102520-97-8

Basic information

• Product Name: N-BOC-2-AMINO-2-METHYL-1-PROPANOL 97
• Synonyms: N-BOC-2-AMINO-2-METHYL-1-PROPANOL 97;1,1-Dimethylethyl (2-hydroxy-1,1-dimethylethyl)carbamate, 2-Hydroxy-1,1-dimethylethyl)carbamic acid 1,1-dimethylethyl ester, (2-Hydroxy-1,1-dimethylethyl)carbamic acid tert-butyl ester;tert-Butyl (1-hydroxy-2-Methylpropan-2-yl)carbaMate;N-Boc-2-aMino-2-Methylpropan-1-ol;N-Boc-2-aMino-2-Methyl-1-propanol 97%;Carbamic acid,N-(2-hydroxy-1,1-dimethylethyl)-, 1,1-dimethylethyl ester;tert-Butyl N-(2-hydroxy-1,1-dimethylethyl)carbamate;tert-Butyl (1-hydroxy-2-methylpropan-2-yl)
• CAS NO: 102520-97-8
• Molecular Formula: C₉H₁₉NO₃
• Molecular Weight: 189.253
• Mol File: 102520-97-8.mol

Chemical Properties

• Melting Point: 57-62 °C
• Boiling Point: 286.543°C at 760 mmHg
• Flash Point: 127.097°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.453
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 12.24±0.46(Predicted)
• CAS DataBase Reference: N-BOC-2-AMINO-2-METHYL-1-PROPANOL 97(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-2-AMINO-2-METHYL-1-PROPANOL 97(102520-97-8)
• EPA Substance Registry System: N-BOC-2-AMINO-2-METHYL-1-PROPANOL 97(102520-97-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 102520-97-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-2-AMINO-2-METHYL-1-PROPANOL 97 is used as an intermediate compound for the synthesis of various pharmaceuticals. Its BOC protecting group plays a crucial role in the selective protection of the amino group during the synthesis process, allowing for the controlled formation of complex molecular structures.
Used in the Synthesis of KCa3.1 Potassium Channel Inhibitors:
N-BOC-2-AMINO-2-METHYL-1-PROPANOL 97 is used as a key building block in the preparation of diamine derivatives, which are known as KCa3.1 potassium channel inhibitors. These inhibitors are essential in the development of drugs targeting the KCa3.1 channel, which plays a vital role in various physiological processes, including blood pressure regulation, immune response, and smooth muscle contraction. By inhibiting the KCa3.1 channel, these diamine derivatives can potentially be used to treat conditions such as hypertension, chronic obstructive pulmonary disease (COPD), and certain types of pain.

InChI:InChI=1/C9H19NO3/c1-8(2,3)13-7(12)10-9(4,5)6-11/h11H,6H2,1-5H3,(H,10,12)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 87413-09-0 Dess-Martin periodane 
• 34619-03-9 tert-butyldicarbonate 
• 30992-29-1 Boc-Aib-OH 
• 500143-63-5 di(tert-butyl) 2-{[tert-butyl(diphenyl)silyl]oxy}-1,1-dimethylethylimidodicarbonate 
• 84758-55-4 N-(tert-butoxycarbonyl)-α-methylalanine methyl ester 

