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6165-68-0

Basic Information
CAS No.: 6165-68-0
Name: Boronicacid, B-2-thienyl-
Article Data: 35
Cas Database
Molecular Structure:
Molecular Structure of 6165-68-0 (Boronicacid, B-2-thienyl-)
Formula: C4H5BO2S
Molecular Weight: 127.959
Synonyms: 2-Thiopheneboronicacid (6CI,7CI,8CI);Boronic acid, 2-thienyl- (9CI);2-Thienylboric acid;Thien-5-ylboronic acid;thiophen-2-ylboronic acid;Thiophene-2-boronic acid;
EINECS: 612-186-6
Density: 1.321 g/cm3
Melting Point: 138-140 °C(lit.)
Boiling Point: 287.917 °C at 760 mmHg
Flash Point: 127.928 °C
Solubility: N/A
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36/37-37/39-36
Transport Information: N/A
PSA: 68.70000
LogP: -0.57210
Synthetic route
1158984-92-9

2-thiopheneboronic acid MIDA ester

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 23℃; for 0.333333h;99%
3437-95-4

2-Iodothiophene

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-Iodothiophene With diisopropopylaminoborane; triethylamine; triphenylphosphine; palladium dichloride In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere;
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;
99%
13061-96-6

dihydroxy-methyl-borane

193978-23-3

2-thiopheneboronic acid pinacol ester

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃;96%
1003-09-4

2-bromothiophene

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere;
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;
87%
With n-butyllithium; diethyl ether at -60℃; anschliessend Behandeln mit Tributylborat und Behandeln des Reaktionsgemisches mit wss. Salzsaeure;
Stage #1: 2-bromothiophene With Trimethyl borate In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; Mg consumable anode, supporting electrolyte;
Stage #2: at 0℃; Acid hydrolysis; Further stages.;
With hydrogenchloride; borane; magnesium In tetrahydrofuran; ice-water

potassium (thiophen-2-yl)trifluoroborate

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With water; silica gel at 20℃; for 3h; Inert atmosphere;84%
1003-09-4

2-bromothiophene

67-56-1

methanol

55124-35-1

diisopropylamine borane

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 2-bromothiophene In tetrahydrofuran at 70℃;
Stage #3: methanol Further stages;
82%
188290-36-0

thiophene

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -78 - -20℃;
Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 20℃;
78%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -78 - -20℃;
Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran Further stages.;
78%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃;
Stage #3: With sulfuric acid In tetrahydrofuran
55%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
1003-09-4

2-bromothiophene

121-43-7

Trimethyl borate

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 4h; Inert atmosphere;
Stage #2: Trimethyl borate In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride In water
78%
1003-09-4

2-bromothiophene

22092-92-8

diisopropopylaminoborane

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-bromothiophene; diisopropopylaminoborane With magnesium In tetrahydrofuran at 65℃; for 4h; Inert atmosphere;
Stage #2: water With hydrogenchloride In tetrahydrofuran at 65℃; for 0.25h; Barbier Coupling Reaction; Inert atmosphere;
74%
5713-61-1

thiophen-2-yl magnesium bromide

6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With water In tetrahydrofuran slow addn. of 10 mmol of the Grignard reagent to a stirred soln. of borane in THF (40 mmol); the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;;68%
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Specification

The 2-Thiopheneboronic acid, with the CAS registry number 6165-68-0, is also known as Boronic acid, B-2-thienyl-. It belongs to the product categories of Boron Compounds; Azoles; Blocks; Boronic Acids; Boron, Nitrile, Thio & TM-Cpds; Heterocycles; Substituted Boronic Acids; Boronic Acids; Boronic Acid; Organoborons; Thiophene; B (Classes of Boron Compounds); Organic or Inorganic Borate. This chemical's molecular formula is C4H5BO2S and molecular weight is 127.96. What's more, its IUPAC name is called Thiophen-2-ylboronic acid. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 2-Thiopheneboronic acid are: (1)ACD/LogP: 1.267; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.27; (4)ACD/LogD (pH 7.4): 1.23; (5)ACD/BCF (pH 5.5): 5.40; (6)ACD/BCF (pH 7.4): 4.93; (7)ACD/KOC (pH 5.5): 116.38; (8)ACD/KOC (pH 7.4): 106.24; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 68.7 Å2; (13)Index of Refraction: 1.562; (14)Molar Refractivity: 31.43 cm3; (15)Molar Volume: 96.885 cm3; (16)Polarizability: 12.46×10-24cm3; (17)Surface Tension: 49.189 dyne/cm; (18)Density: 1.321 g/cm3; (19)Flash Point: 127.928 °C; (20)Enthalpy of Vaporization: 55.672 kJ/mol; (21)Boiling Point: 287.917 °C at 760 mmHg; (22)Vapour Pressure: 0.00100 mmHg at 25 °C.

Uses of 2-Thiopheneboronic acid: (1) it is used as synthetic intermediates; (2) it is used to produce other chemicals. For example, it can react with 2,6-dibromo-pyridine to get 2,6-di-thiophen-2-yl-pyridine. This reaction needs reagent tetrakis-(triphenylphosphine)palladium and solvent 1,2-dimethoxy-ethane. The reaction time is 4 hours. The yield is 55 %.

2-Thiopheneboronic acid can react with 2,6-dibromo-pyridine to get 2,6-di-thiophen-2-yl-pyridine.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: B(c1cccs1)(O)O
(2) InChI: InChI=1S/C4H5BO2S/c6-5(7)4-2-1-3-8-4/h1-3,6-7H
(3) InChIKey: ARYHTUPFQTUBBG-UHFFFAOYSA-N