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4-Borono-L-phenylalanine
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Name

4-Borono-L-phenylalanine

 EINECS N/A
CAS No. 76410-58-7 Density 1.34 g/cm3
PSA 103.78000 LogP -0.97890
Solubility N/A Melting Point 285-293oC (dec.)
Formula C9H12BNO4 Boiling Point 449.3 °C at 760 mmHg
Molecular Weight 209.01 Flash Point 225.5 °C
Transport Information N/A Appearance N/A
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 76410-58-7 (4-BORONO-L-PHENYLALANINE) Hazard Symbols IrritantXi
Synonyms

4-Borono-L-phenylalanine;L-BPA;L-p-Boronophenylalanine;4-boronophenylalanine;4-(dihydroxyboranyl)-L-phenylalanine;4-(Dihydroxyboryl)-L-phenylalanine;L-Phenylalanine, 4-borono-;p-Borono-L-phenylalanine;4-Borono-L-phenylalanine B10 enriched;

Article Data 8

4-Borono-L-phenylalanine Synthetic route

119771-23-2

N-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-1-phenylalanine

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 55℃; for 1.5h;93.2%
With hydrogenchloride In water; acetone for 4h; Heating;70.18%
With sulfuric acid In 1,4-dioxane at 20℃; for 1h; Hydrolysis;67%
262604-05-7

4-borono-N,N-dibenzyl-L-phenylalanine benzyl ester

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In ethanol; water at 60℃; under 3750.38 - 9000.9 Torr; Reagent/catalyst; Temperature; Autoclave;91%
With hydrogenchloride; hydrogen; palladium dihydroxide In ethanol at 20℃; for 19h; Hydrogenolysis;44%
7732-18-5

water

262604-04-6

(4S)-3-t-butyloxycarbonyl-4-[4-(2,3-dimethyl-2,3-butanediolatoboryl)benzyl]-5-oxazolidinone

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide; sodium periodate; sulfuric acid In 1,4-dioxane; water; acetone 1) NaIO4, NH4OAc, acetone/water, room temp., 48 h; 2) aq. NaOH, 1 h; 3)aq. H2SO4, 1,4-dioxane, room temp., 1 h; removal of solvent, neutralization with aq. NaOH;67%
164203-33-2

N-benzyloxycarbonyl-4-borono-L-phenylalanine

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium dihydroxide In ethanol at 20℃; for 19h; Hydrogenolysis;63%
1333-74-0

hydrogen

164203-33-2

N-benzyloxycarbonyl-4-borono-L-phenylalanine

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In ethanol Pd(OH)2/C, room temp., 19 h; filtration, neutralization to pH 7.0 (aq. NaOH), filtration of solid, washing with water;63%
1333-74-0

hydrogen

262604-05-7

4-borono-N,N-dibenzyl-L-phenylalanine benzyl ester

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In ethanol Pd(OH)2/C, room temp., 19 h; filtration, neutralization to pH 7.0 (aq. NaOH), filtration of solid, washing with water;44%
5513-40-6

benzyl N-carbobenzyloxy-L-tyrosine

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99.8 percent / triethylamine / CH2Cl2 / 28 h / 0 - 20 °C
2: 58 percent / Et3N / [PdCl2(PPh3)2] / dioxane / Heating
3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C
4: 207 mg / aq. NaOH / 1 h
5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C
View Scheme
1991-81-7, 14173-41-2, 24250-85-9, 62561-75-5

4-iodo-L-phenylalanine

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 57 percent / NaCO3 / H2O / 24 h / 130 °C
2: 84 percent / Et3N / [PdCl2(dppf)] / dioxane / 36 h / 80 °C
3: 81 percent / NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C
4: 44 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / 1,4-dioxane; water / 19 °C
1.2: 8 h / 0 - 30 °C
2.1: 1,5-bis(methylamino)-3-oxapentane; tert-butylmagnesium chloride; sodium hydride / mineral oil; tetrahydrofuran / 22.5 h / 0 - 30 °C / Inert atmosphere
3.1: hydrogenchloride / water; acetone / 4 h / Heating
View Scheme
220400-04-4

N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / p-TsOH*H2O / toluene / 3 h / Heating
2: 72 percent / Et3N / [PdCl2(dppf)] / dioxane / 27 h / 80 °C
3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C
4: 1.30 g / aq. NaOH / 1 h
5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 96 percent / Cs2CO3 / methanol; dimethylformamide / 2 h / 20 °C
2: 82 percent / Et3N / [PdCl2(dppf)] / dioxane / 100 °C
3: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C
4: 207 mg / aq. NaOH / 1 h
5: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C
View Scheme
183070-41-9

L-Nα-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester

76410-58-7

p-borono-L-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 5 percent / Et3N / [PdCl2(dppf)] / dioxane / 80 °C
2: NaIO4; NH4OAc / acetone; H2O / 48 h / 20 °C
3: 207 mg / aq. NaOH / 1 h
4: 63 percent / hydrogen; aq. HCl / Pd(OH)2/C / ethanol / 19 h / 20 °C
View Scheme

4-Borono-L-phenylalanine Specification

The L-Phenylalanine,4-borono-, with the CAS registry number 76410-58-7, has the systematic name and IUPAC name of 4-(dihydroxyboranyl)-L-phenylalanine. It is a kind of white to off-white powder, and belongs to the product category of Boronic Acids. And the molecular formula of the chemical is C9H12BNO4. What's more, it should be stored at 2-8°C. Neutron absorbing (10)B-cpd used in thermal neutron capturetherapy of malignant melanoma. It is a white to off-white powder.

The characteristics of  4-Borono-L-phenylalanine are as followings:
 (1)ACD/LogP: 0.49; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -2.01; (4)ACD/LogD (pH 7.4): -2.05; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 48 Å2; (13)Index of Refraction: 1.59; (14)Molar Refractivity: 52.42 cm3; (15)Molar Volume: 155.1 cm3; (16)Polarizability: 20.78×10-24cm3; (17)Surface Tension: 64.6 dyne/cm; (18)Density: 1.34 g/cm3; (19)Flash Point: 225.5 °C; (20)Enthalpy of Vaporization: 74.61 kJ/mol; (21)Boiling Point: 449.3 °C at 760 mmHg; (22)Vapour Pressure: 7.39E-09 mmHg at 25°C. 

Safety Information of 4-Borono-L-phenylalanine :
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(O)[C@@H](N)Cc1ccc(cc1)B(O)O
(2)InChI: InChI=1/C9H12BNO4/c11-8(9(12)13)5-6-1-3-7(4-2-6)10(14)15/h1-4,8,14-15H,5,11H2,(H,12,13)/t8-/m0/s1
(3)InChIKey: NFIVJOSXJDORSP-QMMMGPOBBD

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