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Chemical Structure| 69620-20-8 Chemical Structure| 69620-20-8

Structure of 69620-20-8

Chemical Structure| 69620-20-8

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Product Details of [ 69620-20-8 ]

CAS No. :69620-20-8
Formula : C20H41Br
M.W : 361.44
SMILES Code : CCCCCCCCC(CBr)CCCCCCCCCC
MDL No. :MFCD28515435
InChI Key :XSQSDBVMLJNZKU-UHFFFAOYSA-N
Pubchem ID :23148745

Safety of [ 69620-20-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 69620-20-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 69620-20-8 ]

[ 69620-20-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1860-99-7 ]
  • [ 6964-21-2 ]
  • [ 69620-20-8 ]
  • 2-octyldodecyl benzo[1,2-b:6,5-b']dithiophene-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In a 250 ml flask, equipped with coolant and magnetic stirring, the following were charged, under argon flow, in the order: <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) (0.711 g; 5 mmoles), palladium(II)acetate [Pd(OAc)2] (Aldrich) (0.023 g; 0.1 mmol), triphenylphosphine [PPh3] (Aldrich) (0.052 g; 0.2 mmol), potassium carbonate [K2CO3] (Aldrich) (1.382 g; 10 mmol), anhydrous N,N- dimethylformamide (DMF) (Aldrich) (30 ml) and 2-bromothiophene-3- carbaldehyde (Aldrich) (0.955 g; 5 mmoles): the reaction mixture was heated to 110C and kept at said temperature, under stirring, for 12 hours. Subsequently, the reaction mixture was cooled to room temperature (25C) and 9- (bromomethyl)nonadecane (Sunatech) (3.614 g; 10 mmol) was added: the reaction mixture was left, under stirring, at room temperature (25C), for 4 hours. Subsequently, the reaction mixture was placed in a 500 ml separating funnel, diluted with a 0.1 M ammonium chloride solution (NH4CI) (Aldrich) (3x 100 ml) and extracted with ethyl acetate (Aldrich) (3 x 100 ml), obtaining an aqueous phase and an organic phase. The entire organic phase (obtained by combining the organic phases deriving from the three extractions) was washed to neutral with water (3 x 50 ml) and subsequently anidrified on sodium sulphate (Aldrich) and evaporated. The residue obtained was purified by elution on a chromatographic column of silica gel [(eluent: n-heptane/ethyl acetate, 9/1, v/v) (Carlo Erba)], obtaining 2.342 g of 2-octyldodecyl-benzo[2,1-b;3,4- b’]dithiophene-4-carboxylate of formula (C) as straw yellow oil (yield 91%).
61% 2-Bromo-3-thiophenecarboxaldehyde (1.91 g, 10 mmol) was added to a solution of <strong>[6964-21-2]3-thiopheneacetic acid</strong> (1.42 g, 10 mmol), Pd(OAc)2 (224 mg, 0.1 mmol), PPh3 (524 mg, 0.2 mmol), and K2CO3 (2.76 g, 20 mmol) in anhyd DMF (50 mL) and the mixture was stirred to 110 C for 24 h. The reaction suspension was then cooled to 50 C and then 2-octyldodecyl bromide (3.61 g, 10 mmol) was added in one portion together with a catalytic amount of Bu4NI (184 mg, 0.5 mmol). The mixture was stirred for a further 24 h. After removal of solvent under reduced pressure, the crude mixture was purified by flash chromatography (SiO2; n-hexanes/EtOAc/CH2Cl2 (10:0.5:0.5). The pure product 6 was obtained as a colorless oil (61%), together with a small amount of 2-octyldodecyl-3-thiophene acetate (11%).6 Yield: 3.14 g (61%); Rf = 0.34 (99:0.5:0.5 hexanes/EtOAc/CH2Cl2). 1H NMR (CDCl3, 300 MHz): δ = 8.56 (s, 1H), 8.36 (d, J = 5.6 Hz, 1H), 7.53 (d, J = 5.6 Hz, 1H), 7.50 (d, J = 5.4 Hz, 1H), 7.44 (d, J = 5.4 Hz, 1H), 4.36 (d, J = 5.7 Hz, 2 H), 1.88 (m, 1H), 1.55-1.20 (m, 34 H), 0.87 (t, J = 7.0 Hz, 6 H). 13C NMR (CDCl3, 75 MHz): δ = 166.9, 137.8, 136.0, 135.6, 134.7, 125.7, 125.4, 125.2, 125.0, 124.2, 122.3, 67.8, 37.4, 31.8, 31.4, 29.9, 29.6, 29.5, 29.4, 29.2, 26.7, 22.6, 14.0. FIA-MS: m/z = 515 [M + 1]+, 1029 [2 M + 1]+. Anal. Calcd for C31H46O2S2: C, 72.32; H, 9.01. Found: C, 72.0; H, 8.8.
