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[ CAS No. 13080-85-8 ] {[proInfo.proName]}

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Chemical Structure| 13080-85-8
Chemical Structure| 13080-85-8
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Product Details of [ 13080-85-8 ]

CAS No. :13080-85-8 MDL No. :MFCD00039151
Formula : C24H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HYDATEKARGDBKU-UHFFFAOYSA-N
M.W : 368.43 Pubchem ID :632695
Synonyms :
4,4'-Bis(4-aminophenoxy)biphenyl
Chemical Name :4,4-Bis(4-aminophenoxy)biphenyl

Calculated chemistry of [ 13080-85-8 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.0
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 113.72
TPSA : 70.5 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.41
Log Po/w (XLOGP3) : 4.4
Log Po/w (WLOGP) : 6.12
Log Po/w (MLOGP) : 4.15
Log Po/w (SILICOS-IT) : 4.24
Consensus Log Po/w : 4.47

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.2
Solubility : 0.00232 mg/ml ; 0.0000063 mol/l
Class : Moderately soluble
Log S (Ali) : -5.6
Solubility : 0.000931 mg/ml ; 0.00000253 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.66
Solubility : 0.00000081 mg/ml ; 0.0000000022 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.3

Safety of [ 13080-85-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13080-85-8 ]

* 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 [ 13080-85-8 ]

[ 13080-85-8 ] Synthesis Path-Downstream   1~58

YieldReaction ConditionsOperation in experiment
Specific examples of amine curing agents useful in this invention are given below: ... 1,4-bis(4-aminophenoxy)benzene bis[4-(3-aminophenoxy)phenyl]sulfone bis[4-(4-aminophenoxy)phenyl]sulfone 4,4'-bis(3-aminophenoxy)biphenyl 4,4'-bis(4-aminophenoxy)biphenyl 2,2-bis[4-(3-aminophenoxy)phenyl]propane 2,2-bis[4-(4-aminophenoxy)phenyl]propane
Preferred examples of additional other diamines are: ethylenediamine, ... 4,4'-diamino-2,2'-dimethylbibenzyl, bis[4-(4-aminophenoxy)phenyl]sulfone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 2,7-diaminofluorene, 9,9-bis(4-aminophenyl)fluorene, 4,4'-methylene-bis(2-chloroaniline), 4,4'-bis(4-aminophenoxy)biphenyl, 2,2',5,5'-tetrachloro-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino-5,5'-dimethoxybiphenyl, 3,3'-dimethoxy-4,4'-diaminobiphenyl, 4,4-(1,4-phenyleneisopropylidene)bisaniline, 4,4'-(1,3-phenyleneisopropylidene)bisaniline, ...
  • 2
  • [ 108-31-6 ]
  • [ 13080-85-8 ]
  • C32H20N2O6 [ No CAS ]
  • 3
  • [ 2540-99-0 ]
  • [ 13080-85-8 ]
  • [ 210492-48-1 ]
  • Polymer; Monomer(s): 1,2-bis(4-aminophenoxy)-4-tert-butylbenzene; 3,3\,,4,4\-diphenylsulfonetetracarboxylic dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl [ No CAS ]
  • 4
  • [ 2540-99-0 ]
  • [ 13080-85-8 ]
  • Polymer; Monomer(s): 3,3\,,4,4\-diphenylsulfonetetracarboxylic dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl [ No CAS ]
  • 5
  • [ 13080-85-8 ]
  • [ 250267-73-3 ]
  • polymer, Mw=48740, Mn=21600; Monomer(s): 5-(4-acetoxybenzamido)isophthaloyl chloride; 4-{4-[4-(p-aminophenoxy)phenyl]phenoxy}aniline [ No CAS ]
  • 6
  • [ 85-44-9 ]
  • [ 13080-85-8 ]
  • [ 18959-91-6 ]
  • C86H50N4O14 [ No CAS ]
  • 7
  • [ 85-44-9 ]
  • [ 13080-85-8 ]
  • dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether [ No CAS ]
  • polymer, Mw 2.4E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl; phthalic anhydride [ No CAS ]
  • 8
