol

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

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

anthranilic acid

butan-1-ol
71-36-3

butan-1-ol

n-butyl anthranilate
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℃;
2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

butan-1-ol
71-36-3

butan-1-ol

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

Conditions
ConditionsYield
With hydrogenchloride
mesityl(3-(pentafluoro-λ6-sulfanyl)phenyl)iodonium trifluoromethanesulfonate

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

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

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

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%
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

3-isopropyl-2-(isopropylamino)quinazolin-4(3H)-one
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%
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

n-butyl 2-azidobenzoate
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℃;
ortho-bromophenylacetic acid
18698-97-0

ortho-bromophenylacetic acid

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

n-butyl 2-(2-(2-bromophenyl)acetamido)benzoate
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%
dibutyl chlorophosphite
4124-92-9

dibutyl chlorophosphite

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

dibutyl phosphoramidite
82754-10-7

dibutyl phosphoramidite

Conditions
ConditionsYield
With triethylamine In benzene for 2h; Ambient temperature;71%
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

(2-fluorophenyl)acetic acid
451-82-1

(2-fluorophenyl)acetic acid

n-butyl 2-(2-(2-fluorophenyl)acetamido)benzoate
1345540-34-2

n-butyl 2-(2-(2-fluorophenyl)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;62%
2'-chloro-benzeneacetic acid
2444-36-2

2'-chloro-benzeneacetic acid

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

n-butyl 2-(2-(2-chlorophenyl)acetamido)benzoate
1345540-36-4

n-butyl 2-(2-(2-chlorophenyl)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;61%
diethyl-phosphoramidous acid dibutyl ester
41075-90-5

diethyl-phosphoramidous acid dibutyl ester

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

dibutyl phosphoramidite
82754-10-7

dibutyl phosphoramidite

Conditions
ConditionsYield
at 115℃;60.2%
embelin
550-24-3

embelin

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

2-(4-Hydroxy-3,6-dioxo-5-undecyl-cyclohexa-1,4-dienylamino)-benzoic acid butyl ester
101689-27-4

2-(4-Hydroxy-3,6-dioxo-5-undecyl-cyclohexa-1,4-dienylamino)-benzoic acid butyl ester

Conditions
ConditionsYield
With acetic acid at 100℃;58%
diisopropyl phosphorochloridite
41662-51-5

diisopropyl phosphorochloridite

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

2-(Diisopropoxy-phosphanylamino)-benzoic acid butyl ester
82754-08-3

2-(Diisopropoxy-phosphanylamino)-benzoic acid butyl ester

Conditions
ConditionsYield
With triethylamine In benzene for 2h; Ambient temperature;48.3%
formaldehyd
50-00-0

formaldehyd

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

butyl 2-(methylamino)benzoate
15236-34-7

butyl 2-(methylamino)benzoate

Conditions
ConditionsYield
With acetic acid; zinc In 1,4-dioxane; water at 50 - 60℃; for 6h;23%
2,5-dimethoxy-3-undecyl-1,4-benzoquinone
14065-83-9

2,5-dimethoxy-3-undecyl-1,4-benzoquinone

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

A

2-(4-Methoxy-3,6-dioxo-5-undecyl-cyclohexa-1,4-dienylamino)-benzoic acid butyl ester
101689-48-9

2-(4-Methoxy-3,6-dioxo-5-undecyl-cyclohexa-1,4-dienylamino)-benzoic acid butyl ester

B

C39H52N2O6
101689-39-8

C39H52N2O6

Conditions
ConditionsYield
With acetic acidA 14%
B 20%
...Expand
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-chloroacetyl-anthranilic acid butyl ester
100614-29-7

N-chloroacetyl-anthranilic acid butyl ester

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

2-(3,4-Dimethoxy-benzoylamino)-benzoic acid butyl ester
67836-65-1

2-(3,4-Dimethoxy-benzoylamino)-benzoic acid butyl ester

Conditions
ConditionsYield
With triethylamine In benzene for 3h; Ambient temperature;
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

2-Butoxycarbonyl-benzenediazonium; chloride

2-Butoxycarbonyl-benzenediazonium; chloride

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 5℃;
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

dimedone
126-81-8

dimedone

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

2-(2-butyloxycarbonylphenyl)aminomethylidene-5,5-dimethylcyclohexane-1,3-dione

2-(2-butyloxycarbonylphenyl)aminomethylidene-5,5-dimethylcyclohexane-1,3-dione

Conditions
ConditionsYield
at 125 - 130℃; for 0.166667h;
...Expand
formic acid
64-18-6

formic acid

n-butyl anthranilate
7756-96-9

n-butyl anthranilate

2-formylamino-benzoic acid butyl ester
360795-64-8

2-formylamino-benzoic acid butyl ester

Conditions
ConditionsYield
In toluene Heating;
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

2-isocyano-benzoic acid butyl ester
360795-69-3

2-isocyano-benzoic acid butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene / Heating
2: POCl3; Et3N / tetrahydrofuran / 0 °C
View Scheme
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

n-butyl 4-hydroxy-3-quinolinecarboxylate

n-butyl 4-hydroxy-3-quinolinecarboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: toluene / Heating
2: POCl3; Et3N / tetrahydrofuran / 0 °C
3: magnesium bis(diisopropylamide) / diethyl ether / 0 °C
4: magnesium bis(diisopropylamide) / diethyl ether / 2 h
View Scheme
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

3-(2-isocyano-phenyl)-3-oxo-propionic acid butyl ester

3-(2-isocyano-phenyl)-3-oxo-propionic acid butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene / Heating
2: POCl3; Et3N / tetrahydrofuran / 0 °C
3: magnesium bis(diisopropylamide) / diethyl ether / 0 °C
View Scheme
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

C17H19N3O2
180335-19-7

C17H19N3O2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaNO2, HCl / H2O / 5 °C
2: NH4OAc / H2O
View Scheme
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

C17H28NO4PSe
82754-13-0

C17H28NO4PSe

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 48.3 percent / triethylamine / benzene / 2 h / Ambient temperature
2: 46.8 percent / selenium
View Scheme
n-butyl anthranilate
7756-96-9

n-butyl anthranilate

O,O-dibutyl phosphoramidothioate
82754-15-2

O,O-dibutyl phosphoramidothioate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / triethylamine / benzene / 2 h / Ambient temperature
2: 84.6 percent / sulfur / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: 60.2 percent / 115 °C
2: 84.6 percent / sulfur / 60 °C
View Scheme

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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