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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
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CAS No. : | 7255-83-6 | MDL No. : | MFCD00051458 |
Formula : | C16H12N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GICPRLWIFVXEPU-UHFFFAOYSA-N |
M.W : | 232.28 | Pubchem ID : | 252356 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P280-P305+P351+P338-P311 | UN#: | 3439 |
Hazard Statements: | H302+H312-H315-H319-H331-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride Behandeln des Reaktionsprodukts mit aethanol. Ammoniak; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium hydroxide In ethanol at 150℃; for 0.0833333h; microwave irradiation; | |
87% | Stage #1: 4,4’-bis(cyanomethyl)-1,1’biphenyl With sulfuric acid In water for 2h; Reflux; Stage #2: With sodium hydroxide In ethanol; water for 24h; Reflux; | 1 Synthesis of 1,1’-biphenyl-4,4’-di(acetic acid) (H2bpda), 1 Compound B (10.9 g, 47 mmol) was added in small portions to half concentrated sulfuric acid (250 mL) while stirring and then refluxed for 2 h. After cooling to room temperature the suspension was poured in iced water (500 mL) and stirred for 15 min and afterwards filtered and washed with iced water (1 L) and dried in vacuum over night at 323 K. The dry compound was added to a mixture of sodium hydroxide solution (12.8 g, 0.32 mmol NaOH in 100 mL water) and ethanol (175 mL) and refluxed for 24 h. After cooling to room temperature half concentrated hydrochloric solution - was added drop wise to the yellow solution to precipitate an off white solid. The suspension was diluted by addition to iced water (500 mL) and stirred for 15 min. Afterwards the precipitate was filtered and washed with iced water (1 L) and dried in vacuum over night at 323 K to afford compound C (11.1 g, 87 %) as an off white solid. 1H-NMR (200 MHz, DMSO-D6): σ 3.61 (s, 4H, -CH2-), 7.34 & 7.60 (d, 8H, -CH-), 12.36 (s, 2H, -COOH). EI-MS at 150 °C (M = C16H14O4 (270.28) m/z (%) 270 (40) [M], 225 (100) [M - COOH], 211 (35) [M - CH2-COOH], 180 (43) [M - 2x COOH], 152 (19) [M - 2x CH2-COOH]. |
73% | Stage #1: 4,4’-bis(cyanomethyl)-1,1’biphenyl With potassium hydroxide In ethanol; water Stage #2: With hydrogenchloride In ethanol; water |
With hydrogenchloride at 130℃; | ||
Stage #1: 4,4’-bis(cyanomethyl)-1,1’biphenyl With potassium hydroxide; ethanol at 150℃; for 0.0833333h; Microwave irradiation; Stage #2: With hydrogenchloride In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Biphenyl mit HBr, Paraformaldehyd und NaCN; | ||
Bis(1,5-Cyclooctadien)Ni, p-Bromphenylacetonitril; | ||
Entspr. Bis-chlormethyl-diphenyl; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 92 percent / KOH / ethanol / 0.08 h / 150 °C / 7500.6 Torr / microwave irradiation 2.1: CDI / tetrahydrofuran / 0.08 h / 130 °C / 7500.6 Torr / microwave irradiation 2.2: 77 percent / tetrahydrofuran / 0.08 h / 130 °C / 7500.6 Torr / microwave irradiation 3.1: 85 percent / RedAl(R) / toluene / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 92 percent / KOH / ethanol / 0.08 h / 150 °C / 7500.6 Torr / microwave irradiation 2.1: CDI / tetrahydrofuran / 0.08 h / 130 °C / 7500.6 Torr / microwave irradiation 2.2: 77 percent / tetrahydrofuran / 0.08 h / 130 °C / 7500.6 Torr / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2SO4 2: LiAlH4; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: petroleum ether; HCl; ZnCl2 / zuletzt unter Erwaermen 2: aqueous ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid / 130 °C 2: hydrogen chloride; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 14% 2: 9% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 100 - 110℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In dimethyl sulfoxide at 40℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium cyanide; In dimethyl sulfoxide; at 20 - 49.84℃; for 44h; | 4,4?-bis(chloromethyl)-1,1?-biphenyl (13.1 g, 52 mmol, 1 eq) A, was added in small portions to a suspension of NaCN (5.35 g, 0.109 mmol, 2.05 eq) in DMSO (50 mL) while stirring. While adding A the suspension will turn pale yellow. After adding of A the mixture was heated under stirring at 323 K for 8 h and afterwards stirred for 36 h at room temperature. The now orange-brown suspension was poured in iced water (500 mL) and a yellow solid precipitated, which was stirred further for 30 min. After filtration and washing with iced water (500 mL) the filter cake was dried over night at 323 C in vacuum to afford the desired intermediate B (10.9 g, 90 %) (1H-NMR (200 MHz, DMSO-D6): sigma 4.08 (s, 2H, -CH2-), 7.44 & 7.71 (d, 8H, -CH-). EI-MS at 100 C (M = C16H12N2 (232.29) m/z (%) 232 (100) [M], 192 (78) [M - CH2-CN], 152 (19) [M - 2x CH2-CN]. |