  • [ 85-44-9 ]
  • [ 13080-85-8 ]
  • dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether [ No CAS ]
  • polymer, Mw 1.3E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl; phthalic anhydride [ No CAS ]
  • 9
  • [ 85-44-9 ]
  • [ 13080-85-8 ]
  • dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether [ No CAS ]
  • polymer, Mw 0.8E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl; phthalic anhydride [ No CAS ]
  • 10
  • [ 85-44-9 ]
  • [ 13080-85-8 ]
  • C40H24N2O6 [ No CAS ]
  • 11
  • [ 623-12-1 ]
  • [ 13080-85-8 ]
  • N-(4-methoxyphenyl)-4-{4-[4-(4-methoxyanilino)phenoxy]phenyl}phenoxyaniline [ No CAS ]
  • 12
  • [ 95-49-8 ]
  • [ 13080-85-8 ]
  • N-(4-{4-[4-(4-aminophenoxy)phenyl]phenoxy}phenyl)-2-methylaniline [ No CAS ]
  • 13
  • [ 13080-85-8 ]
  • dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether [ No CAS ]
  • polymer, Mw 2.0E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl [ No CAS ]
  • 14
  • [ 13080-85-8 ]
  • dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether [ No CAS ]
  • polymer, Mw 2.9E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl [ No CAS ]
  • 15
  • [ 13080-85-8 ]
  • dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether [ No CAS ]
  • polymer, Mw 15.0E4; monomer(s): 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride; 4,4\-bis(4-aminophenoxy)biphenyl [ No CAS ]
  • 16
  • [ 13080-85-8 ]
  • [ 108-90-7 ]
  • N-phenyl-4-{4-[4-(4-anilinophenoxy)phenyl]phenoxy}aniline [ No CAS ]
  • 17
  • [ 50961-54-1 ]
  • [ 13080-85-8 ]
  • C50H34N4O8 [ No CAS ]
  • 18
  • 4-[(α-cyano)acetoxy]benzaldehyde [ No CAS ]
  • [ 13080-85-8 ]
  • Cyano-acetic acid 4-({(E)-4-[4'-(4-[1-[4-(2-cyano-acetoxy)-phenyl]-meth-(E)-ylidene]-amino}-phenoxy)-biphenyl-4-yloxy]-phenylimino}-methyl)-phenyl ester [ No CAS ]
  • 19
  • 4-(m-nitrophenoxy)benzaldehyde [ No CAS ]
  • [ 13080-85-8 ]
  • C50H34N4O8 [ No CAS ]
  • 20
  • 4-(p-nonylphenoxy)benzaldehyde [ No CAS ]
  • [ 13080-85-8 ]
  • C68H72N2O4 [ No CAS ]
  • 21
  • [ 13080-85-8 ]
  • [ 104-88-1 ]
  • C38H26Cl2N2O2 [ No CAS ]
  • 22
  • [ 13080-85-8 ]
  • [ 555-16-8 ]
  • C38H26N4O6 [ No CAS ]
  • 23
  • [ 13080-85-8 ]
  • [ 100-52-7 ]
  • C38H28N2O2 [ No CAS ]
  • 24
  • [ 13080-85-8 ]
  • [ 123-08-0 ]
  • C38H28N2O4 [ No CAS ]
  • 25
  • [ 13080-85-8 ]
  • [ 120-21-8 ]
  • C46H46N4O2 [ No CAS ]
  • 26
  • [ 13080-85-8 ]
  • [ 100-10-7 ]
  • C42H38N4O2 [ No CAS ]
  • 27
  • [ 135771-48-1 ]
  • [ 13080-85-8 ]
  • poly(ether)amide, Mp = 394 kg/mol; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 28
  • [ 915415-25-7 ]
  • [ 13080-85-8 ]
  • poly(amic)acid; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 29
  • [ 52256-80-1 ]
  • [ 13080-85-8 ]
  • poly(amic)acid; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 30
  • [ 52256-80-1 ]
  • [ 13080-85-8 ]
  • poly(ether)amide, Mp = 105 kg/mol; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 31
  • [ 135771-46-9 ]
  • [ 13080-85-8 ]
  • poly(ether)amide, Mp = 51 kg/mol; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 32
  • [ 915414-96-9 ]
  • [ 13080-85-8 ]
  • poly(amic)acid; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 33
  • [ 150314-48-0 ]
  • [ 13080-85-8 ]
  • poly(amic)acid; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 34
  • [ 150314-48-0 ]
  • [ 13080-85-8 ]
  • poly(ether)amide, Mp = 64 kg/mol; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 35
