Product Name

  • Name

    2,5-DIMETHOXY-BETA-NITROSTYRENE

  • EINECS
  • CAS No. 40276-11-7
  • Article Data10
  • CAS DataBase
  • Density 1.197g/cm3
  • Solubility
  • Melting Point 116-120 °C(lit.)
  • Formula C10H11NO4
  • Boiling Point 350.8oC at 760mmHg
  • Molecular Weight 209.202
  • Flash Point 163.2oC
  • Transport Information
  • Appearance orange crystalline powder
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 40276-11-7 (2,5-DIMETHOXY-BETA-NITROSTYRENE)
  • Hazard Symbols
  • Synonyms Styrene,2,5-dimethoxy-b-nitro-(6CI,7CI);2,5-Dimethoxy-b-nitrostyrene;NSC 158921;NSC 610188;
  • PSA 64.28000
  • LogP 2.47440

Synthetic route

nitromethane
75-52-5

nitromethane

2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

Conditions
ConditionsYield
With ethylenediamine diacetic acid In isopropyl alcohol at 20℃; for 24h;92%
With potassium hydroxide; ethanol Behandeln des Reaktionsproduktes mit Salzsaeure;
(i) Et3N, (ii) NaOAc, Ac2O; Multistep reaction;
nitromethane
75-52-5

nitromethane

ethanol
64-17-5

ethanol

2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

methanolic KOH-solution

methanolic KOH-solution

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

...Expand
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

(E)-ethyl 2-hydroxy-4-(2,5-dimethoxyphenyl)-3-nitrobut-3-enoate

(E)-ethyl 2-hydroxy-4-(2,5-dimethoxyphenyl)-3-nitrobut-3-enoate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 0.0833333h; Morita-Baylis-Hillman reaction;99%
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

5-(2,5-dimethoxyphenyl)-1H-1,2,3-triazole

5-(2,5-dimethoxyphenyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
With sodium azide; acetic acid In N,N-dimethyl-formamide at 200℃; Sealed tube;91%
1-benzyl-2,3-dihydro-1H-indole
6037-73-6

1-benzyl-2,3-dihydro-1H-indole

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

(±)-1-benzyl-5-(1-(2,5-dimethoxyphenyl)-2-nitroethyl)indoline

(±)-1-benzyl-5-(1-(2,5-dimethoxyphenyl)-2-nitroethyl)indoline

Conditions
ConditionsYield
Stage #1: (E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene With zinc trifluoromethanesulfonate In ethanol at 20℃; for 0.5h;
Stage #2: 1-benzyl-2,3-dihydro-1H-indole In ethanol at 20℃; for 12.08h;		89%
indole
120-72-9

indole

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

3-(1-(2,5-dimethoxyphenyl)-2-nitroethyl)-1H-indole
1335106-54-1

3-(1-(2,5-dimethoxyphenyl)-2-nitroethyl)-1H-indole

Conditions
ConditionsYield
With C84H114F9N3O12S3 In water at 37℃; for 16h; Michael Addition;88%
With graphite oxide In tetrahydrofuran; water at 20℃; for 36h; Friedel Crafts addition;40%
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

methyl (E)-4-(((2-nitrophenyl)sulfonamido)oxy)but-2-enoate

methyl (E)-4-(((2-nitrophenyl)sulfonamido)oxy)but-2-enoate

methyl 2-((3R,4S,5S)-3-(2,5-dimethoxyphenyl)-4-nitro-2-((2-nitrophenyl)sulfonyl)-1,2-oxazinan-5-yl)acetate

methyl 2-((3R,4S,5S)-3-(2,5-dimethoxyphenyl)-4-nitro-2-((2-nitrophenyl)sulfonyl)-1,2-oxazinan-5-yl)acetate

Conditions
ConditionsYield
Stage #1: methyl (E)-4-(((2-nitrophenyl)sulfonamido)oxy)but-2-enoate With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinu clidin-2-yl)methyl)thiourea In toluene for 0.0833333h; Sealed tube;
Stage #2: (E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene In toluene at 20℃; for 144h; Sealed tube; stereoselective reaction;		87%
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2-sulfanylpyrimidine
131242-36-9

2-sulfanylpyrimidine

2-((1-(2,5-dimethoxyphenyl)-2-nitroethyl)thio)pyrimidine

2-((1-(2,5-dimethoxyphenyl)-2-nitroethyl)thio)pyrimidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h; Michael Addition;85%
(E)-4-phenyl-2-butenal
55177-35-0

(E)-4-phenyl-2-butenal

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2-((1R,2S,3R,4R)-3-(2,5-dimethoxyphenyl)-2-nitro-4-phenylcyclobutyl)acetaldehyde
1356935-68-6

2-((1R,2S,3R,4R)-3-(2,5-dimethoxyphenyl)-2-nitro-4-phenylcyclobutyl)acetaldehyde

Conditions
ConditionsYield
With diethylacetamide; (S)-3-(3,5-bis(trifluoromethyl)phenylamino)-4-(pyrrolidin-2-ylmethylamino)cyclobut-3-ene-1,2-dione; water In dichloromethane at 20℃; for 40h; optical yield given as %ee; stereoselective reaction;83%
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

