TERT-BUTYL HYDROXYCARBAMATE

Tert-Butyl Hydroxycarbamate is used intermediates for the preparation of oxyoxamic acids.
Tert-Butyl Hydroxycarbamate is used mild oxidation of oxime to acyl nitroso compounds and cycloaddition reactions.
Tert-Butyl Hydroxycarbamate is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts.

CAS Number: 36016-38-3 
EC Number: 252-836-2 
MDL Number: MFCD00002107
Molecular Formula: C₅H₁₁NO₃ 
Molecular Weight: ~ 133.15 g/mol

SYNONYMS:
tert-Butyl hydroxycarbamate, N-BOC-HYDROXYLAMINE, BOC-NH-OH, BOC-HNOH, N-Boc-hydroxylamine, N-Boc-hydroxyL, BOC hydroxylamine, N-T-BOC HYDROXYLAMINE, LABOTEST-BB LT00233206, N-(tert-Butoxycarbonyl)hydroxylamine, N-Hydroxycarbamic Acid tert-Butyl Ester, tert-Butyl N-hydroxycarbamate, 36016-38-3, N-Boc-hydroxylamine, N-tert-Butoxycarbonylhydroxylamine, tert-Butyl hydroxycarbamate, Carbamic acid, hydroxy-, 1,1-dimethylethyl ester, GJV9GPX5T3, n-boc-hydroxyamine, EINECS 252-836-2, 1,1-dimethylethyl N-hydroxycarbamate, NSC-131086, NSC-144620, DTXSID60189587, NSC 131086, NSC 144620, CARBAMIC ACID, N-HYDROXY-, 1,1-DIMETHYLETHYL ESTER, RefChem:188210, DTXCID20112078, 252-836-2, DRDVJQOGFWAVLH-UHFFFAOYSA-N, MFCD00002107, Boc-amino alcohol, tert-butyl-N-hydroxycarbamate, N-Hydroxycarbamic Acid tert-Butyl Ester, (tert-butyl)oxycarbohydroxamic acid, boc-hydroxylamine, Boc hydroxylamine, BOC-amino-alcohol, BocNHOH, HONHBoc, N-Boc hydroxylamine, N-boc amino alcohol, NSC144620, 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%, SCHEMBL1363554, tert-butoxycarbonyl-hydroxylamine, CHEMBL1916775, SCHEMBL10423459, T-BUTYL N-HYDROXYCARBAMATE, N-tert-butoxycarbonyl hydroxylamine, N-tert-butoxycarbonyl-hydroxylamine, ALBB-022859, N-(tert-Butoxycarbonyl)hydroxylamine, 2-Methyl-2-propanyl hydroxycarbamate, NSC131086, SBB059490, N-(tert-butyloxycarbonyl)hydroxylamine, AKOS005256769, AB00205, CS-W001934, FB36017, GS-3593, N-hydroxy-carbamic acid tert-butyl ester, BP-10643, BP-13432, SY006734, DB-007787, H0848, NS00029966, ST50998285, EN300-91975, N-Boc-hydroxylamine, purum, >=98.0% (N), 016B383, F044878, F8889-1872, N-Boc-hydroxylamine, N-BOC-HYDROXYLAMINE, N-Boc hydroxylamine, N-T-BOC HYDROXYLAMINE, t-Butyl N-hydroxycarbomate, tert-butyl hydroxycarbamate, tert-Butyl N-hydroxycarbamate, N-(T-BUTOXYCARBONYL)-HYDROXYLAMINE, N-HYDROXYCARBAMIC ACID TERT-BUTYL ESTER, Benzotriazol-1-YL 9-Fluorenylmethyl Carbonate, N-(tert-Butoxycarbonyl)hydroxylamine~tert-ButylN-hydroxycarbamate, 2-Methyl-2-propanylhydroxycarbamate, Boc-N-hydroxylamine, Boc-nhoh, Carbamic acid, hydroxy-, 1,1-dimethylethyl ester, Carbamic acid, N-hydroxy-, 1,1-dimethylethyl ester, N-(T-butoxycarbonyl)-hydroxylamine, N-BOC-hydroxylamine, N-hydroxycarbamic acid tert-butyl ester, N-T-boc hydroxylamine, N-T-butyloxycarbonyl-hydroxylamine, N-tert-BOC-hydroxylamine, N-tert-butoxycarbonylhydroxylamine, N-tert-butyloxycarbonylhydroxylamine, T-butyl N-hydroxycarbamate, Tert-butyl hydroxycarbamate
boc-hydroxylamine, BocNHOH, BOC-NHOH, (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-methylpentanoic acid, n-boc-hydroxyamine, N-(tert-Butoxycarbonyl)hydroxylamine, 1,1-dimethylethyl N-hydroxycarbamate, N-Boc-hydroxylamine, >=98%, tert-Butyl hydroxycarbamate, N-BOC-HYDROXYLAMINE, BOC-NH-OH, BOC-HNOH, N-Boc-hydroxyL, BOC hydroxylamine, N-Boc-Hydroxyamine, N-hydroxycarbamate, N-T-BOC HYDROXYLAMINE, LABOTEST-BB LT00233206, Tert-Butyl hydroxycarbamate, Carbamic acid, hydroxy-, 1,1-dimethylethyl ester, Carbamic acid, hydroxy-, tert-butyl ester, 1,1-Dimethylethyl N-hydroxycarbamate, N-(tert-Butoxycarbonyl)hydroxylamine, N-(tert-Butyloxycarbonyl)hydroxylamine,