  • [ 915414-52-7 ]
  • [ 13080-85-8 ]
  • poly(amic)acid; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 36
  • [ 915414-52-7 ]
  • [ 13080-85-8 ]
  • poly(ether)amide, Mp = 68 kg/mol; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 37
  • [ 61778-79-8 ]
  • [ 13080-85-8 ]
  • poly(ether)amide, Mp = 71 kg/mol; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 38
  • [ 915415-30-4 ]
  • [ 13080-85-8 ]
  • poly(ether)amide, Mp = 114 kg/mol; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 39
  • [ 13080-85-8 ]
  • [ 38103-06-9 ]
  • poly(amic)acid; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 40
  • [ 13080-85-8 ]
  • [ 38103-06-9 ]
  • poly(ether)amide, Mp = 130 kg/mol; monomer(s): 4,4\-bis(4\'\-aminophenoxy)biphenyl [ No CAS ]
  • 41
  • [ 393570-77-9 ]
  • [ 1823-59-2 ]
  • [ 13080-85-8 ]
  • polymer, elong = 9.5%; monomer(s): [2,4-bis(3-aminophenoxy)phenyl]diphenylphosphine oxide; 4,4'-oxydiphthalic dianhydride; 4,4'-bis(4-aminophenoxy)biphenyl [ No CAS ]
  • 42
  • [ 393570-77-9 ]
  • [ 13080-85-8 ]
  • [ 1107-00-2 ]
  • polymer, elong = 5.0%; monomer(s): [2,4-bis(3-aminophenoxy)phenyl]diphenylphosphine oxide; 6FDA; 4,4'-bis(4-aminophenoxy)biphenyl [ No CAS ]
  • 43
  • [ 13080-85-8 ]
  • [ 173393-55-0 ]
  • polyisophthalamide, synthesized by polycondensation of 5-(3,4,5,6-tetrachlorophthalimid-N-yl)isophthaloyl dichloride and aromatic diamine containing ether linkages, inherent viscosity 0.88 dl/g [ No CAS ]
  • 44
  • [ 13080-85-8 ]
  • [ 250267-73-3 ]
  • polyisophthalamide, synthesized by polycondensation of 5-(4-acetoxybenzamido)-isophthaloyl dichloride and aromatic diamine containing ether linkages, inherent viscosity 0.54 dl/g [ No CAS ]
  • 45
  • [ 873794-21-9 ]
  • [ 13080-85-8 ]
  • polymer, Mn=48000, Mw/Mn=1.74; monomer(s): bis[N-(3-carboxyphenyl)phthalimid-5-yl]dimethylsilane; 4,4'-bis(p-aminophenoxy)biphenyl [ No CAS ]
  • 46
  • [ 634585-36-7 ]
  • [ 13080-85-8 ]
  • polymer, Mn=92000, Mw/Mn=2.3; monomer(s): bis[N-(4-chlorocarbonylphenyl)phthalimid-5-yl]dimethylsilane; 4,4'-bis(p-aminophenoxy)biphenyl [ No CAS ]
  • 47
  • [ 13080-85-8 ]
  • N-(4-{4-[4-(4-anilinophenoxy)phenyl]phenoxy}phenyl)-2-methylaniline [ No CAS ]
  • 48
  • [ 883859-87-8 ]
  • [ 13080-85-8 ]
  • polymer; Mn = 41500; monomer(s): diacid chloride of 5-[N-(4-carboxyphenyl)succinimido]-3-methyl-[N-(4-carboxyphenyl)]-1,2,5,6-tetrahydrophthalimide; 4,4'-bis(p-aminophenoxy)-biphenyl [ No CAS ]
  • 49
  • [ 13080-85-8 ]
  • [ 500295-67-0 ]
YieldReaction ConditionsOperation in experiment
100% With sulfuric acid; at 50℃; Preparation of sulfonated BAPB [42] BAPB (11 g, 30 mmol) dissolved in 18 mL of sulfuric acid was charged into a round-bottom flask and kept at about 0 C with ice. 4.2 mL of fumed sulfuric acid was added to the flask dropwise. The reactant mixture was kept at 0 C for 0.5 h, heated to 50 C slowly, and then reacted at 50 C for 2 h. After being cooled to room temperature, the solution was poured into an excess ice-water mixture. The precipitate was collected with filtration, washed with water, and dried at 90 C under vacuum for 3 h. Sulfonated BAPB (sBAPB) was obtained with a yield of 100%. FTIR (KBr): 631, 1015, 1092, and 1177 cm-1 (-SO3H), 1470 cm-1 (trisubstituted phenyl group); 1H NMR (DMSO-d6, ppm): delta = 7.96 (2H), delta = 7.41 (2H), delta = 6.75 (4H), delta = 6.67 (2H), delta = 6.58 (4H), delta = 4.87 (4H).
