18437-66-6

Basic information

• Product Name: 4-CHLORO-(N-BOC)ANILINE 97
• Synonyms: 4-CHLORO-(N-BOC)ANILINE 97;N-tert-Butoxycarbonyl-4-chloroaniline;(4-Chlorophenyl)carbamic acid tert-butyl ester;1-(tert-Butoxycarbonylamino)-4-chlorobenzene;4-Chlorophenylcarbamic acid tert-butyl ester;N-(4-Chlorophenyl)carbamic acid tert-butyl ester;N-(tert-Butyloxycarbonyl)-4-chloroaniline;N-BOC-4-Chloroaniline, 98%
• CAS NO: 18437-66-6
• Molecular Formula: C₁₁H₁₄ClNO₂
• Molecular Weight: 227.69
• Product Categories: Protected Amines;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 18437-66-6.mol
• Article Data: 78

Chemical Properties

• Melting Point: 102-106 °C(lit.)
• Boiling Point: 265.2°C at 760 mmHg
• Flash Point: 114.2°C
• Appearance: White/Crystalline Powder
• Density: 1.195g/cm³
• Vapor Pressure: 0.00929mmHg at 25°C
• Refractive Index: 1.554
• PKA: 12.99±0.70(Predicted)
• CAS DataBase Reference: 4-CHLORO-(N-BOC)ANILINE 97(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-(N-BOC)ANILINE 97(18437-66-6)
• EPA Substance Registry System: 4-CHLORO-(N-BOC)ANILINE 97(18437-66-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 18437-66-6(Hazardous Substances Data)

Usage

Description

4-Chloro-(N-Boc)aniline, also known as 4-chloro-N-(tert-butoxycarbonyl)aniline, is an organic compound that serves as an important intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is characterized by the presence of a chloro group attached to an aniline moiety, which is protected by a bulky tert-butoxycarbonyl (Boc) group. This protection allows for selective reactions to occur at the chloro group without affecting the aniline functionality.

Uses

Used in Pharmaceutical Synthesis:
4-Chloro-(N-Boc)aniline is used as a key intermediate in the synthesis of various pharmaceutical compounds, specifically for the preparation of drug candidates with potential therapeutic applications.
Used in the Synthesis of MLN8054:
In the pharmaceutical industry, 4-Chloro-(N-Boc)aniline is used as a starting material for the synthesis of 4-[[9–chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]-amino] benzoic acid (MLN8054), a drug candidate with potential applications in the treatment of various diseases.
Used in the Synthesis of 5-(4-aminophenyl)-3H-1,2-dithiol-3-thione (E):
4-Chloro-(N-Boc)aniline is also utilized in the synthesis of 5-(4-aminophenyl)-3H-1,2-dithiol-3-thione (E), a compound with potential applications in the development of new drugs and therapeutic agents.
Used in the Synthesis of (4(prop-1-en-1-yl)phenyl)carbamate:
Furthermore, 4-Chloro-(N-Boc)aniline is employed in the synthesis of (4(prop-1-en-1-yl)phenyl)carbamate, a compound that may have potential applications in the development of agrochemicals or pharmaceuticals.

InChI:InChI=1/C11H14ClNO2/c1-11(2,3)15-10(14)13-9-6-4-8(12)5-7-9/h4-7H,1-3H3,(H,13,14)

Upstream product

• 2617-79-0 N-(4-chlorophenyl)formamide 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 106-47-8 4-chloro-aniline 
• 106-39-8 bromochlorobenzene 
• 4248-19-5 tert-butyl carbazate 
• 380430-49-9 [4-(tert-butoxycarbonylamino)phenyl]boronic acid 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 100-00-5 4-chlorobenzonitrile 
• 24608-52-4 tert-butyl chloroformate 
• 110-05-4 di-tert-butyl peroxide 
• 1885-81-0 p-chlorophenyl isocyanide 
• 108-90-7 chlorobenzene 
• 3422-01-3 tert-butyl phenylcarbamate 

Downstream Products

• 612-57-7 6-chloroquinoline 
• 105688-75-3 3-phenyl-6-chloroquinoline 
• 106-47-8 4-chloro-aniline 
• 564483-40-5 (4-morpholin-4-ylphenyl)carbamic acid tert-butyl ester 
• 561304-62-9 tert-butyl N-[4-chloro-2-[α-hydroxy-α-(2-trifluoromethoxyphenyl)methyl]phenyl]carbamate 
• 201218-07-7 tert-butyl-4-chloro-2-(2,2,2-trifluoroacetyl)phenyl carbamate 
• 1020416-34-5 C₂₄H₂₅N₃O₃ 
• 1161439-61-7 C₂₇H₃₂N₂O₆ 
• 1259391-55-3 C₂₀H₂₂ClNO₃ 
• 1186637-27-3 N-(tert-butoxycarbonyl)-4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 1450821-91-6 tert-butyl 4-chlorophenyl(4,6-dichloropyrimidin-2-yl)carbamate 
• 1802013-08-6 C₁₈H₁₈ClNOS 
• 1802013-08-6 C₁₈H₁₈ClNOS 
• 2866-82-2 N-(4-chlorophenyl)benzamide 

Relevant articles and documents

Lewis acid-mediated cyclizations of (2'-amino-N'-tert-butoxycarbonyl- benzylidene)-3-alkenylamines

Depending on the method of activation, (2'-amino-N'-tert- butoxycarbonyl-benzylidene)-3-alkenylamines (1) react with Lewis acids (TiCl4 or TMSOTf) to afford either a novel Boc-assisted iminium ion formation/trapping sequence (giving hexahydropy

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Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate

The sulfated polyborate catalyzed an efficient and chemoselective N-tert-butyloxycarbonylation of amines under ultrasonic irradiation is developed. A broad substrate scope has been demonstrated for N-Boc protection of various primary/secondary amines. It allows converting several aliphatic/aryl/heteroaryl amines, amino alcohol, aminoester, and chiral amines to their N-Boc-protected derivatives under solvent-free conditions with excellent yields. The protocol has several advantages such as easy catalyst, and product isolation, short reaction time, excellent yields, outstanding chemoselectivity, and catalyst recyclability, among others. This makes the process practicable, economical, and environmentally benign.

Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines

Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.