156866-52-3

Basic information

• Product Name: TERT-BUTYL N-(4-FORMYLBENZYL)CARBAMATE
• Synonyms: 4-(N-TERTBUTOXYAMINOMETHYL)BENZALDEHYDE;TERT-BUTYL N-(4-FORMYLBENZYL)CARBAMATE;4-(Aminomethyl)benzaldehyde, N-BOC protected;Tert-butylN-[(4-formylphenyl)methyl]carbamate;tert-butyl 4-formylbenzylcarbamate;tert-Butyl (4-formylbenzyl)carbamate, 4-{[(tert-Butoxycarbonyl)amino]methyl}benzaldehyde;CarbaMic acid, [(4-forMylphenyl)Methyl]-, 1,1-diMethylethyl ester;(4-Formylbenzyl)carbamic acid tert-butyl ester
• CAS NO: 156866-52-3
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.28
• Mol File: 156866-52-3.mol

Chemical Properties

• Melting Point: 83 °C
• Boiling Point: 389.019 °C at 760 mmHg
• Flash Point: 189.072 °C
• Appearance: /
• Density: 1.108±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 11.92±0.46(Predicted)
• CAS DataBase Reference: TERT-BUTYL N-(4-FORMYLBENZYL)CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL N-(4-FORMYLBENZYL)CARBAMATE(156866-52-3)
• EPA Substance Registry System: TERT-BUTYL N-(4-FORMYLBENZYL)CARBAMATE(156866-52-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-51
• Safety Statements: 22-26-36/37/39
• Hazardous Substances Data: 156866-52-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TERT-BUTYL N-(4-FORMYLBENZYL)CARBAMATE is used as a reagent or intermediate in chemical reactions for the synthesis of various organic compounds. Its specific properties and reactivity make it a valuable component in the creation of complex molecules and structures in the field of organic chemistry.

InChI:InChI=1/C13H17NO3/c1-13(2,3)17-12(16)14-8-10-4-6-11(9-15)7-5-10/h4-7,9H,8H2,1-3H3,(H,14,16)

Upstream product

• 56-91-7 p-aminomethylbenzoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 39895-56-2 4-hydroxymethyl-benzylamine 
• 510772-10-8 4-(azidomethyl)benzaldehyde 
• 439691-96-0 [4-(azidomethyl)phenyl]methanol 
• 52010-97-6 4-(hydroxylmethyl)benzaldehyde 
• 51359-78-5 4-(bromomethyl)benzaldehyde 
• 81172-89-6 terephthalaldehyde mono(diethylacetal) 
• 125734-44-3 4-(hydroxymethyl)benzaldehyde diethyl acetal 
• 1314538-55-0 potassium tert-butyl N-[(trifluorolambda-4-boranyl)methyl]carbamate 
• 69088-97-7 methanesulfonic acid 4-formylphenyl ester 
• 314732-37-1 tert-butyl 4-(methoxy(methyl)carbamoyl)benzylcarbamate 
• 104-88-1 4-chlorobenzaldehyde 
• 33233-67-9 4-(tert-Butoxycarbonylaminomethyl)benzoic acid 