  • 50
  • [ 23911-26-4 ]
  • [ 13080-85-8 ]
  • [ 1364601-70-6 ]
  • 51
  • [ 13080-85-8 ]
  • C32H24N2O14S2 [ No CAS ]
  • 52
  • [ 13080-85-8 ]
  • C32H22N2O12S2(2-)*2Na(1+) [ No CAS ]
  • 53
  • [ 13080-85-8 ]
  • [ 108-95-2 ]
  • 4,4'-bis(4-hydroxyphenyldiazenyl-4-phenoxy)biphenyl [ No CAS ]
  • 54
  • [ 17095-00-0 ]
  • [ 13080-85-8 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen; nickel; triethylamine; In ethyl acetate; at 20 - 60℃; under 11400.8 Torr;Inert atmosphere; In the 20 ~ 30 C nitrogen (50-80ml / min) protection,210 g of 4,4'-bis (4-nitrophenoxy) biphenyl was used as a starting material,Plus lg of triethylamine,16. 8 g ofNi, 840 ml of ethyl acetate at a pressure of 15 atm and a temperature of 40 to 60 C,The reaction was carried out for 5 to 8 hours and cooled to 20 to 30 C. The material was taken out, filtered, stripped of solvent and dried to obtain 178. 8 g of 4,4'-bis (4-aminophenoxy) biphenyl as a white solid powder,The purity was 99.91%
63% With hydrogenchloride; tin(ll) chloride; In water; at 60℃; for 3h; General procedure: Compound 3 (250 mg, 1.25 mmol) was dissolved in 20 mL of DMF and mixed with 1.5 g (10.21 mmol) of K2CO3 and 1.40 g (7.0 mmol) of 4-nitrobromobenzene. The reaction mixture was stirred at 120C for 12 h; H2O (50 mL) was added to quench the reaction. The separated crude product was purified by column chromatography (hexane : ethyl acetate, 6 : 4) affording 4a. The compound 4a (100 mg, 0.233 mmol) was reduced by stirring in a mixture with 15 mL of HCl and 315 mg (1.398 mmol) of SnCl2 at 60C for 3 h. Potassium carbonate (10 mL, 2 M) was added to quench the reaction. The isolated compound 4b was purified by column chromatography (CH2Cl2 : hexane, 3 : 7). Refluxing of compound 3 (50 mg, 0.25 mmol) with 345 mg (2.5 mmol) of K2CO3 and 0.21 mL (2 mmol) of dibromopropane in 15 mL of ethanol for 6 h gave the product 4c. The product was extracted by CH2Cl2 (50 mL) and purified by column chromatography (CH2Cl2 : hexane, 4 : 6). Compound 4d was obtained by refluxing a mixture of 100 mg (0.50 mmol) of compound 3 with K2CO3 (345 mg, 2.5 mmol) and propargyl bromide (0.2 mL, 2 mmol) in 20 mL of ethanol for 2 h.