(benzoylmethylene)dimethylsulfurane
5633-34-1

(benzoylmethylene)dimethylsulfurane

A

(4R,5S)-5-benzoyl-4-(2,5-dimethoxyphenyl)oxazolidin-2-one
1380095-15-7

(4R,5S)-5-benzoyl-4-(2,5-dimethoxyphenyl)oxazolidin-2-one

B

(4S,5R)-5-Benzoyl-4-(2,5-dimethoxyphenyl)oxazolidin-2-one

(4S,5R)-5-Benzoyl-4-(2,5-dimethoxyphenyl)oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene With dmap; 1,1'-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)urea); o-chlorophenylthiourea In 5,5-dimethyl-1,3-cyclohexadiene at -35℃; for 0.5h;
Stage #2: (benzoylmethylene)dimethylsulfurane In 5,5-dimethyl-1,3-cyclohexadiene at -35 - 35℃; for 120h; optical yield given as %ee; enantioselective reaction;		A 83%
B n/a
...Expand
1-benzyl-2-methylindoline
954-89-2

1-benzyl-2-methylindoline

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

1-benzyl-5-(1-(2,5-dimethoxyphenyl)-2-nitroethyl)-2-methylindoline

1-benzyl-5-(1-(2,5-dimethoxyphenyl)-2-nitroethyl)-2-methylindoline

Conditions
ConditionsYield
Stage #1: (E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene With zinc trifluoromethanesulfonate In ethanol at 20℃; for 0.5h;
Stage #2: 2-methyl-1-benzylindoline In ethanol at 20℃; for 12.08h;		83%
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2,5-dimethoxyphenethylamine
3600-86-0

2,5-dimethoxyphenethylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;76%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;55%
With hydrogenchloride; ethanol; acetic acid bei der Reduktion an Blei-Elektroden;
Bromoform
75-25-2

Bromoform

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2-(1,1,1-tribromo-3-nitropropan-2-yl)-1,4-dimethoxybenzene
1133892-33-7

2-(1,1,1-tribromo-3-nitropropan-2-yl)-1,4-dimethoxybenzene

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at 0 - 20℃; for 0.666667h; Michael condensation;74%
methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

C14H14F3NO7
1190132-28-5

C14H14F3NO7

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 4h; Morita-Baylis-Hillman reaction;71%
2-(cyclohexylidene)malononitrile
4354-73-8

2-(cyclohexylidene)malononitrile

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2-(2-(1-(2,5-dimethoxyphenyl)-2-nitroethyl)cyclohexylidene)malononitrile

2-(2-(1-(2,5-dimethoxyphenyl)-2-nitroethyl)cyclohexylidene)malononitrile

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃;45%
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2-oxopropanal
78-98-8

2-oxopropanal

(E)-3-hydroxy-5-(2,5-dimethoxyphenyl)-4-nitropent-4-en-2-one

(E)-3-hydroxy-5-(2,5-dimethoxyphenyl)-4-nitropent-4-en-2-one

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 48h; Morita-Baylis-Hillman reaction;32%
2-nitropropane
79-46-9

2-nitropropane

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2,5-Dimethoxy-1-<1,3-dinitro-3-methyl-butyl-2>-benzol
10125-70-9

2,5-Dimethoxy-1-<1,3-dinitro-3-methyl-butyl-2>-benzol

Conditions
ConditionsYield
With piperidine In ethanol
1,1-dinitroethane
600-40-8

1,1-dinitroethane

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2,5-Dimethoxy-1-(1,3,3-trinitro-butyl-2)-benzol
10125-71-0

2,5-Dimethoxy-1-(1,3,3-trinitro-butyl-2)-benzol

Conditions
ConditionsYield
With piperidine In ethanol
1,1-dinitropropane
601-76-3

1,1-dinitropropane

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2,5-Dimethoxy-1-<1,3,3-trinitro-pentyl-2>-benzol
10125-72-1

2,5-Dimethoxy-1-<1,3,3-trinitro-pentyl-2>-benzol

Conditions
ConditionsYield
With piperidine In ethanol
L-Cysteine
52-90-4

L-Cysteine

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

(R)-2-Amino-3-[1-(2,5-dimethoxy-phenyl)-2-nitro-ethylsulfanyl]-propionic acid

(R)-2-Amino-3-[1-(2,5-dimethoxy-phenyl)-2-nitro-ethylsulfanyl]-propionic acid

Conditions
ConditionsYield
With triethylamine In methanol; water
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

3-(2,5-Dimethoxyphenyl)-N,N-dimethyl-4-nitrobutyramid
33877-55-3

3-(2,5-Dimethoxyphenyl)-N,N-dimethyl-4-nitrobutyramid

Conditions
ConditionsYield
(i) LDA, THF, hexane, (ii) /BRN= 2505663/, AcOH; Multistep reaction;
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2,5-dihydroxyphenylethylamine
21581-41-9