Tert-Butyl Hydroxycarbamate is a white to light pink crystalline powder
Tert-Butyl Hydroxycarbamate is a derivative of carbamic acid, specifically classified as an O-protected N-hydroxycarbamate.
At room temperature, Tert-Butyl Hydroxycarbamate exists as a white to off-white solid with a faint characteristic odor often associated with organic nitrogen compounds.

Tert-Butyl Hydroxycarbamate is generally stable under ambient conditions but may exhibit limited solubility in water, while being more soluble in common organic solvents such as ethanol and acetone.
Tert-Butyl Hydroxycarbamate has been synthesized primarily for use in organic synthesis and pharmaceutical chemistry.

Tert-Butyl Hydroxycarbamate's preparation was first reported in the late 20th century as part of efforts to develop protected hydroxylamine derivatives for controlled chemical reactions.
The synthesis typically involves the reaction of tert-butyl chloroformate with N-hydroxyurea or hydroxylamine in a basic aqueous or alcoholic medium under controlled temperature conditions.

Tert-Butyl Hydroxycarbamate serves as a valuable reagent in peptide chemistry and medicinal research due to its ability to act as a nitrenium ion precursor or participate in oxime ligation strategies.
Tert-Butyl Hydroxycarbamate finds applications particularly in the pharmaceutical industry for the synthesis of heterocyclic compounds and drug intermediates.

There are no known natural sources of Tert-Butyl Hydroxycarbamate; it is exclusively prepared through synthetic routes.
Industrially, Tert-Butyl Hydroxycarbamate is manufactured via scalable processes involving the aforementioned reagents, with purification steps ensuring high purity for commercial use.

Tert-Butyl Hydroxycarbamate is considered to have low to moderate toxicity, though specific data on long-term exposure effects are limited.
Tert-Butyl Hydroxycarbamate is not currently classified as a carcinogen by major regulatory agencies such as the International Agency for Research on Cancer (IARC) or the U.S. Environmental Protection Agency (EPA).

Appropriate personal protective equipment should be used when handling the compound.
For safe storage, Tert-Butyl Hydroxycarbamate should be kept in a cool, dry, and well-ventilated area, away from strong acids and oxidizing agents.
The container should remain tightly sealed to prevent moisture absorption and degradation.

USES and APPLICATIONS of TERT-BUTYL HYDROXYCARBAMATE:
Uses of Tert-Butyl Hydroxycarbamate: Reagents for the synthesis of hydroxylamine derivatives, tert-butyl-N-(acyloxy) carbamates and N,O-diacylated N-hydroxyaryl sulfonamides.
Tert-Butyl Hydroxycarbamate is used preparation of aziridines by cycloaddition of azide and nitroso-Diels-Alder adducts.