  • 2
  • [ 6964-21-2 ]
  • [ 69620-20-8 ]
  • [ 6630-33-7 ]
  • 2-octyldodecyl naphthol[1,2-b]thiophene-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% 2-Bromobenzaldehyde (1.16 mL, 10 mmol) was added to a solution of <strong>[6964-21-2]3-thiopheneacetic acid</strong> (1.42 g, 10 mmol), Pd(OAc)2 (224 mg, 0.1 mmol), PPh3 (524 mg, 0.2 mmol), K2CO3 (2.76 g, 20 mmol) in anhyd DMF (50 mL) and then stirred to 110 C for 24 h. The reaction suspension was then cooled to 50 C and then 2-octyldodecyl bromide (3.61 g, 10 mmol) was added in one portion together with catalytic amount of Bu4NI (184 mg, 0.5 mmol). The reaction mixture was kept stirring under the same conditions for a further 24 h. After removal of solvent under reduced pressure, the crude reaction mixture was purified by flash chromatography (SiO2; n-hexanes/EtOAc 10:1). Pure product was obtained as a colorless oil; yield: 4.63 g (91%). 1H NMR (CDCl3, 300 MHz): δ = 8.56 (s, 1H), 8.36 (d, J = 5.5 Hz, 1H), 8.17 (d, J = 8.1Hz, 1H), 8.03 (d, J = 8.0 Hz, 1H), 7.67 (t, J = 8.0 Hz, 1H), 7.61 (d, J = 5.5 Hz, 1H), 7.56 (t, J = 8.0 Hz, 1H), 4.37 (d, J = 5.7 Hz, 2 H), 1.89 (m, 1H), 1.38-1.18 (m, 32 H), 0.88 (t, J = 6.2 Hz, 6 H). 13H NMR (CDCl3, 75 MHz): δ = 166.78, 138.99, 135.10, 130.81, 130.24, 130.06, 129.40, 128.82, 126.04, 125.87, 125.60, 123.71, 123.48, 67.94, 37.43, 31.80, 31.46, 29.88, 29.55, 29.52, 29.48, 29.23, 26.71, 22.57, 14.00. ESI-MS: m/z = 509 [M + 1]+, 1017 [2 M + 1]+. Anal. Calcd for C33H48O2S: C, 77.9; H, 9.5. Found: C, 77.4; H, 9.1.
  • 3
  • [ 6964-21-2 ]
  • [ 69620-20-8 ]
  • [ 63525-48-4 ]
  • bis(2-octyldecyl)anthra[1,2-b:5,6-b’]dithiophene-4,10-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% In a 100 ml flask, with a magnetic stirrer, thermometer and coolant, in an inert atmosphere, 2,5-dibromobenzene-1 ,4-dicarbaldehyde having formula (IV) obtained as described in Example 2 (0.292 g; 1.0 mmol) and potassium carbonate (K2CO3) (Aldrich) (0.691 g; 5.0 mmol) were added to a mixture of <strong>[6964-21-2]3-thiopheneacetic acid</strong> [heteroaryl compound having general formula (V) wherein Y = oxygen and Z = sulfur] (Aldrich) (0.312 g; 2.2 mmol), triphenylphosphine (Aldrich) (0.026 g; 0.1 mmol), palladium(ll)acetate (0233) [Pd(OAc)2] (0.112 g; 0.5 mmol) in L/,/V-dimethylformamide anhydrous (DMF) (Aldrich) (5 ml): the resulting reaction mixture was heated to 80C and maintained under stirring, at said temperature, for 24 hours. Subsequently, 1 -bromo-2-octyldodecane (Aldrich) [alkyl halide having general formula (VI) wherein R1 = 2-octyldodecyl and X - bromine] (0.672 g; 2.2 mmol) was added in a single portion: the reaction mixture obtained was left, under stirring, at 80C, for 24 hours. Subsequently, after cooling to room temperature (25C), the reaction mixture was placed in a 500 ml separator funnel: a solution of ammonium chloride (NH4CI) 0.1 M (Aldrich) (3 x 100 ml) was added to said reaction mixture and everything was extracted with ethyl acetate (Aldrich) (3 x 100 ml) obtaining an aqueous phase and an organic phase. The entire organic phase (obtained by joining the organic phases deriving from the three extractions) was separated and subsequently anhydrified on sodium sulfate (Aldrich) and evaporated. The residue obtained is purified through elution on a silica gel chromatography column [(eluent: n-heptane/ethylacetate 98/2) (Carlo Erba)], obtaining 0.083 g of bis(2-hexyldecyl)anthra[1 ,2-b:5,6-b’]dithiophene-4, 10- dicarboxylate having formula (la) as a white solid (yield 10%).
 

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