  • 55
  • [ 13080-85-8 ]
  • [ 3127-08-0 ]
  • 1<SUP>3</SUP>,1<SUP>7</SUP>,8<SUP>3</SUP>,8<SUP>7</SUP>-tetraphenyl-3,6,10,13-tetraoxa-1,8(1,5)-di(1,5-diaza-3,7-diphosphacyclooctana)-2,4,5,7,9,11,12,14(1,4)-octabenzenacyclotetradecaphane [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.21 g In N,N-dimethyl-formamide; at 110℃; for 36h;Inert atmosphere; A mixture of phenylphosphine (0.48 g, 4.36 mmol) and paraformaldehyde (0.26 g,8.67 mmol) was heated at 100-110 C until homogenization. Then, the reaction mixture was dissolved in anhydrous degassed DMF (3 mL), followed by the addition of a solution of 4,4bis(4aminophenoxy)biphenyl (0.82 g, 2.22 mmol) in anhydrous degassed DMF (13 mL). The reaction mixture was stirred for 1.5 days at 110 C. A precipitate formed was filtered, washed once with DMF and three times with acetonitrile, and dried for 4 h at 0.1 Torr. The filtrate of the reaction mixture was concentrated in vacuo approximately to 1/4 of the initial volume. A precipitate formed subsequently was allowed to stand for 1 dayat -20 C, filtered, washed thrice with acetonitrile, recrystallized from DMF, and washed with acetonitrile. After drying, the powder obtained was combined with the first portion. The yield of compound 1 was 0.21 g (15%), m.p. 231 C. Found (%): C, 75.13;H, 5.68; N, 4.51; P, 9.46. C80H68N4O4P4. M = 1273.32. Calculated (%): C, 75.46; H, 5.38; N, 4.40; P, 9.73. MS FABpos, m/z(Irel (%)): 1273 [M + H]+ (96), 1289 [M + O + H]+ (100), 1305[M + 2 O + H]+ (76), 1321 [M + 3 O + H]+ (38). 1H NMR (DMSOd6), delta: 4.19 (dd, 8 H, H(1,1)eq, 2JHH = 13.7 Hz, 2JPH == 11.2 Hz); 4.59 (br.d, 8 H, H(1,1)ax, 2JHH = 13.7 Hz); 6.71 (d,8 H, H(3), 3JHH = 7.8 Hz); 6.96 (d, 4 H, H(7), 3JHH = 7.8 Hz);6.98 (d, 4 H, H(7), 3JHH = 7.8 Hz); 7.04 (d, 8 H, H(4), 3JHH == 7.8 Hz); 7.40-7.55 (m, 12 H, H(11,13)); 7.57 (d, 8 H, H(8,8),3JHH = 7.8 Hz); 7.61-7.70 (m, 8 H, H(12)). 31P{1H} NMR (DMSOd6), delta: -51.20 (s). 31P{1H} NMR (DMF), delta: -50.18 (s).
  • 56
  • [ 13080-85-8 ]
  • (1R,3R,4S)-(-)-Di(hydroxymethyl)menthylphosphan [ No CAS ]
  • 1<SUP>3</SUP>,1<SUP>7</SUP>,8<SUP>3</SUP>,8<SUP>7</SUP>-tetra(l-menthyl)-3,6,10,13-tetraoxa-1,8(1,5)-di(1,5-diaza-3,7-diphosphacyclooctana)-2,4,5,7,9,11,12,14(1,4)-octabenzenacyclotetradecaphane [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.57 g In toluene; at 100℃; for 60h;Inert atmosphere; A mixture of menthylphosphine (1.01 g, 5.87 mmol) and paraformaldehyde (0.35 g,11.66 mmol) was heated at 110-115 C until homogenization. Then, the dense liquid obtained was dissolved in anhydrous degassed toluene (5 mL). 4,4Bis(4aminophenoxy)biphenyl(1.08 g, 2.93 mmol) in toluene (28 mL) was added to the warmedup suspension, the reaction mixture was stirred for 2.5 days at100 C. A precipitate formed was filtered, washed once with toluene, then thrice with acetonitrile, and dried for 4 h at 0.1 Torr.The yield of compound 2 was 0.57 g (24%), m.p. 200-204 C.Found (%): C, 75.41; H, 8.37; N, 3.81; P, 8.25. C96H124N4O4P4.M = 1521.93. Calculated (%): C, 75.76; H, 8.21; N, 3.68;P, 8.14. MS ESIpos, m/z (Irel. (%)): 1521 [M + H]+ (100). 