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ChemicalBook--->CAS DataBase List--->39827-11-7

39827-11-7

39827-11-7 Structure

39827-11-7 Structure
IdentificationMore
[Name]

BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE
[CAS]

39827-11-7
[Synonyms]

AKOS 92494
BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE
BUTTPARK 98\04-18
1-Benzothiophene-2-carbonyl chloride
Thianaphthene-2-carbonyl chloride
Benzothiophene-2-Carbonyl Chloride
Benzo[b]thiophene-2-carbonyl chloride (6CI, 7CI, 9CI)
Benzobüthiophene-2-carbonyl chloride, 98%
1-Benzothiophene 2-carboxylic acid chloride
Benzo[b]thiophene-2-carboxylic acid chloride
[EINECS(EC#)]

679-311-4
[Molecular Formula]

C9H5ClOS
[MDL Number]

MFCD00051635
[Molecular Weight]

196.65
[MOL File]

39827-11-7.mol
Chemical PropertiesBack Directory
[Melting point ]

85-86°C
[Boiling point ]

176°C/17mmHg(lit.)
[density ]

1.410±0.06 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[form ]

powder to crystal
[color ]

White to Orange to Green
[Sensitive ]

Moisture Sensitive
[Detection Methods]

HPLC
[BRN ]

125174
[CAS DataBase Reference]

39827-11-7(CAS DataBase Reference)
[Storage Precautions]

Store under nitrogen;Moisture sensitive
Safety DataBack Directory
[Hazard Codes ]

C
[Risk Statements ]

R34:Causes burns.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[RIDADR ]

3261
[Hazard Note ]

Corrosive
[HazardClass ]

8
[PackingGroup ]

III
[HS Code ]

2934999090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Tetrahydrofuran-->N,N-Dimethylformamide-->Thionyl chloride-->n-Butyllithium-->Thianaphthene-->Thianaphthene-2-carboxylic acid-->Toluene
[Preparation Products]

N,N-diethyl-1-benzothiophene-2-carboxamide
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

benzo[b]thiophene-2-carbonyl chloride(39827-11-7)
[Alfa Aesar]

Benzo[b]thiophene-2-carbonyl chloride, 98%(39827-11-7)
Hazard InformationBack Directory
[Synthesis]

Thianaphthene-2-carboxylic acid

6314-28-9

BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE

39827-11-7

The general procedure for the synthesis of benz[b]thiophene-2-carboxylic acid from benz[b]thiophene-2-carboxylic acid was as follows: benz[b]thiophene-2-carboxylic acid (356.42 mg, 2 mmol) was suspended in anhydrous toluene (6 mL) and thionyl chloride (4.4 mL, 60 mmol) and N,N-dimethylformamide (DMF, 0.05 mL) were added. After stirring at room temperature, the mixture was heated to reflux for 8 hours. Upon completion of the reaction, the volatiles were removed under reduced pressure to afford benzo[b]thiophene-2-carbonyl chloride as a yellow powder. Purification by rapid chromatography on silica gel using ethyl acetate/hexane (1:9, v/v) as eluent gave the target product (393.64 mg, 94.9% yield) as a white powder. The spectral data of the product were in agreement with those reported in the literature.1H NMR (300 MHz, CDCl3): δ 8.31 (s, 1H), 7.04-7.89 (m, 2H), 7.60-7.46 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 161.14, 144.07, 138.05, 136.59, 135.89, 128.75, 126.68, 125.66, 122.91.

[References]

[1] Journal of the American Chemical Society, 2011, vol. 133, # 11, p. 3764 - 3767
[2] Patent: WO2012/99785, 2012, A2. Location in patent: Page/Page column 25
[3] Tetrahedron Asymmetry, 2003, vol. 14, # 3, p. 339 - 346
[4] Organometallics, 2015, vol. 34, # 12, p. 3065 - 3071
[5] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15010 - 15011
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