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N-DECYLBORONIC ACID

N-DECYLBORONIC ACID structure

N-DECYLBORONIC ACID 

structure
  • CAS No:

    24464-63-9

  • Formula:

    C10H23BO2

  • Chemical Name:

    N-DECYLBORONIC ACID

  • Synonyms:

    1-Decylboronic acid, 98%;Decylboronic acid;1-Decaneboronicacid (6CI);RARECHEM AH PB 0104;N-DECYLBORONIC ACID;Decylboronic acid, 98.8%

  • Categories:

    Chemical Reagents  >  Organic Reagents

N-DECYLBORONIC ACID Basic Attributes

186.1

186.179108

1743934

DTXSID70400492

2931900090

Characteristics

40.5

0.9±0.1 g/cm3

76-78°C

297.1°C at 760 mmHg

133.5±22.6 °C

1.434

Safety Information

36/37/38

26-36

N-DECYLBORONIC ACID Use and Manufacturing

Methods of Manufacturing

A 100mL flask was charged with 2.1M HBBr2Me2S in CH2Cl2(26.2 mL, ca. 55.0 mmol) and 1-decene (9.5 mL, 50.0 mmol) wasadded dropwise to the stirred solution at 20 °C. One molar BBr3 inCH2Cl2 (2.5 mL, 2.5 mmol) was added dropwise while the reactionmixture was cooled to 0 °C; the reaction was stirred for 15 min;then warmed spontaneously to 20 °C; and stirred for 30 min. Thesolution of boraneswas hydrolyzed by dropwise transfer to another flask containing a stirred mixture of Et2O (100 mL) and H2O (20 mL)at 0 °C then stirred for 20 min. The solution was transferred to aseparatory funnel with minimal exposure to air; the aqueous layerwas separated and discarded; the organic phase was washed withH2O (2 30 mL) and brine (2 30 mL); dried over MgSO4 andfiltered; then concentrated on a rotary evaporator. The yield of freeflowingwhite powder was 8.71 g, 93percent. 1H NMR δ 6.50 (s, 2H), 1.41(p, J 7.8, 7.2 Hz, 2H), 1.28 (s, 14H), 0.92-0.84 (m, 3H), 0.71 (t, J 7.8 Hz, 2H). 13C NMR δ 32.55, 32.07, 29.79, 29.73, 29.62, 29.50, 24.53, 23.50, 22.85, 14.28. 11B NMR d 32.32.

Uses

suzuki reaction

Computed Properties

Molecular Weight:186.10
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:9
Exact Mass:186.1791101
Monoisotopic Mass:186.1791101
Topological Polar Surface Area:40.5
Heavy Atom Count:13
Complexity:96.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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