3-(BOC-AMINO)-1-PROPANOL Chemical Properties

Boiling point:

293℃

Density 

1.025 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.453

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Sparingly)

form 

clear liquid

pka

12.57±0.46(Predicted)

color 

Colorless to Almost colorless

BRN 

1860807

InChI

InChI=1S/C8H17NO3/c1-8(2,3)12-7(11)9-5-4-6-10/h10H,4-6H2,1-3H3,(H,9,11)

InChIKey

XDJCYKMWJCYQJM-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCCO

CAS DataBase Reference

58885-58-8(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

23-24/25-37/39-26

WGK Germany 

3

F 

10-21

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

3-(BOC-AMINO)-1-PROPANOL Usage And Synthesis

Chemical Properties

colorless to yellow or brown liquid

Uses

Amine protected, difunctional reagent employed in the synthesis of phosphatidyl ethanolamines and ornithine.

reaction suitability

reagent type: cross-linking reagent

Synthesis

General procedure for the synthesis of tert-butyl N-(3-hydroxypropyl)carbamate: 1. an anhydrous dichloromethane (DCM, 50 mL) solution of di-tert-butyl dicarbonate ((Boc)2O, 25.0 g, 114.5 mmol) was added slowly and dropwise under nitrogen protection to an anhydrous DCM solution (100 mL) of 3-amino-1-propanol (41, 7.8 g, 104.5 mmol) under stirring. 2. The reaction mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by thin layer chromatography (TLC, 50% petroleum ether/ethyl acetate) to confirm complete consumption of the feedstock. 3. Upon completion of the reaction, the reaction solution was diluted with ether (Et2O, 150 mL) and washed sequentially with phosphate buffer (0.5 M, pH 5.4, 2 × 70 mL), saturated aqueous sodium bicarbonate (70 mL) and brine (2 × 70 mL). 4. The organic phase was dried with anhydrous magnesium sulfate (MgSO4), filtered and the excess solvent was removed by evaporation under reduced pressure to afford the colorless viscous oily product tert-butyl N-(3-hydroxypropyl)carbamate (42, 18.3 g, 100% yield). Product characterization data: 1H NMR (270 MHz, CDCl3): δ 1.44 (s, 9H, CH3), 1.67 (m, 2H, H2'), 3.26 (q, 2H, J = 6.23 Hz, H3'), 3.65 (dd, 2H, J = 5.86, 5.68 Hz, H1'), 3.78 (dt, 1H, J = 6.04, 5.87 Hz, OH), 5.18 (br, 1H, NH). 13C NMR (67.8 MHz, CDCl3): δ 28.4 (CH3), 32.6 (C2'), 37.1 (C3'), 59.3 (C1'), 79.4 (Cquater), 157.1 (CO); MS (E/I) m/l, 1H, J = 6.04, 5.87 Hz, OH, 5.18 (br, 1H, NH). MS (E/I) m/z (relative strength): 176 (M+, 30), 120 (100), 119 (31), 102 (49), 83 (33), 76 (67), 74 (36). HRMS (E/I) Calculated value C8H17O3N: m/e 175.1200, measured value m/e 175.1208; IR (Nujol) ν IR (Nujol) ν (cm-1): 3355, 2976, 2936, 2878, 1810, 1694, 1531, 1455, 1392, 1366, 1278, 1253, 1173, 1072, 996, 914, 870, 781, 752, 638.

References

[1] Synthesis, 1990, p. 366 - 368
[2] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 21, p. 3059 - 3064
[3] Patent: US6414148, 2002, B1
[4] Patent: US6747144, 2004, B1. Location in patent: Page column 28
[5] Patent: US2010/222324, 2010, A1. Location in patent: Page/Page column 50

3-(BOC-AMINO)-1-PROPANOL(58885-58-8)Related Product Information

• tert-Butyl N-(3-aminopropyl)-N-methylcarbamate
• tert-butyl (3-bromo-2-fluorophenyl)carbamate
• tert-butyl (3-(2-(3-((5-cyanopyrazin-2-yl)amino)-1H-pyrazol-5-yl)-5-fluoro-3-methoxyphenoxy)propyl)carbamate
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• Boc-Hyp-OH
• BOC-ASP(OBZL)-OSU
• Boc-Asp(Ochx)-OH
• Boc-beta-alanine
• BOC-HYP(BZL)-OH
• N-Boc-L-Homoserine
• Boc-Asp-OH
• Boc-D-aspartic acid 4-benzyl ester
• 4-tert-Butyl N-[(tert-butoxy)carbonyl]-L-aspartate dicyclohexylamine salt
• Boc-D-aspartic acid 4-cyslohexyl ester
• (R)-1-(Boc-amino)-2-propanol, 98%
• 2R-BOC-AMINO-1-PROPANOL,(R)-(+)-2-(BOC-AMINO)-1-PROPANOL,(R)-2-(BOC-AMINO)-1-PROPANOL
• (S)-(-)-2-(BOC-AMINO)-1-PROPANOL,(S)-2-(BOC-AMINO)-1-PROPANOL,(S)-2-(Boc-amino)-1-propanol=N-(tert-Butoxycarbonyl)-L-alaninol