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821-11-4

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821-11-4 Usage

Chemical Properties

Light yellow liquid

Uses

trans-2-Butene-1,4-diol can be used as an extender in polyurethanes and as a catalyst precursor in the preparation of α,ω,kentro-telechelic poly(THF).

Check Digit Verification of cas no

The CAS Registry Mumber 821-11-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 1 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 821-11:
(5*8)+(4*2)+(3*1)+(2*1)+(1*1)=54
54 % 10 = 4
So 821-11-4 is a valid CAS Registry Number.
InChI:InChI=1S/C4H8O2/c5-3-1-2-4-6/h1-2,5-6H,3-4H2/b2-1+

821-11-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-BUTENE-1,4-DIOL

1.2 Other means of identification

Product number -
Other names (E)-2-butene-1,4-diol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:821-11-4 SDS

821-11-4Synthetic route

1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 48h; Inert atmosphere;100%
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reduction; Heating;99%
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Heating;90%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

A

trans-4-Octene
14850-23-8

trans-4-Octene

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With C37H40Cl2N2ORuS2 In tetrahydrofuran-d8 at 45℃; for 1h; Inert atmosphere;A 100%
B 100%
allyl alcohol
107-18-6

allyl alcohol

(R)-3-allylsulfanyl-2-tert-butoxycarbonylaminopropionic acid methyl ester
232953-12-7

(R)-3-allylsulfanyl-2-tert-butoxycarbonylaminopropionic acid methyl ester

A

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

B

C13H23NO5S
1043521-67-0

C13H23NO5S

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst second generation In water; tert-butyl alcohol at 32℃; for 2.5h; optical yield given as %de;A 99%
B 56%
trans-1,4-diacetoxy-2-butene
1576-98-3

trans-1,4-diacetoxy-2-butene

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether; water In ethanol for 16h; Inert atmosphere; Reflux;98%
With hydrogenchloride In ethanol; water at 80℃; for 12h;72%
Trifluoro-acetic acid (E)-4-(2,2,2-trifluoro-acetoxy)-but-2-enyl ester

Trifluoro-acetic acid (E)-4-(2,2,2-trifluoro-acetoxy)-but-2-enyl ester

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With silica gel; triethylamine In diethyl ether; Petroleum ether Substitution; Detrifluoroacetylation;95%
(E)-1,4-bis(2-tetrahydropyranyloxy)-2-butene

(E)-1,4-bis(2-tetrahydropyranyloxy)-2-butene

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol at 20℃; for 0.16h;95%
diethyl Fumarate
623-91-6

diethyl Fumarate

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at 20℃; for 12h;79%
With diisobutylaluminium hydride In toluene at 20℃; Inert atmosphere;60%
With diethylaluminium hydride; benzene
With diisobutylaluminium hydride; benzene
With diisobutylaluminium hydride In hexane; benzene at 5 - 20℃; for 3h;
butyne-1,4-diol
628-23-9

butyne-1,4-diol

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 12.3333h; Inert atmosphere;67%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 12h;67%
allyl alcohol
107-18-6

allyl alcohol

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst second generation; 5,17-bis[(3-(2,6-diisopropylphenyl)imidazolium)methyl]-25,26,27,28-tetrapropoxycalix[4]arene dichloride In water at 45℃; for 24h; optical yield given as %de;54%
methylene-pyridinium-tagged Hoveyda-Grubbs pre-catalyst at 25℃; for 3.5h;99 % Chromat.
epoxybutene
930-22-3

epoxybutene

A

3,4-butenediol
497-06-3

3,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With water
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

A

3,4-butenediol
497-06-3

3,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With sodium carbonate
With sodium carbonate at 90 - 95℃;
(E)-1,4-dibromobutene
821-06-7

(E)-1,4-dibromobutene

A

3,4-butenediol
497-06-3

3,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With sodium carbonate at 90 - 95℃;
(E)-1,4-dibromobutene
821-06-7

