198572-71-3

Basic information

• Product Name: N-(TERT-BUTOXYCARBONYL)-2-NITROBENZENESULFONAMIDE
• Synonyms: N-Boc-2-nitrophenylsulfonamide;tert-butyl N-[(2-nitrobenzene)sulfonyl]carbaMate;N-Boc o-nitro phenylsulfonaMide;tert-Butyl (2-nitrophenyl)sulfonylcarbamate;N-(tert-Butoxycarbonyl)-2-nitrobenzenesulfonamide;N-BOC-O-NITROBENZENESULFONAMIDE;N-BOC-2-NITROBENZENESULFONAMIDE;N-(TERT-BUTOXYCARBONYL)-2-NITROBENZENESULFONAMIDE
• CAS NO: 198572-71-3
• Molecular Formula: C₁₁H₁₄N₂O₆S
• Molecular Weight: 302.3
• Product Categories: Amination;Synthetic Organic Chemistry
• Mol File: 198572-71-3.mol

Chemical Properties

• Melting Point: approximate 147℃(dec.)
• Appearance: /
• Density: 1.365g/cm³
• Refractive Index: 1.547
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.32±0.10(Predicted)
• CAS DataBase Reference: N-(TERT-BUTOXYCARBONYL)-2-NITROBENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(TERT-BUTOXYCARBONYL)-2-NITROBENZENESULFONAMIDE(198572-71-3)
• EPA Substance Registry System: N-(TERT-BUTOXYCARBONYL)-2-NITROBENZENESULFONAMIDE(198572-71-3)

Safety Data

• Hazardous Substances Data: 198572-71-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide is used as a reagent for the protection of amine groups in organic synthesis. Its Boc protecting group allows chemists to temporarily block the reactivity of amine groups, facilitating the selective modification of other functional groups within a molecule.
Used in Peptide Chemistry:
In the field of peptide chemistry, N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide is employed as a protecting agent for amine groups during the synthesis of peptides. The Boc group can be selectively removed under mild acidic conditions, enabling the controlled stepwise assembly of peptide chains.
Used in the Modification and Functionalization of Organic Molecules:
The nitrobenzenesulfonamide group in n-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide can participate in various chemical reactions, making N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide useful for the modification and functionalization of organic molecules. This allows for the introduction of new functional groups or the alteration of existing ones, expanding the compound's applicability in diverse chemical processes.
Used in Pharmaceutical and Biochemical Research:
Due to its ability to protect and later deprotect amine groups, N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide is utilized in the development of new pharmaceuticals and biochemicals. It aids in the synthesis of complex molecules with specific biological activities, contributing to the advancement of drug discovery and design.
Used in the Synthesis of Complex Organic Compounds:
N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide is a key component in the synthesis of complex organic compounds, where its dual functionality allows for the controlled assembly and modification of molecules. This makes it an important tool in the creation of advanced materials, specialty chemicals, and other high-value organic products.

InChI:InChI=1/C11H14N2O6S/c1-11(2,3)19-10(14)12-20(17,18)9-7-5-4-6-8(9)13(15)16/h4-7H,1-3H3,(H,12,14)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 5455-59-4 2-Nitrobenzenesulfonamide 
• 4248-19-5 tert-butyl carbazate 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 

Downstream Products

• 334996-58-6 4-[N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamido]cyclopentene 
• 245364-48-1 C₁₈H₂₈N₂O₆S 
• 245364-50-5 (R)-N-Boc-N-o-nitrobenzenesulfonylalanine ethyl ester 
• 31612-63-2 (R)-3,3-dimethylbutane-1,2-diol 
• 84994-66-1 (R)-hexane-1,2-diol 
• 765908-10-9 C₁₇H₂₆N₂O₇S 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 10303-88-5 methyl L-glycerate 
• 1026546-72-4 C₁₅H₂₀N₂O₉S 

Relevant articles and documents

Direct Synthesis of Allyl Amines with 2-Nitrosulfonamide Derivatives via the Tsuji-Trost Reaction

The Tsuji-Trost Reaction is a palladium-catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen-based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2-nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2-nitrosulfonyl groups are well-known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2-nitrosulfonamide derivatives are ideal substrates for the Tsuji-Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives.

