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(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate

Product Name
(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate
CAS No.
89985-86-4
Chemical Name
(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate
Synonyms
(R)-2-(Boc-amino)-3-buten-1-ol;(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate;tert-Butyl (1R)-1-(hydroxymethyl)prop-2-enylcarbamate;tert-Butyl [(1R)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate;Carbamic acid, N-[(1R)-1-(hydroxymethyl)-2-propen-1-yl]-, 1,1-dimethylethyl ester
CBNumber
CB32546136
Molecular Formula
C9H17NO3
Formula Weight
187.24
MOL File
89985-86-4.mol
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(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate Property

Boiling point:
302.9±35.0 °C(Predicted)
Density 
1.026±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
pka
11.60±0.46(Predicted)
Appearance
Colorless to off-white Solid
InChI
InChI=1S/C9H17NO3/c1-5-7(6-11)10-8(12)13-9(2,3)4/h5,7,11H,1,6H2,2-4H3,(H,10,12)/t7-/m1/s1
InChIKey
HYVYNSIWYIWTCK-SSDOTTSWSA-N
SMILES
C(OC(C)(C)C)(=O)N[C@@H](CO)C=C
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

ChemScene
Product number
CS-W000577
Product name
(R)-tert-butyl(1-hydroxybut-3-en-2-yl)carbamate
Packaging
100mg
Price
$259
Updated
2021/12/16
AK Scientific
Product number
1883AQ
Product name
(R)-tert-butyl(1-hydroxybut-3-en-2-yl)carbamate
Packaging
100mg
Price
$414.8
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CCH0033074
Product name
(R)-TERT-BUTYL-(1-HYDROXYBUT-3-EN-2-YL)CARBAMATE
Purity
95.00%
Packaging
5MG
Price
$499.96
Updated
2021/12/16
Chemenu
Product number
CM194718
Product name
tert-butyl(R)-(1-hydroxybut-3-en-2-yl)carbamate
Purity
95%
Packaging
1g
Price
$611
Updated
2021/12/16
Crysdot
Product number
CD13001742
Product name
(R)-tert-Butyl(1-hydroxybut-3-en-2-yl)carbamate
Purity
95+%
Packaging
1g
Price
$640
Updated
2021/12/16
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(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate Chemical Properties,Usage,Production

Synthesis

115378-31-9

89985-86-4

General procedure for the synthesis of tert-butyl (R)-(1-hydroxybut-3-en-2-yl)carbamate from (R)-N-Boc-2,2-dimethyl-4-vinyl oxazolidine: vinyl oxazolidine 11 (500 mg, 2.2 mmol) was dissolved in ethanol (10 mL) under ice-bath cooling conditions, and p-toluenesulfonic acid monohydrate (42 mg, 0.22 mmol). The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the reaction was quenched with aqueous sodium bicarbonate and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, washed sequentially with saturated aqueous sodium bicarbonate (2 x 10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (eluent: hexane-ethyl acetate, v/v 9:1) to give 330 mg (80% yield) of colorless oily target compound. The 1H NMR and 13C NMR spectra of the product were in agreement with literature data [59]. Infrared spectra (ATR, cm?1) ν: 3344, 2998, 2932, 1692, 1522, 1366, 1171, 1053; 1H NMR (400 MHz, CDCl3) δ: 5.81 (m, 1H, =CH?), 5.25 (m, 2H, =CH2), 4.94 (br s, 1H, NH), 4.25 ( br s, 1H, CH?N), 3.65 (m, 2H, CH2?OH), 2.39 (br s, 1H, OH), 1.46 (s, 9H, Boc); 13C NMR (100 MHz, CDCl3) δ: 156.0, 135.4, 116.6, 79.8, 65.2, 54.7, 28.3; high-resolution mass spectra ( ESI): calculated value C9H17NO3Na [M+Na]+ m/z 210.1106, measured value 210.1109.

References

[1] Synthesis, 1994, # 12, p. 1463 - 1466
[2] Chemical Communications, 1999, # 3, p. 245 - 246
[3] Tetrahedron, 2018, vol. 74, # 38, p. 5392 - 5398
[4] Journal of Organic Chemistry, 2009, vol. 74, # 22, p. 8852 - 8855
[5] Synthesis, 1994, # 1, p. 31 - 33

(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate Preparation Products And Raw materials

Raw materials

Preparation Products

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(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate Suppliers

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89985-86-4, (R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMateRelated Search:


  • (R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate
  • (R)-2-(Boc-amino)-3-buten-1-ol
  • tert-Butyl [(1R)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate
  • Carbamic acid, N-[(1R)-1-(hydroxymethyl)-2-propen-1-yl]-, 1,1-dimethylethyl ester
  • tert-Butyl (1R)-1-(hydroxymethyl)prop-2-enylcarbamate
  • 89985-86-4