(E)-1,4-dibromobutene

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With water; lead(II) oxide
With lead(II) oxide In water Heating;
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
Acetylenedicarboxylic acid
142-45-0

Acetylenedicarboxylic acid

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
buta-1,3-diene
106-99-0

buta-1,3-diene

A

3,4-butenediol
497-06-3

3,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With sodium perchlorate In water; acetonitrile (electrolysis);
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With hydrogen; ruthenium palladium In propan-1-ol at 89.9℃; Rate constant;
With hydrogen; copper(II) sulfate; nickel In ammonium hydroxide; water at 40℃; under 5250.4 Torr; Title compound not separated from byproducts;
With hydrogen In isopropyl alcohol at 30℃; under 7500.75 Torr; for 1h; Autoclave; optical yield given as %de; stereoselective reaction;
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Formic acid (2S,3S)-4-formyloxy-2,3-dihydroxy-butyl ester

Formic acid (2S,3S)-4-formyloxy-2,3-dihydroxy-butyl ester

A

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

B

(R)-(+)-3,4-dihydroxy-1-butene
86106-09-4

(R)-(+)-3,4-dihydroxy-1-butene

Conditions
ConditionsYield
With sodium methylate In methanol Ambient temperature; Yield given;
dimethylfumarate
624-49-7

dimethylfumarate

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene 1.) -78 deg C, 90 min, 2.) 0 deg C, 30 min;
With diisobutylaluminium hydride In toluene at -10 - 20℃; for 18h;
With diisobutylaluminium hydride In toluene at -10 - 20℃; for 18h;
dl-2,3-dibromo-1,4-butanediol
1947-58-6

dl-2,3-dibromo-1,4-butanediol

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With samarium In methanol for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
epoxybutene
930-22-3

epoxybutene

A

2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

B

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

C

3,4-butenediol
497-06-3

3,4-butenediol

D

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

E

4-iodo-2-butene-1-ol

4-iodo-2-butene-1-ol

Conditions
ConditionsYield
With potassium iodide; USY zeolite In various solvent(s) at 74.85℃; for 24h; Product distribution; Mechanism; var. nucleophiles and acids; var. solv. and time;
diethyl ether
60-29-7

diethyl ether

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

lithium alanate

lithium alanate

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

diethyl ether
60-29-7

diethyl ether

Acetylenedicarboxylic acid
142-45-0

Acetylenedicarboxylic acid

lithium alanate

lithium alanate

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

palladium/charcoal

palladium/charcoal

ethanolic NaOH-solution

ethanolic NaOH-solution

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

ethanol
64-17-5

ethanol

Raney nickel

Raney nickel

A

2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

C

1,4-butenediol
6117-80-2

1,4-butenediol

D

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
Produkt5: But-2ξ-en-1-ol.Hydrogenation;
diacetate of trans-butene-(2)-diol-(1.4)

diacetate of trans-butene-(2)-diol-(1.4)

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With barium dihydroxide
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

aqueous natrium carbonate

aqueous natrium carbonate

A

3,4-butenediol
497-06-3

3,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

1-chloro-2-hydroxy-3-butene
671-56-7

1-chloro-2-hydroxy-3-butene

NaHCO3

NaHCO3

A

epoxybutene
930-22-3

epoxybutene

B

3,4-butenediol
497-06-3

3,4-butenediol

C

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(E)-1,4-ditosyloxybut-2-ene
49837-05-0

(E)-1,4-ditosyloxybut-2-ene

Conditions
ConditionsYield
With sodium t-butanolate In tetrahydrofuran at 0 - 20℃;100%
With sodium t-butanolate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;82%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In 1,4-dioxane at -3 - 20℃; for 3.5h;
With sodium t-butanolate
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

acetic anhydride
108-24-7

acetic anhydride

trans-1-hydroxy-4-acetoxy-2-butene
27977-16-8, 64196-68-5, 70940-89-5

trans-1-hydroxy-4-acetoxy-2-butene

Conditions
ConditionsYield
With pyridine at 20℃; for 24h;95%
With sodium hydride In tetrahydrofuran Ambient temperature;70%
Stage #1: trans-butene-1,4-diol With pyridine In toluene for 0.166667h;
Stage #2: acetic anhydride In toluene at 0 - 20℃; for 24h;
45%
In pyridine
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