Downstream Products

• 184766-37-8 4-{4-[(2-tert-Butoxycarbonylamino-2-methyl-propyl)-methyl-amino]-phenyl}-3-methyl-4-oxo-butyric acid methyl ester 
• 184766-30-1 4-[4-(2-tert-Butoxycarbonylamino-2-methyl-propylamino)-phenyl]-3-methyl-4-oxo-butyric acid methyl ester 
• 184766-43-6 (1,1-Dimethyl-2-{methyl-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-amino}-ethyl)-carbamic acid tert-butyl ester 
• 114856-90-5 {1,1-Dimethyl-2-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenylamino]-ethyl}-carbamic acid tert-butyl ester 
• 454248-55-6 3-(tert-butyloxycarbonyl)-4,4-dimethyl-[1,2,3]-oxathiazolidine-2,2-dioxide 
• 193085-32-4 (2-tert-butoxycarbonylamino-2-methylpropoxy)acetic acid 
• 193086-04-3 {1,1-dimethyl-2-[(methyl-{1-[methyl-(1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-2-naphthalen-2-yl-ethyl}-carbamoyl)-methoxy]-ethyl}-carbamic acid tert-butyl ester 
• 204707-34-6 tert-butyl (1-methoxy-2-methylpropan-2-yl)carbamate 
• 109608-77-7 2-tert-butoxycarbonylamino-2-methylpropanal 
• 27646-80-6 N-Methyl-2-amino-2-methyl-1-propanol 
• 134597-95-8 tert-butyl (2-methyl-1-(methylamino)propan-2-yl)carbamate 

Relevant articles and documents

N-Alkyl-5,5-dimethyl-2-oxomorpholin-3-yl radicals. Characterization and reaction with molecular oxygen

The synthesis of bi(4,5,5-trimethyl-2-oxomorpholin-3-yl) (TM-3′ dimer), bi(5,5-dimethyl-4-cthyl-2-oxomorpholin-3-yl) (DEM-3 dimer), and bi(5,5-dimethyl-4-isopropyl-2-oxomorpholin-3-yl) (DIM-3 dimer) by one-electron oxidation of 4,5,5-trimethyl-2-oxomorpholine (8), 5,5-dimethyl-4-ethyl-2-oxomorpholine (9), and 5,5-dimethyl-4-isopropyl-2-oxomorpholine (10), respectively, with photochemically generated rert-butoxyl radical is described. dl-TM-3′ dimer, meso-DEM-3 dimer, and meso-DIM-3 dimer were characterized from spectra and by X-ray crystallography. In solution the radical dimers existed in equilibrium with the captodatively substituted radicals, 4,5,5-trimethyl-2-oxomorpholin-3-yl (TM-3′), 5,5-dimethyl-4-ethyl-2-oxomorpholin-3-yl (DEM-3), and 5,5-dimethyl-4-isopropyl-2-oxomorpholin-3-yl (DIM-3), respectively, as indicated by EPR spectroscopy. The activation parameters for bond homolysis in ethanol solvent were measured by oxidatively trapping the radicals with diphenylpicrylhydrazyl (DPPH). The half-lives for bond homolysis vary by S orders of magnitude at 25°C with a value of only 2.3 s for DIM-3 dimer. DIM-3 dimer reacted quantitatively with molecular oxygen to form a mixture of meso- and dl-bis(5,5-dimethyl-4-isopropyl-2-oxomorpholin-3-yl) peroxides (DIM-3 peroxides), which were isolated and characterized spectroscopically and analytically. At ambient temperature the peroxides fragmented by C-O bond homolysis to release the DIM-3 radical as indicated by EPR spectroscopy and were solvolyzed by protic solvent with release of hydrogen peroxide. The solvolysis was reversed by evaporation of the protic solvent, which restored most of the DIM-3 peroxides. The peroxides also slowly fragmented irreversibly to 5,5-dimethyl-3-hydroxy-4-isopropyl-2-oxomorpholine (21) and 5,5-dimethyl-2,3-dioxo-4-isopropylmorpholine (23) in polar aprotic solvent.

New routes to N-alkylated cyclic sulfamidates

BOC- and dibenzosuberyl-protected chiral and hindered cyclic sulfamidates ([1,2,3]-oxathiazolidine-2,2-dioxides) were synthesized and subsequently deprotected using trifluoroacetic acid. The resulting crystalline sulfamidates were then used in several alk

New methods for the preparation of 2-amino-2-methylpropanesulfonic acid

2-Amino-2-methylpropanesulfonic acid 3 was prepared either from 2-N-[(1,1-dimethylethoxy)carbonyl]amino-2-methyl-1-propanol 4 or from 1-N-[(1,1-dimethylethoxy)carbonyl]amino-2-methyl-2-propanol 5 in good overall yields.

