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Cyclopropylboronic acid

Cyclopropylboronic acid structure

CAS No:
411235-57-9
Formula:
C3H7BO2
Chemical Name:
Cyclopropylboronic acid
Synonyms:
Boronic acid,B-cyclopropyl-;Boronic acid,cyclopropyl-;B-Cyclopropylboronic acid;Cyclopropylboronic acid;Cyclopropaneboronic acid
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

White to off-white powder

Cyclopropylboronic acid Basic Attributes

Molecular Weight：

85.9

Exact Mass：

85.90

DSSTox ID：

DTXSID00375402

HScode：

2931900090

Characteristics

PSA：

40.5

XLogP3：

-0.37680

Appearance：

white powder

Density：

1.1±0.1 g/cm3

Melting Point：

90-95 °C(lit.)

Boiling Point：

205.1°C at 760 mmHg

Flash Point：

77.9±22.6 °C

Refractive Index：

1.443

Storage Conditions：

Store below -20ºC

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R22

safety instructions：

S26-S36

Marks：

Xn:Harmful

Precautionary statement(s)：

P201-P280-P305 + P351 + P338-P308 + P313

Hazard Statements：

H302-H318-H360FD

GHS Classification：

|Warning|H242 (21.43%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]|P210, P220, P234, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P411, P420, and P501|Aggregated GHS information provided by 14 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Cyclopropylboronic acid Use and Manufacturing

Methods of Manufacturing

To a stirred solution of TRIMETHYLBORATE (1.69g, 1.81 ML, 16. 25MMOL) in THF (7ML) AT-78C under a N2 atmosphere was added, by drop wise addition, cyclopropylmagnesium bromide (0.5M in THF, 25ML, 12. 5mmol). A white precipitate formed. After 1 hr the reaction was warmed to room temperature and stirred overnight. The reaction was quenched with HCI aq. (20ML, 2. ON) and the mixture stirred for 1 hour. After extracting with DCM (15ml) and back extracting with H20 (2XL5ML), the aqueous fractions were combined and extracted using TBME (4X40ML). The combined organic extracts were dried over MgS04 and concentrated under reduced pressure to give a white solid. Recrystallisation from DCM and hexane (twice) furnished a white solid 25, 297mg, 27percent yield. H nmr (250MHz, CDCl3) ; 0.56-0. 50 (2H, m, CH2), 0.42-0. 40 (2H, m, CH2), -0. 08--0. 20 (1 H, m, CH).

Uses

Cyclopropylboronic Acid is an organoboronic acid commonly used in highly efficient Suzuki coupling reactions. Reagent used for• ;Microwave-assisted copper(II)-catalyzed N-cyclopropylation1• ;Nickel- and copper-catalyzed Suzuki-Miyaura coupling reaction of arenes2• ;Palladacycle-catalyzed Suzuki-cross coupling of aryl halides with cyclopropylboronic acid3• ;Palladium(0)-catalyzed cyclopropane C-H bond functionalization4• ;Palladium-catalyzed decarboxylative coupling5• ;Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes6• ;Palladium-catalyzed Suzuki coupling reaction7Reagent used in Preparation of• ;Diaryl ketones by arylation suzuki reaction

Computed Properties

Molecular Weight:85.90
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:86.0539096
Monoisotopic Mass:86.0539096
Topological Polar Surface Area:40.5
Heavy Atom Count:6
Complexity:50.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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