Downstream Products

• 1022928-42-2 C₂₄H₃₈N₂O₄ 
• 1272015-90-3 {4-[2-(4-iodo-2,5-dimethoxyphenyl)vinyl]benzyl}carbamic acid tert-butyl ester 
• 1360616-36-9 tert-butyl 4-(oxazol-5-yl)benzylcarbamate 
• 1360616-38-1 (4-(oxazol-5-yl)phenyl)methanamine trifluoroacetate salt 
• 875582-76-6 (S)-6-Benzyloxycarbonylamino-2-({2-[1-[4-(tert-butoxycarbonylamino-methyl)-phenyl]-meth-(Z)-ylidene]-3-oxo-2,3-dihydro-benzo[b]thiophene-7-carbonyl}-amino)-hexanoic acid methyl ester 
• 1018674-41-3 cyclopentyl (2S)-[(4-{[(tert-butoxycarbonyl)amino]methyl}benzyl)amino](cyclohexyl)acetate 
• 695171-96-1 diphenyl benzyloxycarbonylamino-(4-(tert-butyloxycarbonylaminomethyl)phenyl)methanephosphonate 
• 675138-34-8 {4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic acid t-butyl ester 
• 914606-08-9 (S)-2-[4-(tert-butoxycarbonylamino-methyl)-benzylamino]-3-phenyl-propionic acid cyclopentyl ester 
• 675138-10-0 {4-[4-(t-butoxycarbonylaminomethyl)-benzylamino]-butyl}-carbamic acid benzyl ester 
• 695172-17-9 diphenyl ((N-benzyloxycarbonyl-O-tert-butyl-D-seryl)-L-alanyl)amino-(4-((N,N'-bis(tert-butyloxycarbonyl)guanyl)methyl)phenyl)methanephosphonate 
• 695172-10-2 diphenyl N-(N-benzyloxycarbonyl-L-alanyl)amino-(4-((N,N'-bis(tert-butyloxycarbonyl)guanyl)methyl)phenyl)methanephosphonate 
• 695172-03-3 diphenyl benzyloxycarbonylamino-(4-((N,N'-bis(tert-butyloxycarbonyl)guanyl)methyl)phenyl)methanephosphonate 

Relevant articles and documents

Discovery of Tetrahydroisoquinoline-Containing CXCR4 Antagonists with Improved in Vitro ADMET Properties

CXCR4 is a seven-transmembrane receptor expressed by hematopoietic stem cells and progeny, as well as by ≥48 different cancers types. CXCL12, the only chemokine ligand of CXCR4, is secreted within the tumor microenvironment, providing sanctuary for CXCR4+ tumor cells from immune surveillance and chemotherapeutic elimination by (1) stimulating prosurvival signaling and (2) recruiting CXCR4+ immunosuppressive leukocytes. Additionally, distant CXCL12-rich niches attract and support CXCR4+ metastatic growths. Accordingly, CXCR4 antagonists can potentially obstruct CXCR4-mediated prosurvival signaling, recondition the CXCR4+ leukocyte infiltrate from immunosuppressive to immunoreactive, and inhibit CXCR4+ cancer cell metastasis. Current small molecule CXCR4 antagonists suffer from poor oral bioavailability and off-target liabilities. Herein, we report a series of novel tetrahydroisoquinoline-containing CXCR4 antagonists designed to improve intestinal absorption and off-target profiles. Structure-activity relationships regarding CXCR4 potency, intestinal permeability, metabolic stability, and cytochrome P450 inhibition are presented.

CHEMOKINE CXCR4 RECEPTOR MODULATORS AND USES RELATED THERETO

The disclosure relates to chemokine CXCR4 receptor modulators and uses related thereto. The receptor modulators can be formulated to form pharmaceutical compositions comprising the disclosed compounds or pharmaceutically acceptable salts or prodrugs thereof. The compositions may be used for managing CXCR4 related conditions, typically prevention or treatment of viral infections abnormal cellular proliferation, retinal degeneration, inflammatory diseases, or as an immunostimulant or immunosuppressant or for managing cancer and may be administered with another active ingredient such as an antiviral agent or chemotherapeutic agent.

Efficient chemoselective hydrogenation of organic azides catalyzed by palladium nanoparticles with alkyne-derived homogeneous supports

Catalytic chemoselective hydrogenation of organic azides using palladium nanoparticles stabilized by alkyne derivatives was studied. A broad range of aromatic and aliphatic azides were smoothly reduced to the corresponding amines in excellent yields with a quite small amount of the catalyst. Hydrogenation of 3-phenylpropylazide gave 3-phenylpropylamine almost quantitatively with a substrate-to-palladium molar ratio (S/Pd) of 12,900 under 8?atm of H2. The reaction under 1?atm of H2also proceeded smoothly with an S/Pd of 1000. Several reduction-sensitive functional groups, such as carbonyl, halide, benzylic OH, and aliphatic nitro were well tolerated under the reaction conditions.