A Synthetic Bioinspired Carbohydrate Polymer with Mucoadhesive Properties

Mucoadhesive polymers are of significant interest to the pharmaceutical, medical device, and cosmetic industries. Polysaccharides possessing charged functional groups, such as chitosan, are known for mucoadhesive properties but suffer from poor chemical d

Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex

A benchtop-stable reagent for the catalytic Nicholas reaction was developed. By combining a propargyl dicobalt hexacarbonyl cluster with an ortho-alkynylbenzoate unit and a fluorous tag, introduction of a propargyl hexacarbonyl complex on various aromatic compounds having acid- or base-sensitive functional groups becomes possible by using a gold(i) catalyst. In addition, the presence of a fluorous tag facilitates convenient separation of the target products from byproducts.

Enantioselective IrI-catalyzed carbocyclization of 1,6-enynes by the chiral counterion strategy

Enantioenriched bicyclo[4.1.0]hept-2-enes were synthesized by Ir I-catalyzed carbocyclization of 1,6-enynes. No chiral ligands were used, CO and PPh3 were the only ligands bound to iridium. Instead, the stereochemical information was

HEAVY-NITROGENIZED NITROBENZENESULFONAMIDE, ITS DERIVATIVE AND PRODUCTION METHOD THEREOF

PROBLEM TO BE SOLVED: To provide a heavy-nitrogenized nitrobenzenesulfonamide derivative and an efficient production method thereof. SOLUTION: The heavy-nitrogenized nitrobenzenesulfonamide compound is represented by general formula [2]. An amino group of

Ruthenium catalyzed ring rearrangement: A rapid entry to substituted aza- and oxacycles

A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloh

New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

A new route for the asymmetric synthesis of 4-aminocyclopent-2-en-1-ols (90% ee) for carbocyclic nucleoside analogue synthesis is described. The approach involves the stereoselective preparation of cis 4-amino-substituted cyclopentene oxides and subsequent chiral base-mediated rearrangement to the corresponding allylic alcohols. Full details on the synthesis and stereoselectivity of epoxidation of 4-amino-substituted cyclopentenes are presented. (C) 2000 Elsevier Science Ltd.

N-carboalkoxy-2-nitrobenzenesulfonamides: A practical preparation of N- Boc-, N-Alloc-, and N-Cbz-protected primary amines

N-Carboalkoxy-2-nitrobenzenesulfonamides, readily prepared by acylation of 2-nitrobenzenesulfonamide (o-NsNH2), can be alkylated by either conventional or Mitsunobu protocols. Since the o-nosyl group can be deprotected under mild conditions, a variety of N-carboalkoxy derivatives of primary amines may be prepared in excellent yields from the corresponding alcohols and/or halides. In addition, allyloxycarbonyl (Alloc), t- butoxycarbonyl (t-Boc), and benzyloxycarbonyl (Cbz) groups can be deprotected in the presence of the o-nosyl group, allowing the resultant N-alkylated 2- nitrobenzenesulfonamides to be used for further preparation of secondary amines.

Heterocycles with a benzothiadiazepine moiety. 5. Derivatives of pyrrolo[2,1-d][1,2,5]benzothiadiazepine, a novel tricyclic ring

The synthesis of pyrrolo[2,1-d][1,2,5]benzothiadiazepin-7(6H)-one 5,5- dioxide has been achieved by reaction between 2-(1H-pyrrol-1- yl)benzenesulfonamide and triphosgene. N-Ethylation of the tricyclic derivative afforded 6-ethylpyrrolo[2,1-d][1,2,5]benzothiadiazepin-7(6H)-one 5,5-dioxide, also obtained by the action of trifosgene on N-ethyl 2-(1H- pyrrol-1-yl)benzenesulfonamide. Preparation of pyrrole derivatives from 2- aminobenzenesulfonamide and its N-ethyl derivative by Clauson-Kaas procedure required preliminary protection of the sulfonamide function.