32961-44-7

Basic information

• Product Name: Isobutyl 3,5-diamino-4-chloro benzoate
• Synonyms: TIMTEC-BB SBB003200;3,5-diamino-4-chloro-benzoicaci2-methylpropylester;ISOBUTYL 3,5-DIAMINO-4-CHLOROBENZOATE;ISOBUTYL 4-CHLORO-3,5-DIAMINOBENZOATE;3,5-DIAMINO-4-CHLORO-BENZOIC ACID ISOBUTYL ESTER;4-chloro-3,5-diaminobenzoic acid isobutyl ester;ISOBUTYL 3,5-DIAMINO-4-CHLOROBENZOATER;Benzoic acid, 3,5-diamino-4-chloro-, 2-methylpropyl ester
• CAS NO: 32961-44-7
• Molecular Formula: C₁₁H₁₅ClN₂O₂
• Molecular Weight: 242.7
• EINECS: 251-311-5
• Product Categories: C10 to C11;Carbonyl Compounds;Esters
• Mol File: 32961-44-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 86-90 °C(lit.)
• Boiling Point: 390.1 °C at 760 mmHg
• Flash Point: 189.7 °C
• Appearance: /
• Density: 1.252 g/cm³
• Vapor Pressure: 1.65E-06mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.75±0.10(Predicted)
• CAS DataBase Reference: Isobutyl 3,5-diamino-4-chloro benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutyl 3,5-diamino-4-chloro benzoate(32961-44-7)
• EPA Substance Registry System: Isobutyl 3,5-diamino-4-chloro benzoate(32961-44-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 32961-44-7(Hazardous Substances Data)

Usage

Uses

Isobutyl 3,5-diamino-4-chloro benzoate

InChI:InChI=1/C11H15ClN2O2/c1-2-3-4-16-11(15)7-5-8(13)10(12)9(14)6-7/h5-6H,2-4,13-14H2,1H3

Synthetic route

isobutyl 3,5-dinitro-4-chlorobenzoate (58263-53-9) → 3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7)

Conditions	Yield
With morpholine; hydrogen In ethanol at 90 - 100℃; under 1500.15 - 22502.3 Torr; for 1.5h; Solvent; Temperature; Autoclave; Green chemistry;	92%

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 3,5-diamino-4-chlorobenzoic acid

Conditions	Yield
With water; sodium hydroxide In ethanol for 1h;	91%

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 3,5-diamino-4-chloro-2-(2-hydroxyphenyl)diazenylbenzoic acid (1426244-74-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 3,5-diamino-4-chloro-2-(2-hydroxy-5-nitrophenylazo)benzoic acid (1426244-75-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 3,5-diamino-4-chloro-2-(2-hydroxy-4-nitrophenylazo)benzoic acid (1426244-76-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 3,5-diamino-4-chloro-2-(2-hydroxy-5-chlorophenylazo)benzoic acid (1426244-78-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 3,5-diamino-4-chloro-2-(2-methoxyphenylazo)benzoic acid (1426244-80-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-7-chloro-2-(2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid (1426244-82-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 10 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-7-chloro-2-(2-hydroxy-5-nitrophenyl)-2H-benzotriazole-4-carboxylic acid (1426244-83-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 20 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-7-chloro-2-(2-hydroxy-4-nitrophenyl)-2H-benzotriazole-4-carboxylic acid (1426244-84-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 30 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-7-chloro-2-(5-chloro-2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid (1426244-86-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 3 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-7-chloro-2-(2-methoxyphenyl)-2H-benzotriazole-4-carboxylic acid (1426244-87-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 5 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-2-(5-amino-2-hydroxyphenyl)-7-chloro-2H-benzotriazole-4-carboxylic acid (1426244-89-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 20 h / Reflux 4.1: sodium dithionite; sodium hydroxide / water / 4.5 h / 20 °C View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-2-(5-amino-2-hydroxyphenyl)-7-chloro-2H-benzotriazole-4-carboxylic acid (1426244-89-4) + 6-amino-2-(5-amino-2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 20 h / Reflux 4.1: sodium dithionite; sodium hydroxide / water / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-2-(4-amino-2-hydroxyphenyl)-7-chloro-2H-benzotriazole-4-carboxylic acid (1426244-90-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 30 h / Reflux 4.1: sodium dithionite; sodium hydroxide / water / 4.5 h / 20 °C View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-2-(4-amino-2-hydroxyphenyl)-7-chloro-2H-benzotriazole-4-carboxylic acid (1426244-90-7) + C13H11N5O3