(E)-1,4-bis(2-tetrahydropyranyloxy)-2-butene

(E)-1,4-bis(2-tetrahydropyranyloxy)-2-butene

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In dichloromethane at 20℃; for 0.5h;95%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

benzyl bromide
100-39-0

benzyl bromide

(E)-1,4-bis(benzyloxy)-2-butene
68972-93-0

(E)-1,4-bis(benzyloxy)-2-butene

Conditions
ConditionsYield
Stage #1: trans-butene-1,4-diol With sodium hydride In tetrahydrofuran at 0℃; for 3.5h; Inert atmosphere; Reflux;
Stage #2: benzyl bromide In tetrahydrofuran for 3.5h; Inert atmosphere; Reflux;
93%
Stage #1: trans-butene-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Reflux;
Stage #2: benzyl bromide In tetrahydrofuran for 3.5h; Inert atmosphere; Reflux;
91%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

4-biphenyl-carboxylic acid chloride
14002-51-8

4-biphenyl-carboxylic acid chloride

Biphenyl-4-carboxylic acid (E)-4-hydroxy-but-2-enyl ester

Biphenyl-4-carboxylic acid (E)-4-hydroxy-but-2-enyl ester

Conditions
ConditionsYield
With pyridine at 20℃; for 72h;92%
C-(N-tert-butoxycarbonylamino)methanol
365572-48-1

C-(N-tert-butoxycarbonylamino)methanol

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

C10H17NO3

C10H17NO3

Conditions
ConditionsYield
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In N,N-dimethyl acetamide at 100℃; Schlenk technique; Inert atmosphere; enantioselective reaction;92%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

trichloroacetonitrile
545-06-2

trichloroacetonitrile

C8H8Cl6N2O2
1256294-08-2

C8H8Cl6N2O2

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at -5℃; for 1h; Molecular sieve;91%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

diethyl octa-2(E),4(E),6(E)-triene-1,8-dioate
5941-43-5

diethyl octa-2(E),4(E),6(E)-triene-1,8-dioate

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 10h;90%
With Dess-Martin periodane; benzoic acid In dichloromethane; dimethyl sulfoxide at 20℃; for 0.5h;64%
methanol
67-56-1

methanol

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

1,4-dihydroxy-3-iodo-2-methoxybutane

1,4-dihydroxy-3-iodo-2-methoxybutane

Conditions
ConditionsYield
With dihydrogen peroxide; iodine at 20℃; for 12h;90%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(E)-4-[(tert-butyldimethylsilyl)oxy]-2-buten-1-ol
91202-69-6

(E)-4-[(tert-butyldimethylsilyl)oxy]-2-buten-1-ol

Conditions
ConditionsYield
Stage #1: trans-butene-1,4-diol With sodium hydride In tetrahydrofuran at 20℃; for 0.75h;
Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 0.75h; Further stages.;
89%
In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;89%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;89%
1H-imidazole
288-32-4

1H-imidazole

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(E)-4-[(tert-butyldimethylsilyl)oxy]-2-buten-1-ol
91202-69-6