Tert-Butyl Hydroxycarbamate is used reagents for the synthesis of α-aminooxyacids.
Tert-Butyl Hydroxycarbamate is used intermediates for the preparation of oxyoxamic acids.
Tert-Butyl Hydroxycarbamate is used mild oxidation of oxime to acyl nitroso compounds and cycloaddition reactions.

Tert-Butyl Hydroxycarbamate is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts.
Tert-Butyl Hydroxycarbamate acts as a reagent for the synthesis of hydroxylamine derivatives t-butyl-N-(acyloxy)carbamates and N,O-diacylated N-hydroxyarylsulfonamides.

Tert-Butyl Hydroxycarbamate is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts.
Tert-Butyl Hydroxycarbamate is used in organic synthesis, particularly as a protected hydroxylamine reagent: “Boc-hydroxylamine” is used in reactions where hydroxylamine functionality is needed but must be protected to avoid unwanted side reactions.

For example, in the preparation of aziridines via cycloaddition of azides with nitroso Diels-Alder adducts.
Tert-Butyl Hydroxycarbamate is used to make hydroxylamine derivatives, N,O-diacylated N-hydroxyarylsulfonamides etc.

BENEFITS / CHARACTERISTICS of TERT-BUTYL HYDROXYCARBAMATE:
The “BOC” (tert-butoxycarbonyl) protecting group allows the hydroxylamine moiety to be handled more safely / stably until needed in the synthetic sequence.
Tert-Butyl Hydroxycarbamate is a solid form, reasonable melting point, modest stability (if kept dry and cool), making handling and storage more practical than using free hydroxylamine in many contexts.
Purity is commonly high (≥ 98%) in commercial samples.

SYNTHESIS of TERT-BUTYL HYDROXYCARBAMATE:
A suspension of NH2OH•HCl (9.7 g, 140mmol) and K2CO3 (9.7 g, 700 mmol) in Et2O (60 mL) and H2O (2 mL)was stirred for about 1 h at r.t. with evolution of CO2 gas.
A solution of Boc2O (20.0 g, 92 mmol) in Et2O (40 mL) was then added dropwise at 0 °C, and the suspension was stirred at r.t for 12 h.

The organic phase was decanted, and the solid was washed with Et2O (3 × 30 mL).
The combined organic layers were concentrated, and the residue was recrystallized from cyclohexane/toluene to afford the desired product tert-butyl N-hydroxycarbamate as a white solid.

PHYSICAL and CHEMICAL PROPERTIES of TERT-BUTYL HYDROXYCARBAMATE:
CBNumber: CB7274369
Molecular Formula: C5H11NO3
Molecular Weight: 133.15
MDL Number: MFCD00002107
MOL File: 36016-38-3.mol
Melting Point: 53-55 °C (lit.)
Boiling Point: 245.66 °C (rough estimate)
Density: 1.2510 (rough estimate)
Refractive Index: 1.4120 (estimate)
Storage Temp.: 2-8°C

Solubility: Chloroform, Methanol
Form: Crystalline Powder
pKa: 9.31 ±0.23 (Predicted)
Color: White to light pink
Water Solubility: Slightly soluble in water
Sensitive: Moisture Sensitive
BRN: 1756546
InChI: InChI=1S/C5H11NO3/c1-5(2,3)9-4(7)6-8/h8H,1-3H3,(H,6,7)
InChIKey: DRDVJQOGFWAVLH-UHFFFAOYSA-N
SMILES: C(OC(C)(C)C)(=O)NO
CAS DataBase Reference: 36016-38-3 (CAS DataBase Reference)

FDA UNII: GJV9GPX5T3
UNSPSC Code: 12352100
NACRES: NA.22
IUPAC Name: tert-butyl N-hydroxycarbamate
InChI: InChI=1S/C5H11NO3/c1-5(2,3)9-4(7)6-8/h8H,1-3H3,(H,6,7)
InChIKey: DRDVJQOGFWAVLH-UHFFFAOYSA-N
Canonical SMILES: CC(C)(C)OC(=O)NO
Isomeric SMILES: CC(C)(C)OC(=O)NO
WGK Germany: 3
Reaxy-Rn: 1756546
CAS: 36016-38-3
EINECS: 252-836-2
Molecular Formula: C5H11NO3