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 30 h / Reflux 4.1: sodium dithionite; sodium hydroxide / water / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-2-(2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid (1426244-92-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 10 h / Reflux 4.1: sodium dithionite; sodium hydroxide / water / 4.5 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-2-(5-chloro-2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid (1426244-93-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 3 h / Reflux 4.1: sodium dithionite; sodium hydroxide / water / 4.5 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-acetylamino-7-chloro-2-(2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid (1426244-95-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 10 h / Reflux 4.1: acetic acid / 7.5 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-acetylamino-7-chloro-2-(2-hydroxy-5-nitrophenyl)-2H-benzotriazole-4-carboxylic acid (1426244-96-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 20 h / Reflux 4.1: acetic acid / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-acetylamino-7-chloro-2-(2-hydroxy-4-nitrophenyl)-2H-benzotriazole-4-carboxylic acid (1426244-98-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 30 h / Reflux 4.1: acetic acid / 7.5 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-acetylamino-7-chloro-2-(5-chloro-2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid (1426245-00-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 3 h / Reflux 4.1: acetic acid / 7.5 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 2-(2-acetoxyphenyl)-6-acetylamino-7-chloro-2H-benzotriazole-4-carboxylic acid (1426245-01-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 10 h / Reflux 4.1: acetic acid / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 2-(2-acetoxy-4-nitrophenyl)-6-acetylamino-7-chloro-2H-benzotriazole-4-carboxylic acid (1426245-02-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 30 h / Reflux 4.1: acetic acid / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 2-(2-acetoxy-5-chlorophenyl)-6-acetylamino-7-chloro-2H-benzotriazole-4-carboxylic acid (1426245-03-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 3 h / Reflux 4.1: acetic acid / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-acetylamino-2-(5-amino-2-hydroxyphenyl)-7-chloro-2H-benzotriazole-4-carboxylic acid (1426245-04-6)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 20 h / Reflux 4.1: acetic acid / Reflux 5.1: sodium dithionite; sodium hydroxide / water / 20 °C View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-acetylamino-7-chloro-2-(2-methoxyphenyl)-2H-benzotriazole-4-carboxylic acid (1426245-05-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 5 h / Reflux 4.1: acetic acid / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-7-chloro-2-(2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid methyl ester (1426245-06-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 10 h / Reflux 4.1: sulfuric acid / 1,4-dioxane / 8 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-7-chloro-2-(2-hydroxy-5-nitrophenyl)-2H-benzotriazole-4-carboxylic acid methyl ester (1426245-07-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 20 h / Reflux 4.1: sulfuric acid / 1,4-dioxane / 8 h / Reflux View Scheme

3,5-diamino-4-chlorobenzoic acid isobutyl ester (32961-44-7) → 6-amino-7-chloro-2-(2-hydroxy-4-nitrophenyl)-2H-benzotriazole-4-carboxylic acid methyl ester (1426245-08-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 1 h 2.1: hydrogenchloride; sodium nitrite / water / 1.25 h / 10 °C 2.2: 3.5 h / pH 6 3.1: copper(ll) sulfate pentahydrate; ammonia / water; isopropyl alcohol / 30 h / Reflux 4.1: sulfuric acid / 1,4-dioxane / 8 h / Reflux View Scheme

Upstream product

• 58263-53-9 isobutyl 3,5-dinitro-4-chlorobenzoate 

Downstream Products

• 1426245-11-5 6-amino-2-(2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid methyl ester 
• 1426245-10-4 6-amino-2-(5-amino-2-hydroxyphenyl)-7-chloro-2H-benzotriazole-4-carboxylic acid methyl ester 
• 1426245-09-1 6-amino-7-chloro-2-(5-chloro-2-hydroxy)-2H-benzotriazole-4-carboxylic acid methyl ester 
• 1426245-08-0 6-amino-7-chloro-2-(2-hydroxy-4-nitrophenyl)-2H-benzotriazole-4-carboxylic acid methyl ester 
• 1426245-07-9 6-amino-7-chloro-2-(2-hydroxy-5-nitrophenyl)-2H-benzotriazole-4-carboxylic acid methyl ester 
• 1426245-06-8 6-amino-7-chloro-2-(2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid methyl ester 
• 1426245-05-7 6-acetylamino-7-chloro-2-(2-methoxyphenyl)-2H-benzotriazole-4-carboxylic acid 
• 1426245-04-6 6-acetylamino-2-(5-amino-2-hydroxyphenyl)-7-chloro-2H-benzotriazole-4-carboxylic acid 
• 1426245-03-5 2-(2-acetoxy-5-chlorophenyl)-6-acetylamino-7-chloro-2H-benzotriazole-4-carboxylic acid 
• 1426245-02-4 2-(2-acetoxy-4-nitrophenyl)-6-acetylamino-7-chloro-2H-benzotriazole-4-carboxylic acid 
• 1426245-01-3 2-(2-acetoxyphenyl)-6-acetylamino-7-chloro-2H-benzotriazole-4-carboxylic acid 
• 1426245-00-2 6-acetylamino-7-chloro-2-(5-chloro-2-hydroxyphenyl)-2H-benzotriazole-4-carboxylic acid 
• 1426244-98-5 6-acetylamino-7-chloro-2-(2-hydroxy-4-nitrophenyl)-2H-benzotriazole-4-carboxylic acid 
• 1426244-96-3 6-acetylamino-7-chloro-2-(2-hydroxy-5-nitrophenyl)-2H-benzotriazole-4-carboxylic acid 

Relevant articles and documents

Preparation method of isobutyl 3,5-diamino-4-chlorobenzoate

A preparation method of isobutyl 3,5-diamino-4-chlorobenzoate comprises the following basic steps: step 1, putting raw material ester compound, a solvent, a catalyst Raney nickel and a dehalogenation inhibitor into a high pressure reaction kettle at one time, sealing, and adopting 0.2-0.3 MPa of nitrogen gas and hydrogen gas for replacing gas in the high pressure reaction kettle for 3 times respectively; step 2, after completely sealing in the step 1, adding the hydrogen gas pressure to 3.0 MPa, increasing the temperature of the high pressure reaction kettle, carrying out a reaction, and timely replenishing the hydrogen gas pressure to ensure that the pressure in the high pressure reaction kettle in the reaction process is maintained at 3.0 MPa; step 3, adding hydrogen gas to maintain the pressure at 3.0 MPa in the step 2, carrying out a reaction for about 1.5-2 hours, finishing the reaction after the system absorbs hydrogen gas no longer, and overall cooling; step 4, after the step 3 is finished, recycling the catalyst Raney nickel; step 5, carrying out reduced pressure concentration of a filtrate to be viscous, putting into a refrigerator, and cooling and crystallizing at low temperature; and step 6, desolventizing the solvent alcohol and the dehalogenation inhibitor, recycling and reusing. The method is low in cost, safe and feasible.