1H NMR (CDCl3), delta: 0.75 (d, 12 H, H(18), 3JHH = 5.9 Hz); 0.86-1.08(m, 32 H, Hment + H(17,19)); 1.09-1.20 (m, 4 H, Hment);1.32-1.48 (m, 8 H, Hment); 1.58-1.88 (m, 16 H, Hment); 2.66-2.79(m, 4 H, H(16)); 3.62 (d, 4 H, H(1)ax, 2JHH = 15.6 Hz); 3.77(d, 4 H, H(1)ax, 2JHH = 15.7 Hz); 4.30 (br.d, 4 H, H(1)eq,2JHH = 15.6 Hz); 4.47 (dd, 4 H, H(1)eq, 2JHH = 15.7 Hz,2JPH = 4.1 Hz); 6.55 (d, 8 H, H(3), 3JHH = 8.3 Hz); 6.96 (d, 8 H,H(4), 3JHH = 8.3 Hz); 7.02 (d, 8 H, H(7,7), 3JHH = 8.3 Hz);7.52 (d, 8 H, H(8,8), 3JHH = 8.3 Hz). 1H NMR (CDCl3-DMSOd6, 9 : 1), delta: 0.76 (d, 12 H, H(18), 3JHH = 6.8 Hz);0.90-0.99 (m, 8 H, Hment); 0.92 (d, 12 H, H(19), 3JHH = 6.3 Hz);0.94 (d, 12 H, H(17), 3JHH = 6.8 Hz); 1.00-1.08 (m, 4 H,Hment); 1.10-1.20 (m, 4 H, Hment); 1.35-1.46 (m, 8 H, Hment);1.67-1.75 (m, 4 H, Hment); 1.75-1.84 (m, 8 H, Hment); 2.66-2.74(m, 4 H, H(16)); 3.66 (dd, 4 H, H(1)ax, 2JHH = 15.7 Hz, 2JPH == 3.2 Hz); 3.82 (br.d, 4 H, H(1)ax, 2JHH = 15.3 Hz); 4.27 (dd, 4 H,H(1)eq, 2JHH = 15.3 Hz, 2JPH = 5.9 Hz); 4.44 (dd, 4 H, H(1)eq,2JHH = 15.7 Hz, 2JPH = 6.8 Hz); 6.53 (d, 8 H, H(3), 3JHH = 9.0 Hz);6.93 (d, 8 H, H(4), 3JHH = 9.0 Hz); 7.01 (d, 8 H, H(7,7),3JHH = 8.6 Hz); 7.52 (d, 8 H, H(8,8), 3JHH = 8.6 Hz). 31P{1H}NMR (CDCl3), delta: -46.54 (s). 31P{1H} NMR (toluene), delta: -50.48(s). [alpha]D20 -63 (c 0.3677, CHCl3).
  • 57
  • [ 75-15-0 ]
  • [ 13080-85-8 ]
  • C26H20N2O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; at 20℃; for 0.5h; General procedure: Diisothiocyanates (compound 4-18) were prepared accordingto the reported procedure [22] with some modifications.CS2 (6.68 g, 88 mmol) and Et3N (888 mg, 8.80 mmol)were added into a solution of the diamine (4.40 mmol) inabsolute ethanol or THF (10 mL). The reaction mixture wasstirred at room temperature for about 30 min or until the diaminewas completely consumed (monitored by TLC). Themixture was then cooled down on an ice bath. Boc2O (1.9 g,8.72 mmol) and DMAP (1 mol%) were added. The reactionmixture was kept in an ice bath for 5 min and allowed toslowly reach room temperature. The reaction mixture wasfurther stirred at room temperature and monitored by TLC.After completion, the mixture was evaporated thoroughly invacuo. The residue was purified by silica gel column chromatographyto yield the desired product. The product structureswere characterized by nuclear magnetic resonance(NMR) and High-Resolution Mass Spectrometry (HRMS)based techniques. The 1H- and 13C-NMR spectra were obtainedon a Bruker NMR spectrometer at 400 and 100 MHzrespectively. The data is reported as follows: chemical shiftsare reported relative to internal chloroform (delta 7.26 for 1H, delta77.15 for 13C) in ppm (delta), multiplicity (s = singlet, d = doublet,dd = doublet of doublets, t = triplet, q=quartet, p= pentet,m = multiplet). Coupling constant (J) are reported inHertz (Hz) and were generated using NMR analyzer software(MestReNova). The HRMS spectra were recorded on Orbitrap FusionTM TribridTM mass spectrometer, ThermoScientificTM.
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  • [ 13080-85-8 ]
  • 4,4'-bis(4-isothiocyanatophenoxy)-1,1'-biphenyl [ No CAS ]
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