2,5-dihydroxyphenylethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / LiAlH4 / tetrahydrofuran / Heating
2: BBr3 / CH2Cl2 / 48 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: LiAlH4; diethyl ether / 170 °C
2: aqueous HBr / auf Siedetemperatur
View Scheme
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

1-(2,5-dimethoxy-4-aminophenyl)-2-(acetylamino)ethane
88441-02-5

1-(2,5-dimethoxy-4-aminophenyl)-2-(acetylamino)ethane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 76 percent / LiAlH4 / tetrahydrofuran / Heating
2: 80 percent / acetic acid, nitric acid / 1 h / 0 °C
3: 48 percent / concd HCl, Sn / 1 h / Heating
View Scheme
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

1-(2,5-dimethoxy-4-nitrophenyl)-2-(acetylamino)ethane
88441-00-3

1-(2,5-dimethoxy-4-nitrophenyl)-2-(acetylamino)ethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / LiAlH4 / tetrahydrofuran / Heating
2: 80 percent / acetic acid, nitric acid / 1 h / 0 °C
View Scheme
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2-(2-aminoethyl)-5-nitrohydroquinone
41241-39-8

2-(2-aminoethyl)-5-nitrohydroquinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 76 percent / LiAlH4 / tetrahydrofuran / Heating
2: 80 percent / acetic acid, nitric acid / 1 h / 0 °C
3: 48percent aq. HBr / 6 h / Heating
View Scheme
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

1-(4-amino-2,5-dihydroxyphenyl)-2-ethylamine
41241-40-1

1-(4-amino-2,5-dihydroxyphenyl)-2-ethylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76 percent / LiAlH4 / tetrahydrofuran / Heating
2: 80 percent / acetic acid, nitric acid / 1 h / 0 °C
3: 48 percent / concd HCl, Sn / 1 h / Heating
4: 48percent aq. HBr / 6 h / Heating
View Scheme
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

methyl-1 dihydro-3,4 dimethoxy-5,8 isoquinoleine
105901-26-6

methyl-1 dihydro-3,4 dimethoxy-5,8 isoquinoleine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous hydrochloric acid; ethanol; acetic acid / bei der Reduktion an Blei-Elektroden
3: phosphoryl chloride; benzene
View Scheme
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

N-<2-(2,5-dimethoxyphenyl)ethyl>acetamide
106274-40-2

N-<2-(2,5-dimethoxyphenyl)ethyl>acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous hydrochloric acid; ethanol; acetic acid / bei der Reduktion an Blei-Elektroden
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux
2: triethylamine / dichloromethane; methanol / 20 °C
View Scheme
(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene
40276-11-7

(E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene

2-(2,5-dimethoxy-phenyl)-N4,N4-dimethyl-butanediyldiamine
46880-50-6

2-(2,5-dimethoxy-phenyl)-N4,N4-dimethyl-butanediyldiamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) LDA, THF, hexane, (ii) /BRN= 2505663/, AcOH
2: LiAlH4
View Scheme

2,5-Dimethoxy-beta-nitrostyrene Specification

The Benzene,1,4-dimethoxy-2-(2-nitroethenyl)-, with CAS registry number 40276-11-7, has the systematic name of 1,4-dimethoxy-2-[(E)-2-nitroethenyl]benzene. This chemical is a kind of orange crystalline powder. When use this chemical, do not breathe dust and avoid contact with skin and eyes.

Physical properties of Benzene,1,4-dimethoxy-2-(2-nitroethenyl)-: (1)ACD/LogP: 2.18; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 5; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 64.28 Å2; (7)Index of Refraction: 1.564; (8)Molar Refractivity: 56.88 cm3; (9)Molar Volume: 174.6 cm3; (10)Polarizability: 22.55×10-24cm3; (11)Surface Tension: 41.1 dyne/cm; (12)Enthalpy of Vaporization: 57.2 kJ/mol; (13)Vapour Pressure: 8.66E-05 mmHg at 25°C.

Uses of p-Chloropropiophenone: it can be used to produce 2,5-dimethoxy-phenethylamine. This reaction will need reagents aqueous hydrochloric acid, ethanol, acetic acid.

You can still convert the following datas into molecular structure:
(1)SMILES: [O-][N+](=O)\C=C\c1cc(OC)ccc1OC
(2)InChI: InChI=1/C10H11NO4/c1-14-9-3-4-10(15-2)8(7-9)5-6-11(12)13/h3-7H,1-2H3/b6-5+
(3)InChIKey: IRRZIWHEPWPPJF-AATRIKPKBS
(4)Std. InChI: InChI=1S/C10H11NO4/c1-14-9-3-4-10(15-2)8(7-9)5-6-11(12)13/h3-7H,1-2H3/b6-5+
(5)Std. InChIKey: IRRZIWHEPWPPJF-AATRIKPKSA-N

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