tert-Butyl N-hydroxycarbamate

Base Information

• Chemical Name: tert-Butyl N-hydroxycarbamate
• CAS No.: 36016-38-3
• Molecular Formula: C5H11NO3
• Molecular Weight: 133.147
• Hs Code.: 29280090
• European Community (EC) Number: 252-836-2
• NSC Number: 144620,131086
• UNII: GJV9GPX5T3
• DSSTox Substance ID: DTXSID60189587
• Nikkaji Number: J150.043K
• Wikidata: Q72503295
• ChEMBL ID: CHEMBL1916775
• Mol file: 36016-38-3.mol

Synonyms:tert-Butyl N-hydroxycarbamate;36016-38-3;N-Boc-hydroxylamine;N-tert-Butoxycarbonylhydroxylamine;tert-Butyl hydroxycarbamate;Carbamic acid, hydroxy-, 1,1-dimethylethyl ester;Boc-amino alcohol;GJV9GPX5T3;tert-butyl-N-hydroxycarbamate;EINECS 252-836-2;1,1-dimethylethyl N-hydroxycarbamate;MFCD00002107;NSC-131086;NSC-144620;N-Hydroxycarbamic Acid tert-Butyl Ester;boc-hydroxylamine;Boc hydroxylamine;n-boc-hydroxyamine;BOC-amino-alcohol;BocNHOH;HONHBoc;N-Boc hydroxylamine;N-boc amino alcohol;NSC144620;N-Boc-Hydroxyl Amine;BOC-NHOH;t-butyl hydroxycarbamate;UNII-GJV9GPX5T3;t-butyl-N-hydroxycarbamate;t-butyl-N-hydroxy-carbamate;SCHEMBL17960;tert-Butyl hydroxycarbamate #;tert-butyl N-hydroxy-carbamate;N-Boc-hydroxylamine, >=98%;N-TERT-BOC-HYDROXYLAMINE;tert-butoxycarbonyl-hydroxylamine;CHEMBL1916775;DTXSID60189587;T-BUTYL N-HYDROXYCARBAMATE;N-tert-butoxycarbonyl hydroxylamine;N-tert-butoxycarbonyl-hydroxylamine;N-(tert-Butoxycarbonyl)hydroxylamine;NSC131086;N-(tert-butyloxycarbonyl)hydroxylamine;AKOS005256769;AB00205;CS-W001934;GS-3593;NSC 131086;NSC 144620;N-hydroxy-carbamic acid tert-butyl ester;BP-10643;BP-13432;SY006734;AM20090572;FT-0600526;H0848;EN300-91975;N-Boc-hydroxylamine, purum, >=98.0% (N);A823094;W-106645;F8889-1872;CARBAMIC ACID, N-HYDROXY-, 1,1-DIMETHYLETHYL ESTER

Chemical Property of tert-Butyl N-hydroxycarbamate

Chemical Property:

• Appearance/Colour: White to light pink crystalline powder
• Vapor Pressure: 0.00344mmHg at 25°C
• Melting Point: 53-55 °C(lit.)
• Refractive Index: 1.443
• Boiling Point: 250.4 °C at 760 mmHg
• PKA: 9.31±0.23(Predicted)
• Flash Point: 105.2 °C
• PSA: 58.56000
• Density: 1.101 g/cm³
• LogP: 1.29120
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform, Methanol
• Water Solubility.: Slightly soluble in water.
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 133.07389321
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-hydroxylamine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NO
• Uses: tert-Butyl N-hydroxycarbamate is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts. N-Boc-hydroxylamine is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts. It acts as a reagent for the synthesis of hydroxylamine derivatives t-butyl-N-(acyloxy)carbamates and N,O-diacylated N-hydroxyarylsulfonamides.

Technology Process of tert-Butyl N-hydroxycarbamate

There total 13 articles about tert-Butyl N-hydroxycarbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) → tert-Butyl N-hydroxycarbamate (36016-38-3)

Guidance literature:

With hydroxylamine hydrochloride; potassium carbonate; In diethyl ether; water; at 20 ℃;

DOI:10.1016/S0040-4020(02)01512-0

Reference yield: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + hydroxylamine hydrochloride (5470-11-1) → tert-Butyl N-hydroxycarbamate (36016-38-3)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 0 - 20 ℃; for 3h;

DOI:10.1016/S0040-4020(98)00459-1

Reference yield: 96.0%

di-tert-butyl tricarbonate (24424-95-1) → tert-Butyl N-hydroxycarbamate (36016-38-3)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1021/jm1010397

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

di-tert-butyl dicarbonate

hydroxylamine hydrochloride

t-butoxycarbonylhydrazine

Downstream raw materials:

N,N-di(tert-butoxycarbonyl)hydroxylamine

(benzyloxy)carbamic acid 1,1-dimethylethyl ester

(acetyloxy)carbamic acid 1,1-dimethyl ethyl ester

tert-butyl N-tosyloxycarbamate

Refernces

• 1、 Voigt et al.. "". . p. 227,229 - 231. Retrieved 1978.
• 2、 Ma, Mingming,Chatterjee, Soumitra,Zhang, Meng,Bong, Dennis. "Stabilization of vesicular and supported membranes by glycolipid oxime polymers". . p. 2853 - 2855. Retrieved 2011.
• 3、 F?hrmann, Jan,Hilt, Gerhard. "Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions". supporting information. p. 20313 - 20317. Retrieved 2021/08/12.
• 4、 Wang, Zheng,Li, Peihe,Fu, Hui,Dai, Qipu,Hu, Changwen. "Palladium-Catalyzed Synthesis of Indolines from Aroyloxycarbamates through a Tandem Decarboxylative Amination/Heck/Annulation Reaction". . p. 192 - 200. Retrieved 2018/11/23.