1,3-Disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable ionic liquid catalyst for the N-Boc protection of amines

1,3-Disulfonic acid imidazolium hydrogen sulfate is easily prepared and used as an efficient and recyclable ionic liquid for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be reused and recovered for several times without loss of activity.

Vinyl Sulfone-Based Inhibitors of Nonstructural Protein 2 Block the Replication of Venezuelan Equine Encephalitis Virus

Emerging infectious diseases like those caused by arboviruses such as Venezuelan equine encephalitis virus (VEEV) pose a serious threat to public health systems. Development of medical countermeasures against emerging infectious diseases are of utmost importance. In this work, an acrylate and vinyl sulfone-based chemical series was investigated as promising starting scaffolds against VEEV and as inhibitors of the cysteine protease domain of VEEV's nonstructural protein 2 (nsP2). Primary screen and dose response studies were performed to evaluate the potency and cytotoxicity of the compounds. The results provide structural insights into a new class of potent nonpeptidic covalent inhibitors of nsP2 cysteine protease represented by compound 11 (VEEV TrD, EC50= 2.4 μM (HeLa), 1.6 μM (Vero E6)). These results may facilitate the evolution of the compounds into selective and broad-spectrum anti-alphaviral drug leads.

Iron(III)triflate as a highly efficient, recyclable and green catalyst for the N-Boc protection of amines

Iron (III) triflate was used as an efficient catalyst for N-t-butoxycarbonylation of amines with di-t-butyl dicarbonate under solvent-free conditions at room temperature. Various aliphatic, aromatic, heterocyclic amines and aminols were protected as their corresponding mono-carbamates in excellent yields and short reaction times. Only two of the 23 monocarbamates were new. No competitive side reactions such as isocyanate, urea, nor N,N-di-Boc formation were observed. The reported method is mild and has the advantages of low cost, chemoselectivity and, because no solvent is used and the catalyst can be recycled, it is classifiable as a green procedure.

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.

Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Substituted chiral diaryl macrocyclic compound as TRK inhibitors

The invention relates to a substituted chiral diaryl macrocyclic compound as a TRK inhibitor, and belongs to the technical field. The structure of the chiral diaryl macrocyclic compound is shown as a general formula (I), and the chiral diaryl macrocyclic

Gem-dimethyl peptide nucleic acid (α/β/γ-gdm-PNA) monomers: synthesis and the role ofgdm-substituents in preferential stabilisation ofZ/E-rotamers

The flexible backbone of aminoethylglycine (aeg) PNA upon substitution becomes sterically constrained to enable conformational pre-organization for preferential binding to DNA or RNA. The bulkygem-dimethyl (gdm) substituent on carbons adjacent to thet-amide sidechain either at Cα (glycyl) or Cβ/Cγ (aminoethylene) sides may influence theZ/Erotamer ratio arising from a restricted rotation around thet-amide bond. Employing 2D NMR (NOESY), it is shown here that the Cα-gdm-PNA-T monomer exhibits exclusively theZ-rotamer, while the Cβ-gdm-PNA-T monomer shows only theE-rotamer. The unsubstitutedaeg-PNA-T and Cγ-gdm-PNA-T monomers display a mixture ofZ/Erotamers. The rotamers witht-amide carbonyl pointing towards thegem-dimethyl group always prevailed. The results are supported by computational studies that suggested that the preferred rotamers are the outcome of a net energetic benefit from the stabilising n-π* interactions of carbonyls (amide backbone andt-amide sidechain), and C-H?O interactions and the destabilising steric clash ofgem-dimethyl groups with the t-amido methylene group. TheE-rotamer structure in Cγ-gdmis also characterised by X-ray crystallography. The exclusiveE-rotamer for the Cβ-gdmmonomer seen in solution here is the first such example among several modified PNA monomers. Since the conformation of the sidechain is important for inducing base stacking and effective base pairing, the exclusiveE-rotamer in the Cβ-gdmmonomer may have significance in the properties of the derived PNA?:?DNA/RNA duplexes with allE-rotamers.