(E)-4-[(tert-butyldimethylsilyl)oxy]-2-buten-1-ol

Conditions
ConditionsYield
In N,N-dimethyl-formamide89%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

propargyl bromide
106-96-7

propargyl bromide

(E)-1,4-bis(prop-2-yn-1-yloxy)but-2-ene
116938-78-4

(E)-1,4-bis(prop-2-yn-1-yloxy)but-2-ene

Conditions
ConditionsYield
Stage #1: trans-butene-1,4-diol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene; mineral oil for 2h; Inert atmosphere;
89%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

benzyl bromide
100-39-0

benzyl bromide

(E)-4-(benzyloxy)-2-buten-1-ol
80885-30-9, 81028-03-7, 69152-88-1

(E)-4-(benzyloxy)-2-buten-1-ol

Conditions
ConditionsYield
Stage #1: trans-butene-1,4-diol With sodium hydride In tetrahydrofuran at 20℃; for 1.5h;
Stage #2: benzyl bromide In tetrahydrofuran for 1h; Reflux;
88.8%
Stage #1: trans-butene-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran; mineral oil at 0 - 75℃; for 1h; Inert atmosphere;
87%
With sodium hydride In N,N-dimethyl-formamide85%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol
92808-78-1

(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;88%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 20h;56%
With 1H-imidazole at 0℃; for 15h;48%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

2-(phenylsulfonyl)acetonitrile
7605-28-9

2-(phenylsulfonyl)acetonitrile

1-phenylsulfonyl-1-cyano-2-vinylcyclopropane

1-phenylsulfonyl-1-cyano-2-vinylcyclopropane

Conditions
ConditionsYield
With 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane In tetrahydrofuran at 22℃; for 4h;88%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

acrylonitrile
107-13-1

acrylonitrile

(E)-3,3'-(but-2-ene-1,4-diylbis(oxy))dipropanenitrile

(E)-3,3'-(but-2-ene-1,4-diylbis(oxy))dipropanenitrile

Conditions
ConditionsYield
With potassium tert-butylate In neat (no solvent) at 20℃; for 0.333333h; Michael Addition; Inert atmosphere;88%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

1,2,4-trihydroxy-3-iodobutane

1,2,4-trihydroxy-3-iodobutane

Conditions
ConditionsYield
With dihydrogen peroxide; iodine In acetonitrile at 20℃; for 13h;87%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

2-[(E)-4-hydroxybut-2-enyloxy]cyclohexanol

2-[(E)-4-hydroxybut-2-enyloxy]cyclohexanol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h;87%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

3-chloro-3-oxopropanoic acid methyl ester
37517-81-0

3-chloro-3-oxopropanoic acid methyl ester

2,2'-(2E)-but-2-ene-1,4-diyl 3,3'-dimethyl dimalonate
915234-98-9

2,2'-(2E)-but-2-ene-1,4-diyl 3,3'-dimethyl dimalonate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 1h;87%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Zn(CD2I)2*DME

Zn(CD2I)2*DME

(R,R)-2,2-dideuterio-1,3-cyclopropanedimethanol
883223-46-9

(R,R)-2,2-dideuterio-1,3-cyclopropanedimethanol

Conditions
ConditionsYield
With (4S,5S)-2-butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide In dichloromethane at -45 - 20℃; Charette cyclopropanation;86%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

methyl iodide
74-88-4

methyl iodide

(E)-1,4-dimethoxy-2-butene
22805-71-6

(E)-1,4-dimethoxy-2-butene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 25℃; for 25h;86%
Stage #1: trans-butene-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 5℃; for 1.33333h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 16 - 19℃; for 16.5h;
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

2-bromoisobutyric acid bromide
20769-85-1

2-bromoisobutyric acid bromide

A

1,2-bis(bromoisobutrylyoxy)-2-butene

1,2-bis(bromoisobutrylyoxy)-2-butene

B

1,2-bis(bromoisobutyryloxy)-2-butene

1,2-bis(bromoisobutyryloxy)-2-butene

Conditions
ConditionsYield
With triethylamine In tetrahydrofuranA n/a
B 85%
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

1-iodononane
4282-42-2

1-iodononane

C22H44O2

C22H44O2

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 80℃; for 72h;85%

821-11-4Relevant articles and documents

Electrolytic reduction of 2-butyne-1,4-diol as a route to trans-2-butene-1,4-diol

Pyatnitsyna,El'chaninov,Savost'yanov

, p. 2037 - 2038 (2006)

The effect of the cathode material on the electrochemical transformations of 2-butyne-1,4-diol at atmospheric pressure was studied by chromatographic analysis. The optimal parameters of the selective synthesis of trans-2-butene-1,4-diol were determined.