Compounds & Methods for the Enhanced Degradation of Targeted Proteins & Other Polypeptides by an E3 Ubiquitin Ligase

The present invention relates to bifunctional compounds, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins that are degraded and/or otherwise inhibited by bifunctional compounds of the present invention. In particular, the present invention is directed to compounds, which contain on one end a VHL ligand that binds to the ubiquitin ligase and on the other end a moiety that binds a target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. The present invention exhibits a broad range of pharmacological activities associated with compounds of the present invention, consistent with the degradation/inhibition of targeted polypeptides.

Quantitative analysis of histone demethylase probes using fluorescence polarization

We previously reported methylstat as a selective inhibitor of jumonji C domain-containing histone demethylases (JHDMs). Herein, we describe the synthesis of a fluorescent analogue of methylstat and its application as a tracer in fluorescence polarization assays. Using this format, we have evaluated the binding affinities of several known JHDM probes, as well as the native cofactor and substrate of JHDM1A. This fluorophore allowed a highly robust and miniaturized competition assay sufficient for high-throughput screening.

Novel atom-economic reaction: Comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts

A novel atom-economic three-component one-pot reaction of a primary amine, an S-alkylisothiouronium salt and a Michael receptor is reported, which affords a guanidinium salt and thioether simultaneously. The guanidine moiety is involved in catalyzing the conjugated Michael addition of the mercaptan. The reaction proceeds under ambient conditions using a non-toxic EtOH-H2O mixture as the solvent, and the two products can be very easily purified. Complete atom economy is achieved by fully utilizing the S-alkylisothiouronium salt and converting the previously wasted mercaptan by-product into the valuable thioether.

COMPOUNDS AND METHODS FOR THE INHIBITION OF VCB E3 UBIQUITIN LIGASE

The present invention relates to novel compounds which find utility as modulators, especially inhibitors of VCB E3 Ubiquitin Ligase and as bioactive agents for use as therapeutics for the stimulation of erythropoiesis in a patient or subject including inducement of EPO production in the patient or subject, for the treatment of chronic anemia and ischemia (limits brain injury during episodes of localized anemia, ischemia and/or stroke and damage to cardiovascular tissue during cardiovascular ischemia), as well as enhancing wound healing processes. Pharmaceutical compositions comprising effective amounts of compounds according to the present invention alone or in combination with an additional erythropoieses stimulating agent such as EPO under the tradename procrit or epogen or darbapoietin alfa under the tradename aranesp. Methods of stimulating erythropoiesis in a subject or patient, including increasing the number of red blood cells and/or hematocrit of the patient, treating anemia, including chronic anemia and anemia associated with chronic kidney disease, dialysis, and cancer chemotherapy, ischemia, stroke and damage to cardiovascular tissue during cardiovascular ischemia as well as enhancing wound healing processes and preventing/reducing scarring secondary to healing represent additional aspects of the present invention. Local enhancement of angiogenesis through induction of VEGF including wound healing and reduction of stent occlusion remain additional aspects of the present invention.

GLUCOSE SENSOR MOLECULE

The present invention provides a glucose sensor having a glucose receptor containing a binding site of formula (I): wherein X, n, m and R1 are defined herein. Also provided is a glucose sensor molecule for use in such a glucose sensor, the glucose sensor molecule containing the binding site of formula (I). The binding site has been found to have particularly good selectivity for glucose.

HISTONE DEACETYLASE INHIBITORS

The disclosure provides compounds of formula I and methods for preparation thereof. The compounds act as inhibitor of histone deacetylase.

Suzuki-Miyaura cross-coupling reactions of potassium boc-protected aminomethyltrifluoroborate with aryl and hetaryl mesylates

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions were studied with potassium Boc-protected aminomethyltrifluoroborate through C-O activation of various mesylate derivatives to afford the corresponding products in moderate to good yields.