Molar Mass: 133.15
Density: 1.2510 (rough estimate)
Melting Point: 53-55 °C (lit.)
Boiling Point: 245.66 °C (rough estimate)
Flash Point: 105.2 °C
Water Solubility: Slightly soluble in water
Solubility: Chloroform, Methanol
Vapor Pressure: 0.00344 mmHg at 25°C
Appearance: Crystallization
Color: White to light pink
BRN: 1756546

pKa: 9.31 ±0.23 (Predicted)
Storage Condition: 2-8°C
Sensitive: Moisture Sensitive
Refractive Index: 1.4120 (estimate)
Physical and Chemical Properties: Melting Point 53-57 °C
Density: 1.1 ±0.1 g/cm³
Boiling Point: 250.4 ±9.0 °C at 760 mmHg
Melting Point: 53-55 °C (lit.)
Molecular Formula: C5H11NO3
Molecular Weight: 133.146
Flash Point: 105.2 ±18.7 °C
Exact Mass: 133.073898

PSA: 58.56000
LogP: 0.82
Vapor Pressure: 0.0 ±1.1 mmHg at 25°C
Index of Refraction: 1.443
Storage Condition: 2-8°C
Compound Is Canonicalized: Yes
Appearance / Form: Crystalline powder, white to light pink (sometimes light yellow) solid
Melting Point: ~ 53-55 °C (lit.) (other sources give 53-57 °C)
Boiling Point: ~ 245.66 °C (estimated)

Density: ~ 1.2510 g/cm³ (estimate)
Refractive Index: ~ 1.4120 (estimate)
Solubility: Slightly soluble in water; soluble in organic solvents (e.g. chloroform, methanol)
Storage Conditions: Store at low temperature (2-8 °C); 
moisture sensitive; 
keep container tightly closed; avoid heat & moisture
Linear Formula: (CH3)3COCONHOH
CAS Number: 36016-38-3
Molecular Weight: 133.15

Beilstein: 1756546
EC Number: 252-836-2
MDL Number: MFCD00002107
UNSPSC Code: 12352100
PubChem Substance ID: 24853547
NACRES: NA.22
Physical State: crystalline
Color: beige
Odor: No data available
Melting Point/Freezing Point: 53 - 55 °C

Initial Boiling Point and Boiling Range: No data available
Flammability (solid, gas): No data available
Upper/Lower Flammability or Explosive Limits: No data available
Flash Point: No data available
Autoignition Temperature: No data available
Decomposition Temperature: No data available
pH: No data available
Viscosity, Kinematic: No data available
Viscosity, Dynamic: No data available
Water Solubility: No data available
Partition Coefficient n-octanol/water: No data available

Vapor Pressure: No data available
Density: No data available
Relative Density: No data available
Relative Vapor Density: No data available
Particle Characteristics: No data available
Explosive Properties: No data available
Oxidizing Properties: No data available
Other Safety Information: No data available
Molecular Weight: 133.15 g/mol
XLogP3-AA: 0.4

Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 2
Exact Mass: 133.07389321 Da
Monoisotopic Mass: 133.07389321 Da
Topological Polar Surface Area: 58.6 Ų
Heavy Atom Count: 9
Formal Charge: 0
Complexity: 105
Isotope Atom Count: 0

Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Molecular Formula / Molecular Weight: C5H11NO3 = 133.15
Physical State (20 °C): Solid
Storage Temperature: Refrigerated (0-10 °C)

Store Under Inert Gas: Store under inert gas
Condition to Avoid: Moisture Sensitive, Heat Sensitive
CAS RN: 36016-38-3
Reaxys Registry Number: 1756546
PubChem Substance ID: 87571206
SDBS (AIST Spectral DB): 21429
MDL Number: MFCD00002107
INCI / Name: tert-Butyl N-hydroxycarbamate, N-Boc-hydroxylamine
Compound Is Canonicalized: Yes

FIRST AID MEASURES of TERT-BUTYL HYDROXYCARBAMATE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of TERT-BUTYL HYDROXYCARBAMATE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of TERT-BUTYL HYDROXYCARBAMATE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of TERT-BUTYL HYDROXYCARBAMATE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of TERT-BUTYL HYDROXYCARBAMATE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of TERT-BUTYL HYDROXYCARBAMATE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available