Design and synthesis of a nucleoside and a phosphonate analogue constructed on a branched-threo-tetrofuranose skeleton

Kiran,Wakamatsu, Hideaki,Natori, Yoshihiro,Takahata, Hiroki,Yoshimura, Yuichi

, p. 3949 - 3952 (2013)

The synthesis of a novel nucleoside phosphonate constructed on a branched-threo-tetrofuranose scaffold, as a potential antiviral agent, is described. The pseudosugar moiety served as the nucleoside skeleton was produced starting from 2-butyne-1,4-diol in

Stereochemistry-Controlled Mechanical Properties and Degradation in 3D-Printable Photosets

Becker, Matthew L.,Dove, Andrew P.,Khalfa, Anissa L.

supporting information, p. 17510 - 17516 (2021/11/04)

Stereochemistry provides an appealing handle by which to control the properties of small molecules and polymers. While it is established that stereochemistry in linear polymers affects their bulk mechanical properties, the application of this concept to photocurable networks could allow for resins that can accommodate the increasing demand for mechanically diverse materials without the need to significantly change their formulation. Herein, we exploit cis and trans stereochemistry in pre-resin oligomers to create photoset materials with mechanical properties and degradation rates that are controlled by their stereochemistry and molecular weight. Both the synthesis of stereopure (cis or trans) acrylate-terminated pre-polymers and the subsequent UV-triggered cross-linking occurred with a retention of stereochemistry, close to 100%. The stereochemistry of a 4 kDa oligomer within the resin enabled the tuning of the formulation to either a fast eroding, soft cis elastomer or a stiff trans plastic that is more resistant to degradation. These results demonstrate that stereochemistry is a powerful tool to modify the stiffness, toughness, and degradability of high-resolution, three-dimensional printed scaffolds from the same formulated ratio of components.

Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**

Browne, Duncan L.,Colombel-Rouen, Sophie,Crévisy, Christophe,Curbet, Idriss,Mauduit, Marc,McBride, Tom,Morvan, Jennifer,Roisnel, Thierry

supporting information, p. 19685 - 19690 (2021/08/06)

The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/ Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors.

Preparation method of N-(4-methylpyridine-3-yl) methyl carbamate

-

Paragraph 0020; 0022; 0025; 0030; 0032; 0035; 0040; 0042, (2021/06/02)

The invention relates to the technical field of preparation methods of N-(4-methylpyridine-3-yl) methyl carbamate, and discloses preparation of potassium tert-butoxide and preparation of the potassium tert-butoxide by using potassium methoxide. According to the preparation method of the N-(4-methylpyridine-3-yl) methyl carbamate, a user uses the potassium methoxide to prepare the potassium tert-butoxide, so that the content of the potassium tert-butoxide is higher, the potassium tert-butoxide and the potassium methoxide are very similar in properties and functions, so that the cost is saved, the method for extracting a THT solvent by using 1, 4-dichlorobutene as a raw material is simple, and the method has the advantages that the use amount of the catalyst is small, the condition is mild, the extraction purity is high, so that the cost is reduced again; and the N-(4-methylpyridine-3-yl) methyl carbamate is obtained by catalyzing two high-purity raw materials through the catalyst carbonic acid diester and stirring, so that the preparation efficiency is improved, the purity of the prepared N-(4-methylpyridine-3-yl) methyl carbamate is improved, the over-high preparation cost of the N-(4-methylpyridine-3-yl) methyl carbamate is avoided, and the use of the user is facilitated.

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